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100+ results
Best Seller
Explore the best that Key West has to offer on this narrated, hop-on, hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Enjoy free admission to the Sails to Rails Museum for extra sightseeing fun.
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Key West Hop-On Hop-Off Trolley Tour
1 hour 30 minutes
Free Cancellation
4.4
(1,677)
from
$56
Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour Jet Ski tour. With several daily tours, you can easily find a time that fits with your schedule. The tour is priced per Jet Ski, so you can ride tandem with a friend at no additional cost. Your guide is on hand at all times to lead the way on your aquatic adventure.
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Key West Island Adventure Jet Ski Tour: Bring a Partner for Free
1 hour 30 minutes
Free Cancellation
4.8
(1,395)
from
$156
Per group
Pedal through the charming streets of Old Town Key West on a guided bike tour, perfect for first-timers exploring the island. Along the way, you’ll uncover its rich history and stop at iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. With morning and afternoon tour options, it’s easy to soak in panoramic ocean views and experience Key West at your own pace.
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Guided Bike Tour of Old Town Key West
2 hours
Free Cancellation
4.9
(2,701)
from
$59
Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.
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Key West Ghosts and Gravestones Trolley Tour
1 hour
Free Cancellation
4.3
(1,306)
from
$40
Enjoy the flexibility of independent travel with the convenience and narration of a guided experience with a hop-on hop-off trolley tour in Key West. With this 1-day pass, board at any of the conveniently located stops and get to know the city in customized fashion, with live onboard commentary from a professional tour conductor.
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Key West Shore Excursion: Hop-On Hop-Off Trolley Tour
1 hour 30 minutes
Free Cancellation
4.3
(81)
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$56
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 West. Departing Key West, look out for dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breezes, and select from a variety of refreshing beverages on board the boat.
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Key West Dolphin Watch and Snorkel Tour - Eco Adventure
3 hours
Free Cancellation
4.7
(1,185)
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$80
Explore the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.
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Southernmost Key West History and Culture Small-Group Walking Tour
1 hour 45 minutes
Free Cancellation
5.0
(133)
from
$40
Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, numbers are restricted to 24 so you have a spot at the rail when it’s time to capture photos of the setting sun.
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Sunset Sail in Key West with Beverages Included
1 hour 30 minutes
Free Cancellation
4.9
(945)
from
$79
Getting out on the water is one of the best ways to explore Key West, but many big tours cram their boats with passengers. This private tour promises an un-crowded experience. Head out onto turquoise water aboard a unique tiki bar boat and look out for marine life such as turtles and dolphins as you cruise to a sandbar where you can swim or just soak up the sun.
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Key West Tiki Bar Boat to Popular Sand Bar with Turquoise Waters
4 hours
Free Cancellation
4.9
(136)
from
$565
Per group
Special Offer
The best way to experience Key West is by getting out on the water, but with so many tours available, it can be hard to choose. This tour company has decades of experience of guiding visitors on jet skis through the waters they know so well and giving everyone plenty of time to let loose on the waves.
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The Original Key West Island Jet Ski Tour from Barefoot Billy's
1 hour 30 minutes
Free Cancellation
4.9
(351)
from
$156
$140
Per group
Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.
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Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
2 hours
Free Cancellation
4.5
(583)
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$32
Likely to Sell Out
Kayaking is a great way to experience the Florida Keys but your views are typically limited to what's above the surface of the water. This small-group tour provides clear kayaks that let you discover the underwater world as well. As you paddle, you just need to look below to spot starfish, tropical fish, nurse sharks, turtles, jellyfish and more.
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Guided Clear Kayak Eco-Tour Near Key West
2 hours
Free Cancellation
4.9
(698)
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$79
Likely to Sell Out
Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat tour will take you on an exhilarating, up-close adventure across crystal-clear waters, winding through lush mangroves, stopping at pristine sandbars, and exploring hidden islands that are off the beaten path. This is your chance to experience Key West like never before — in a fun, fast, and eco-friendly CraigCat boat! Perfect for All Levels: Whether you're an experienced boater or a first-time adventurer, the Craigcat is easy to handle and designed for fun and comfort. With a small, nimble design, you’ll have the freedom to explore areas that larger boats or jet skis can’t reach. Up to 4 boats per tour. 2 guests max per boat. If you have 4 people in your group please make two separate bookings to accommodate your party and so forth up to 8 guests.
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2 Hour Key West Mini Catamaran Eco Tour
2 hours
Free Cancellation
4.6
(159)
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$285
Per group
See the Key West lagoons in a whole new way. Go on a nocturnal adventure with clear kayaks and LED lights that illuminate the surroundings so you can see underwater. A local guide takes you and a small group to the best spots and you’ll experience a unique and memorable way of spotting marine life.
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Guided Night Kayak Adventure Tour in Luminous Lagoon
1 hour 30 minutes
Free Cancellation
4.5
(154)
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$90
Soak up sunset views from the water's edge, and admire a perspective many visitors miss, on this Key West sailing tour. Sample up to eight different wines and/or five different beers as you sail, and indulge in a selection of gourmet hors d'oeuvres to accompany them. As you go, learn more from your crew, and enjoy a festive and celebratory way to toast to your trip.
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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
2 hours
Free Cancellation
4.9
(1,433)
from
$135
Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
2 hours
Free Cancellation
4.9
(879)
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$123
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 environment. This guided tour is the perfect way to spot Florida wildlife in a natural habitat.
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Key West Mangrove Kayak Eco Tour
2 hours
Free Cancellation
4.9
(2,327)
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$80
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. Discover the backcountry waters and secluded sandbars around the busy island, all while sipping on cold drinks. This guided kayak ecotour takes you into the mangrove isles to spot dazzling marine life before heading to a sandy beach to knock back a few alcoholic or nonalcoholic beverages.
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Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks
5 hours
Free Cancellation
4.8
(353)
from
$150
Likely to Sell Out
Head out into the open waters on this small-group kayaking and snorkeling ecotour adventure. Follow your captain through scenic mangrove tunnels and over calm waters as you make your way to one of the area's most-stunning snorkeling destinations. Learn about local wildlife before taking a dip and get an underwater look. Gear is provided on this tour that's perfect for all levels.
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Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco
4 hours 30 minutes
Free Cancellation
5.0
(190)
from
$156
Go sightseeing in the Florida Keys at your own pace with a private self-guided audio tour. Choose a northbound or southbound itinerary and learn about local landmarks, history, and more during the drive. Set out on a road trip through the Florida Keys and learn about highlights such as Seven Mile Bridge and John Pennekamp State Park along the way. Tour offline using GPS, with no cell service needed.
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Self-Guided Audio Tour in Florida Keys
1 day
Free Cancellation
4.7
(92)
from
$17
Per group
Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees, and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.
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Ultimate Sea Doo Jet Ski Tour of Key West-Additional Rider Free!
1 hour 30 minutes
Free Cancellation
4.6
(651)
from
$150
Per group
Have all the fun of a private tour from the comfort of your own vehicle and at your own pace to boot. Enjoy this informative self-driven tour for 100 miles, from Key Largo all the way to Key West, making as many stops along the way as you want to eat, rest, and take pictures.
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Florida Key West Self-Guided Driving Tour (7 Mile Bridge)
2 to 3 hours
Free Cancellation
4.5
(73)
from
$17
Per group
Get a different perspective of Key West and visit some lively local spots at the same time during this haunted pub crawl tour. Take a journey through the streets of Key West as your guide regales you with scary stories. From eerie tales of possessed dolls to creepy encounters with the macabre, enjoy the entertainment as you visit various landmarks.
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Key West Haunted Pub Crawl Walking Tour
2 hours
Free Cancellation
4.4
(102)
from
$35
Try something new in Key West: parasailing. Adventure seekers who've booked this trip will love soaring over the Key West Seaport. The experience is available for singles, doubles, and even triples so it's a fantastic activity for a group of friends or a family. You'll board a state-of-the-art boat, get briefed by the crew, and then fly over the city—free as a bird.
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Parasailing over the Historic Key West Seaport
1 hour
Free Cancellation
4.7
(223)
from
$60
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Top Attractions in Key West
1 / 2
Attractions
Mallory Square
From $12
Attractions
South Beach
From $11
Attractions
Harry S. Truman Little White House
From $12
Attractions
Dry Tortugas National Park
From $899
Attractions
Florida Keys National Marine Sanctuary
From $60
Attractions
Southernmost Point of the Continental USA
From $12
Attractions
Mallory Square
From $12
Attractions
South Beach
From $11
Attractions
Harry S. Truman Little White House
From $12
Attractions
Dry Tortugas National Park
From $899
Attractions
Florida Keys National Marine Sanctuary
From $60
Attractions
Southernmost Point of the Continental USA
From $12
Attractions
Mallory Square
From $12
Attractions
South Beach
From $11
Attractions
Harry S. Truman Little White House
From $12
Attractions
Dry Tortugas National Park
From $899
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