Points, Cards and Travel

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 137 of Points, Cards, and Travel, join us as Ross Alcorn sits down with Henah Velez to make the BILT Card feel simple again. If you have rent or a mortgage and you want travel rewards without adding more complexity, this episode breaks down what matters, what changed, and how to think through it without getting stuck in the math.Henah shares how she originally got the Built Card as a renter paying around $4,000 in rent, why earning something beats earning nothing, and how she uses BILT points to book trips like Atlanta to Europe on Flying Blue promos, plus a 4.5K Alaska redemption that replaced a $400 cash ticket. They also unpack housing only vs BILT cash, how transaction fees really work, and why using a calculator can save you from guessing. If you want a cleaner credit card strategy that matches your real spending, this is your roadmap.Credit Card Resources:⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsHenah’s Social Media:InstagramNewsletterItinerary Boss Socials:⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 136 of Points, Cards, and Travel, join us as Ross sits down with real estate investor Chris Reichenbach to show how points and miles can fund real travel while helping you move faster in business. If you are paying renovation costs by check or ACH, you might be missing a safer, more flexible way to pay, earn rewards, and keep projects moving.Chris shares how he went from fearing credit cards to using 0% APR business credit cards to cover materials, float expenses between hard money draws, and rack up points and miles without chasing random offers. You will hear how he handled a nightmare renovation that jumped to $140,000, why contractor payment methods matter, and how credit cards can protect you when work is not delivered. He also breaks down how he used points and miles to book a Hawaii trip that saved over $6,000 and created a life moment he will never forget.Credit Card Resources:⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for TravelMelio: Pay vendors who don't take card with credit card to earn more pointsChris’s Social Media:InstagramYouTubeSpotifyItinerary Boss Socials:⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 135 of World Travel Made Easy With Itinerary Boss, Ross sits down with Kerry Krull, founder of The Wedding App, to break down what actually makes destination weddings stressful and how couples can avoid it. Most destination weddings don’t fall apart because of travel costs or venues. They fail because guests don’t know what’s going on.Join us as Kerry shares insights from her background in corporate events and wedding planning, explaining why destination weddings should be treated like multi-day experiences, not just a single ceremony. From missed welcome parties to flight cancellations and last-minute schedule changes, Kerry explains how lack of communication creates chaos and how real-time updates can completely change the guest experience.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources: ⁠⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠⁠⁠Best Credit Cards for Travel⁠⁠⁠⁠Bonus Offer Notifications⁠⁠⁠⁠Transfer Bonus Notifications⁠⁠⁠⁠Melio⁠⁠: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Kerry’s Social Media:InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 134 of World Travel Made Easy With Itinerary Boss, Ross sits down with Jacob Goldberg, co-founder of SkyKey, to break down one of the biggest hidden problems in airfare pricing and the simplest solution most travelers are missing.Airlines constantly change prices, and most travelers never check their ticket again after booking. Jacob explains why 40–50% of flights drop in price after purchase and how SkyKey monitors flights 24/7 to automatically secure refunds or flight credits when prices fall. With average savings of $130 per flight, SkyKey removes the stress of timing airfare purchases, deal alerts, and mental gymnastics especially for families, business travelers, and anyone booking peak travel dates.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources: ⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠⁠Best Credit Cards for Travel⁠⁠Bonus Offer Notifications⁠⁠Transfer Bonus Notifications⁠⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Jacob’s Social Media:InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 133 of World Travel Made Easy With Itinerary Boss, Discover how positioning flights can turn “I don’t live near a hub” into real business-class options. Hunter Threadgill aka the Professor of Points breaks down what positioning flights are, why they work, and how to use them without blowing up your trip when delays happen.You’ll learn how to spot the best airports to position through (think Chicago, Boston, Seattle, Vancouver, and more), how to protect the long-haul seat you actually care about, and how to plan stress-free buffers especially when you’re on separate tickets or switching airports. Hunter also shares how he uses hotel points (like Hyatt and free-night certificates) to turn an overnight into a bonus vacation day, plus a simple way to think about fuel surcharges and smarter Europe gateways like Paris and Amsterdam. We also touch award availability patterns and why competition at “someone else’s hub” can create opportunities.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources: ⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠⁠Best Credit Cards for Travel⁠⁠Bonus Offer Notifications⁠⁠Transfer Bonus Notifications⁠⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Hunter’s Social Media:InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 132 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with JT Genter, Editor-in-Chief at AwardWallet, to break down how travelers can finally get organized with points and miles without spreadsheets, stress, or lost rewards. If you’ve ever forgotten expiration dates, redeemed points poorly, or felt overwhelmed managing multiple loyalty programs, this episode delivers clarity.Join us as JT shares how AwardWallet helps track credit card points, airline miles, hotel rewards, expiration alerts, and even flight repricing opportunities, all in one dashboard. You’ll hear how beginners can avoid analysis paralysis, how advanced travelers spot better redemptions, and why flexibility across programs leads to stronger value. JT also reveals common mistakes he sees, including why redeeming points for gift cards quietly destroys value.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources: ⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠⁠Best Credit Cards for Travel⁠⁠Bonus Offer Notifications⁠⁠Transfer Bonus Notifications⁠⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!JT’s Social Media:InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 131 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with Spencer Johnson to break down how to build a simple, sustainable credit card strategy that actually leads to travel. Instead of chasing every shiny offer, Spencer explains how to start with the right foundation, choose cards that fit your real spending, and use transferable points to unlock better flights and hotels.This conversation covers annual fee math, welcome bonus timing, and why most people overcomplicate points and miles far too early. Spencer also explains how “cash back” cards can quietly become powerful travel tools, when diversification across banks actually helps, and how to avoid getting stuck with points you can’t use. If you want a clear roadmap whether you’re brand new or trying to clean up a messy setup, this episode delivers practical advice you can apply immediately. Subscribe to make sure you don’t miss future expert breakdowns.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You ThereBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMelio: Pay vendors who don't take card with credit card to earn more pointsFavorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Spencer’s Social Media:InstagramTiktokWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 130 of World Travel Made Easy With Itinerary Boss, Ross sits down with Max Craig (“Points to the Max”) for a practical Southwest Companion Pass playbook that works in 2025 and 2026 without the timing mistakes that kill your value. Discover how the Southwest Companion Pass really works (true buy-one-get-one for just taxes and fees), why earning it early in the year can unlock up to 21+ months of upside, and how to approach the two-card method using P1/P2 strategy and the 24-month rules. Max also breaks down the recent Southwest changes, basic fare limits, fare multipliers, assigned seating, and bag fees and the simple math that can make a card’s annual fee pay for itself fast. You’ll also hear a smart repositioning flight framework (like Nashville → Chicago) to reach better international award deals, plus the most common Companion Pass pitfalls, spend tracker surprises, returns, and companion-change headaches (and why calling is often better).Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus Notifications Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Max’s Social Media:InstagramFacebook PageWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 129 of World Travel Made Easy With Itinerary Boss, we dive into the world of military credit cards with Spencer Rees from Military Money Manual. If you’re active duty, Guard/Reserve, or a military spouse, this episode shows how fee-waived premium cards can unlock premium travel, elite hotel status, and thousands in yearly savings. Learn exactly how to confirm MLA eligibility, why Amex Platinum and Chase Sapphire Reserve are the heavy hitters, and how to avoid the most common mistakes service members make with points and miles.Join us as Spencer breaks down the Military Lending Act, reveals the difference between active duty and veteran benefits, and shares real stories of flying business class on PCS moves, stacking hotel status overseas, and converting unused credits into real-life wealth (including Roth IRA contributions). You’ll also learn simple systems for batching credits, tracking cards, protecting your credit score, and maximizing rewards without overwhelm.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Spencer’s Social Media:InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 128 of World Travel Made Easy With Itinerary Boss, Ross sits down with Steve Domino, co-founder of Crew, to show how a smart banking setup makes travel goals actually happen. Credit Card Points are only valuable when your money system is simple, automatic, and built to prevent overspending. Steve walks through Crew’s pockets, paycheck rules, joint accounts, and kid allowances so your bills, savings, and travel budget move themselves.Join us as we connect Credit Card Points strategy to real-life family finances: auto bill pay from a bills pocket, overspend protection tied to your budget, and a month-in-review that spotlights where to earn more. Crew offers a high-yield checking account (with Itinerary Boss code, a limited APY boost) and is building a smart charge card that pays down daily or weekly so you get rewards without carrying a balance. If you’ve tried tools like Greenlight, Monarch, or YNAB, Crew combines the pieces in one place for Points & Miles beginners and busy parents. Subscribe for more practical systems that help you travel more without debt.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Steve’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 127 of World Travel Made Easy With Itinerary Boss, Ross sits down with money coach and podcaster Suzy May to break down how world schooling really works for regular families. You’ll hear how her family splits time between Colorado and Spain, why world schooling isn’t just for digital nomad influencers, and how the cost of preschool at home can equal a full school year abroad. If you’ve ever wondered whether world schooling and slow family travel are only for the ultra-rich, this conversation will fix that fast.They dig into choosing locations, navigating visas like Schengen and Mexico’s 180-day rule, and comparing real numbers on daycare, private schools, and programs like international schools or world schooling hubs. Then they tie it all back to points and miles, how slow travel uses fewer flights, why positioning flights and trains matter, and how business owners can turn everyday spending into long-haul family trips. If you want your kids learning from the world instead of just worksheets, this episode will give you a clear, practical roadmap.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Suzy’s Social Media:FacebookInstagramWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 126 of World Travel Made Easy With Itinerary Boss, we sit down with Ben from Ben’s Big Deals to break open the world of hotel upgrades and real-life elite status strategy. If you’ve ever wondered why some people always seem to snag better rooms, free nights, and special treatment, this hotel upgrade deep dive is your playbook.Ben shares how he went from La Quinta business trips to luxury stays using hotel upgrades, elite status, and smart use of free night certificates instead of just chasing flashy flights. You’ll learn why emailing the property before arrival matters, how ownership and brand relationships affect your stay, and when to pay cash vs. points. We get into IHG, Hyatt, Marriott, Hilton, best rate guarantees, elite status shortcuts, and how to think like a VIP guest without overcomplicating the game. If you want your next trip to feel like an intentional experience instead of a random hotel night, this is one you’ll want to replay and take notes on.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Ben’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 125 of World Travel Made Easy With Itinerary Boss, licensed mental health clinician Mariah Hudler unpacks the link between money mindset and travel freedom. Join us as we explore Points & Miles through the lens of financial therapy, identifying money scripts (avoidance, vigilance, status, worship), healing financial trauma, and building calm, repeatable systems that actually lead to more trips.Mariah shares practical steps: monthly money dates, values-based spending, clear goals, and vision boards that connect emotions to action. We discuss paying in full, automating savings, and aligning Points & Miles with your “rich life” priorities so award travel feels intentional, not impulsive. You’ll hear how couples can increase transparency, communicate better, and use Points & Miles to reward consistent habits. Expect simple frameworks you can use today, from transferring wisely to tracking net worth plus examples across Chase Ultimate Rewards, Capital One, and Southwest. Ready to become an “optionaire” and design travel that fits your life? Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Mariah’s Social Media:LinkedInWebsiteItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 124 of World Travel Made Easy with Itinerary Boss, we revisit one of the most practical tutorials ever released on how to earn more from the shopping you already do.This replay dives back into shopping portals like Rakuten and SaveWise, showing how simple browser extensions can multiply your points and cash back with zero extra effort. You’ll learn how to link your American Express account to convert Rakuten cash back into Membership Rewards, how to stack SaveWise alerts for Amex, Chase, and SimplyMiles, and how these small tweaks can add up to free flights and upgraded stays.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Itinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 123 of World Travel Made Easy With Itinerary Boss, Ross sits down with Ali for a hands-on Hyatt deep dive. Join us as we unpack why Hyatt delivers outsized value in Points & Miles, from reliable award charts and a powerful Points Calendar to elite perks that actually show up at check-in. You’ll hear how Globalist benefits, suite upgrades, free breakfast, and waived resort fees combine with simple tactics like billing everything to the room for 9x to stretch every stay.We cover Points & Miles fundamentals most travelers miss: Chase and Bilt transfer partners for Hyatt, when to earn & burn, how to time off-peak redemptions, and smart scenarios for buying points (hello, Alila Ventana). Families get practical booking paths (Guest of Honor, points-plus-cash), and American Airlines flyers learn why linking accounts and status matching multiplies returns. If you’re choosing between Hyatt, Marriott, and Hilton, this conversation shows where the real cents-per-point value lives. Ready to plan Park Hyatt-level memories without Park Hyatt cash?Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Ali’s Social Media:InstagramFacebookBeaconsItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 122 of World Travel Made Easy With Itinerary Boss, Ross sits down with Matthew Dong (WuHoo Group  LLC) to demystify Dulles (IAD) as a Star Alliance springboard. If you’ve ever asked why that United flight often prices cheaper with Air Canada Aeroplan or how to find saver awards without spending hours, this one’s for you. We cover Points & Miles basics that work today: partner booking, hub-to-hub domestic routes, real award comparisons (80k vs 60k vs 45k), and when to use tools like seats.aero.Join us as Mattew shares family travel tactics, what lap-infant fees really cost internationally, how Aeroplan shows seats left, and why Capital One Venture X plus Priority Pass lounges at IAD/DCA simplify airport days. You’ll learn how Points & Miles stretch further with transfer bonuses, why diversification matters across Amex/Chase/Capital One, and how to sanity-check award availability fast. Whether you’re eyeing Paris on Air France or a last-minute Turkish business class, this is a clear path from Dulles to “booked.”Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Matthew’s Social Media:⁠LinkedIn⁠Itinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 121 of World Travel Made Easy With Itinerary Boss, Ross sits down with Betsey Wilson, founder of Become Travel Rich, to decode how everyday travelers can use Alaska Airlines Atmos points for real value. If you fly from American hubs or you are new to Points & Miles, this is a clear blueprint to upgrade faster, spend less, and book trips that fit actual family calendars.Join us as Betsey breaks down practical redemptions like 4,500-point economy seats and 35,000-point lie-flats, how American elite benefits map on Alaska metal, why partner bookings matter, and when to pay cash versus use points. You will learn companion award differences, smart same-day change tactics, and why Condor is a standout partner for Europe and beyond. We also hit status-earning via non-airline partners and how to think about premium cards without fear of annual fees. If you want points to translate into better seats and better trips, this one’s for you. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Betsey's Social Media:⁠LinkedIn⁠InstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 120 of World Travel Made Easy With Itinerary Boss, Ross sits down with Vodacy CEO Shawn Moore to unpack the real playbook behind lifestyle assets, short term rentals, and smarter travel. If you care about ROI and real memories, this one’s for you. Learn how to balance cash flow with appreciation, when to trade up, and why setup and furnishing matter more than most spreadsheets admit. You’ll also hear how to align your Itinerary with shoulder season for better rates and quieter trips.Shawn breaks down conservative investing habits, return on equity, and the four pillars of real estate returns, plus simple ways business owners and high W2 earners can use Credit Card Points without overextending. We also talk about tax advantages like bonus depreciation and how to protect time by outsourcing management. If you want to turn business spend into Credit Card Points and smarter Credit Card Points redemptions while building a travel-friendly portfolio, this is your roadmap. Discover how lifestyle assets support long term wealth and stress free travel. Subscribe.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Shawn’s Social Media:LinkedInVodysseyInstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 119 of World Travel Made Easy With Itinerary Boss, we sit down with Brooke from CardPointers to show you how to turn everyday spending into real travel. If picking the right card at checkout feels confusing, CardPointers simplifies it so you earn more rewards with less effort. From the Best Card wizard to the browser extension that activates hundreds of bank offers in seconds, you will capture value you are probably leaving on the table.Discover how Autopilot on iPhone surfaces the best card on your lock screen as you shop, why profiles help families and teams earn smarter, and how stacking portal rewards with card offers multiplies points fast. We keep it beginner friendly while sharing power user strategies that respect YourBestCreditCards.com guidelines. If you want practical, repeatable systems for Travel rewards and Points & Miles, this one is packed with tips. Subscribe to never miss future episodes.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:TravelPayouts: Turn your trips into income and earn!Gondola AI: Find better hotels, earn more points, travel for free!Rakuten: Earn cash back/rewards on every purchase!Seats.aero: Discover the best flights for your pointsSaveWise: Maximize Cashback, Miles, & PointsAwardWallet: Organize & track your points and milesRoveMiles: Earn and redeem miles on flights/hotels without a credit cardCardPointers: Earn more from your credit cards daily Our Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Brooke’s Social Media:LinkedInCardPointersItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

(Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired.In episode 118 of World Travel Made Easy With Itinerary Boss, Ross sits down with Alex Maiersperger, global marketing lead at SAS, host of The Health Pulse podcast, and cofounder of the Young Health Leader Summit. Together, they explore the realities of traveling with kids, the mistakes families often make, and how to turn everyday expenses into memorable international trips.Join us as Alex shares how his family planned meaningful journeys to Japan and Spain, the lessons learned from navigating hotels in Europe with three kids, and why prioritizing family experiences matters more than work deadlines. You’ll also hear strategies for stretching your budget, avoiding common pitfalls like paying full price, and even creative lodging ideas like home exchanges.Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comCredit Card Resources:Points and Miles Cheat SheetBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsMesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus points Favorite Travel & Points Tools:⁠TravelPayouts⁠: Turn your trips into income and earn!⁠Gondola AI:⁠ Find better hotels, earn more points, travel for free!⁠Rakuten⁠: Earn cash back/rewards on every purchase!⁠Seats.aero⁠: Discover the best flights for your points⁠SaveWise⁠: Maximize Cashback, Miles, & Points⁠AwardWallet⁠: Organize & track your points and miles⁠RoveMiles⁠: Earn and redeem miles on flights/hotels without a credit card⁠CardPointers⁠: Earn more from your credit cards dailyOur Favorite Daily Personal & Business Tools:Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsFunction Health: Optimize your health, explore the world!Alex’s Social Media:LinkedInInstagramItinerary Boss Socials:LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners. Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.