Don’t Plan a Key West Trip Until You Watch This

Planning a trip to Key West? This is the perfect 5-day Key West itinerary — designed to help you experience the best of the Florida Keys without feeling rushed. In this video, I walk through our exact day-by-day plan for an upcoming trip to Key West — including iconic spots, hidden gems, the best food, and one of the most scenic drives in the country along the Overseas Highway. We’re staying right in Old Town near Duval Street and built this itinerary to balance adventure, relaxation, and incredible local experiences. 👉 Highlights include: Exploring Duval Street + Old Town Key West Visiting the Southernmost Point & Hemingway House A full-day road trip across the Florida Keys (Seven Mile Bridge 🚗) Snorkeling + boat day options The best Key West food spots and must-try experiences I also show how I used ChatGPT to plan this entire trip, saving hours of research and helping optimize the schedule. 0:00 Intro 0:30 Using ChatGPT to help plan the trip 1:46 Day 1: Arriving in Key West 1:57 Day 2: Drive up the Overseas Highway and Seven Mile Bridge 3:20 Picking a hotel 4:15 Sunset celebration 4:43 Day 3: Local lower key activities 5:41 Day 4: Seaplane to Dry Tortugas National Park 7:25 Day 5: Open itinerary to go with the flow with restaurant ideas 8:48 Wrap up 🎥 COMING NEXT: After the trip, I’ll be posting the full experience — what was actually worth it, what I’d skip, and what surprised me most. 👉 Make sure to subscribe so you don’t miss it. 🚗 Car Rental for the Overseas Highway Drive We used Turo to find the exact car we wanted for the trip — perfect for cruising the Keys with the top down. 🌴 Whether you’re planning your first Key West vacation, a Florida Keys road trip, or just looking for travel inspiration, this itinerary will help you make the most of your time. Watch us get crushed by rapids in the New River Gorge    • We Took Our Kids Whitewater Rafting… This ...