Michele O'Connor

Fun in Key West Podcast

Society EN ↓ 168 episodes

🌴 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 oc...

Author

Michele O'Connor

Category

Society

Podcast website

funinkeywest.com

Latest episode

Jul 6, 2026

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Episodes

Exploring the Marine Hospital: Key West's Historic Gem 16.11.2025

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 signi...

Exploring Key West Through Food: The Ultimate Guide to Tasty Tuesday 10.11.2025

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 Exper...

The Outer Mole: Key West's Historic Evolution 09.11.2025

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 co...

Exploring the World of Low-Carb Mocktails 02.11.2025

Exploring the World of Low-Carb Mocktails In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the vibrant and refreshing world of mocktails. Whether you're participating in Sober October, gearing up for Dry January, or simply looking for healthier, low-carb drink options, this episode is packed with tips and recipes. Michele discusses the art of creating balanced mockt...

Exploring Key West and the Beach Bum Book Series with HR Gordon 02.11.2025

Exploring Key West and the Beach Bum Book Series with HR Gordon In this episode of the Fun in Key West podcast, host Michele O'Connor introduces listeners to the book club edition featuring HR Gordon, author of the Beach Bum book series. HR Gordon discusses her inspiration behind the series, her connection to Key West, and the importance of Jimmy Buffett's music in her work. The conversation cover...

Key West: A Literary Haven 02.11.2025

Key West: A Literary Haven   In this episode of the Fun in Key West podcast, host Michele O'Connor welcomes listeners to explore the creative soul of Key West. The episode serves as an insider's guide to the island, diving deep into its rich literary history. The discussion covers famous authors who have been inspired by Key West, including Ernest Hemingway, Tennessee Williams, Robert Frost, and J...

Raising a Glass to Tiki Culture: History, Drinks, and Mocktails 02.11.2025

Raising a Glass to Tiki Culture: History, Drinks, and Mocktails   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor dives into the tropical vibes of tiki culture. The podcast covers the history of tiki bars, starting from the 1930s with Don the Beachcomber, and highlights significant tiki landmarks like Trader Vic's. Michele discusses what makes a drink 'tiki,' from ingredien...

The Impact of Steam Power on Key West 02.11.2025

The Impact of Steam Power on Key West   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor takes listeners on a journey through the fascinating history of steam power and its transformative impact on Key West. From enabling quicker maritime travel and aiding in the fight against piracy to powering trains and lighting up homes, steam power turned Key West into a vital hub of co...

Exploring October Festivities in Key West: Weather, Events, and More 13.10.2025

Exploring October Festivities in Key West: Weather, Events, and More In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to enjoying Key West in October. She highlights the area's perfect weather, foodie adventures, music festivals, and the legendary Fantasy Fest. Listeners get a rundown of weekly and monthly events, including the Truman Annex Farmer's...

The Ultimate Guide to Key West Sunset Sails 13.10.2025

The Ultimate Guide to Key West Sunset Sails In this episode of the 'Fun in Key West' podcast, host Michelle O'Connor provides an insider's guide to experiencing the best sunset sails Key West has to offer. Whether you're a first-time visitor or a seasoned island dweller, this episode covers a range of sunset sail options from the luxurious Danger Charters' Wind and Wine Sail to the vibrant Fury's...

Uncovering the Wild History of Key West's Old Custom House 13.10.2025

Uncovering the Wild History of Key West's Old Custom House In this episode of the Fun in Key West podcast, host Michele O'Connor explores the fascinating history of Key West's old Custom House. From its pivotal role in the wrecking industry, which turned Key West into one of America's wealthiest cities, to its transformation into the current Custom House Inn, Michele dives into thrilling tales of...

The Ultimate First Timer's Guide to Key West 05.10.2025

The Ultimate First Timer's Guide to Key West In this episode of the Fun in Key West podcast, host Michele O'Connor offers a detailed guide for first-time visitors planning a 2-3 day trip to Key West. She covers top dining spots like Cuban Coffee Queen, Blue Heaven, and Latitudes, along with must-visit locations such as the Hemingway House and Mallory Square. Michele provides insights on activities...

Game Day in Paradise: Best Sports Bars in Key West 05.10.2025

Game Day in Paradise: Best Sports Bars in Key West   In this episode of the 'Fun in Key West' podcast, host Michele O'Connor dives into the best sports bars on the island where you can catch your favorite game while enjoying the laid-back, tropical ambiance of Key West. Highlights include Jack Flats with its team-based seating arrangement, Pickles Pub boasting 40 TVs and a late-night kitchen, Brad...

Exploring Key West's Hidden Gems: The Benjamin Curry House 05.10.2025

Exploring Key West's Hidden Gems: The Benjamin Curry House   In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on an in-depth exploration of the historic Benjamin Curry House, a private residence in Key West that has been in the Curry family for over 150 years. Michele discusses the house's unique architectural features, its historical significance, and its conn...

Life Stories from Key West: Interview with Richie 'Conch Boy' Gomez 05.10.2025

Life Stories from Key West: Interview with Richie 'Conch Boy' Gomez   In this episode of the Fun in Key West podcast, host Michele O'Connor interviews Richie 'Conch Boy' Gomez, a third-generation Conch and author of 'Key West, A Smuggler's Tale.' Richie shares his rich and adventurous life growing up in Key West, from his childhood memories and smuggling adventures in the 1960s and 1970s to his ti...

Historic Marker Monday: The Great Havana Hurricane of 1846 28.09.2025

Historic Marker Monday: The Great Havana Hurricane of 1846   In this episode of the Fun in Key West podcast, host Michele O'Connor delves into the devastating Great Havana Hurricane of 1846. Michele describes the hurricane's catastrophic impact on Key West, including the loss of lives, the disappearance of a lighthouse, and the uprooting of the Key West Cemetery. She highlights the subsequent rebu...

Key West Festival Guide: Finding the Perfect Time to Visit 19.09.2025

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...

Pirates, Shipwrecks, and the Wild History of Key West 19.09.2025

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. Mi...

Unveiling the Mysteries of St. Mary's Star of the Sea 14.09.2025

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 explor...

Exploring Key West's History: The Rise and Fall of the Mallory Steamship Line 06.09.2025

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 C...

Exploring Key West with Lucy Burdette: Inside the Key West Food Critic Mysteries 31.08.2025

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 i...

Romantic Getaways in Key West: Top Activities and Tips 23.08.2025

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...

Key West Roosters: From Fighters to Feathery Celebrities 23.08.2025

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 episo...

Sipping Through Summer: Key West Cocktails & Island Vibes 23.08.2025

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 dr...

Exploring The Best Brunch Spots in Key West 18.08.2025

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 va...

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