Fun in Key West Podcast

Fun in Key West Podcast

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Fun in Key West Podcast episodes

  • Key West Travel Tips and Booking Smarter with Savvy.com (Guest: Eric Goldreyer)
    Key West Travel Tips and Booking Smarter with Savvy.com (Guest: Eric Goldreyer) Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and interviews hospitality entrepreneur Eric Goldreyer, who has 30+ years of experience spanning bed and breakfasts, boutique hotels, mega-yacht inflatables, and vacation rental property management. Eric shares his background (founding BedandBreakfast.com, selling it to HomeAway in 2010; co-founding TurnKey Vacation Rentals and selling to Vacasa in 2021; and launching FunAir) and explains why he created Savvy.com after experiencing high platform fees when booking a trip. He outlines common frustrations with Airbnb/VRBO and other OTAs, including 15–20% platform fees, restricted guest-host communication, temporary phone numbers, and complications when changes are needed (similar to booking hotels via Expedia). Eric describes Savvy as a book-direct marketplace that avoids platform fees, shows Savvy pricing alongside Airbnb pricing, and focuses on enabling direct communication with professional property managers (no rent-by-owner listings), with internal vetting and planned third-party trust/ID verification for hosts and travelers. The conversation covers how travelers can avoid scams by checking reviews, what fees are normal (taxes and cleaning) versus frustrating (platform fees), and why professional local management helps during high-demand destinations like Key West. Eric notes Savvy has been live about a year, lists about 150,000 North American properties from 2,500+ property management companies, is adding thousands of listings monthly, and aims to expand internationally by year-end, sharing how to reach him via Savvy.com, LinkedIn, and [email protected]. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Today's Guest: Hospitality Veteran Eric Goldreyer Joins the Show 02:00 Theme Song & Kickoff: Setting the Island Vibe 03:26 Eric's Origin Story: BedandBreakfast.com to Boutique Hotels 04:36 From Mega-Yacht Inflatables to Vacation Rental Tech 05:40 Why Savvy.com Exists: Beating Airbnb/VRBO Fees 07:42 Behind the Scenes of OTAs: Hidden Fees & Blocked Communication 10:49 Avoiding Scams: Reviews, Vetting, and Booking with Pros 14:42 What Fees Are Legit vs. Junk Fees (and Price Comparison Tools) 17:40 How Travel Has Changed: From Hospitality to Transaction 18:19 Tech vs. Hospitality: Why Human Hosts Still Matter 19:09 Real-World Trip Planning: Nuance, Off-Market Homes & Concierge Help 21:02 Savvy for Peak Season: Direct Communication + No Rent-by-Owner Safety Net 23:01 Quality Control: Reviews, Background Checks & Removing Bad Apples 24:47 Key West Love Letter: B&Bs, Longer Stays & Local Vibes 28:15 Food, Coffee & Duval Street: Gluten-Free Finds and Must-Do Spots 30:23 Booking Habits to Break: Save Money by Booking Direct on Savvy 31:55 Wrap-Up: Savvy's Growth Plans, How to Reach Eric, and Final Thanks www.funinkeywest.com www.savvy.com
    35 min
  • First Timer Friday: Why Marathon Is the Perfect Home Base in the Florida Keys
    First Timer Friday: Why Marathon Is the Perfect Home Base in the Florida Keys Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and presents a First Timer Friday episode that detours from Key West to highlight Marathon as a laid-back, centrally located Florida Keys home base. She explains Marathon's position halfway between Miami and Key West across 13 islands and why it offers quieter mornings, easier parking, and strong water access for day trips up to Key Largo, Island Morada, Big Pine Key, and Key West. Activities and highlights include snorkeling at Sombrero Reef, kayaking and paddleboarding on both ocean and bay sides through mangroves and seagrass with possible manatee, turtle, and bird sightings, and fishing options (deep sea, reef, and flats). She recommends experiencing the Seven Mile Bridge via the old bridge for walking, biking, fishing, and views, plus visiting Pigeon Key by trolley for tours, museum history, snorkeling, and fishing while bringing your own essentials. Wildlife stops include the Dolphin Research Center's educational and conservation focus and the Turtle Hospital's guided tours and rehabilitation work, with advice to book ahead and consider supporting both. She also spotlights Curry Hammock State Park for trails, kayaking, picnics, birdwatching, and competitive seasonal camping. For food, she recommends Keys Fisheries for marina views and classic Keys atmosphere, noting popular items like the lobster Reuben, seasonal stone crab claws, and award-winning key lime pie, along with a cash-only note and arriving early for sunset. The episode closes by describing who Marathon best fits (families, nature lovers, water-focused travelers) versus those seeking nightlife or luxury, and directs listeners to funinkeywest.com for guides, an ultimate road trip guide, newsletter (including a Key West happy hour list), and book club updates. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Today's Detour: Why Marathon Is a Hidden Gem in the Keys 02:57 First Timer Friday: Marathon as the Perfect Home Base 04:12 Where Marathon Sits + Why the Middle of the Keys Matters 06:29 Snorkeling in Marathon: Easy Reefs, Clear Water & Tour Tips 08:03 Kayaking & Paddleboarding: Mangroves, Manatees and Quiet Water 09:30 Fishing Capital Vibes + Experiencing the Seven Mile Bridge 10:42 Pigeon Key: Old Bridge Walks, History Tours & Island Time 11:38 Wildlife Must-Dos: Dolphin Research Center & The Turtle Hospital 13:13 Curry Hammock State Park: Trails, Camping and Nature Escapes 14:11 Where to Eat in Marathon: Keys Fisheries & Local Favorites 15:17 Is Marathon Right for You? Day Trips, Travel Styles & Final Take 17:30 Wrap-Up + Resources: Guides, Newsletter, Happy Hour List & Book Club 19:08 Final Outro: Marathon, the Unsung Hero of the Florida Keys www.funinkeywest.com
    21 min
  • Historic Marker Monday: The Birth of the Conch Republic and the Great Battle of 1982
    Historic Marker Monday: The Birth of the Conch Republic and the Great Battle of 1982 Host Michele O'Connor introduces the Fun in Key West podcast and a Historic Marker Monday episode about the 1982 events that led to the creation of the Conch Republic. She recounts how a U.S. Border Patrol roadblock at Last Chance Saloon in Florida City stopped and searched every car entering and leaving the Keys, creating massive traffic jams, generating national and international press, and causing major economic harm as tourists canceled trips and hotels sat empty. After community leaders pushed Mayor Dennis Wardlow to respond, a legal effort led by David Paul Horan failed in federal court in Miami; outside the courthouse Wardlow told reporters Key West would "go home and secede." On April 23, 1982, the Conch Republic declared itself, raised its flag over City Hall, and staged a humorous protest known as the "Great Battle of the Conch Republic," involving the schooner Western Union (captained by John Cross) jokingly attacking the U.S. Coast Guard cutter Diligence with water balloons, conch fritters, and stale Cuban bread, while the cutter responded with fire hoses. Wardlow, now acting as prime minister, immediately surrendered and requested foreign aid and war relief; the episode notes they are still waiting to be paid, but the roadblock was removed and tourism was saved. The script emphasizes the protest was not anti-American and the Coast Guard was never considered an enemy, describing the Conch Republic as a "sovereign state of mind" rooted in humor, community, and independence. Listeners are directed to the historic marker at 402 Wall Street and invited to attend Conch Republic Days, described as the 44th year of the celebration, with 2026 dates April 17–26, 30+ events, multiple parades (including one spanning from the Atlantic to the Gulf), and a reenactment at Mallory Square featuring boats, water balloons, stale bread, a Coast Guard fire hose response, and a plane dropping toilet paper. The episode points viewers to funinkeywest.com for details, free guides, a newsletter, and the podcast's book club and author interviews on YouTube, including a 2025 selection by Richie "Conch Boy" Gomez. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Historic Marker Monday Teaser: The Conch Republic Origin Story 02:57 March 1982: The Border Patrol Roadblock & 17-Mile Traffic Jam 05:45 Tourism Takes a Hit: Empty Hotels and Economic Fallout 07:05 From Courtroom to Secession: 'We're Going Home and Secede' 07:56 April 23, 1982: Flag Raised & The 'Great Battle' (Water Balloons + Cuban Bread) 09:33 Quiet Victory: Roadblock Removed and the Real Point of the Protest 10:51 Conch Republic Today: A 'Sovereign State of Mind' + Where to See the Marker 11:36 Conch Republic Days 2026: Dates, Parades, and the Battle Reenactment 13:25 Wrap-Up & Where to Learn More (Website, Guides, YouTube, Newsletter) 14:16 Final Sendoff: Keep the Conch Republic Spirit Alive www.funinkeywest.com
    15 min
  • Exploring Key West in February: Festivals, Events, and Warm Weather Delights
    Exploring Key West in February: Festivals, Events, and Warm Weather Delights In this episode of the Fun in Key West podcast, host Michele O'Connor offers a comprehensive guide to enjoying Key West in February. From highlighting warm weather and sunny skies to detailing a variety of festivals and events including arts and crafts fairs, theaters, Mardi Gras celebrations, and foodie exhibitions, Michele provides valuable insider tips for both first-time visitors and Key West veterans. The episode also discusses upcoming key events and attractions throughout the month, including the Red Barn Theater's plays, various tribute band performances at the Key West Theater, and the Smithsonian-sponsored food history exhibit. Tune in to discover why February is an ideal time to visit Key West and how to make the most out of your island getaway. 00:00 Welcome to Fun in Key West Podcast 01:26 First Timer Friday: Why Visit Key West in February? 04:50 February Events and Activities in Key West 06:16 Key West Arts and Entertainment Highlights 10:57 Wrapping Up: Stay Connected and Informed www.funinkeywest.com
    13 min
  • Crispy Conch Fritters and Key West Delights: Tasty Tuesday Special
    Crispy Conch Fritters and Key West Delights: Tasty Tuesday Special In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a culinary journey through Key West, with a focus on the iconic conch fritters. Michele covers everything from the perfect texture and seasoning of these crispy treats to the best spots on the island to enjoy them. She also dives into the origins of conch fritters, their preparation, and tips for ensuring you get the best ones. Whether you're planning a visit to Key West or simply daydreaming about island life, this episode is packed with insights and recommendations to savor the tastes of paradise. 00:00 Welcome to Fun in Key West Podcast 01:26 Tasty Tuesday: Conch Fritters Introduction 04:39 The Perfect Conch Fritter: What to Look For 09:17 Top Spots for Conch Fritters in Key West 12:56 Tips for Enjoying Conch Fritters 16:06 Wrapping Up: Join Us Next Time www.funinkeywest.com
    18 min
  • Exploring Clinton Square: A Civil War Landmark in Key West
    Exploring Clinton Square: A Civil War Landmark in Key West In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to Key West, focusing on Clinton Square's rich and layered history. She highlights its significance during the Civil War as the only southern city occupied by the Union throughout the conflict. Michele explains the unique dual commemoration within Clinton Square, where both Union and Confederate memories are honored in the same space, making it a fascinating site of coexistence and historic significance. The episode encourages listeners to slow down and appreciate the history surrounding them, with tips on exploring more historic markers in Key West. 00:00 Welcome to Fun in Key West Podcast 01:28 Historic Marker Monday Introduction 01:49 Exploring Clinton Square's Civil War History 06:36 Union and Confederate Memorials in Key West 09:38 Key West's Military Significance 11:09 Wrapping Up and Exploring More Markers www.funinkeywest.com
    13 min
  • Discovering Key West with Salty Paw Charters
    Discovering Key West with Salty Paw Charters In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the idyllic world of Key West with Zach from Salty Paw Charters. Learn about Zach's journey from aspiring teacher to captain, and how he launched his own charter business in Key West. The episode explores unique experiences offered by Salty Paw Charters, including sandbar adventures, brunch cruises, sunset charters, and a new family-friendly pirate-themed scavenger hunt. Discover what sets Salty Paw Charters apart, the breathtaking sights, and the must-bring essentials for your trip. Get insider tips on local dining and enjoy a special offer to save on your next Key West adventure. 00:00 Welcome to Fun in Key West Podcast 01:26 Introducing Zach from Salty Paw Charters 03:37 Zach's Journey to Becoming a Captain 06:04 Unique Offerings of Salty Paw Charters 10:56 Experiencing Key West Sandbars 15:13 Sunset and Brunch Cruises 19:17 Upcoming Pirate Adventure for Families 22:06 Tips for a Great Charter Experience 24:59 Zach's Personal Favorites in Key West 27:02 Conclusion and Special Offers SALTYDEAL to save $100 www.funinkeywest.com https://saltypawskeywest.com/
    29 min
  • Discovering the Hidden Gems of Key West: West Martello Tower
    Discovering the Hidden Gems of Key West: West Martello Tower In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a journey to explore the transformation of the West Martello Tower, a Civil War fort that has been reclaimed by nature and community efforts. From its initial construction in 1862 to its current status as a lush garden and butterfly habitat managed by the Key West Garden Club, Michele delves into the rich history and vibrant present of this unique landmark. Whether you're a history buff, nature lover, or just looking for a serene escape, this episode offers a fascinating look at one of Key West's hidden gems. Tune in to learn more about its indestructible design, historical significance, and the dedicated community that keeps its legacy alive. Plus, get insider tips for your next Key West adventure. 00:00 Welcome to Fun in Key West Podcast 01:26 Exploring the West Martello Tower 02:59 Historic Marker Monday: West Martello's Rich History 08:26 West Martello's Modern Transformation 10:10 Visiting the West Martello Today 14:26 Conclusion and Key West Adventures www.funinkeywest.com
    17 min
  • First Timer's Guide to Choosing Bed and Breakfasts in Key West
    First Timer's Guide to Choosing Bed and Breakfasts in Key West In this episode of the 'Fun in Key West' podcast, host Michele O'Connor offers practical tips and historical insights for selecting the perfect bed and breakfast in Key West. She covers essential considerations such as location, amenities, and the unique characteristics of various Key West properties. Michele delves into the history of Key West's hospitality and provides a rundown of specific accommodations, touching on their individual quirks and advantages. She also addresses factors like breakfast offerings, room comfort, and additional fees. Listeners are encouraged to reach out for personalized recommendations and visit the Fun in Key West website for more travel tips and ideas. 00:00 Welcome to Fun in Key West Podcast 01:26 Choosing the Perfect Bed and Breakfast 02:32 First Timer Friday Tips 03:59 Key Considerations for Your Stay 05:48 Understanding Breakfast Options 07:36 Location, Location, Location 10:01 Amenities and Must-Haves 12:40 Room Comfort and Style 16:03 Adult-Only vs. Social Vibes 17:09 Fees, Rates, and Hidden Costs 18:38 Historical Stays in Key West 20:03 Narrowing Down Your Options 25:13 Final Tips and Resources www.funinkeywest.com
    28 min
  • Exploring Key West's Best Breakfast Spots: A Tasty Tuesday Guide
    Exploring Key West's Best Breakfast Spots: A Tasty Tuesday Guide In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to the best breakfast spots in Key West. From iconic locations like Blue Heaven and Pepe's Cafe to hidden gems like Sandy's Cafe and Glazed Donuts, Michele lists must-try places that offer delicious breakfast options. Additionally, she introduces the different 'Key West Breakfast Personalities,' including the Slow Sipper, Recovery Specialist, Brunch Maximalist, and Local Looper. Michele offers pro tips on avoiding the breakfast rush and maximizing your morning meal experience in Key West. The episode also highlights where to find the best coffee and cocktails, and emphasizes that vacation calories don't count. Listeners are encouraged to visit funinkeywest.com for more guides, tips, and foodie inspiration. 00:00 Welcome to Fun in Key West Podcast 01:28 Exploring Key West Breakfast Spots 06:10 Iconic Key West Breakfast Experiences 07:33 Coffee First: Key West's Best Cafes 10:17 Vacation Calories Don't Count: Indulgent Breakfasts 12:28 Healthy Options and Vegetarian-Friendly Spots 13:33 Breakfast with a View: Scenic Spots 14:31 Finding Your Key West Breakfast Personality 16:16 Tips for Enjoying Breakfast in Key West 21:36 Conclusion and Community Engagement www.funinkeywest.com
    25 min

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