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22 results | All Key West Tours

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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
1153
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

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
313
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
From
$61.46
From
$61.46

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
435
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
From
$124.95
From
$124.95

Key West Sunset Champagne Catamaran Cruise
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Key West Sunset Champagne Catamaran Cruise

star-4.5
335
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
$51.95
From
$51.95

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

star-5
461
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

Florida Keys Afternoon Reef Snorkel & Sail Adventure
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Florida Keys Afternoon Reef Snorkel & Sail Adventure

star-5
90
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
$79.00
From
$79.00

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out

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

star-5
241
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
From
$99.95
From
$99.95

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

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

star-4.5
593
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
$209.95
From
$209.95

Key West Snorkel and Sunset Sail: Rum n' Reggae

Key West Snorkel and Sunset Sail: Rum n' Reggae

star-4
169
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.
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  • 3 hours
  • Free Cancellation
From
$56.12
From
$56.12

Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak

Key West Schooner Backcountry Eco-Tour: Sail, Snorkel & Kayak

star-4.5
102
Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes breakfast, lunch, and access to an open bar on the return sail to Key West.
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  • 5 hours
  • Free Cancellation
From
$119.95
From
$119.95

Key West Wild Dolphin Sail and Shallow-Water Snorkel
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Key West Wild Dolphin Sail and Shallow-Water Snorkel

star-4.5
214
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.
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  • 4 hours
From
$97.91
From
$97.91

Morning Reef Snorkel & Sail Adventure from Key West
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Morning Reef Snorkel & Sail Adventure from Key West

star-5
46
Sail to a gorgeous snorkeling spot off the coast of Key West to explore a coral reef home to rainbow-colored fish, anemones, eels, and more. On the hour-long sailing trip to the reef, sip included wine, beer, or soft drinks while watching for dolphins and sea turtles. The captain chooses the snorkeling spot according to each day’s conditions, ensuring the best experience for your group.
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  • 3 hours
  • Free Cancellation
From
$79.00
From
$79.00

Adults only Champagne Celebration Sunset Cruise from Key West
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Adults only Champagne Celebration Sunset Cruise from Key West

star-5
376
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
From
$81.40
From
$81.40

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

star-4.5
89
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
$79.95
From
$79.95

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
43
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
$74.95
From
$74.95

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-4.5
55
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.
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  • 3 hours
  • Free Cancellation
From
$74.95
From
$74.95

Key West Private Morning Sail on Schooner America 2.0
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Key West Private Morning Sail on Schooner America 2.0

star-5
2
Getting out on the water is key when traveling in the Keys. But many sailing trips can feel crowded and impersonal. This private tour, however, lets you enjoy the experience of having your very own yacht, without the hard work. As the crew work, you can simply lay back and enjoy the views and cool breeze.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$1,032.00
per group
From
$1,032.00
per group

Key West Sunset Sail Aboard Schooner
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Key West Sunset Sail Aboard Schooner

star-5
249
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
From
$103.20
From
$103.20

Schooner Key West Day and Sunset Cruises with Full Bar
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Schooner Key West Day and Sunset Cruises with Full Bar

star-4.5
116
Set sail on the schooner Appledore for a scenic cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail.. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.
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  • 2 hours
  • Free Cancellation
From
$44.95
From
$44.95

Key West Day Sail Aboard Schooner
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Key West Day Sail Aboard Schooner

star-5
74
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
From
$60.20
From
$60.20

Private 2-Hour Wind and Wine Sunset Sail in Key West
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Private 2-Hour Wind and Wine Sunset Sail in Key West

star-4.5
19
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There will be hors d'oeuvres passed around throughout the trip. A great way to have a private sail with your friends, family, or co-workers.
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  • 2 hours
From
$2,299.00
per group
From
$2,299.00
per group

3-Hour Private Catamaran Sunset Sail of Key West with 1 Activity

3-Hour Private Catamaran Sunset Sail of Key West with 1 Activity

star-4
4
Combine a private, sunset sailing tour along Key West’s picturesque coastline with one activity of your choice: snorkeling, paddleboarding, fishing, or kayaking. Excursions can accommodate up to six people, making it an ideal option for families or friends. Snacks and refreshments are included, and you can bring alcoholic drinks to enjoy as you cruise.
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  • 3 hours
  • Free Cancellation
From
$799.00
per group
From
$799.00
per group

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