Choose your trip length, interests, and pace to build a flexible Key West itinerary. Add other destinations, compare experiences, and reserve time for travel between stops.
Plan my Key West trip →Explore more in Florida.
December–March
Seasonal guidance is a starting point; check weather and dates for your chosen experiences.
Old Town: Central, historic neighborhoods within easy walking distance of major sights and nightlife. Duval Street area: Best for nightlife, restaurants, and easy access to bars and shops. Key West Historic Seaport: Good for seafood restaurants, boat tours, and quieter waterfront stays.
Browse these experiences as a starting point. The planner considers your interests, pace, and published schedules when building your days.
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sippin…
Approx. 120 minutesView on Viator →
This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to view the sharks. Delight in close-up views of sharks and a variety…
Approx. 120 minutesView on Viator →
Ride with Key Lime Bike Tours for a truly unique and unforgettable Key West experience! See the islands top attractions with your own friendly knowledgable guide! Cruise Old Town, …
Approx. 120 minutesView on Viator →
Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West. You will glide through the wi…
Approx. 120 minutesView on Viator →
Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in historic old town, dining on t…
Approx. 180 minutesView on Viator →
Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar. Climb aboard our custom luxury catamaran …
Approx. 120 minutesView on Viator →Start with the number of days you have, then choose an unhurried, balanced, or fuller pace. Review the suggested route before generating your daily plan. Transport allowances are estimates; confirm services and meeting points before booking.
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