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70 results
Best Seller
Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.
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Southernmost Food & Cultural Walking Tour by Key West Food Tours
3 hours
Free Cancellation
4.9
(1,852)
from
$90
Likely to Sell Out
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 Key West. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef teeming with marine life. Snacks, beer, wine, and soft drinks are included.
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Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset
4 hours 30 minutes
Free Cancellation
4.9
(1,750)
from
$125
Likely to Sell Out
Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.
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Key West Craft Cocktail Crawl
3 hours
Free Cancellation
4.9
(569)
from
$94
Likely to Sell Out
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.
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Key West Historic Seaport Food & Walking Tour
3 hours
Free Cancellation
4.9
(663)
from
$93
Likely to Sell Out
Discover the enchanting beauty of the Florida Keys with Island Girls Excursions. This adventure combines relaxing sandbar experiences with stunning sunset cruises. Unwind on your spacious 52’ catamaran, complete with complimentary snacks and drinks while soaking up the sun or exploring the crystal-clear waters. Your experienced crew will ensure a smooth sailing experience, showcasing the best spots in the area. Perfect for groups seeking relaxation, celebration, or exploration, this tour promises unforgettable memories in paradise. - Enjoy a leisurely sandbar trip with paddleboarding and floats - Experience breathtaking sunset views while sipping drinks - Spacious and comfortable 52’ catamaran with Wi-Fi - Friendly and knowledgeable crew dedicated to your safety and enjoyment
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Sandbar Adventure Cruise in the Florida Keys
4 hours
Free Cancellation
4.9
(7)
from
$85
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
Go sightseeing along the Overseas Highway without having to sort out your own transportation on this day tour from Key West, which includes pickup from your hotel. Discover the wonders of the Florida Keys including the Florida Keys Aquarium Encounters, Bahia Honda State Park, National Key Deer Refuge, and Seven Mile Bridge.
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Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
7 hours
Free Cancellation
4.9
(35)
from
$169
Price varies by group size
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 packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.
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Key West Historic Old Town Food Tour with 5 Authentic Tastings
2 hours 30 minutes
Free Cancellation
4.8
(306)
from
$108
Price varies by group size
Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering hidden gems and local lore along the way . Explore the vast wetlands of Everglades National Park, encountering unique wildlife and ecosystems . Delve into the rich history and biodiversity of Big Cypress National Preserve . Finally, discover the underwater wonders of Biscayne National Park, from coral reefs to mangrove forests . With GPS-triggered narration, offline maps, and expert storytelling, enjoy the freedom to explore at your own pace without the constraints of group tours. Join thousands of travelers who have transformed their Florida road trips into enriching experiences—download now and let the Sunshine State's natural beauty and history captivate you!
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Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours
4 days
Free Cancellation
5.0
(1)
from
$40
Per group
Likely to Sell Out
The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.
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Shark and Wildlife Viewing Adventure in Key West
2 hours
Free Cancellation
5.0
(3,205)
from
$99
Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic landmarks as your crew shares information about the local area and points out interesting sights along the way. Once you arrive at the sandbar, step into shallow turquoise water perfect for swimming, floating, and relaxing. Use the provided water floats and noodles, or simply unwind on deck and enjoy the sunshine and music. This relaxed and family-friendly tour offers plenty of space to move around the boat, shaded seating, onboard restrooms, and a cooler with ice, soda, and water. Ideal for couples, families, and groups, this experience lets you enjoy Marathon’s sandbars the way locals do—easygoing, fun, and surrounded by the natural beauty of the Keys.
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Island Sandbar Tour Catamaran Cruise in Marathon FL
4 hours
Free Cancellation
4.0
(4)
from
$130
Experience an Unforgettable Fishing Adventure in Key West! Join us for an exhilarating private deep-sea fishing adventure on the vibrant waters of Key West. Led by a skilled and experienced captain, our charters cater to both seasoned anglers and first-timers, ensuring an unforgettable experience. Reel in magnificent mahi, wahoo, sailfish, and more. Our knowledgeable crew will guide you to prime fishing spots, employing techniques like trolling, reef, or wreck fishing and many more to maximize your chances of landing a trophy catch. Choose from flexible charter options: 1/2-day, 3/4-day, full-day, or extended 10-12 hour trips tailored to your preferences. Our 36-foot Hatteras "Cowboy" offers comfort and safety with clean facilities, restrooms, , a flybridge, and state-of-the-art equipment. Book now and discover why our private charters are the ultimate choice for a thrilling day on the water in Key West.
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Key West Private Fishing Charters- 4 HRS 36 FT HATTERAS COWBOY
4 to 12 hours
Free Cancellation
5.0
(5)
from
$850
Per group
Unlike standard boat rides, this tour takes you to a unique sandbar location where you can enjoy shallow waters and natural beauty. With expert guidance and a well-planned itinerary, you’ll experience one of the Florida Keys’ most iconic coastal spots.
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Sandbar Boat Tour in Marathon Florida
3 hours
Free Cancellation
1.0
(1)
from
$80
Set sail for a full-day escape to the hidden gems off Key West’s coast—where pristine beaches and secluded islands await. Whether you're soaking up the sun, taking in the coastal views, or just unwinding with your group, this experience blends the excitement of the open water with the comfort of premium onboard amenities. Perfect for history lovers and adventure seekers alike, this guided journey offers something for everyone.
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Dry Tortugas National Park Day Trip by Luxury Private Boat
8 hours
Free Cancellation
3.9
(11)
from
$1,500
Price varies by group size
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
Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat for an easy day out. Whether you’re a beginner or an experienced angler, your captain and crew assist with your fishing skills. Fish for reef species like snapper, grouper, and mackerel. A fishing license and all bait are included, and the boat features restrooms, shaded seating, and a small galley with snacks and drinks for your convenience.
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Key West 6-Hour Party Boat Fishing Trip – Affordable Reef Fishing
6 hours
Free Cancellation
4.4
(332)
from
$89
Ideal for travelers short on time, this private tour covers the best of Key West in one day from Marathon. Highlights include stops at the Hemingway House, Mile Marker Zero, and Mallory Square at sunset. Enjoy roughly three hours of free time to explore at your own pace. Upgrade to include a sunset sail, dinner cruise, or other Key West attractions.
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Marathon to Key West Private Tour of Florida Keys
8 hours
Free Cancellation
5.0
(27)
from
$137
Price varies by group size
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.
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Schooner Appledore Day Sail with Full Bar in Key West
2 hours
Free Cancellation
4.9
(113)
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$49
Experience the beauty of the Florida Keys on this guided 4-hour VIP tour! Travel the iconic Overseas Highway, cross the famous 7-Mile Bridge, and explore Bahia Honda State Park. Spot endangered Key Deer, visit the Blue Hole, and enjoy live commentary, island music, and breathtaking views. Hotel pickup and drop-off included. Perfect for nature lovers, history buffs, and adventure seekers!
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Florida Keys Nature & History Tour from Key West
4 hours
Free Cancellation
4.9
(115)
from
$119
Price varies by group size
Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike roadside rentals, this tour transports you by boat to the untouched Mud Keys, a hidden paradise of mangrove tunnels, crystal-clear waters, and diverse marine life. What to Expect: Boat Ride to a Remote Kayaking Spot – No roads, no noise, just backcountry beauty Guided Kayak Tour – Paddle through winding mangroves and spot stingrays, tropical fish, and sea turtles Wildlife Sightings – Keep an eye out for dolphins, sharks, and exotic birds ️ Sandbar Stop – Relax in pristine waters after kayaking Drinks & Lunch Included – Enjoy unlimited drinks and a delicious meal Why This Tour is Unique: Exclusive Location – No other company goes here No Crowds, No Roads – A peaceful, off-the-grid experience Perfect for All Skill Levels – Easy and enjoyable for everyone
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Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks
5 hours
Free Cancellation
4.7
(6)
from
$150
Watch the sun set and the moon rise off the coast of Key West on this relaxing sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer, and soft drinks are included.
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Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
2 hours
Free Cancellation
4.7
(3,705)
from
$79
Explore the best that Key West has to offer on this narrated tour aboard a miniature train. See Key West’s top attractions and learn about the Conch Republic’s history and residents, including Ernest Hemingway and Harry Truman. Get to know Old Town Key West, from the Front Street Depot to Mallory Square, and learn the stories behind the sights from the live on-board commentary.
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Key West Conch Tour Train
1 hour 30 minutes
Free Cancellation
4.4
(848)
from
$45
Our US Coast Guard licensed captains have decades of combined excursion experience in the Middle Keys and look forward to sharing our lovely paradise with you! Your captain will provide all the tips to have you exploring our local sea-life in no time. We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, our boats are clean and comfortable offering multiple seating options, and maintained regularly. After your 2 hour excursion, you’ll fall in love with the Keys! Florida Mom owned, voted Best in Marathon 2023, 2024
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Marathon: Local Sandbar Escape
2 hours
Free Cancellation
5.0
(4)
from
$119
Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.
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Key West Sunset Cruise: Dinner, Live Music & Drinks Included
2 hours
Free Cancellation
4.3
(1,803)
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$93
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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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