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Key West Getaway for Outdoor Enthusiasts

5 to 7+ Nights from $1,496*
* Sample price: priced within the past 7 days for a 1/11/2026 arrival, departing Atlanta ATL (GA), US. Choose departure city, cabin and dates.

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Add Outbound & Return Flights

This 5 night sample itinerary includes:

  • Flight into out of Key West
  • Hotel for 5 nights in Key West

    Sample of Included Tours:
  • Daytime Sailing and Watersport Adventure Excursion in Key West
  • Parasail Adventure in Key West
  • Kayak Tour Adventure from Key West
  • Sunset Cruise Experience in Key West

    Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.

An epic vacation at one of Florida`s best cities specially for Outdoor Enthusiasts!. Get ready to discover Key West (island city that is part of the Florida Keys archipelago, known for its coral reefs, famous for water sports, lively nightlife, beaches, historic sites and its pastel, conch-style architecture)... from chilling on a Cruise and watching the sunset on the water, to sailing, doing water sports, or even going on a Parasail and Kayak Adventure. You won't get bored here with all the fun stuff to do!.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
Live phone and chat support

Flexible Itinerary

  • Key West, FL

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USA

Customer Reviews

Trip Summary

  • Key West, FL
    Key West, FL

    At the end of the 113-mile Overseas Highway in the Florida Keys is the vibrant town of Key West, the southernmost point in the continental United States. The `Conch Republic`, just 90 miles from Cuba, has a flair and attitude all its own, which you can see out on Duval Street and Mallory Square, places to see and be seen. Grab a cold drink and enjoy the relaxing and welcoming tropical atmosphere only Key West knows how to provide.

    Visit and discover the Ernest Hemingway House and Museum, Southernmost Point Marker, Mallory Square, Duval Street, Fort Zachary Taylor, Smathers Beach, Truman Little White House, Key West Lighthouse, Key West Aquarium, Key West Butterfly and Nature Conservatory, and so much more!

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