Fun in Key West Podcast

Michele O'Connor
  • 4.7 (11)
  • 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. 4d ago

    Mikki Bennett on Writing the Florida Keys Romance Series

    Miki Bennett on Writing the Florida Keys Romance Series as Therapy and the Inspiration Behind Runaway to the Keys On the Fun in Key West podcast, Michele O'Connor interviews Charleston-based author and artist Miki Bennett, September book club pick author of Runaway to the Keys. Bennett explains she never planned to write until a doctor urged her to share her and her daughter's medical experiences; unable to write a memoir, she turned it into fiction, launching the Keys to Love series. She describes why the Florida Keys inspire her (Caribbean feel, clear water, relaxed, friendly culture) and how characters often earn their own books after she finishes each story; she wrote her first novel in 30 days and ultimately created five novels and two novellas. They discuss Skylar's theme of choosing your own path, her writing routine, travel's impact, her Camping in High Heels series, a brain injury that paused her writing, future books, favorite Keys spots, and where to find her online. 00:00 From Nonwriter to Fiction 00:40 Meet Miki Bennett 02:50 Why the Florida Keys 04:10 Water Island Vibes 05:18 African Queen Spotlight 06:04 Keys to Love Origin Story 08:50 Building a Book Series 09:44 Writing as Therapy 12:34 Skylar Choosing Her Path 14:55 Garrett and Love Themes 16:10 Real Keys in Fiction 17:28 Rapid Fire Favorites 19:40 Camping in High Heels 21:16 Key West Series Tease 21:33 Wild Travel Mishaps 23:06 Writing From Real Life 23:52 Art After Injury 25:30 Next Books In The Keys 26:25 How Travel Changes You 28:14 Family Vacation Planning 30:04 Keys Rapid Fire Favorites 33:51 Mallory Square Must Do 35:44 Mosaic Sea Turtle Brand 36:38 Where To Find Miki 37:47 Final Thanks And Wrap www.funinkeywest.com/africanqueen

  2. 4d ago ·  Bonus

    You Might Also Like: Math & Magic: Stories from the Frontiers of Marketing with Bob Pittman

    Introducing Hoda Kotb: “Joy’s in us, it’s about unearthing it.” from Math & Magic: Stories from the Frontiers of Marketing with Bob Pittman. Follow the show: Math & Magic: Stories from the Frontiers of Marketing with Bob Pittman Millions of Americans feel like Hoda Kotb is a good friend. She’s an acclaimed journalist and TV pioneer, best known for her years at NBC and the TODAY Show. More recently, she’s turned her focus to joy, stepping into entrepreneurship with her company Joy 101 and launching a new podcast with iHeartPodcasts centered around joy. Born in Oklahoma to Egyptian immigrant parents and raised in West Virginia, Hoda built her career step by step, starting at Greenville News Center 15 in Mississippi and working her way to the top. She has plenty to share about perseverance, hard work, and the lessons she’s learned along the way. Plus, she talks about what’s surprised her about podcasting, how she thinks about joy, and what she imagines for the future of news media. See omnystudio.com/listener for privacy information. DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

    You Might Also Like: Math & Magic: Stories from the Frontiers of Marketing with Bob Pittman

  3. Sep 20

    Key West's Old Coca-Cola Bottling Court and the Rumor of Rainwater Coke

    Historic Marker #65: Key West's Old Coca-Cola Bottling Court and the Rumor of Rainwater Coke Michele O'Connor explores Key West Historic Marker #65 at 103 Simonton Street, tracing one site's many lives and how they reflect Key West history. The original building was destroyed in the Great Fire of 1886, which burned about 12 hours, destroyed over 200 buildings across 50 acres, devastated the cigar industry, and may have been linked to tensions around the Cuban Independence Movement. A hardware store rose on the lot by 1892, followed by Jack and Rosa Williams' Jack's Saloon in 1914. In 1923 the building became a Coca-Cola bottling plant, with a local rumor that the Coke may have used cistern-collected rainwater, reflecting Key West's historic freshwater scarcity. The episode also notes reusable deposit glass bottles, the contour bottle, and how the 1938 Overseas Highway made local bottling unnecessary; later uses included offices, clothing stores, liquor distribution, and a key lime pie factory. 00:00 Key West Coke Legend 00:43 Welcome and Setup 02:15 Great Fire of 1886 03:42 Rebuilding and Hardware Era 04:49 Jacks Saloon Days 05:29 Coca Cola Arrives 07:16 Rainwater Cistern Rumor 08:32 Bottles Reuse and Design 09:54 Overseas Highway Changes 11:09 Many Lives of One Building 12:15 Marker Wrap Up and Question 12:58 Final Sign Off

  4. Sep 13

    Before the Treasure: The Navy Storehouse Behind the Mel Fisher Maritime Museum

    Before the Treasure: The Navy Storehouse Behind the Mel Fisher Maritime Museum Michele O'Connor explores the history of the building at 200 Green Street—now the Mel Fisher Maritime Museum—focusing on its earlier life as a U.S. Navy storehouse. Planned in 1902, built from 1908–1910 for $54,791, it was among Key West's most technologically advanced structures, featuring a steel frame constructed by the Penn Bridge Company. The episode explains Key West's strategic naval importance, the working waterfront of the early 1900s, and the role of coal in fueling steam-powered vessels as navies began shifting toward oil and diesel. After 1970s military cutbacks, the property moved to the GSA; Mel Fisher leased it in the early 1980s, purchased it in 1987, and the museum acquired it in 2000. The building's strength supports heavy artifacts and conservation tanks, making it part of the story it now preserves. 00:00 Treasure Building Teaser 00:20 Podcast Welcome Setup 01:32 Meet the Museum Building 02:09 Navy Storehouse Origins 03:37 Why Key West Mattered 04:30 Steel Frame Innovation 05:29 Coal Steamship Era 07:19 Waterfront Transformed 08:19 Sponsor Flora Days 09:21 From Navy to Mel Fisher 10:34 Built for Heavy Artifacts 11:34 Building Is the Exhibit 12:50 Final Takeaway Outro https://funinkeywest.com/floridays/

  5. Sep 13

    Unusual and Unique Things to Do in Key West

    Unusual and Unique Things to Do in Key West (Thursday Night Live) Michele hosts the Fun in Key West Thursday Night Live show and invites viewers to share unusual Key West experiences beyond staples like Duval Street, Mallory Square sunset, the Southernmost Point, and key lime pie. She recommends exploring Truman Annex, including the Truman Little White House white-glove tour, historic markers, and Art & Historical Society walking tours; and watching Friday sunset from the US Coast Guard Cutter Ingham with 1940s music and drinks. Other ideas include rolling a die for happy-hour cocktail pricing at General Horseplay, taking key lime pie-making classes at the Key West Key Lime Pie Company, attending Key West Cooking Show demonstrations and cocktail classes (with Bar One), touring iWitness True Crime (real crimes, 17+), visiting Robert the Doll, exploring West Martello's gardens, visiting Nancy Forrester's Secret Garden parrot sanctuary, seeing rescued birds at the Key West Wildlife Center and animals at the Sheriff's Animal Farm, taking alternative sunset options (Fort Zachary Taylor, sails, sandbar charters), and biking with local guide Lloyd. 00:00 Welcome and Theme Song 01:49 Why Go Beyond Duval 03:55 Explore Truman Annex 07:36 Sunset on the Ingham 08:59 Dice Roll Happy Hour 10:40 Make Your Own Key Lime 12:42 Cocktail Classes and Rum 14:14 True Crime Walking Tour 16:06 Robert the Doll and Forts 18:41 Secret Garden Parrots 20:09 Alternative Sunsets 22:10 Wildlife Rescues and Bike Tour 24:15 Wrap Up and Next Week www.funinkeywest.com/crime www.funinkeywest.com/unusual things to do in Key West

  6. Sep 6

    The San Carlos Institute: Key West's "House of Cuba" on Duval Street

    The San Carlos Institute: Key West's "House of Cuba" on Duval Street Michele O'Connor of the Fun in Key West podcast tells the story of the San Carlos Institute at 516 Duval Street, a pivotal site for Cuban exiles and Cuba's independence movement. Founded in 1871 on Ann Street by leaders José Dolores Pollo and Juan Maria Reyes and funded largely by Cuban cigar workers, it became an early bilingual, integrated school teaching in English and Spanish. José Martí addressed a major gathering there on January 3, 1892, urging unity that helped lead to the Cuban Revolutionary Party, and he called it "La Casa Cuba." The institute celebrated Cuban independence on May 20, 1902, survived fires, hurricanes, and collapse, was rebuilt with $80,000 from the Republic of Cuba and architect Francisco Centurion, closed in 1973 after condemnation, then was restored and reopened in January 1992. Today it operates as a free-admission museum, library, gallery, theater, and educational space. 00:00 Duval Street Mystery 01:19 Sponsor Key West Food 02:01 Meet San Carlos 03:11 Origins on Ann 04:16 Bilingual School Firsts 05:28 Marti Unites Exiles 07:28 Independence Celebration 08:12 Fire Hurricane Rebuilds 09:53 Politics Closure Collapse 10:55 Restoration Comeback 11:51 Visit San Carlos Today 12:22 Why It Matters 13:31 Wrap Up and Subscribe www.funinkeywest.com/foodtour

  7. Sep 6

    Key West in September: Weather, Crowds, and Can't-Miss Events

    Key West in September: Weather, Crowds, and Can't-Miss Events The host explains why September can be an overlooked but rewarding time to visit Key West: summer crowds are gone, the island is quieter, and you may find lodging deals, though some businesses close so visitors should check schedules. They address hurricane season expectations, noting heat (highs around 89–90°F), frequent but typically brief showers, and the need for flexible plans, refundable bookings, and possibly travel insurance. Suggestions include wandering less-busy streets, the historic seaport and Bahama Village, visiting galleries, historic sites (Hemingway House, Truman Little White House, Audubon House), and trying activities like snorkeling, food tours, sunset sails, and the Dry Tortugas (which books ahead). Featured September events include Women's Fest, Just a Few Friends (Jimmy Buffett celebration), Brew Fest, First Fridays on Fleming, the Barbecue Rib Battle, Monday night jazz jams, Walk on White, Comedy Key West, Happy Hour with the Historian, and other regional activities. 00:00 September Trip Question 01:09 Show Intro And Theme 02:40 September Island Vibe 04:53 Weather And Hurricanes 10:04 Wandering And Local Spots 14:21 Try New Experiences 15:18 September Events Guide 21:46 How To Plan Your Days 24:17 Who Should Visit 26:29 Wrap Up And Resources https://funinkeywest.com/key-west-in-september/

  8. Aug 30

    Winging It in Key West: Trip Recap, New Favorites, and Classic Tours

    Winging It in Key West: Trip Recap, New Favorites, and Classic Tours Michele O'Connor hosts the Fun in Key West podcast with her husband Kevin, recapping their recent Key West trip and announcing a new weekly Thursday 8:00 PM ET live format. They highlight their first-night tradition at Conch Republic Seafood Company (mahi sandwich, Key West shrimp) and meeting travelers who were "winging it," then visiting the Green Parrot for live music. They review staying at La Concha (Marriott) for its unbeatable Duval location and live music but note limited nighttime outdoor space and bar crowding. New favorites include Kaya Eats (weekend breakfast, snapper sandwich, karaoke room) and Red Shoe Bistro (reservation-only seatings, standout flavors, lavender cheesecake). They also discuss Key West Island Books, Lobsterfest, the Mel Fisher Museum, Hemingway House gardens, Bali Bar, First Legal Rum Distillery piña colada, Doing Work Coffee, Squirrel & Grouper, and tours via Old Town Trolley/Conch Train/Graves & Gravestones with a promo code, plus scooter safety and Kevin's travel services. 00:00 Winging Key West Intro 00:50 Live Show and Guest 02:38 Sponsor Old Town Trolley 03:26 Conch Republic Bar Night 07:34 Green Parrot Music Stop 09:27 Staying at La Concha 12:41 La Concha Pros and Cons 15:10 Kaya Eats Hidden Gem 18:54 Books and Lobsterfest 20:36 Mel Fisher Museum Visit 22:53 Red Shoe Bistro Find 27:13 Back to Sponsor and Tours 28:24 Conch Train Teaser 28:52 Conch Train Tips 31:23 Old Town Trolley Guide 34:42 Graves and Gravestones 37:50 Tour Discounts Link 38:15 Kevin Top Three 41:29 Michele Favorites 46:00 Doing Work Coffee 49:21 Trip Highlights Recap 50:32 Scooter Safety Warning 55:56 Travel Planning Outro www.funinkeywest.com/conch promo code 7219

See All (181)

Trailer

4.7
out of 5
11 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
    181
  • Rating
    Clean
  • Copyright
    © Fun In Key West 2026
  • Show Website
    Fun in Key West Podcast

You Might Also Like