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Fun in Key West Podcast
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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
102 Episodes
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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/  
Exploring Key West with Lucy Burdette: Inside the Key West Food Critic Mysteries   In this episode of the Fun in Key West podcast, host Michele O'Connor interviews Lucy Burdette, the author behind the Key West Food Critic Mysteries. The conversation delves into how Burdette's accidental love for Key West inspired her 15-book mystery series. Topics include the origins of her characters, real-life inspirations, the local flair of Key West, and sneak peeks into her upcoming 16th book. Listeners will also discover Burdette's favorite Key West spots, culinary delights, and unique anecdotes, making it a must-listen for any Key West enthusiast.   00:00 Welcome to Fun in Key West Podcast 01:26 Meet Lucy Burdette: The Key West Food Critic Mysteries 02:37 The Inspiration Behind the Characters 06:27 Writing Authentic Key West 15:02 Character Development and Personal Connections 22:46 Introduction to the Author's Personal Life 23:44 Food and Cooking Preferences 24:37 Restaurant Reviews and Key West Favorites 26:58 Impact of the Pandemic on Key West 32:44 Upcoming Book Releases and Writing Process 38:01 Final Thoughts and Fun Facts 40:40 Conclusion and Book Club Invitation   Lucy's website: https://lucyburdette.com/   Amazon Link - Buy Lucy's Books: https://amzn.to/3VsMhnq As an Amazon Affiliate I will earn a commission on qualifying purchases.  Thanks for your support!   Fun in Key West Book Club:  https://funinkeywest.com/fun-in-key-west-book-club/    
Romantic Getaways in Key West: Top Activities and Tips   In this episode of the Fun in Key West podcast, host Michele O'Connor discusses why Key West is an ideal destination for couples seeking a romantic getaway. She covers a wide range of activities from sunset sails, butterfly gardens, and meeting flamingos to visiting historic sites like the Ernest Hemingway Home and the Audubon House. Michele also shares insider tips on the best times to visit Key West for romance, where to stay, and how to make the trip Instagram-worthy. Listeners will learn about romantic dining options, fun tours, relaxing activities, and special events that capture the charm of Key West. Whether planning an anniversary, honeymoon, or just a magical weekend, this episode serves as a comprehensive guide for making the most of a couple's retreat in Key West.   00:00 Welcome to Fun in Key West 01:26 Romantic Key West Getaways 03:04 Wandering Wednesday: Exploring Key West 04:06 Top Romantic Activities in Key West 05:39 Best Times to Visit Key West 06:46 Unique Experiences for Couples 13:14 Dining and Food Tours 14:29 Off the Beaten Path Adventures 18:30 Final Tips and Farewell   https://funinkeywest.com/things-for-couples-to-do-in-key-west/  
Key West Roosters: From Fighters to Feathery Celebrities   In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the fascinating history and cultural significance of Key West's most iconic residents — the roosters. Michele discusses how these birds transitioned from being food sources to fighters and ultimately becoming the free-range celebrities of the island. The episode covers their historical origins, their role in tourism, and the mixed feelings locals have about them. Michele also introduces the Key West Chicken Law, which protects these quirky birds. Tune in for fun rooster stories, explore more through Michele's blog post, and join the Fun in Key West newsletter and book club for additional island insights.   00:00 Welcome to Fun in Key West 01:26 Key West Roosters: The Island's Feathered Celebrities 02:44 The History and Cultural Significance of Key West Roosters 04:47 Roosters: From Fighters to Free-Range Icons 07:48 Rooster Controversies and Legal Protections 08:53 Roosters as Symbols of Key West Spirit 10:04 Share Your Rooster Stories 12:18 Conclusion and Community Engagement   https://funinkeywest.com/key-west-roosters/  
Sipping Through Summer: Key West Cocktails & Island Vibes   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a vibrant journey through the world of summer cocktails. The show kicks off with a warm welcome to new and returning listeners, promising insider tips on the best eats, drinks, and stays in Key West. Michele then dives into an exploration of summer drinks, shedding light on the fascinating stories and science behind favorite sips, including how cognac has become a summer star. The episode offers practical tips for setting up a backyard tiki bar, featuring summer ingredients like citrus, rum, pineapple, and coconut. Michele also encourages creativity with cocktails, suggesting flavor combinations and debunking common myths about ice and dilution. Throughout the episode, she emphasizes the fun, freedom, and freshness of summer drinks, inviting listeners to share their own creations and join the Fun in Key West newsletter and book club for more island-inspired content.   00:00 Welcome to Fun in Key West 01:26 Exploring Summer Cocktails 02:41 Thirsty Thursday Special 03:27 The Science and Stories Behind Summer Drinks 09:38 Setting Up Your Backyard Tiki Bar 14:41 Wrapping Up and Final Thoughts https://funinkeywest.com/5-hennessy-drink-recipes-for-summer/  
Exploring The Best Brunch Spots in Key West   In this episode of the Fun in Key West podcast, host Michele O'Connor dives deep into the best brunch options Key West has to offer. Michele discusses iconic must-visit spots like Blue Heaven and Bagatelle, as well as hidden gems like Moondog Cafe and Anna's Cafe. The episode also covers brunch cruises and local favorites, making sure to highlight a variety of options for every type of brunch lover. Michele invites listeners to share their favorite brunch spots and reminds them to check out the Fun in Key West blog for more detailed guides. Whether you're planning a trip or just dreaming of lazy mornings by the ocean, this episode provides a comprehensive guide to enjoying brunch in Key West.   00:00 Welcome to Fun in Key West 01:26 Best Brunch Spots in Key West 04:18 Iconic Brunch Locations 06:36 Brunch with a View 09:40 Hidden Gems and Local Favorites 14:48 Wrapping Up Your Key West Brunch Adventure https://funinkeywest.com/best-brunch-in-key-west/  
Unveiling Bruce Hall: Key West's Resilient Historical Gem   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a deep dive into the history of Bruce Hall, the last remaining structure of the historic Ruth Hargrove Seminary. Michele explores the building's multifaceted past, from its roots as an educational hub in 1889, to serving as a wartime hospital during both World Wars, and later transitioning into a Navy commissary and ultimately back to an educational facility. This journey through Bruce Hall reflects the resilience, innovation, and sense of community in Key West, making it an essential stop for any history enthusiast. Michele also encourages listeners to explore other historic markers in Key West and offers practical tips for a self-guided tour on funinkeywest.com.   00:00 Welcome to Fun in Key West Podcast 01:26 Exploring Bruce Hall: A Hidden Gem 02:27 Historic Marker Monday: Discovering Bruce Hall 07:44 The Evolution of Bruce Hall 08:59 Full Circle: Bruce Hall's Return to Education 10:52 Exploring Key West's Historic Markers 11:40 Join the Fun in Key West Community 12:38 Conclusion: Keep Exploring Key West https://funinkeywest.com/bruce-hall/  
Key West's Best Lunch Spots Revealed   In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to the best lunch destinations in Key West. From iconic eateries on Deval Street to hidden gems, Michele covers a wide array of culinary delights including Cuban cuisine, fresh seafood, and hearty comfort food. The episode highlights notable spots such as Garbos Grill, Blue Heaven, Eaton Street Market, and many more. Michele also invites listeners to share their favorite lunch spots and keeps them informed about additional guides and resources available on the Fun in Key West website.   00:00 Welcome to Fun in Key West 01:26 Epic Lunch Spots in Key West 05:12 Iconic Eateries and Hidden Gems 07:24 Exploring Beyond Key West 07:59 Cuban Cuisine and Local Favorites 10:44 Special Mentions and Tips 19:02 Wrapping Up and Final Thoughts   https://funinkeywest.com/best-lunch-in-key-west/  
Exploring Key West's Iconic Conch Fritters: A Tasty Island Adventure   In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the delicious world of Key West conch fritters. Listeners get an insider's guide to the best places to savor this iconic island snack, from Louis's Backyard to Hogfish Bar and Grill. Michele also shares the history and cultural significance of conch fritters, along with tips on what makes a great fritter and which dipping sauces to try. Listeners are encouraged to share their favorite spots and join the conversation. The episode also highlights additional foodie guides and resources available on funandkeywest.com, including a book club and happy hour recommendations.   00:00 Welcome to Fun in Key West 01:26 Key West Conch Fritters: A Culinary Journey 06:03 Top Spots for Conch Fritters in Key West 11:22 Conch Fritters: Tips and Tricks 14:18 Explore More with Fun in Key West 15:51 Final Thoughts and Farewell   https://funinkeywest.com/best-conch-fritters-in-key-west/  
Tequila & Tiki Bars: Elevate Your Summer Cocktails   In this episode of the Fun in Key West podcast, host Michele O'Connor guides listeners through the vibrant world of tequila cocktails, perfect for enhancing any backyard tiki bar setup. Michele delves into the history and varieties of tequila, from Blanco to Reposado to Añejo, and offers practical tips for selecting the right bottle. The episode features recipes for classic margaritas, skinny margaritas, ranch water, Paloma cocktails, and more, including mocktail options for non-drinkers. Michele also shares tips for setting up a tiki bar, highlights the importance of using fresh ingredients, and encourages listeners to explore more recipes and cocktail tips at funandkeywest.com. This episode is a treasure trove of advice for cocktail enthusiasts eager to impress at their next gathering.   00:00 Welcome to Fun in Key West Podcast 01:26 Tequila Cocktails 101 08:30 Setting Up Your Backyard Tiki Bar 15:29 Mocktails: Fun Without the Hangover 21:23 Join the Fun in Key West Community 23:08 Wrapping Up: Keep It Key Westie   https://funinkeywest.com/light-tequila-drink/  
Discovering the Rich Cigar History of Key West   In this episode of the Fun in Key West podcast, host Michele O'Connor delves into the intriguing history of Key West's cigar industry. She explores how Key West was transformed into the cigar capital of the world in the late 19th century by Cuban exiles and their expertise in hand-rolling cigars. Michele provides fascinating insights into key figures like William Wall and pivotal locations like Green Street, and discusses the cultural impact that the cigar industry has had on the island. She also highlights the lingering Cuban influence in Key West's food, music, and remaining cigar shops while offering practical tips for visitors interested in exploring this rich history.   00:00 Welcome to Fun in Key West! 01:26 Diving into Key West's Cigar History 02:38 The Rise of Key West as the Cigar Capital 04:49 Cuban Influence and the Decline of the Cigar Industry 10:23 Exploring Key West's Cigar Legacy Today 14:38 Final Thoughts and Fun Facts 16:37 Stay Connected with Fun in Key West   https://funinkeywest.com/    
Discover the Best Kayaking Adventures in Key West   In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the top experiences for kayaking around Key West and the Florida Keys. Michele shares tips for both beginners and experienced kayakers, highlighting the serene mangrove tunnels, crystal-clear waters, and vibrant marine life you can encounter. She also recommends various tours, including clear kayak tours and moonlit paddles, as well as places to rent kayaks and important safety tips for your adventure. Tune in for insights on the best times to go, must-visit spots, and recommendations for enhancing your kayaking journey.   00:00 Welcome to Fun in Key West 01:26 Kayaking Adventures in Key West 02:33 First Timer Friday: Kayaking Tips 04:36 Exploring Key West's Marine Life 08:05 Kayak Tours and Rentals 12:35 Final Thoughts and Recommendations https://funinkeywest.com/best-kayaking-in-key-west/ https://funinkeywest.com/category/what-to-do/  
Exploring the Best Pizza Spots in Key West   In this episode of the Fun in Key West podcast, host Michele O'Connor offers an insider's guide to the best pizza places in Key West. Michele begins with an engaging introduction about the laid-back vibe and unique offerings of Key West. She highlights various pizza spots, including Only Wood Pizzeria with its authentic Italian ingredients and brick oven from Naples, Clemente’s Trolley Pizzeria known for its family-friendly atmosphere and gluten-free options, and Duetto Pizza which combines pizza, pints, and gelato for budget-friendly dining. Other notable mentions include Tica Wood-Fired Pizza with its Neapolitan and deep-dish pizzas, White Street Pizza for New York-style slices, and Mr. Z’s for late-night cravings. Michele also recommends Seaside Cafe at the Mansion for its renowned lobster pizza and ocean views, Moondog Cafe for its grilled pizzas and proximity to the Hemingway House, and Bruta Francesca for authentic Sicilian flavors. Michele encourages listeners to share their favorite pizza spots and orders, and to explore more dining options and island-inspired recipes on the Fun in Key West website. She also invites listeners to sign up for the newsletter for insider tips and updates.   00:00 Welcome to Fun in Key West Podcast 01:26 Exploring Key West's Best Pizza Spots 03:50 Wood-Fired and Neapolitan Pizzas 04:38 Family-Friendly and Budget Pizzerias 06:20 Late Night and Unique Pizza Experiences 07:03 Seafood Pizzas and Scenic Views 08:07 Authentic Italian and Sicilian Pizzas 09:20 Wrapping Up and Additional Resources https://funinkeywest.com/best-pizza-in-key-west/  
Exploring Key West History: The Cosgrove House and Banyan Resort   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor delves into the rich history of Key West, with a special focus on the Cosgrove House, now known as the Banyan Resort. The episode covers the house's origins with founding father John Whitehead, its purchase by Captain Philip Cosgrove, and the impressive landscaping by Myrtle Cosgrove, including a famous banyan tree. Michele also shares ghost stories linked to the house, adding a spooky twist to its historical charm. Listeners can explore Key West's history through its many historic markers and learn more about local events and tours available on funinkeywest.com.   00:00 Welcome to Fun in Key West Podcast 01:26 Exploring the Historic Cosgrove House 02:47 The Cosgrove House's Rich History 06:24 Ghostly Tales and Architectural Marvels 09:13 Discover More Key West Adventures 10:01 Conclusion and Farewell https://funinkeywest.com/the-cosgrove-house-historic-walking-tour/  
Key West Cocktail Adventures: Iconic Drinks and Hidden Gems   In this episode of the Fun in Key West podcast, hosted by Michele O'Connor, listeners are taken on a vibrant tour of Key West's iconic cocktail scene. From the legendary Sloppy Rita at Sloppy Joe's to the flaming zombie at the Tiki House, Michele explores must-try beverages that offer a taste of the island's spirit. The episode also features unique drink experiences at various local establishments, including Irish Kevin's, Hogs Breath Saloon, General Horseplay, the Roost, and Mary Ellen's. Michele encourages listeners to step out of their comfort zones and try these iconic cocktails, with tips on recreating them at home for a slice of tropical paradise. Listeners are prompted to share their favorite Key West drinks and explore more tips and updates at FuninKeyWest.com.   00:00 Welcome to Fun in Key West 01:26 Iconic Key West Cocktails 03:34 Sloppy Joe's Must-Try Drinks 04:51 Exploring Irish Kevin's and Hogs Breath Saloon 07:10 Craft Cocktails at General Horseplay and The Roost 09:17 Tiki House and Other Unique Spots 12:08 Final Thoughts and More Key West Tips   https://funinkeywest.com/key-west-bars-and-the-must-try-cocktails/ https://funinkeywest.com/category/recipes/cocktails-recipes/  
Mapping Out Your Journey from Tampa to Key West   Join host Michele O'Connor in this episode of the Fun in Key West podcast as she answers the frequently asked question: 'How far is Tampa from Key West?' Michele provides a detailed guide covering multiple travel options, including driving, flying, and cruising. She shares insights on scenic drives, pit stops, flight details, and even cruise itineraries. Michele also offers practical travel tips and resources to ensure a seamless trip. Listeners are encouraged to explore the hidden gems, dining spots, and activities that make the journey as delightful as the destination. Get ready to dive into the ultimate travel planning guide!   00:00 Welcome to Fun in Key West 01:26 Travel Options from Tampa to Key West 02:21 Driving from Tampa to Key West 06:32 Flying from Tampa to Key West 07:26 Cruising from Tampa to Key West 09:28 Final Tips and Resources 10:16 Conclusion and Farewell   https://funinkeywest.com/how-far-is-key-west-from-tampa/   https://funinkeywest.com/category/the-keys/  
Lobster Delights in Key West: Tasty Tuesday Special   In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the world of Key West lobster. From the distinct characteristics of Florida's spiny lobster to the best spots to enjoy lobster dishes, Michele covers all you need to know for a perfect seafood adventure. You'll learn about the different lobster seasons, where to indulge in culinary experiences like Blue Heaven’s lobster benedict or DJ’s Clam Shack’s lobster roll, and even tips for catching your own lobster using snorkel gear and a tickle stick. This comprehensive guide is packed with fun facts, restaurant recommendations, and practical advice for both foodies and adventurous spirits alike. Don't forget to sign up for the Fun in Key West newsletter to stay updated on all things Key West!   00:00 Welcome to Fun in Key West 01:26 Diving into Key West Lobster 02:40 Understanding Florida Spiny Lobster 06:14 Top Lobster Spots in Key West 09:34 Catching Your Own Lobster 13:05 Wrapping Up and Final Tips   https://funinkeywest.com/best-lobster-in-key-west/    
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