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Top Key West Cruises & Sailing

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45 results | All Key West Tours

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

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

star-5
866
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
$69.95
From
$69.95
Taking safety measures

Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

star-5
170
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$103.20
From
$103.20
Taking safety measures

Key West Sunset Champagne Catamaran Cruise

Key West Sunset Champagne Catamaran Cruise

star-4.5
280
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
  • Taking safety measures
From
$49.95
From
$49.95
Taking safety measures

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Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
328
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$69.82
From
$69.82
Taking safety measures

Small-Group Key West Sunset Sail with Wine

Small-Group Key West Sunset Sail with Wine

star-5
280
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
$91.38
From
$91.38
Taking safety measures

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
121
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 Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar

star-5
182
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.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$79.95
From
$79.95
Taking safety measures

Key West Sunset Dinner Cruise with Tropical Buffet

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
222
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
$67.65
From
$67.65
Taking safety measures

Key West Day Sail Aboard Schooner

Key West Day Sail Aboard Schooner

star-5
55
Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$60.20
From
$60.20
Taking safety measures

Key West Sunset and Cocktail Cruise

Key West Sunset and Cocktail Cruise

star-5
29
After a long day of work or sightseeing, treat yourself to a relaxing 2-hour sunset cruise in Key West. Climb aboard the 47-foot catamaran and set sail along the scenic Floridian coast as the sun sinks into the water. Enjoy unlimited South Florida craft beer, California wine, and hand-crafted cocktails for the duration of the tour. A selection of fresh bread and spreads are also provided.
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  • 2 hours
  • Free Cancellation
From
$60.00
From
$60.00

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

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

star-4.5
26
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
  • Taking safety measures
From
$57.50
From
$57.50
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
167
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$49.77
From
$49.77
Taking safety measures

Adults only Champagne Celebration Sunset Cruise from Key West

Adults only Champagne Celebration Sunset Cruise from Key West

star-5
266
Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. 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
  • Taking safety measures
From
$81.40
From
$81.40
Taking safety measures

Shark and Wildlife Viewing Adventure in Key West

Shark and Wildlife Viewing Adventure in Key West

star-5
474
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

2-Hour Private Sunset Cruise around Key West

2-Hour Private Sunset Cruise around Key West

star-5
16
This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter. Feel free to bring food or beverages of your choice. Price is $375 TOTAL and includes up to 6 people. Looking forward to seeing you on the dock!
More
  • 2 hours
  • Free Cancellation
From
$200.00
Price varies by group size
From
$200.00
Price varies by group size

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

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

star-4.5
31
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West. As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures. With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset. A chef’s selection of Tapas including shrimp cocktail and tuna poke are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$79.95
From
$79.95
Taking safety measures

Key West Snorkel and Sunset Sail: Rum n' Reggae

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4
118
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
$49.34
From
$49.34
Taking safety measures

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

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

star-5
38
Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.
More
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$57.50
From
$57.50
Taking safety measures

Luxury Sailing Catamaran - Private and Group Charters

Luxury Sailing Catamaran - Private and Group Charters

star-5
8
While there are a number of catamarans to chose from in Key West, Bimini charters is unique in that we offer private and public charters. Our private charters hold up to 10 people, and we limit our public charters to 6 people, so you can have a comfortable and safe sail distanced from others, or with just your friends and family, with much room to spread out. This is a very different experience from other charters where they jam over 20 people in the boat with you. We also allow you to bring your own food and cocktails on the boat to create your own perfect experience. You can rent the entire boat out for a 1/2 day (3 hour) or full day (6 hour) sail to host family and friends on a private charter, or choose a 2-hr public sail for a shorter trip. The S/V Liberty is a luxurious 44-ft cat, offering 5 different seating areas, so you can spread out and savor the coastline as we sail by. Enjoy a romantic sunset cruise, host a cocktail party, all aboard this luxurious yacht.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$125.00
From
$125.00
Taking safety measures

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

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

star-5
366
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

Private Sunset Boat Charter Key West

Private Sunset Boat Charter Key West

star-4
4
Enjoy a private 2 hour sunset cruise in Key West with your family and friends. Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter while you take in the gorgeous sunsets that Key West celebrates nightly. Feel free to bring food or beverages of your choice, the cooler is full of ice. Looking forward to seeing you on the dock!
More
  • 2 hours
  • Free Cancellation
From
$208.34
Price varies by group size
From
$208.34
Price varies by group size

Key West Dolphin Watch and Snorkel Cruise

Key West Dolphin Watch and Snorkel Cruise

star-4.5
393
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
$68.00
From
$68.00
Taking safety measures

Key West Wild Dolphin Sail and Shallow-Water Snorkel

Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
157
Take a half-day sailing adventure off the coast of Key West, Florida and observe wildlife. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
More
  • 4 hours
  • Taking safety measures
From
$97.91
From
$97.91
Taking safety measures

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

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

star-4.5
2
Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Our boats feature a large thatch roof for shade, bluetooth tv and stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure. Keep your eyes on the horizon for a chance to see the famous Green Flash as the sun goes down.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$456.88
per group
From
$456.88
per group
Taking safety measures

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