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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
1104
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
  • Taking safety measures
From
$89.95
From
$89.95
Taking safety measures

Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
475
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
  • Taking safety measures
From
$73.75
From
$73.75
Taking safety measures

Key West Mangrove Kayak Eco Tour

Key West Mangrove Kayak Eco Tour

star-5
660
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
  • Taking safety measures
From
$50.00
From
$50.00
Taking safety measures

Key West Sunset Dinner Cruise with Tropical Buffet

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
411
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
  • Taking safety measures
From
$88.95
From
$88.95
Taking safety measures

Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
679
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
  • Taking safety measures
From
$45.95
From
$45.95
Taking safety measures

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

star-5
424
Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$124.95
From
$124.95
Taking safety measures

Dry Tortugas National Park Day Trip by Catamaran from Key West
Likely to Sell OutLikely to Sell Out

Dry Tortugas National Park Day Trip by Catamaran from Key West

star-4.5
271
Escape to the secluded islands and tropical beaches off the coast of Key West on this guided, full-day adventure to historic Dry Tortugas National Park. History buffs and outdoor enthusiasts alike will love this unique voyage, where getting there is half the fun on board the Yankee Freedom III, a luxurious, state-of-the-art catamaran. Enjoy snorkeling (equipment provided) in the crystal blue waters and take in the military fort, national park, campground, sandy beaches and coral reefs that make this area special. Breakfast and lunch included.
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  • 10 hours
  • Taking safety measures
From
$190.00
From
$190.00
Taking safety measures

Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
282
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
  • Taking safety measures
From
$38.80
From
$38.80
Taking safety measures

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

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

star-4.5
585
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
  • Taking safety measures
From
$209.95
From
$209.95
Taking safety measures

Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
728
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
  • Taking safety measures
From
$84.27
From
$84.27
Taking safety measures

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
272
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, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$61.46
From
$61.46
Taking safety measures

Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
523
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
  • Taking safety measures
From
$50.35
From
$50.35
Taking safety measures

Key West Parasailing Adventure

Key West Parasailing Adventure

star-5
145
Go parasailing above the emerald waters of Key West for a thrilling 1-hour tour that provides sweeping views of Florida’s southernmost city and its surroundings. Head out in a 12-passenger state-of-the-art parasailing boat out to the ocean, then your guide secures you into a double or triple-person parasailing device for a ride that gently lifts off and glides above the water, all without getting wet.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$85.95
From
$85.95
Taking safety measures

Ultimate Adventure from Key West including Breakfast, Lunch and Drinks

Ultimate Adventure from Key West including Breakfast, Lunch and Drinks

star-4.5
233
Enjoy an amazing day out on the water in Florida’s Key West with this ultimate adventure tour. Spend the day partaking in water sports such as parasailing, jet skiing, and and a ride on a the Banana Boat. You can also go snorkeling, and try to catch sight of angelfish and other brightly colored fish. Sunbathe on the boat’s spacious deck, or just take in the sights of the Key West area. Breakfast, a buffet lunch, and drinks are included with your tour.
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  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$214.95
From
$214.95
Taking safety measures

Small-Group Key West Sunset Sail with Wine
Likely to Sell OutLikely to Sell Out

Small-Group Key West Sunset Sail with Wine

star-5
418
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
  • Taking safety measures
From
$99.95
From
$99.95
Taking safety measures

Key West Dolphin Watch and Snorkel Cruise

Key West Dolphin Watch and Snorkel Cruise

star-4.5
537
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
  • Taking safety measures
From
$75.20
From
$75.20
Taking safety measures

Island Adventure Snorkel Kayak and Tour from Key West

Island Adventure Snorkel Kayak and Tour from Key West

star-4.5
290
Get access to a remote nature sanctuary, known only to Key West locals, during this island adventure. Choose to paddleboard, kayak, snorkel, or just lounge on the sandbar and take in the natural ambiance. Snack, lunch, and use of snorkel equipment included; wine and beer available after activities.
More
  • 4 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$128.95
From
$128.95
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-3.5
220
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$53.70
From
$53.70
Taking safety measures

Key West Snorkel and Sunset Sail: Rum n' Reggae

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4
163
Combine a snorkel session on North America's only living coral reef with a Key West sunset during this catamaran cruise. Listen to lively reggae beats, snorkel using the provided equipment, and watch the sunset with a rum punch in hand.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$56.12
From
$56.12
Taking safety measures

All-Inclusive Water Adventure Excursion in Key West

All-Inclusive Water Adventure Excursion in Key West

star-5
256
Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.
More
  • 6 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$129.00
From
$129.00
Taking safety measures

Key West Living Coral Reef Snorkel Adventure

Key West Living Coral Reef Snorkel Adventure

star-4
282
Explore the only living coral reef in North America during this snorkeling adventure from Key West. Sail aboard a state-of-the-art catamaran as you voyage toward the reef. Receive snorkeling guidance from your knowledgeable crew, making this experience perfect for first-time snorkelers. Use of sanitized snorkel gear and beer, water, and champagne on the morning trip or margaritas on the afternoon trip provided.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$46.92
From
$46.92
Taking safety measures

Key West Jet Ski Tour: Free 2nd Rider

Key West Jet Ski Tour: Free 2nd Rider

star-5
356
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
  • Taking safety measures
From
$173.27
From
$173.27
Taking safety measures

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
532
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
  • Taking safety measures
From
$88.68
From
$88.68
Taking safety measures

2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
Likely to Sell OutLikely to Sell Out

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

star-5
9
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.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$456.88
per group
From
$456.88
per group
Taking safety measures

Filters

What people are saying about Key West

star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"Had the best time. Great staff, good food, music and food. And the view was absolutely beautiful!! I would totally recommend this trip!! Well worth the money."..."
star-5
Key West Sunset Cruise with Live Island Music
"The band and crew were extremely friendly & fun. My sister and I enjoyed the music, breath taking views and wine."..."
star-5
Key West Mangrove Kayak Eco Tour
"We went on the Key West Eco Tour with Peyton as our guide. It was a great experience: out guide made the trip interactive, fun and brought it to life. The water was very calm and the mangrove tunnels were exceptionally peaceful. I would highly recommend this tour to anyone visiting the Keys!!"..."
star-5
Key West Sunset Dinner Cruise with Tropical Buffet
"We had so much fun dancing to the wonderful live reggae music while we watched the beautiful sunset. The food was excellent and there was plenty of it. We loved being welcomed on the boat with a tasty cocktail! The staff were all friendly with smiling faces. Thank you for a great vacation memory."..."
star-5
Key West Florida Reef Half-Day Snorkeling Excursion
"With Captain Nick, TJ, and Jordan. Great time with a great crew. Definitely be back with these guys. Weather was awesome, met new friends."..."
star-5
Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel
"Snorkeling was fun but the water wasn’t as clear as we had hoped. Those who get a clear day are in for a treat. Kayaking was peaceful, fun and they go over lots of history. Both were such a fun experience and the crew was helpful and fun as well"..."
star-5
Dry Tortugas National Park Day Trip by Catamaran from Key West
"This trip was amazing! Fort Jefferson and snorkeling were magnificent! The yankee freedom was clean and comfortable but the staff was even better!! This is a must do/see trip!"..."
star-5
Key West Ghosts and Gravestones Trolley Tour
"Had a great interactive experience. Heard the footsteps in the shipwreck museum which was cool. Ms Rose was very informative and told great stories! Ms Lydia was a great driver and handled those streets like the pro that she is."..."
star-5
Key West Full-Day Power Adventure: Sailing & Watersports Package
"We had a great time! Best part of our trip. Highly recommend! Staff was super nice. Alcohol served was very limited, only drawback. A margarita would have been nice. They only had Landshark beer and red and white wine. Wine is just kind of unfitting for a day playing in the sun."..."
star-5
Shark and Wildlife Viewing Adventure in Key West
"This was such an awesome experience! Knowledgeable, friendly and enjoyable tour guides. Made sure everyone was able to get a good view. Clean boat with plenty of seating, shade, and open sides. Saw sharks, sea turtles and jellyfish! Definitely worth the price. Would go again!"..."
star-5
Sunset Sail in Key West with Beverages Included
"Beautiful scenery and the best captain and mate. Very friendly and excellent service with a smile.👍👍👍"..."
star-5
Key West Hop-On Hop-Off Trolley Tour
"Very good experience. Funny commentary and informative. Easy on and off. Good experienced driver. Polite and informative agents at ticket booth also."..."
star-5
Key West Parasailing Adventure
"This was so much fun! Our crew Alex and Tony were professional, safe and very fun! It is so peaceful up in the air. Nothing to be afraid of. Would definitely do again!"..."
star-5
Ultimate Adventure from Key West including Breakfast, Lunch and Drinks
"Great staff, fun time for all!!!Couples would love this.Gotta do this in Key West, staff takes care of you."..."
star-5
Small-Group Key West Sunset Sail with Wine
"Great service, great food. Crew was super helpful and friendly! Played great music, too. We will definitely do the trip again"..."
star-5
Key West Dolphin Watch and Snorkel Cruise
"We enjoyed seeing many dolphins on our trip! The crew, Capt Nicole and Amanda, were fantastic! Knowledgeable, friendly and fun. Couldn’t have asked for a better day on the water. We’re so glad we did this during our short trip to Key West!!"..."
star-5
Island Adventure Snorkel Kayak and Tour from Key West
"This was a must do trip in Key West. If you are lucky enough to get Rachel on your tour, you hit the jackpot. Such an asset to company. Very informative and super attentive to passengers."..."
star-5
Key West Glass-Bottom Boat Tour with Sunset Option
"Ruth and Grace were very knowledgeable. We were able to talk to Grace for a little bit and she knew everything we asked about the island."..."
star-5
Key West Snorkel and Sunset Sail: Rum n' Reggae
"Great crew, perfect snorkeling location, amazing sunset. We had an amazing time. This was for 20th wedding anniversary and I couldn't want anything more."..."
star-5
All-Inclusive Water Adventure Excursion in Key West
"Crew was outstanding! Very knowledgeable and fun! The sharks and dolphins didn’t disappoint either! Great time, would highly recommend!"..."
star-5
Key West Living Coral Reef Snorkel Adventure
"The crew we went with was absolutely incredible, kind, responsible and fun. The spot we went to was beautiful, plenty of colorful and curious fish to look at. It was the best part of our vacation in the keys!"..."
star-5
Key West Jet Ski Tour: Free 2nd Rider
"Awesome ride with Jake and BJ.. Tour was a blast and they were very patient. Smooth sailing. Highly recommend."..."
star-5
Key West Southernmost Food and Cultural Walking Tour
"We had a great tour with Dana. The food was delicious and she shared interesting pieces of island history. We had Cuban at El Siboney’s, conch fritters at Mangoes, rum punch at the Rum Bar, jerk fish at Kaya Island Eats and key lime pie at Cuban Coffee Queen."..."
star-5
2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
"We all had a great time. We brought our two teenagers with us and our captain had lots of fun stories. He made sure the teenagers had fun by veering off track about and letting them swim on a sandbar near by. Even though the sunset ended up behind clouds, we still all had a wonderful time."..."

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