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Fun in Key West Podcast

Author: Michele O'Connor

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🌴 Welcome to the Fun in Key West Podcast! 🌴

Get ready to dive into all things Key West—the southernmost island where the sunsets are breathtaking, the food is unforgettable, and the drinks are always cold! 🍹

In this podcast, we bring you insider tips on:
✅ The best places to eat (yes, there will be conch fritters 🥥).
✅ Where to drink and enjoy the island's famous cocktails 🍸.
✅ The coolest spots to stay, from cozy inns to luxury getaways 🏝️.
✅ And so much more—from quirky local events to can't-miss festivals! 🎉

We'll also keep you up to date on the latest happenings around the island and occasionally chat with special guests who know Key West like the back of their sandy hand. 🐚

Whether you're planning your first trip, a frequent visitor, or just daydreaming about island life, this podcast is your ultimate guide to enjoying paradise.

🎙️ New episodes every wek—so don't forget to subscribe! Hit the like button if you're as obsessed with Key West as we are, and share the island love with your friends!

💌 Connect with us!
👉 Website: www.FunInKeyWest.com
👉 Follow us on Facebook, Instagram, and Twitter for even more island vibes.

🌊 So grab your flip-flops, pour yourself a cold drink, and escape to the island state of mind with the Fun in Key West Podcast!

#FunInKeyWest #KeyWestPodcast #IslandLifeVibes
116 Episodes
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Exploring the Marine Hospital: Key West's Historic Gem In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the rich history of the Marine Hospital in Key West. From its origins in the 1840s as a life-saving medical facility, through hurricanes and yellow fever outbreaks, to its current status as condos in the Truman Annex, the building has witnessed a plethora of significant events. The episode explores Key West's ability to adapt and preserve its heritage while offering listeners an insider's guide to historical markers around the island. Tune in to learn fascinating stories, uncover potential connections to Ernest Hemingway, and enjoy the laid-back vibe of Key West history. Don't forget to visit funinkeywest.com for self-guided walking tours and more Key West fun. 00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: Marine Hospital 02:59 The Marine Hospital's Storied Past 06:46 Hemingway's Rumored Connection 08:02 From Hospital to Condos 09:29 Exploring Key West's Historical Markers 11:32 Conclusion and More Key West Fun   https://funinkeywest.com/marine-hospital/    
Exploring Key West Through Food: The Ultimate Guide to Tasty Tuesday   In this episode of the Fun in Key West podcast, host Michele O'Connor introduces listeners to the vibrant food scene of Key West through a variety of food tours. She details four main tours: the Southernmost Food and Cultural Walking Tour, the Historic Seaport Seafood Lovers Tour, a Craft Cocktail Crawl, and the Hemingway Experience. Michele explains each tour's unique offerings, highlights their durations, what visitors can expect to taste, and offers practical tips for making the most of each experience. The episode emphasizes the importance of booking tours early, wearing comfortable shoes, and staying hydrated. Listeners are encouraged to interact by sharing their favorite food tour experiences and dishes.   00:00 Welcome to Fun in Key West Podcast 01:26 Exploring Key West Through Food 02:20 Key West Food Tours Overview 04:35 Southernmost Food and Cultural Walking Tour 07:27 Historic Seaport Seafood Lovers Tour 08:24 Craft Cocktail Crawl 10:10 Hemingway Experience Tour 11:59 Tips for Enjoying Key West Food Tours 16:51 Conclusion and Final Thoughts https://funinkeywest.com/key-west-food-tours-2/  
The Outer Mole: Key West's Historic Evolution   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor delves into the fascinating history of the Outer Mole at Key West. Michele guides listeners through the transformation of the Outer Mole from wooden docks built before the Civil War to its current role as a concrete pier for large cruise ships and military vessels. The episode covers the Outer Mole's evolution, including its role during World War I and II and the transition to modern times when the Navy sold most of its property but retained this crucial docking spot. Listeners are invited to explore Key West's rich history, visit historic markers, and stay updated on the latest happenings in the island paradise.   00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday Introduction 01:47 Exploring the Outer Mole's Rich History 05:30 The Evolution of Key West's Naval Base 09:07 Modern Day Outer Mole and Cruise Ships 12:13 Connecting Key West's Past and Present 15:33 Upcoming Events and Community Engagement 17:35 Conclusion and Farewell   https://funinkeywest.com/outer-mole-key-west/  
Exploring the World of Low-Carb Mocktails In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the vibrant and refreshing world of mocktails. Whether you're participating in Sober October, gearing up for Dry January, or simply looking for healthier, low-carb drink options, this episode is packed with tips and recipes. Michele discusses the art of creating balanced mocktails using fresh ingredients, keto-friendly sweeteners, and non-alcoholic alternatives. She also touches on the growing acceptance and popularity of mocktails in social settings and offers ideas for incorporating them into your daily routine. Listeners are encouraged to share their favorite mocktail recipes and non-alcoholic wine recommendations. The episode concludes with an invitation to join the Fun in Key West community and partake in the many engaging activities and resources offered. 00:00 Welcome to Fun in Key West Podcast 01:26 Exploring the World of Mocktails 01:55 Mocktail Series: Tips and Recipes 06:11 Crafting the Perfect Low Carb Mocktail 09:48 Building Your Low Carb Drink Bar 14:35 Join Our Fun Community 16:23 Final Thoughts and Farewell   Sign up for the newsletter - get the happy hour list Join the book club Join the VIP Club https://funinkeywest.com/low-carb-non-alcoholic-drinks/    
Exploring Key West and the Beach Bum Book Series with HR Gordon In this episode of the Fun in Key West podcast, host Michele O'Connor introduces listeners to the book club edition featuring HR Gordon, author of the Beach Bum book series. HR Gordon discusses her inspiration behind the series, her connection to Key West, and the importance of Jimmy Buffett's music in her work. The conversation covers her experiences living on the island, her favorite locations and meals, and the vibrant characters that influence her stories. Listeners will learn about the different books in the series, writing process, and the unique way the proceeds support the Save the Manatee organization. The episode is filled with island vibes, personal anecdotes, and insights into the idyllic life of Key West. 00:00 Welcome to Fun in Key West Podcast 01:28 Introducing HR Gordon and the Beach Bum Book Series 02:30 HR Gordon's Journey to Writing 03:29 The Inspiration Behind Fins and Flames 06:06 Creating Authentic Key West Characters 07:00 Exploring Key West Locations in the Books 08:52 The Beach Bum Books Series and Charity Work 12:30 Challenges in Writing Romance and Key West Stories 18:14 Book Signing Experience in Key West 20:24 Connecting Through Books 21:54 Key West Inspirations 23:08 Dreaming of Key West 25:25 Favorite Key West Activities 29:16 Writing Process and Inspirations 33:48 Key West Culinary Delights 37:06 Final Thoughts and Farewell     Sign up for the newsletter - get the happy hour list Join the book club Join the VIP Club https://hannahrgordon.com/ Buy Fins and Flames - on Amazon (This is an Amazon affiliate link.  I will earn a commission on qualifing purchases.  
Key West: A Literary Haven   In this episode of the Fun in Key West podcast, host Michele O'Connor welcomes listeners to explore the creative soul of Key West. The episode serves as an insider's guide to the island, diving deep into its rich literary history. The discussion covers famous authors who have been inspired by Key West, including Ernest Hemingway, Tennessee Williams, Robert Frost, and Judy Blume. Michele highlights notable spots such as Hemingway's home, the Tennessee Williams Museum, and other local literary landmarks. The episode also promotes the podcast's book club, VIP club, and upcoming events, encouraging listeners to engage with the Key West literary community. Tune in for a blend of storytelling, book recommendations, and island culture.   00:00 Welcome to Fun in Key West 01:26 Exploring Key West's Literary Magic 02:03 First Timer Friday: Key West Highlights 03:34 Key West: A Haven for Famous Authors 06:50 Hemingway's Key West Legacy 11:43 Tennessee Williams' Sanctuary 13:48 Robert Frost and Other Literary Greats 17:17 Key West Festivals and Landmarks 19:32 Join Our Book Club and VIP Club 21:16 Conclusion: Keep the Stories Alive   Sign up for the newsletter - get the happy hour list   Join the book club   Join the VIP Club
Raising a Glass to Tiki Culture: History, Drinks, and Mocktails   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor dives into the tropical vibes of tiki culture. The podcast covers the history of tiki bars, starting from the 1930s with Don the Beachcomber, and highlights significant tiki landmarks like Trader Vic's. Michele discusses what makes a drink 'tiki,' from ingredients like pineapple juice and coconut cream to unique garnishes. The episode also focuses on creating non-alcoholic tiki mocktails, offering recipes and tips for enjoyable, alcohol-free beverages. Listeners are encouraged to participate in the Key West community by joining a book club, signing up for the newsletter, and engaging in contests for Key West swag.   00:00 Welcome to Fun in Key West Podcast 01:26 Thirsty Thursday: Tiki Culture and Drinks 07:44 Crafting the Perfect Tiki Mocktail 15:20 Essential Tools for Your Home Tiki Bar 17:41 Must-Try Virgin Tiki Drinks 20:22 Wrapping Up: Key West Vibes and More   Sign up for the newsletter   Sign up for the book club
The Impact of Steam Power on Key West   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor takes listeners on a journey through the fascinating history of steam power and its transformative impact on Key West. From enabling quicker maritime travel and aiding in the fight against piracy to powering trains and lighting up homes, steam power turned Key West into a vital hub of commerce, travel, and military strategy. Michele highlights how steam power contributed to significant historical events like the Civil War and the California Gold Rush. She encourages listeners to explore Key West's historic markers for more captivating stories and gives a shout-out to various local events and activities. Tune in to learn how steam power reshaped Key West and made it the unique paradise it is today.   00:00 Welcome to Fun in Key West Podcast 01:27 Historic Marker Monday Introduction 01:59 The Impact of Steam Power on Key West 03:25 Steam Power in the Industrial Revolution 05:19 Key West's Role in Maritime and Military History 07:21 Steam Power's Broader Influence 09:01 Conclusion and Community Engagement   Sign up for our newsletter: https://funinkeywest.kit.com/765a844435  
Exploring October Festivities in Key West: Weather, Events, and More In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to enjoying Key West in October. She highlights the area's perfect weather, foodie adventures, music festivals, and the legendary Fantasy Fest. Listeners get a rundown of weekly and monthly events, including the Truman Annex Farmer's Market, fly fishing championships, and the Key West Music Festival. Michele emphasizes the impact of hurricane season and offers flexible travel tips. Additionally, she discusses unique activities such as ghost tours, the annual Zombie Bike Ride, and various local parades. The episode concludes with information on upcoming holidays and a call to check out more details and guides on funinkeywest.com. 00:00 Welcome to Fun in Key West Podcast 01:26 October Excitement in Key West 02:16 Weather and Tips for October 03:16 Events and Activities in October 05:05 Fantasy Fest Highlights 09:06 Halloween and Haunted Key West 10:22 Wrapping Up and Final Thoughts   www.funinkeywest.com    
The Ultimate Guide to Key West Sunset Sails In this episode of the 'Fun in Key West' podcast, host Michelle O'Connor provides an insider's guide to experiencing the best sunset sails Key West has to offer. Whether you're a first-time visitor or a seasoned island dweller, this episode covers a range of sunset sail options from the luxurious Danger Charters' Wind and Wine Sail to the vibrant Fury's Commotion on the Ocean. Michelle also shares practical tips on booking, what to expect, and highlights unique experiences like floating tiki bars and private sandbar charters. Tune in to discover the magic of Key West sunsets and make your next trip unforgettable. 00:00 Welcome to Fun in Key West Podcast 01:26 The Magic of Key West Sunsets 01:51 Exploring Sunset Sails 04:44 Top Sunset Sail Experiences 17:11 Insider Tips for Sunset Sails 21:40 Recap and Final Thoughts 24:34 Farewell and Next Steps www.funinkeywest.com  
Uncovering the Wild History of Key West's Old Custom House In this episode of the Fun in Key West podcast, host Michele O'Connor explores the fascinating history of Key West's old Custom House. From its pivotal role in the wrecking industry, which turned Key West into one of America's wealthiest cities, to its transformation into the current Custom House Inn, Michele dives into thrilling tales of shipwrecks, treasure hunts, and the lawlessness of the 19th century. The episode also includes interesting facts about the structure's relocation and its continued historical significance. She encourages listeners to explore Key West's historic markers for a richer understanding of the island's adventurous spirit and history. For more Key West insights, listeners are invited to join the podcast's book club and VIP community. 00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: The Old Custom House 03:21 The Wrecking Industry: Key West's Treasure Hunting Past 07:26 The Custom House: From Wrecking Hub to Cozy Inn 10:27 Exploring Key West's Rich History 10:59 Join Our Community and Keep Exploring www.funinkeywest.com    
The Ultimate First Timer's Guide to Key West In this episode of the Fun in Key West podcast, host Michele O'Connor offers a detailed guide for first-time visitors planning a 2-3 day trip to Key West. She covers top dining spots like Cuban Coffee Queen, Blue Heaven, and Latitudes, along with must-visit locations such as the Hemingway House and Mallory Square. Michele provides insights on activities ranging from snorkeling to sunset cruises, emphasizing the importance of spontaneity and local tips like hydration and sunscreen. Listeners are encouraged to enjoy the laid-back island vibes and start planning their return trip even before leaving. 00:00 Welcome to Fun in Key West 01:26 First Timer Friday: Your Perfect Itinerary 02:22 Exploring Key West: Hidden Gems and Local Tips 05:02 Day One: Arrival and Initial Adventures 10:17 Day Two: Adventure and Relaxation 13:15 Day Three: Final Day Highlights 16:08 Bonus Tips and Local Secrets 18:51 Wrapping Up Your Key West Adventure   https://funinkeywest.com/category/what-to-do/must-see/    
Game Day in Paradise: Best Sports Bars in Key West   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor dives into the best sports bars on the island where you can catch your favorite game while enjoying the laid-back, tropical ambiance of Key West. Highlights include Jack Flats with its team-based seating arrangement, Pickles Pub boasting 40 TVs and a late-night kitchen, Brady's Pub's relaxed atmosphere, and other notable venues like Old Town Tavern, Celtic Kunk Pub, and Mary Ellen's. Michele also provides additional tips on where to dine, drink, and explore, making this episode essential for both sports enthusiasts and Key West visitors. 00:00 Welcome to Fun in Key West Podcast 01:26 Game Day in Paradise: Best Sports Bars 04:13 Top Picks for Watching Sports in Key West 06:45 Hidden Gems and Local Favorites 09:06 Plan Your Perfect Key West Experience 09:50 Conclusion and Farewell https://funinkeywest.com/best-sports-bars-in-key-west/  
Exploring Key West's Hidden Gems: The Benjamin Curry House   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on an in-depth exploration of the historic Benjamin Curry House, a private residence in Key West that has been in the Curry family for over 150 years. Michele discusses the house's unique architectural features, its historical significance, and its connection to one of Key West's most famous residents, Ernest Hemingway. The episode highlights the Curry family's influence on Key West, from Florida's first millionaire to the design of Old Town streets and the establishment of the Sunset celebration at Mallory Square. Listeners are encouraged to visit funinkeywest.com for more self-guided historic marker tours and to join the podcast's book club and happy hour newsletter.   00:00 Welcome to Fun in Key West 01:27 Historic Marker Monday: The Benjamin Curry House 03:30 The Curry Family Legacy 04:38 Architectural Marvels and Historical Artifacts 06:52 Connections to Ernest Hemingway 09:18 Exploring Key West's Historic Markers 09:53 Join the Fun in Key West Community 10:45 Conclusion and Farewell   www.funinkeywest.com  
Life Stories from Key West: Interview with Richie 'Conch Boy' Gomez   In this episode of the Fun in Key West podcast, host Michele O'Connor interviews Richie 'Conch Boy' Gomez, a third-generation Conch and author of 'Key West, A Smuggler's Tale.' Richie shares his rich and adventurous life growing up in Key West, from his childhood memories and smuggling adventures in the 1960s and 1970s to his time as a commercial fisherman and charter business owner. Throughout the conversation, Richie highlights real-life characters from his book, the dangers and excitement of his smuggling days, and the personal impacts on his family life. The episode also touches on Richie's writing journey and his plans for future books.   00:00 Welcome to Fun in Key West Podcast 01:28 Introducing Richie Conk Boy Gomez 02:57 Richie's Early Life in Key West 03:17 Fishing Adventures and Family Legacy 09:08 Smuggling Tales and Book Insights 18:05 The Writing Journey Begins 26:21 Brotherly Bonds and Heartache 28:25 Hints and Reflections on Relationships 29:58 Memories of Elizabeth Street 32:23 Truth and Embellishment in Storytelling 33:39 Starting a Charter Company in Key West 37:23 New Book and Writer's Block 40:28 Favorite Spots in Key West 44:48 Reflections on Friends and Memories 49:13 Conclusion and Final Thoughts   Amazon Affiliate link  - As an Amazon Affiliate I earn on qualifying purchases. Key West: A Smugglers Tale   Want to reach out to Richie? Here's his Facebook Page https://www.facebook.com/richard.gomez.9085790    
Historic Marker Monday: The Great Havana Hurricane of 1846   In this episode of the Fun in Key West podcast, host Michele O'Connor delves into the devastating Great Havana Hurricane of 1846. Michele describes the hurricane's catastrophic impact on Key West, including the loss of lives, the disappearance of a lighthouse, and the uprooting of the Key West Cemetery. She highlights the subsequent rebuilding efforts which led to a 300% increase in the population and improved construction techniques. Michele also discusses the importance of hurricane preparedness and shares some fun facts about Key West's geography and history. The episode aims to give listeners a comprehensive understanding of this significant event in Key West's past. 00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: The Great Havana Hurricane 03:05 The Devastation of the 1846 Havana Hurricane 09:12 Rebuilding and Resilience in Key West 12:33 Key West Today and Final Thoughts   www.funinkeywest.com  
Key West Festival Guide: Finding the Perfect Time to Visit   In this episode of the Fun in Key West podcast, host Michele O'Connor provides a lively and comprehensive guide to the festivals and events in Key West throughout the year. Michele emphasizes the importance of checking the festival calendar first when planning your trip to avoid surprises and strategically plan your visit around or away from the bustling events. The episode covers major events from October's Fantasy Fest to July's Hemingway Days and beyond. Michele also discusses the value of staying informed about Key West's vibrant scene through resources on funinkeywest.com, including a calendar of events, a newsletter, and a book club. Whether you're looking for a party or a quiet getaway, this guide will help you navigate Key West's year-round celebrations.   00:00 Welcome to Fun in Key West 01:26 Planning Your Key West Adventure 03:45 Festival Highlights: October to December 06:35 Festival Highlights: January to April 08:49 Festival Highlights: May to August 10:05 Festival Highlights: September to December 10:50 Staying Updated and Signing Off   https://funinkeywest.com/category/what-to-do/calendar-of-events/  
Pirates, Shipwrecks, and the Wild History of Key West   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a historical journey through Key West's intriguing past, covering pirates, naval missions, and shipwreck salvage. The story begins in the 1820s with the US Navy's efforts to eliminate pirates in the Caribbean, leading to the rise of the Mosquito Fleet. Michele details Commodore David Porter's pivotal role and the emergence of legal wreckers who turned shipwrecks into lucrative ventures, contributing to Key West becoming one of the wealthiest cities per capita in the United States. The episode also highlights notable sights in Key West, such as the Key West Shipwreck Museum and various historical markers.   00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: Pirates and Treasure Hunters 05:04 The Rise of the Mosquito Fleet 09:21 The Wreckers: Turning Disaster into Fortune 13:14 Exploring Key West's Rich History 16:32 Wrapping Up and What's Next  
Unveiling the Mysteries of St. Mary's Star of the Sea   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a journey through the rich history of St. Mary's Star of the Sea, Key West's oldest Roman Catholic parish. Michele delves into legends, key events, and architectural marvels of the church that has stood against hurricanes and other adversities. She explores its origins in the 1840s, the devastating fire of 1901, and its stunning rebirth thanks to Jesuit architect Brother Cornelius Otten. The episode also highlights the grotto built by Sister Louise Gabriel, which locals believe protects the island from direct hurricane hits. Michele connects the maritime, multicultural, and resilient spirit of Key West embodied in this historical site.   00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: Key West's Unofficial Force Field 03:36 The Origins of St. Mary's Star of the Sea 08:03 Rebuilding After the Fire 09:27 Architectural Marvels and Wartime Stories 12:52 The Grotto and Its Hurricane Legend 15:01 Modern Day St. Mary's and Community Impact 17:50 Conclusion and Call to Action     https://funinkeywest.com/fun-in-key-west-book-club/                  
Exploring Key West's History: The Rise and Fall of the Mallory Steamship Line   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a journey back to the 1870s to explore the history of the Mallory Steamship Line, a vital link between the North and South that significantly impacted the development of Key West. The episode covers the founding of the company by Charles Henry Mallory, its contributions during the Civil War, and its golden age of steam travel before being overshadowed by Henry Flagler's railroad. The story also touches on the evolution of transportation technology and its impact on tourism and local culture in Key West. Michele concludes the episode by encouraging listeners to explore Key West's historic markers and hints at upcoming podcast topics.   00:00 Welcome to Fun in Key West Podcast 01:26 Historic Marker Monday: The Mallory Steamship Line 03:34 The Rise and Fall of the Mallory Steamship Line 09:20 Mallory Square: A Living Legacy 11:57 Conclusion and Future Episodes   https://funinkeywest.com/fun-in-key-west-book-club/ https://funinkeywest.com/category/what-to-do/historic-walking-tour/  
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