Fun in Key West Podcast

Michele O'Connor
  • 4.7 (10)
  • Places & Travel
  • Updated Weekly

🌴 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

  1. 2d ago

    Key West in June: Weather, Packing Tips, Events, and a 3-Day Itinerary

    Key West in June: Weather, Packing Tips, Events, and a 3-Day Itinerary Host Michele O'Connor introduces the Fun in Key West podcast and shares a practical guide to visiting Key West in June, covering warm, humid upper-80s weather, comfortable water temps, and typical quick afternoon showers during the start of hurricane season. She recommends booking midweek for better hotel deals, packing breathable clothes, comfy shoes, reef-safe sunscreen, a hat, a refillable water bottle, and light rain gear, and planning outdoor activities earlier in the day. June highlights include Pride Month events, water excursions (snorkeling, kayaking, sandbar trips, dolphin watching, sunset cruises), Old Town staples like Mallory Square and Duval Street, beaches (noting possible sargassum), museums and historic sites, and day trips like Dry Tortugas (book early). She lists June 2026 happenings (Walk on White, Comedy Key West shows, farmers market, jazz jams, Mango Mania) and offers rainy-day indoor options plus a sample 3-day itinerary. Sponsor: Up the Keys Tours. 00:00 Welcome to Key West 01:26 June Trip Overview 03:48 Why Visit in June 05:50 Weather and Rain 07:33 What to Pack 08:51 Pride and Events 09:39 Best Things to Do 12:59 Museums and Day Trips 15:09 June 2026 Calendar 18:10 Rainy Day Plans 19:30 Where to Stay 21:21 Getting There 21:45 Three Day Itinerary 24:26 Final June Tips 25:31 Wrap Up and Thanks   https://funinkeywest.com/key-west-in-june/ www.funinkeywest.com/up

    28 min

  2. May 31

    The Ultimate Couples Guide to Key West: Sunsets, Food Tours, and Quirky Date Ideas

    The Ultimate Couples Guide to Key West: Sunsets, Food Tours, and Quirky Date Ideas Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to where to eat, drink, stay, and what to do on the island, then focuses on experiencing Key West as a couple with a laid-back, spontaneous vibe. She recommends balancing iconic activities—Mallory Square Sunset Celebration, sunset cruises (Fury's Commotion on the Ocean, Flora Days, and Danger's Wind and Wine Sail), and Duval Street strolling—with unique options like ghost tours, cocktail classes, jet ski tours, kayaking, and private sandbar charters with Make It So Charters. Additional highlights include the Butterfly and Nature Conservatory (including flamingo meet-and-greets), Fort Zachary Taylor, Dry Tortugas, West Martello Tower, Hemingway Home, Truman Little White House, Audubon House, Rodriguez Cigars, Key West Island Bookstore, and date ideas like brunch, dessert stops, and wine at Vino's. The episode is sponsored by Key West Food Tours, promoting multiple tours and emphasizing booking ahead, staying hydrated, wearing comfortable shoes, avoiding driving, and planning one main activity per day. 00:00 Welcome to Key West 01:26 Couples Episode Setup 02:09 Key West Food Tours 05:03 Island Vibe for Two 07:05 How We Plan Days 09:20 Classic Sunset Staples 11:41 Duval and Food Tours 14:32 Cocktails and Water Fun 17:09 Nature and History Stops 19:06 Quirky Finds and Books 20:59 Dates and Itineraries 24:45 Practical Trip Tips 27:37 Sponsor and Farewell   www.funinkeywest.com/foodtour www.funinkeywest.com https://www.keywestcookingshow.com/     Other episodes to check out -   Key West Trip Recap: Coconut Beach Resort, Hidden Gem Cocktail & Cooking Classes, and Local Favorites Exploring Key West: From Sunrise to Sunset with Fun in Key West

    30 min

  3. May 24

    Family-Friendly Florida Keys Road Trip: Key Largo to Key West (Summer Travel Tips)

    Family-Friendly Florida Keys Road Trip: Key Largo to Key West (Summer Travel Tips) Host Michele O'Connor introduces the Fun in Key West podcast and shares family-travel tips for a Florida Keys road trip from Key Largo to Key West heading into Memorial Day weekend 2026. She argues the Keys are a great multi-generational destination if approached with a relaxed mindset: plan one major activity per day, build in pool/beach downtime, pack snacks and water, plan around morning weather and afternoon showers, and check age/height requirements and booking needs. Suggested stops include Key Largo's John Pennekamp Coral Reef State Park (snorkeling or glass-bottom boats); Islamorada's Rain Barrel Village (Betsy lobster), Robbie's tarpon feeding, and Theater of the Sea; Marathon/Middle Keys attractions like the Turtle Hospital, Dolphin Research Center, aquarium, Pigeon Key/Seven Mile Bridge history, and Sombrero Beach; Duck Key's Hawks Cay Resort; Bahia Honda State Park; Big Pine Key's Key Deer Refuge; and Key West activities such as the conch train/trolley, Fort Zachary Taylor, Eco-Discovery Center, splash park, Southernmost Point replica, Butterfly Conservatory, aquarium, Hemingway Home, Shipwreck Museum, Mallory Square sunset celebration, and Dry Tortugas. The episode is sponsored by Fury Water Adventures. 00:00 Welcome to Key West 01:26 Family Trip Overview 02:28 Travel Tips and Sponsor 06:22 Keys Trip Mindset 07:43 Key Largo Adventures 09:48 Islamorada Road Stops 14:17 Marathon and Middle Keys 19:35 Lower Keys Highlights 21:49 Key West With Kids 28:06 Key West Eats and Treats 29:42 Dry Tortugas Day Trip 30:25 Sample Road Trip Itinerary 31:18 Final Tips and Wrap Up 35:45 Closing Thanks and Goodbye   www.funinkeywest.com/fury

    37 min

  4. May 24

    David Sloan Returns: How Key West Killed JFK, Bum Farto, Beatles Tales, and Haunted History

    David Sloan Returns: How Key West Killed JFK, Bum Farto, Beatles Tales, and Haunted History Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and interviews returning guest David Sloan, a longtime Key West author and researcher known for haunted history, Robert the Doll, and key lime pie expertise. Sloan explains how he moved to Key West after seeing ghost tours abroad and describes his work as entertainment-driven historical storytelling, including a personal connection to the Civil War fort where Robert the Doll is housed. They discuss his book How Key West Killed JFK, prompted by FBI files from research into missing fire chief Bum Farto and by JFK-assassination documents tying figures like Jack Ruby and Lee Harvey Oswald to the Keys; Sloan also details suspect Gilberto Lopez, newly found photos, and information from Lopez's daughter. He previews upcoming books on Bomfarto and The Beatles' 1964 Key West stay, addresses evolving ghost lore and misconceptions about Robert the Doll, shares local recommendations, and notes where to find him, his books, and tours, with sponsorship from iWitness Crime Tours. 00:00 Welcome to Key West 01:27 Meet David Sloan 02:20 Sponsor Crime Tour 05:57 David Origin Story 07:07 Mystorian Mindset 08:23 Guided to Key West 09:10 Why Write JFK Book 09:31 Bum Farto Files 10:47 Key West JFK Links 13:57 Cold War Power Players 17:25 Writing Without Conspiracies 18:40 Gilberto Lopez Breakthrough 24:42 Mafia Culture Revealed 27:22 Digging Unredacted Files 29:07 Hoffa and Teamsters Tales 31:54 Audience Q and Pivot 32:23 Prolific Books and Hits 33:48 Bucket List Lifestyle Brand 35:00 Tutu Hemingway Cat Story 36:36 Key Lime Passion Project 37:19 Key Lime Pie Debate 38:25 Best First Book Picks 40:17 Bonfardo Mystery Unpacked 45:58 Beatles Hurricane Detour 50:14 Haunted Research Origins 54:03 Robert the Doll Truths 58:04 Stories Still to Chase 58:55 Key West Food Favorites 01:01:51 Where to Find David 01:05:27 Final Thanks and Sponsor   www.funinkeywest.com/crime-tour   Grab a copy of the book over at Amazon (Click Here) As an Amazon Affiliate I will earn a commission on qualified purchases, at no extra charge to you.  It helps support our little corner of the world.

    1h 6m

  5. May 10

    Visiting Key West in May: Weather, Events, Packing Tips, and Travel Planning

    Visiting Key West in May: Weather, Events, Packing Tips, and Travel Planning Host Michele O'Connor introduces the Fun in Key West podcast and shares an insider guide to visiting Key West in May, calling it a sweet spot with fewer crowds, mid-80s daytime highs, upper-70s evenings, less rain, and generally more forgiving hotel rates before hurricane season begins June 1. She covers what to pack (reef-safe sunscreen, hat, breathable clothes, comfortable shoes, lightweight jacket, reusable water bottle) and how to get there by driving the Overseas Highway, flying into the updated Key West International Airport, or taking the Key West Express ferry. Lodging choices depend on desired vibe and proximity to Duval. Recommended activities include Mallory Square Sunset Celebration, Fort Zachary Taylor Historic State Park, booking Dry Tortugas far in advance, museums, and water excursions. May highlights include Songwriters Festival, Walk on White, First Fridays on Fleming, markets, Monday night jazz jams, and the Schooner Wharf Minimal Regatta. Tips include skipping a rental car, not overpacking, not overplanning, and hydrating. 00:00 Welcome to Key West 01:26 Why Visit in May 04:49 May Weather Guide 06:35 What to Pack 08:48 Getting to Key West 11:44 Where to Stay 14:38 Must Do Highlights 18:23 May Events Calendar 23:46 Perfect May Day Plan 24:48 Common Travel Mistakes 27:32 Wrap Up and Resources 29:20 Final Farewell https://funinkeywest.com/key-west-in-may/

    30 min

  6. May 10

    Historic Marker Monday: Key West's Old Stone Church (Marker #55)

    Historic Marker Monday: Key West's Old Stone Church (Marker #55) Host Michele O'Connor introduces the Fun in Key West podcast and a Historic Marker Monday episode focused on historic marker #55, the Old Stone Church (United Methodist Church) at 600 Eaton Street at Simonton and Elizabeth in Old Town. She explains how Methodist missionaries began services in 1832 in Bahamian settler Samuel Kemp's home for 12 years before a series of wooden church buildings were damaged by fire and hurricanes. Commissioned around 1870, architect William Kerr built the current coral-rock church by quarrying stone on the grounds and constructing it around the existing wooden church, later dismantling the interior structure after the roof went on in 1884. The quarry became a rainwater cistern, and 1950s excavation revealed the church sits on a small cemetery. The church remains active, with some Kemp descendants still attending, and listeners are directed to FunInKeyWest.com for a free walking tour and newsletter trivia drawing. 00:00 Welcome to Fun in Key West 01:26 Historic Marker Monday Begins 03:34 Finding the Old Stone Church 04:26 Key West in the 1800s 05:21 From Living Room to Churches 07:10 Building in Coral Rock 09:01 Cistern and Cemetery Surprise 10:07 Visit Today and Location Tips 11:06 Walking Tour and Newsletter 12:26 Final Wrap Up and Goodbye

    13 min

  7. Apr 26

    Key West's Hidden WWII Submarine Base, Sonar School, and the Truman Annex

    Fun Fact Friday: Key West's Hidden WWII Submarine Base, Sonar School, and the Truman Annex Host Michele O'Connor introduces a "Fun Fact Friday" episode focused on Historic Marker #57 near the Outer Mole and the US Coast Guard Cutter Ingham Museum area, explaining how today's calm Truman Annex was once a major WWII submarine hub. She describes the site's evolution from the 1845 Fort Zachary Taylor Army installation to Navy control, the construction of five metal finger docks for submarines, and Key West's wartime role countering German U-boats that sank thousands of ships, including nearly 50 off Florida in 1942. Key West submarines escorted supply convoys and helped support the Pacific War, while the Fleet Sonar School relocated there in 1940, training thousands in sonar. The base was designated in 1946, became obsolete with nuclear submarines, and was decommissioned in 1974, later transforming into today's parks, amphitheater, cruise-ship pier, and tourist area. 00:00 Welcome to Fun in Key West 01:26 Episode teaser WWII waters 02:50 Fun Fact Friday kickoff 03:51 Marker 57 location today 05:17 Base origins and docks 07:12 U-boats off Florida 08:42 Key West wartime missions 10:08 Sonar school revolution 11:22 Decommission to Truman Annex 13:09 Questions and reflections 14:29 Live comments and travel tips 17:25 Final recap and subscribe

    19 min

  8. Apr 18

    Mile Marker Zero: William McKeen on Key West's Wild 1970s Creative Scene

    Mile Marker Zero: William McKeen on Key West's Wild 1970s Creative Scene Host Michele O'Connor introduces the Fun in Key West podcast and welcomes William McKeen, Boston University journalism professor and author of Mile Marker Zero, to discuss 1970s Key West and the artists, writers, musicians, and actors drawn to its cheap, funky, under-the-radar culture. McKeen explains his drive as a lifelong storyteller, how Tom Corcoran (author of The Mango Opera) inspired and enabled the book after sharing a final Hunter S. Thompson message about documenting the "missing" Key West years, and why Corcoran became the narrative gateway linking figures like Thomas McGuane, Jim Harrison, Russell Chatham, Jimmy Buffett. They discuss balancing revelry with serious creative work, editing out some raunchier material (with extras on McKeen's website), Key West's sensory pull and rising costs, and the book's themes of friendship, survival, and tragedy, including Corcoran's missing wife. 00:00 Welcome to Fun in Key West 01:26 Episode teaser and guest 02:12 Podcast theme and intro 03:10 Meet author William McKean 04:40 Addicted to storytelling 07:24 Hunter Thompson voicemail 10:45 Writing Mile Marker Zero 11:59 Keeping the art focus 14:57 Why Key West drew artists 17:49 Then vs now costs 22:29 Structuring the big cast 26:17 Cut scenes and bonus tales 28:23 Wild stories reaction 28:49 Wild Key West Tales 29:36 Why Editors Matter 32:04 Sex Drugs and Context 33:24 Keeping Key West Lit 35:34 Writing With Senses 38:25 Friendship and Survival 41:34 Paradise With a Price 45:39 Can Creativity Return 48:11 Coffee Dinner and Favorites 50:52 Key West State of Mind 53:27 Final Thanks and Signoff https://www.williammckeen.com/ https://funinkeywest.com/fun-in-key-west-book-club/

    55 min
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4.7
out of 5
10 Ratings

About

🌴 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

Information

  • Creator
    Michele O'Connor
  • Years Active
    2018 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © Fun In Key West 2026
  • Show Website
    Fun in Key West Podcast

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