Episodes

  • December Delights in Key West: Your Ultimate Guide to Holiday Happenings

    December Delights in Key West: Your Ultimate Guide to Holiday Happenings
    Jan 11 2026
    December Delights in Key West: Your Ultimate Guide to Holiday Happenings In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to the vibrant December events in Key West and the Florida Keys. From holiday parades, boat parades, and festive light tours to concerts, art walks, and fishing tournaments, listeners will discover a plethora of activities to enjoy. Michele highlights key events such as the Key West Christmas Parade, the Key West Lighted Boat Parade, and various theater performances. She also shares tips on weather and packing for the trip, and encourages listeners to visit funinkeywest.com for more details and event updates. This episode is perfect for anyone planning a visit to Key West or simply daydreaming about a tropical holiday escape. 00:00 Welcome to Fun in Key West Podcast 01:35 Holiday Magic in Key West 02:57 December Events in Key West 04:55 Key West Holiday Activities 08:00 Upcoming Events and Activities 16:26 Wrapping Up and Final Thoughts
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    19 mins
  • Unveiling Key West's Civil War Legacy: The Story Behind the Blockade

    Unveiling Key West's Civil War Legacy: The Story Behind the Blockade
    Jan 11 2026
    Unveiling Key West's Civil War Legacy: The Story Behind the Blockade In this episode of the Fun in Key West podcast, host Michele O'Connor explores Key West's surprising role during the Civil War. Dive into the history of the Union blockade, the strategic importance of Key West, and the role of British blockade running ships. O'Connor also provides insights into local historic markers and encourages listeners to explore these hidden stories through the self-guided walking tour. Additionally, listeners can sign up for the newsletter for trivia, happy hour tips, and a chance to win the monthly Key West surprise box. The episode wraps up with an invitation to join the free book club, featuring books connected to Key West. 00:00 Welcome to Fun in Key West Podcast 01:37 Historic Marker Monday: Key West in the Civil War 04:30 The Strategic Importance of Key West 07:56 The Role of Blockade Runners 09:11 British Involvement and Economic Impact 12:09 Exploring Key West's Historic Markers 14:24 Join Our Community and Stay Connected 15:52 Conclusion and Farewell www.funinkeywest.com
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    17 mins
  • Exploring Key West: From Sunrise to Sunset with Fun in Key West

    Exploring Key West: From Sunrise to Sunset with Fun in Key West
    Jan 11 2026
    Exploring Key West: From Sunrise to Sunset with Fun in Key West In this episode of Fun in Key West, host Michele O'Connor and her husband Kevin from Out A Here Travel, provide a comprehensive recap of their recent Key West adventure. They discuss updates at key locations like Pittsburgh International and Key West airports, and their stay at the Southernmost Beach Resort. The episode includes recommendations for dining, coffee spots, new breweries, and unique tours like the Eyewitness Crime Tour. They also touch on practical travel tips and changes to popular attractions and transit services. Whether you're a first-time visitor or a seasoned traveler, this episode offers valuable insights for your next Key West escapade. 00:00 Welcome to Fun in Key West Podcast 02:01 Special Guest: Kevin from Out of Here Travel 03:43 Travel Insights: Pittsburgh to Key West 04:58 Exploring the New Key West Airport 10:10 Staying at the Southernmost Beach Resort 13:50 Sunrise Photography and Resort Activities 19:15 Key West Coffee and Dining Options 20:40 Discovering the Southernmost Brewery 23:18 Eyewitness Crime Tour and Key Lime Pie Tasting 26:16 Exploring Local Dining Gems 27:47 Reviving Outta Here Travel 29:40 Cruising Adventures and Destinations 33:06 Key West Trolley and Transportation Tips 35:05 Changes at Kermit's Key Lime Pie Shop 36:32 Top 10 Things We Love About Key West 46:42 Final Thoughts and Travel Tips https://funinkeywest.com/ https://www.outaheretravel.com/
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    51 mins
  • Exploring Key Largo: Your First Stop on the Road to Paradise

    Exploring Key Largo: Your First Stop on the Road to Paradise
    Dec 1 2025
    Exploring Key Largo: Your First Stop on the Road to Paradise Join Michele O'Connor on the Fun in Key West podcast as she kicks off 'Wandering Wednesday' with a detailed exploration of Key Largo. Discover Key Largo's unique charm, from the underwater adventures at John Pennekamp Coral Reef State Park to bird-watching at the Laura Quinn Wild Bird Sanctuary. Learn about local tips for dining, happy hours, and nightlife, and get recommendations on where to stay. Whether it's your first visit or you're a seasoned traveler, Michele provides an insider's guide to maximizing your Key Largo experience. Complete with activity suggestions, nature spots, and sunset views, this episode is your ultimate guide to making the most of Key Largo before continuing your journey through the Florida Keys. 00:00 Welcome to Fun in Key West Podcast 01:35 Exploring Key Largo: First Stop on the Road to Paradise 02:06 Key Largo Daytime Adventures 14:54 Nightlife and Dining in Key Largo 20:28 Where to Stay in Key Largo 22:30 Best Time to Visit and Travel Tips 27:01 Conclusion and Community Engagement https://funinkeywest.com/ https://funinkeywest.com/fun-in-key-west-book-club/ https://funinkeywest.com/things-to-do-in-key-largo-at-night/
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    29 mins
  • Diving into Key West's Sponging History

    Diving into Key West's Sponging History
    Nov 30 2025
    Diving into Key West's Sponging History Welcome to the Fun in Key West podcast, hosted by Michele O'Connor. In this episode with a fresh theme song and intro, Michele explores the fascinating history of the sponging industry in Key West. Discover how this unexpected industry blossomed in the 1820s, peaked in the 1890s, and eventually declined due to overharvesting and environmental damage. Learn about the economic impact on Key West, the influence of Greek divers, and the modern-day connections to this historic trade. Michele also highlights the importance of Key West's historic markers and encourages visiting funinkeywest.com for more information, including a self-guided walking tour, happy hour list, and book club. Tune in for a blend of history, local insights, and a celebration of Key West's unique culture. 00:00 Welcome to Fun in Key West Podcast 01:35 Historic Marker Monday: The Sponging Industry 04:12 The Rise and Fall of Sponging in Key West 11:46 Modern Connections to Key West's Sponging Past 14:14 Exploring Key West's Historic Markers 14:59 Stay Connected with Fun in Key West 15:58 Conclusion and Farewell https://funinkeywest.com/ https://funinkeywest.com/fun-in-key-west-book-club/ https://funinkeywest.com/sponging-more-than-a-shopping-trip/
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    17 mins
  • Exploring the Marine Hospital: Key West's Historic Gem

    Exploring the Marine Hospital: Key West's Historic Gem
    Nov 16 2025
    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/
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    13 mins
  • Exploring Key West Through Food: The Ultimate Guide to Tasty Tuesday

    Exploring Key West Through Food: The Ultimate Guide to Tasty Tuesday
    Nov 10 2025
    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/
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    19 mins
  • The Outer Mole: Key West's Historic Evolution

    The Outer Mole: Key West's Historic Evolution
    Nov 9 2025
    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/
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    18 mins