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Key West Tours

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223 results

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Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

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

star-4.5
1808
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
US$79.95
From
US$79.95

Key West Sunset Cruise with Tropical Buffet Dinner

Key West Sunset Cruise with Tropical Buffet Dinner

star-4
772
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
US$88.95
From
US$88.95

Small-Group Key West Sunset Sail with Wine

Small-Group Key West Sunset Sail with Wine

star-5
721
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
US$99.95
From
US$99.95

Shark and Wildlife Viewing Adventure in Key West

Shark and Wildlife Viewing Adventure in Key West

star-5
1231
Get up close with 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 of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
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  • 2 hours
  • Free Cancellation
From
US$89.00
From
US$89.00

Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
1016
Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.
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  • 3 hours
  • Free Cancellation
From
US$45.95
From
US$45.95

Key West Mangrove Kayak Eco Tour

Key West Mangrove Kayak Eco Tour

star-5
1113
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
US$55.00
From
US$55.00

Key West Full-Day Power Adventure: Sailing & Watersports Package

Key West Full-Day Power Adventure: Sailing & Watersports Package

star-4.5
681
Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.
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  • 6 hours
  • Free Cancellation
From
US$189.95
From
US$189.95

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
Likely to Sell OutLikely to Sell Out

Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

star-4.5
254
Limited to an intimate number of passengers, this small-group sunset sail includes an up-close look at dolphins as well as views of Key West landmarks like the legendary Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Then, relax on the luxury catamaran to watch the sunset as nibble on tapas such as shrimp cocktail served with wine and champagne.
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  • 2 hours 30 minutes
  • Free Cancellation
From
US$89.95
From
US$89.95

Key West Dolphin Watch and Snorkel Cruise
Likely to Sell OutLikely to Sell Out

Key West Dolphin Watch and Snorkel Cruise

star-4.5
771
Get ready for fun in the sun on this dolphin watch and snorkeling adventure off the coast of Key West. Cruise away from the island city of Key West and see 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 breeze and select from a variety of refreshing beverages on board the boat.
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  • 3 hours
  • Free Cancellation
From
US$75.20
From
US$75.20

Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
772
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. Select from an unlimited 1- or 2-day pass to suit your schedule.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$50.36
From
US$50.36

Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
590
Discover some of Key West’s deepest, darkest secrets on a 60-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.
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  • 1 hour
  • Free Cancellation
From
US$39.86
From
US$39.86

Key West Jet Ski Tour: Free 2nd Rider

Key West Jet Ski Tour: Free 2nd Rider

star-5
694
Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour jet ski tour. With four 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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  • 1 hour 30 minutes
  • Free Cancellation
From
US$155.95
From
US$155.95

Half-Day Cruise from Key West with Kayaking and Snorkeling
Likely to Sell OutLikely to Sell Out

Half-Day Cruise from Key West with Kayaking and Snorkeling

star-5
973
Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. 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 with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.
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  • 4 hours 30 minutes
  • Free Cancellation
From
US$106.00
From
US$106.00

Florida Keys Reef Snorkel & Sail Adventure
Likely to Sell OutLikely to Sell Out

Florida Keys Reef Snorkel & Sail Adventure

star-5
229
Explore the only living coral reef in North America on this small-group snorkeling adventure aboard a sailing yacht in Key West. You will receive instruction on how to use the equipment, but it’s recommended that participants be comfortable underwater and have the ability to swim. Common sightings include tropical fish, eels, turtles, dolphins, anemones, and urchins.
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  • 3 hours
  • Free Cancellation
From
US$89.00
From
US$89.00

Key West Southernmost Food and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Southernmost Food and Cultural Walking Tour

star-5
857
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
US$88.68
From
US$88.68

Key West Sunset Champagne Catamaran Cruise
Likely to Sell OutLikely to Sell Out

Key West Sunset Champagne Catamaran Cruise

star-4.5
437
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$59.95
From
US$59.95

Sunset Tiki Boat Tour in Key West
Likely to Sell OutLikely to Sell Out

Sunset Tiki Boat Tour in Key West

star-5
66
Key West is famous for its sunsets. Rather than joining the crowds at Mallory Square, you can enjoy a more personal, uncrowded experience on this small-group sunset cruise. Aboard a custom tiki bar boat, you can toast the sunset (byob) while taking in the sights as you cruise around the Key West harbor.
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  • 2 hours
  • Free Cancellation
From
US$80.58
From
US$80.58

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
667
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
More
  • 2 hours
  • Free Cancellation
From
US$90.75
From
US$90.75

Key West Premium Sunset Sail aboard Schooner with Full Bar
Likely to Sell OutLikely to Sell Out

Key West Premium Sunset Sail aboard Schooner with Full Bar

star-5
363
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
More
  • 2 hours
  • Free Cancellation
From
US$99.95
From
US$99.95

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
330
For the aquatic adventure of a lifetime, take this cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy a glass of Champagne as the sun settles into the Gulf of Mexico.
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  • 1 hour 45 minutes to 2 hours
  • Free Cancellation
From
US$64.45
From
US$64.45

Key West Conch Tour Train

Key West Conch Tour Train

star-4.5
377
Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$39.98
From
US$39.98

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

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

star-5
47
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
US$564.90
per group
From
US$564.90
per group

Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West
Likely to Sell OutLikely to Sell Out

Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West

star-4.5
91
Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.
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  • 2 hours
  • Free Cancellation
From
US$74.95
From
US$74.95

Key West Craft Cocktail Crawl
Likely to Sell OutLikely to Sell Out

Key West Craft Cocktail Crawl

star-5
256
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.
More
  • 3 hours
  • Free Cancellation
From
US$93.68
From
US$93.68

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What people are saying about Key West Tours

star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"It was the highlight of our trip we enjoyed the singing and dancing & wonderful food The whole staff was amazing the sunset was awesome And we highly recommend it"..."
star-5
Key West Sunset Cruise with Tropical Buffet Dinner
"The staff was very helpful with my 91 year old mother the atmosphere was fun and the good was good. The live band was a bonus."..."
star-5
Small-Group Key West Sunset Sail with Wine
"A fantastic way to see the sunset. The crew were very friendly and kept the wine flowing. A very relaxed and friendly vibe. I would definitely do it again on our next trip to Key West."..."
star-5
Shark and Wildlife Viewing Adventure in Key West
"A small family operation with a very nice and welcoming crew. The crew was informative about the wildlife and answered any questions you had."..."
star-5
Key West Florida Reef Half-Day Snorkeling Excursion
"We took the afternoon trip on 1.20.23 and we just loved how clear the water was. From the fish to the sea turtle and the staff, it was a wonderful excursion."..."
star-5
Key West Mangrove Kayak Eco Tour
"Great kayak tour of the Mangroves McGill, our guide was great! Pointed out lots of great things Crew at check in was also courteous & patient"..."
star-5
Key West Full-Day Power Adventure: Sailing & Watersports Package
"We had a great time. The water was a little rough the day we went but at the end parasailing made up for it 100%"..."
star-5
Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings
"Great time. Saw lots of dolphins. Beautiful sunset with wine and tapas. Enjoyed all. Very much recommend."..."
star-5
Key West Dolphin Watch and Snorkel Cruise
"Thanks Captain Amanda! Kept us informed, narrated well, knowledgeable about dolphins! Made sure we had fun!"..."
star-5
Key West Hop-On Hop-Off Trolley Tour
"Every driver was very knowledgeable and had a great sense of humor. It was a fantastic way to get around, worry free and easy. The wait was never very long."..."
star-5
Key West Ghosts and Gravestones Trolley Tour
"My daughter was down visiting and my family and I took her on the ghost tour which I have been on several times. But it was so much better than it had been because it wasn’t just me going. I had family there. You had the gentleman on the bus who was the bartender““ that had died at Captain Tony’s. And he made the trip so amazing."..."
star-5
Key West Jet Ski Tour: Free 2nd Rider
"So much fun!! Gavyn did a great job taking us around the island and making sure we were having fun. Saw dolphins, stingray, and a sea turtle. We had so much fun we went a second time after our first tour."..."
star-5
Half-Day Cruise from Key West with Kayaking and Snorkeling
"Cap'n Dan and first mate Olivia were awesome. Small intimate trip...skip the crowds and do this trip"..."
star-5
Florida Keys Reef Snorkel & Sail Adventure
"There’s nothing better than out on the ocean on a beautiful day! With a lovely, attentive, and friendly crew!! 5 Stars!!"..."
star-5
Key West Southernmost Food and Cultural Walking Tour
"Maxwell was the best tour guide! Loved all of the stops and the interesting information he shared with us. Highly recommend!"..."
star-5
Key West Sunset Champagne Catamaran Cruise
"Lovely evening, calm seas, lovely sunset, lots of champagne. The 3 person crew of the Cubed was great!"..."
star-5
Sunset Tiki Boat Tour in Key West
"We had a blast! You can’t ask for a better way to watch the sunset. Nick our boat captain was sensational! Make sure you ask for him when you book~he played the best music! Great experience, would book again!"..."
star-5
Key West Sunset Cruise with Live Island Music
"Excellent customer service, friendly and accommodating staff, great food and drinks!! Beautiful sunset!!"..."
star-5
Key West Premium Sunset Sail aboard Schooner with Full Bar
"Captn Ross, Bradley, and Wade were fantastic hosts! Very attentive and pleasant. Top notch experience with yummy hors d'oeuvres, and a large variety of beverages. Can't say enough good about this wonderful sunset sail!"..."
star-5
Key West Glass-Bottom Boat Tour with Sunset Option
"Excellent tour and history of the Key. Saw lots of fish. Beautiful day to be out on a boat! Would recommend to others."..."
star-5
Key West Conch Tour Train
"We had a great time. It was very interesting learning about the history of the island. Our tour guide, Danilo, was very entertaining and a wealth of knowledge. I would definitely recommend this tour to our friends."..."
star-5
4-Hour Private Sand Bar Cruise on a Tiki Bar Boat in Key West
"Our captain was AWESOME!!!! Got to go boating throughout this beautiful area and around little islands! Loved it! Too windy to go out to all the sandbars which we knew in advance but great time! Will be back ! Nice bar on board to chill out. Smooth ride"..."
star-5
Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West
"Best bar tenders ever! Clean safe and fun! Food was good and kept coming. Musician was lively and entertaining. We would do it again…."..."
star-5
Key West Craft Cocktail Crawl
"I loved all of the different drinks. The history was great to hear and our group was so friendly. We all went to the comedy club after."..."
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