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

The House That Moved: The Sawyer-Navarro House's Key West Adventure Michele O'Connor shares the story of the Sawyer-Navarro House, a two-and-a-half story classic revival home now at 426 Elizabeth Street in Key West that originally stood at Duval and Fleming. Built for master ship carpenter and businessman John T. Sawyer after the Great Fire of April 7, 1886 destroyed his first mansion, the rebuilt home reflected Sawyer's wide-ranging ventures, including ship-related businesses, banking, city service, and operating the steamboat City of Key West with service to Baltimore. As Duval Street became more commercial, Sawyer sold the property in 1912 for a planned Kress five-and-dime store site, and the entire house was moved to Elizabeth and Fleming. Daniel and Eva Navarro later bought it; Daniel built an automobile business, and the family kept the home for 70 years. The house was added to the National Register of Historic Places in 1970. 00:00 A House That Moved 03:09 Meet the Sawyer Navarro 04:11 John Sawyer Builder Extraordinaire 04:19 Great Fire of 1886 07:12 Duval Street Turns Commercial 08:10 Moving a Mansion in 1912 09:00 Navarro and the Auto Era 10:16 What the House Witnessed 11:25 Walk the Story Yourself 12:38 Historic Status and Key Takeaway 13:21 Wrap Up and Subscribe www.funinkeywest.com/ghost

Ridley House: Richard Kemp, the Rarest Sea Turtle, and a Key West Legend Michele O'Connor of the Fun in Key West podcast shares the story behind Ridley House at 601 Caroline Street, now part of the Key West Historic Inns Collection. The property dates to 1845 when the Bahamian-settler Kemp family bought land and remained connected to it for 72 years. Richard Moore Kemp, a Key West furniture dealer, merchant, fisherman, and amateur naturalist, helped introduce Key West sponges to the New York market, contributing to the rise of the late-1800s sponge industry. Around 1880 he identified an unusual sea turtle later recognized as the Kemp's ridley, described by the National Park Service as the rarest sea turtle species. After the Great Fire of 1886 destroyed the original home, Kemp rebuilt in 1888; ship carpenter John Sawyer constructed the Bahamian-architecture house. The episode also recounts local legend of caretaker "Mr. Mosby," buried treasure, and possible hauntings, and includes sponsorship mentions of Key West Food Tours. 00:00 Turtle House Teaser 02:08 Meet Ridley House 03:23 Kemp Family Roots 04:27 Richard Kemp Origins 05:19 Sponges Become Business 07:23 Kemps Ridley Discovery 09:04 Great Fire Rebuild 10:38 Ghost And Treasure 13:05 Ridley House Today 14:50 Walk Slower Outro www.funinkeywest.com/foodtour

From Jimmy Buffett to 25 Tropical Crime Adventures with Chip Bell

What happens when a rainy weekend, a Jimmy Buffett song, and a longtime trial attorney collide?

You get Come Monday, the first book in a tropical crime series that eventually grew into 25 Jake Sullivan adventures.

In this episode of the Fun in Key West Podcast, Michele sits down with author Charles "Chip" Bell to talk about the real stories, friendships, music, and Key West places behind the Jake Sullivan series.

Chip shares how a chance encounter with Jimmy Buffett at the Soggy Dollar Bar helped inspire him to finally write a book, why his real-life best friend became the model for Jake's sidekick Mike, and how his nearly 50 years as a trial attorney shaped the way he writes about justice, the law, and people caught between the two.

We also talk about the evolution of Jake Sullivan across 25 books, the research that brings Chip's settings to life, and the Key West bars and characters that helped shape the series.

Along the way, we wander into Trop Rock music, Hollywood scripts, a Jake Sullivan Caribbean lager, an almost-rum adventure, and the very important regional debate between Pittsburgh pierogies and West Virginia pepperoni rolls.

In This Episode

🌴 How Chip Bell became a tropical crime author

🎶 The Jimmy Buffett encounter that helped spark Come Monday

📚 The real friendship behind Jake and Mike

⚖️ Why justice and the law are not always the same thing

🗺️ How Chip researches locations, legends, and local history

🍺 The story behind the Jake Sullivan Caribbean Lager

🥃 Why the Jake Sullivan rum never made it to market

🎬 Chip's dream casting choices for Jake and Mike

🎵 The musicians who helped bring the Jake Sullivan world to life

🍹 Chip's favorite Key West bars, restaurants, and island memories

Read Along

Get your copy of Come Monday: https://amzn.to/4z5T9Km

Explore the complete Jake Sullivan series: https://amzn.to/4fK0WEs

A quick island-sized disclosure: As an Amazon Associate I earn from qualifying purchases. The book links above are affiliate links, which means I may earn a small commission if you make a purchase, at no additional cost to you. Your support helps keep the microphones on, the books open, and the Key West stories coming. 🌴📚

Learn More About Chip Bell

Visit Chip Bell's website: http://www.chipbellauthor.com/

Listen to the Music

John McDonald on Spotify: https://open.spotify.com/artist/5sG9ecAhtnZuFMcrZJK3Bc?si=ZwOeSYz6SL2LVwd3FHg0uw

Donnie Brewer on Spotify: https://open.spotify.com/artist/4nI1bYqONqWFnHPlSL9k35?si=2quwmqoxSMapg6nyProtJg

Eric Stone on Spotify: https://open.spotify.com/artist/09w2nmrWDRCL0wtRqoNLdM?si=zGmXUy0HRxyBTw68IfIZjA

Today's Sponsor

This episode is sponsored by the iWitness Key West True Crime Tour.

Key West may look like sunshine, cocktails, colorful houses, and postcard-perfect streets, but those same streets have witnessed real scandals, smugglers, gamblers, crimes, and characters behaving very badly.

This is not a ghost tour. These are true stories connected to real people and real places, shared as you walk through the streets where they unfolded.

Learn more or book your tour: https://funinkeywest.com/crime

Episode Chapters

00:00 Welcome and Guest Intro 01:31 True Crime Tour Sponsor 02:27 Meet Author Chip Bell 04:34 The Pitt vs. WVU Rivalry 05:48 Pierogi vs. Pepperoni Roll 07:02 Meeting Jimmy Buffett 10:13 The Story Behind Come Monday 12:20 Chip's Dictation Writing Process 13:48 Creating Jake Sullivan 15:11 Using Jimmy Buffett Song Titles 17:20 What Chip Would Change 20:25 Jake's Evolution Across 25 Books 21:52 Justice Versus the Law 27:17 Plotting, Research, and Story Hooks 29:53 Key West Places and People 33:12 Theme Songs and Trop Rock 36:34 Creating the Concept Album 36:59 What "Everything's Jake" Means 38:46 Chip's Key West Jukebox Picks 39:19 The Desert Yacht Club Story 41:23 The Jake Sullivan Beer 43:54 Rum Plans and Legal Red Tape 44:49 How Writing Made Chip a Better Lawyer 47:01 The Reality of Hollywood Scripts 48:54 Casting Jake and Mike 50:30 Linda and the Jukebox Meeting 52:52 Rapid-Fire Key West Favorites 56:42 Chip's Dream Barstool Guest 59:33 What's Next for Chip Bell

About Fun in Key West

Fun in Key West shares the stories, people, history, food, books, drinks, and wonderfully unusual characters that make Key West unforgettable.

Explore more Key West stories, travel tips, hidden gems, interviews, and island inspiration at: https://www.funinkeywest.com

Thank you for spending part of your day with me. Until next time, keep reading, keep exploring, and remember: in Key West, paradise usually has a backstory.

Dani Hoy on Trop Rock, Island Life, and the Old Stone Church in Key West Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and introduces guest Dani Hoy, a Key West singer-songwriter, artist, and member of The Shanty Hounds who also manages social media and communications for the historic Old Stone Church (Key West United Methodist Church). Dani shares how Jimmy Buffett, the Parrothead community, and trop rock led her to start writing music in her 40s, release her album Tropigal, and eventually move to Key West in 2013, with "Drunk on Mallory Square" becoming her most popular Spotify track. They discuss what daily life on the island is really like beyond Duval Street, plus the church's history, architecture, music-centered services, Old Stone Coffee House live music, the bell choir "The Southernmost Ding Dongs," weddings, and outreach partnerships. Episode sponsor: Tart Tales key lime pie walking tours. 00:00 Welcome to Key West 01:26 Meet Dani Hoy 05:03 Music Life on Island 06:08 Sponsor Tart Tales 07:01 Jimmy Buffett to Key West 11:19 From Snow to Sun 16:07 Real Key West Living 19:00 Finding Old Stone Church 19:50 Coffee House and Choir 24:00 Church History and Spaces 32:01 Visiting Sunday Service 34:33 Music Program and Bells 35:53 Bell Choir Highlights 36:34 Holiday Music Traditions 37:39 Community Outreach Partners 38:10 Congregation Size and Services 39:00 Weddings and Accessibility 41:52 Interfaith and Cuba Missions 43:17 Programs and Weekly Schedule 45:44 Songwriting Mini Movies 48:23 Live Set Requests and Style 54:06 New Projects and Rapid Fire 01:00:14 Where to Find Dani 01:04:19 Final Thanks and Wrap Up https://theshantyhounds.com/ https://youtu.be/v37NUl0sJ4Y https://danihoy.com/welcome www.funinkeywest.com/tart www.funinkeywest.com/dani-hoy

Key West Easter Eggs at Disney's Old Key West Resort: Exploring Conch Flats Host Michele O'Connor takes a detour from the Florida Keys to Disney's Old Key West Resort in Central Florida to explore Key West-inspired "Easter eggs" built into an imaginary Keys town called Conch Flats. She explains the resort's history (opened Dec. 20, 1991 as the first Disney Vacation Club resort; renamed in 1996) and how its bridge entrance echoes the Overseas Highway and Flagler's Overseas Railroad, reinforced by a model train display in the lobby. Highlights include the Hospitality House as a town center; Olivia's Café and its fictional backstory and menu items like conch fritters and key lime pie; Hemingway nods in Papa's Den; the Gurgling Suitcase bar tied to Prohibition smuggling lore; Trumbo Canal references; and turtle-themed names connected to Key West turtle kraals. She concludes that Disney captures Keys mood and details but not the real island's layered history, personalities, and roosters. 00:00 Disney Detour Setup 01:19 Podcast Welcome 03:40 Why Old Key West 06:15 Sponsor Break 08:32 Resort Origins 10:09 Crossing the Bridge 12:47 Hospitality House Hub 14:47 Flagler Railroad Easter Egg 18:50 Conch Flats Lore 19:55 General Store Stop 20:59 Porches and Haint Blue 26:13 Olivia's Cafe Story 28:43 Papa's Den Hemingway Nod 30:53 Sponsor Reminder 32:02 Gurgling Suitcase Bar 33:16 Waterways and Trumbo Canal 35:00 Turtles and Turtle Kraals 36:30 Pool Lighthouse Symbols 38:06 Key Lime Pie Taste Test 39:08 What Disney Got Right 41:30 What Disney Can't Copy 43:21 Should You Stay Here 44:29 Getting There Tips 45:38 Final Wrap and Questions 49:33 Outro and Resources www.outaheretravel.com www.funinkeywest.com

Key West in July: Key Lime Festival, 4th of July, Hemingway Days & Lobster Mini Season Host Michele O'Connor introduces the Fun in Key West podcast and shares an insider guide to visiting Key West in July, emphasizing the heat, humidity, and typical afternoon showers during hurricane season, along with tips on packing breathable clothes, reef-safe sunscreen, and planning around the weather with air-conditioned breaks. She highlights July's slower tourist pace, warm water, and major events including the five-day Key Lime Festival (through July 5) with tastings, a sip-and-stroll, and contests; 4th of July celebrations including a Truman Little White House cookout (July 3) and the Rotary Club 5K at Higgs Beach (July 4); Hemingway Days (July 21–26) featuring the Sloppy Joe's lookalike contest, running of the bulls, and a 5K; and lobster mini season (July 29–30). She recommends local museums and indoor spots, advises skipping rental cars, spotlights sponsor Danger Charters, and promotes her weekly newsletter and swag-box trivia. 00:00 Welcome to Key West 01:26 July Episode Preview 04:43 Sponsor Danger Charters 05:29 July Vibe and Tips 07:05 Weather and Packing 09:10 Beat the Heat Indoors 10:34 Why Visit in July 12:36 Key Lime Festival Guide 13:54 Fourth of July Events 14:53 Hemingway Days Highlights 17:02 Lobster Mini Season 18:14 Getting Around in Summer 19:17 More July Events List 21:07 Wrap Up and Newsletter 23:42 Final July Recap www.funinkeywest/danger www.funinkeywest.com

Nick Shuck on The Green Flash at Sunset: Reinvention, Key West Grit, and Hope Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and introduces the June 2026 book club pick, The Green Flash at Sunset by Nick Shuck, with Shuck joining to discuss the story behind the story, why Key West is a "world capital of reinvention," and how a book can feel dark yet hopeful. Shuck shares his background as a Pensacola senior English teacher, tour company owner (Emerald Coast Tours), father, and writer inspired by Hemingway, and explains he began the novel from its ending, sparked by watching Mallory Square street performers. He describes the green flash as a metaphor for chasing dreams despite risk and uncertainty, talks about crafting four central characters and Key West as an essential setting with layered history, and addresses reader reactions to the book's darkness as honesty about the world. The episode also spotlights sponsor Cruises and Tikis of Key West and mentions Key West Island Books. 00:00 Welcome to Fun in Key West 01:26 June Book Club Preview 03:13 Meet Author Nick Shuck 04:30 Nick's Origin Story 08:06 Cruising Tikis Sponsor Break 09:32 How Green Flash Began 12:53 Meaning of the Green Flash 16:37 Key West as Reinvention 21:07 Seeing Places in Layers 24:29 Meet Janet and Her Fight 27:11 Dark Stories Hopeful Endings 31:23 Writing Without an Outline 33:14 Endings and Lessons Learned 35:36 Writing Is Showing Up 37:17 Starting Emerald Coast Tours 38:50 Segway Tours Spark 40:44 Pub Tours Drunk History 42:07 Characters Walk Into Bar 43:22 Reinvention And Past 46:16 What Readers Should Feel 48:42 Next Projects And Research 51:06 Key West Favorites Rapid Fire 54:49 Coffee Rum And Local Tips 59:44 Thanks Sponsors And Wrap 01:02:40 Final Outro And Call To Action https://emeraldcoasttours.net/ https://bookshop.org/shop/PanhandleBooks

Historic Marker Monday: Truman's Little White House (Marker #59) in Key West Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and spotlights Historic Marker Monday episode #59: the Harry S. Truman Little White House in Truman Annex. She describes the house's origins (built in 1890 as Quarters A and B, becoming a single-family residence by 1911) and notable early stays, including President William Howard Taft's 1912 visit and Thomas Edison's six-month World War I stay. The episode focuses on Truman's 11 working vacations from 1946–1953 totaling 175 days, when major issues were discussed there, including the Marshall Plan, Truman Doctrine, recognition of Israel, civil rights executive orders, the Korean War ceasefire efforts, and the merger creating the Department of Defense. She notes later presidential connections (Eisenhower, Kennedy, Carter, Clinton) and promotes Trusted Tours' small-group "White Glove Tour," featuring behind-the-scenes access, exhibits, refreshments, a keepsake, and a ride in Truman's 1950 Lincoln limousine. 00:00 Welcome to Fun in Key West 01:26 Marker Monday Setup 04:30 Sponsor White Glove Tour 05:45 Origins of the House 06:54 Early VIP Visitors 08:18 Truman Arrives in 1946 09:53 Big Decisions Made Here 12:11 Truman Daily Rhythm 14:00 Other Presidential Ties 15:31 Why Historic Markers Matter 17:00 Tour Highlights and Questions 19:15 Explore More Key West Markers 20:24 Final Wrap and Call to Visit www.funinkeywest.com/truman

Wreck Ashore: How Key West Wreckers Built a Fortune Host Michele O'Connor introduces the Fun in Key West podcast and explains Key West's historic wrecking industry, highlighted by Historic Marker #58 near Mallory Square and the Wrecker Memorial by the Memorial Sculpture Garden. She describes wrecking as licensed marine salvage under maritime law—rescuing crews first, salvaging cargo, and settling claims through admiralty court at the Custom House—rather than piracy, noting myths like false lights lack evidence. The Florida Keys' reefs, storms, and limited navigation led to frequent wrecks, with NOAA estimates of hundreds to over 1,000 shipwrecks and an average of one per week in the 1800s; wrecking drove 60–90% of Florida exports by the 1830s and made Key West a leading port and home to Florida's first millionaire. She recommends visiting the Key West Shipwreck Museum tower, the Mel Fisher Museum about the 1622 Atocha found in 1985, and other related sites, and notes lighthouses and navigation improvements ended wrecking's profitability. 00:00 Welcome to Key West 01:26 Wreck Ashore Hook 03:18 Historic Marker 58 06:29 What Wrecking Means 08:04 Why Ships Wrecked Here 10:38 Key West Gets Rich 12:34 Custom House and Courts 15:01 Myths and Methods 18:45 Mel Fisher and Atocha 20:57 Shipwreck Museum Tower 21:42 End of Wrecking Era 22:43 Where to See It Today 24:33 Final Thoughts and Wrap 28:18 Recap and Call to Action