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Top Key West Private Sightseeing Tours

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44 results | All Key West Tours

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Gulfstream Fishing - Key West
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Gulfstream Fishing - Key West

star-4.5
185
Going fishing while in Key West is a must, and this deep-sea fishing tour takes you on a comfortable boat that can fit up to 60 passengers. Whether you’re a beginner or an experienced fisherman, your captain and crew helps you with your skills. Try to catch snapper, grouper, mackerel, or shark. A license and all bait are included, and restrooms are on board for convenience.
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  • 6 hours
  • Free Cancellation
From
$76.97
From
$76.97

Key West Southernmost Food and Cultural Walking Tour
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Key West Southernmost Food and Cultural Walking Tour

star-5
536
Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, 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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  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

2-Hour Private Sunset Cruise around Key West
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2-Hour Private Sunset Cruise around Key West

star-5
26
Key West is famed for its sunsets but the scene in town tends to be crowded. Sidestep the big crowds by getting out onto the water on a private tour. In the company of just your party and the captain, relax as you cruise around the island and the captain points out all the important landmarks.
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  • 2 hours
  • Free Cancellation
From
$200.00
Price varies by group size
From
$200.00
Price varies by group size

Key West Sunset Dinner Cruise with Tropical Buffet
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Key West Sunset Dinner Cruise with Tropical Buffet

star-4
428
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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  • 2 hours
  • Free Cancellation
From
$88.95
From
$88.95

2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
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2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West

star-5
13
Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.
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  • 2 hours
  • Free Cancellation
From
$456.88
per group
From
$456.88
per group

Key West Craft Cocktail Crawl
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Key West Craft Cocktail Crawl

star-5
137
Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, 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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  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Kayak Tour of Mangrove Maze from Key West

Kayak Tour of Mangrove Maze from Key West

star-5
37
Paddle through the mangroves, located at the southwest corner of the island, before reaching the salt ponds on this guided kayaking tour. Learn about the history of Key West and South Florida, as well as the local flora and fauna along the way. You also paddle through the Gulf of Mexico and Cow Key Channel as you head to the mangroves.
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  • 3 hours
  • Free Cancellation
From
$75.00
From
$75.00

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
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Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1125
Watch the sun set and the moon rise off the coast of Key West on this 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. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
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  • 2 hours
  • Free Cancellation
From
$89.95
From
$89.95

Key West Historic Seaport Food Tasting and Cultural Walking Tour
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Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
253
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West 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, and group size is limited to 10 people to ensure personal service from your guide.
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  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1229
Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.
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  • 3 hours
  • Free Cancellation
From
$49.81
From
$49.81

Key West Mangrove Kayak Eco Tour

Key West Mangrove Kayak Eco Tour

star-5
669
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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  • 2 hours
  • Free Cancellation
From
$50.00
From
$50.00

Small-Group Key West Sunset Sail with Wine
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Small-Group Key West Sunset Sail with Wine

star-5
433
Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
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  • 2 hours
  • Free Cancellation
From
$99.95
From
$99.95

Beach Day in Key West with Picnic Lunch

Beach Day in Key West with Picnic Lunch

star-5
30
Visit Fort Zachary Taylor Historic State Park on a tour that introduces you to both the history and natural beauty of Key West. Located on the southwestern tip of the island, the park is a relaxing place to spend a few hours snorkeling, sunbathing, and discovering historical sites. This tour provides an easy way to see more of Key West for those short on time.
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  • 3 to 5 hours
  • Free Cancellation
From
$125.00
From
$125.00

4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West
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4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West

star-4.5
9
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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  • 4 hours
  • Free Cancellation
From
$564.90
per group
From
$564.90
per group

Private Sunset Booze Cruise in Key West

Private Sunset Booze Cruise in Key West

star-1
1
This is the only private guided booze cruise in Key West. We provide you with dockside access to three different watering holes on three different keys in Key West. First stop is at The Geiger Key Marina Restaurant. This is a Tiki bar and restaurant located approx. 5 miles north of the City of Key West. Access is gained through a beautiful mangrove inlet. Second stop is located at The Boat House Bar located on Cow Key Channel in the City of Key West. See the sites while enjoying a cold beverage. The third and final stop is The Hogfish Bar & Grill located in the "Old Florida" fishing village of Stock Island. This is the quintessential locals experience that you don't want to miss. Book it today!
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  • 3 hours
  • Free Cancellation
From
$258.34
Price varies by group size
From
$258.34
Price varies by group size

Private Looe Key Snorkel from Big Pine Key

Private Looe Key Snorkel from Big Pine Key

star-5
349
Discover the Great Florida Reef while visiting the Florida Keys on this private snorkel excursion. Board a private boat and depart from Big Pine Key towards Looe Key, where you can jump in the water and explore the extensive coral reef system. Snorkel alongside your captain and learn about the various species you encounter such as barracuda, parrotfish, and rays.
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  • 3 hours
From
$545.00
per group
From
$545.00
per group

Glass Bottom Boat Island Eco Adventure
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Glass Bottom Boat Island Eco Adventure

star-5
21
Regular boat tours around Key West provide excellent views, but miss the most important view of all: the underwater world beneath the boat. This private glass-bottom boat tour provides the full, 360-degree experience of the waters around Key West. Exclusively for your group, this tour lets you create your own adventure, whether you want to snorkel the reef, explore an offshore island or simply relax on a sandbar.
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  • 3 hours 30 minutes
  • Free Cancellation
From
$645.00
per group
From
$645.00
per group

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

star-5
17
Swap crowded bus tours for a private and personalized tour of Key West on a comfortable, and unique, tiki bike. Your driver will pedal you around the streets of Old Town and the Historic District to top attractions and places that cannot be reached by bus. You'll also be treated to a slice of famous Kermit's Key lime pie.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$224.99
per group
From
$224.99
per group

PRIVATE Welcome to Key West Walking Tour
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PRIVATE Welcome to Key West Walking Tour

star-5
9
This private tour is ideal if you want to see it all in Key West, but are not a fan of crowded group tours. In the company of just your group and a guide, hit the streets and stroll to all the top attractions, including the Southernmost Point and Mallory Square. Best of all, the tour can be customized to your own interests.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$137.50
Price varies by group size
From
$137.50
Price varies by group size

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

4-Hour Private Cruise to a Sand Bar on a Boat in Key West

star-5
9
Getting out on the water is a must-do in Key West, but big boat tours tend to be crowded. Enjoy a personalized, crowd-free experience on this private cruise. Head into the backcountry of the Florida Keys that larger boats can’t access, then anchor at a sandbar where you can swim in the clear water or relax on a floating raft.
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  • 4 hours
  • Free Cancellation
From
$475.00
per group
From
$475.00
per group

Private Florida Keys tour from 7-Mile Bridge to Key Deer and Overseas Highway
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Private Florida Keys tour from 7-Mile Bridge to Key Deer and Overseas Highway

star-5
8
Discover the islands near Key West on this private land-based tour of the Florida Keys. Designed for small groups of up to 12 people, this tour travels along the Overseas Highway, and experience the Seven Mile Bridge, relax on Bahia Honda Beach, and snap photos of endangered Key Deer on Big Pine Key. The guide will offer fun facts and information about the Florida Keys and the islands along the way.
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  • 5 hours
  • Free Cancellation
From
$294.00
Price varies by group size
From
$294.00
Price varies by group size

Road Trip through the Lower Keys Audio Tour

Road Trip through the Lower Keys Audio Tour

star-5
7
Turn your phone or tablet into a local tour guide with this location-aware audio/multimedia tour! CAR RENTAL/DRIVER ARE NOT INCLUDED. There’s so much to see and do in just one-and-a-half hours of driving between Key West and Marathon. Visit the Keys’ most beautiful state park, tan on a secret nude beach, check out a limestone quarry inhabited by American alligators, spot rare Key deer, find the Keys’ best shrimp pizza, and jump off an abandoned bridge into a cool-water canal. You’ll have historic photos, a map linked to your GPS, plus websites and restaurant menus at your fingertips. Soon after booking, you'll receive a confirmation email with login instructions and a coupon code.
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  • 2 to 5 hours
From
$9.99
From
$9.99

Boat Excursion in Florida Keys with Snorkeling Equipment

Boat Excursion in Florida Keys with Snorkeling Equipment

star-5
6
Some big boat tours in the Florida Keys can feel crowded and impersonal. This private tour instead offers a personalized and customizable experience of the Lower Keys. Where you go and what you do is largely up to you, whether it's snorkeling, kayaking, dolphin-watching or simply chilling out on the water.
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  • 4 hours
  • Free Cancellation
From
$600.00
per group
From
$600.00
per group

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
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Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

star-5
6
Go sightseeing along the Overseas Highway on a full-day tour from the island of Key West. 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. Lunch, snacks, entrance fees, and hotel pickup and drop-off are included on this small-group tour with numbers limited to 10 people.
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  • 6 hours
  • Free Cancellation
From
$389.50
Price varies by group size
From
$389.50
Price varies by group size

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