
Key West, Florida
Dry Tortugas National Park Day Trip by Luxury Private Boat
Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await.
★ 5.0 (11 reviews)
From $1,500
Key West, Florida
Robert the Doll After Dark is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and center. Expect a steady pace, local context, and a comfortable rhythm that lets you focus on the landscape.
Robert the Doll After Dark delivers a guided day adventure experience with a relaxed Florida, the route focuses on standout viewpoints and comfortable timing so you can enjoy the setting without feeling rushed.
We classify the skill level as All levels with guided support, with the day structured around a flexible half-day window. Guides adapt the flow for the group, offering helpful context and optional pauses while keeping the outing smooth and approachable.
Scenery and local insight are the highlights. Expect thoughtful stops, clear guidance, and a route that balances exploration with comfort.
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Key West, Florida
Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await.
★ 5.0 (11 reviews)
From $1,500

Key West, Florida
Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters.
★ 5.0 (31 reviews)
From $810

Key West, Florida
Discover the Great Florida Reef while visiting the Florida Keys on this private snorkel excursion.
★ 5.0 (444 reviews)
From $599

Key West, Florida
Getting out on the water is one of the best ways to explore Key West, but many big tours cram their boats with passengers.
★ 5.0 (137 reviews)
From $564.90

Key West, Florida
Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters.
★ 5.0 (180 reviews)
From $284.95

Key West, Florida
Cruise from Key West into deeper waters where you can fish for tuna, mahi-mahi, and kingfish—species you won’t see in coastal areas.
★ 5.0 (22 reviews)
From $250

Key West, Florida
Cool off in Key West on a half-day water sports tour that features 10 different water activities for you to try, from jet skiing to parasailing to…
★ 5.0 (368 reviews)
From $179.95

Key West, Florida
One of the only Adult Only experiences offered in Key West, our excursions are top-notch, with the vessel, all equipment, food and beverage service…
★ 5.0 (26 reviews)
From $161.24

Key West, Florida
Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour Jet Ski tour.
★ 5.0 (1426 reviews)
From $155.95

Key West, Florida
Spend a stunning afternoon soaking up the sights of the Gulf of Mexico, chilling out at a sandbar, and watching dolphins at the Florida Marine…
★ 5.0 (602 reviews)
From $149.95

Key West, Florida
Get ready to spend a half-day soaking up the sun and enjoying Key West’s diverse ecology during this fun sandbar and mangrove tour.
★ 5.0 (386 reviews)
From $149.95

Key West, Florida
Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour.
★ 5.0 (1457 reviews)
From $135

Key West, Florida
Get ready for fun in the sun—and leave all the planning to someone else—on this half-day sailing, kayaking, and snorkeling adventure off the coast of…
★ 5.0 (1788 reviews)
From $125

Key West, Florida
Set sail on a replica of the 1851 Schooner America on a cruise from Key West.
★ 5.0 (893 reviews)
From $122.59

Key West, Florida
Enjoy an amazing day out on the water in Florida’s Key West with this ultimate adventure tour aboard a catamaran.
★ 5.0 (447 reviews)
From $129.96

Key West, Florida
Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar.
★ 5.0 (143 reviews)
From $139

Key West, Florida
The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West.
★ 5.0 (3305 reviews)
From $99

Key West, Florida
Watch Key West's sunset — a main island attraction — on an evening dinner cruise.
★ 5.0 (1864 reviews)
From $92.95

Key West, Florida
Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district.
★ 5.0 (1904 reviews)
From $90.19

Key West, Florida
From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town…
★ 5.0 (309 reviews)
From $108

Key West, Florida
See the Key West lagoons in a whole new way.
★ 5.0 (179 reviews)
From $89.95

Key West, Florida
Paddle a kayak through mangrove creeks and shallow water on a Key West kayaking tour that offers an up-close look that this unique coastal…
★ 5.0 (2359 reviews)
From $80

Key West, Florida
Get ready for fun in the sun—and check off two top experiences in just one trip—on this dolphin-watching and snorkeling tour off the coast of Key…
★ 5.0 (1205 reviews)
From $73.21

Key West, Florida
Take in rare birds–eye views of Key West on a parasailing adventure over Smathers Beach.
★ 5.0 (148 reviews)
From $59.95
Key West, Florida
Guided Bike Tour of Old Town Key West is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front…
Key West, Florida
GPS Guided E-Bike History FunTour is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and…
Key West, Florida
Key West After Dark - Santeria, Voodoo & Ghost Tiki Bike Tour by Kokomo Cabs is a guided outdoor experience based in Key West, Florida that keeps the…
Key West, Florida
Private sandbar charter in Key West, held away from a crowd of other boats.
From $750
Key West, Florida
Namaste All Day is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and center. Expect a…
Key West, Florida
Upper Keys Road Trip & Bike Ride is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and…
Key West, Florida
Day adventure
Private sandbar charter of about five hours on a Boston Whaler in Key West, with a captain aboard.
★ 5.0 (187 reviews) · Google
From $749
Key West, Florida
Day adventure
Four-hour private charter on a Boston Whaler 230 Vantage bow-rider in Key West, with a captain and seating for six.
★ 5.0 (187 reviews) · Google
From $649
Key West, Florida
Day adventure
Six-hour private charter on a newer Boston Whaler 230 Vantage bow-rider in Key West, with a captain and seating for six.
★ 5.0 (187 reviews) · Google
From $849
Key West, Florida
Private offshore fishing charter on a 45-foot Hatteras out of Key West for up to six guests, offered for 4, 6, 8, 10, or 12 hours. A captain, a mate, and tackle are included.
★ 4.8 (1,022 reviews) · Google
From $1,050
Key West, Florida
Two-hour guided jet ski circumnavigation of Key West from the Perry Hotel and Marina, on Yamaha VX Waverunners with a Coast Guard-licensed lead guide.
From $209
Key West, Florida
Morning two-tank dive on the USNS General Hoyt S. Vandenberg, sunk in 2009 about six miles from Key West. Divers are limited to the deck at 100 feet.
From $65
Key West, Florida
Tennessee Williams Museum is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and center.…
Key West, Florida
Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs is a guided outdoor experience based in Key West, Florida that keeps the logistics…
Key West, Florida
Walking tour of Key West historic districts and Old Town. The group stays on foot while a guide talks at each site.
From $56.99
Key West, Florida
Walking tour in Key West with time at the Southernmost Point while a guide explains each outdoor stop.
From $49.99
Key West, Florida
Two-hour sunset sail in Key West, passing the Historic Seaport, Key West Bight, Mallory Square, and Fort Zachary Taylor.
★ 4.9 (487 reviews) · Google
From $95
Key West, Florida
Private charter of the 64-foot Atlantia power catamaran in Key West, booked for four to eight hours, with six staterooms and room for up to 12 guests.
From $6,000
Key West, Florida
Two-hour evening charter in Key West on the 64-foot Atlantia power catamaran, for up to 12 guests, with six staterooms and a full galley.
From $2,000
Key West, Florida
Two-hour evening charter in Key West on the Lagoon 450 F flybridge catamaran Somewhere, for up to 12 guests, with four cabins and a flybridge.
From $1,500
Key West, Florida
Charter of the Lagoon 450 F flybridge catamaran Somewhere in Key West for four to eight hours, for up to 12 guests, with four cabins and a flybridge.
From $4,500
Key West, Florida
Blind Squirrel is a guided outdoor experience based in Key West, Florida that keeps the logistics simple and the scenery front and center. Expect a…
Key West, Florida
Day adventure
Two-hour Key West walk for up to 20 guests, starting at Glazed Donuts and continuing through Old Town for rotating sweets and island history.
★ 5.0 (1,463 reviews) · TripAdvisor
From $65