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Top Key West Sunset Cruises

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After a long day soaking up the Florida sun, there’s nothing quite like relaxing on a sunset cruise off the shores of Key West. From a casual sightseeing cruise to a private Champagne toast for two, here are your options.

Sightseeing Cruises
As the sun begins to sink, sail past Mallory Square, Sunset Pier, and Sand Key Tower Lighthouse on a sunset cruise departing from the Historic Seaport. During an evening sail, families looking for a kid-friendly sunset cruise can head out on a glass-bottom catamaran to gaze down at the marine life inhabiting North America’s only living coral barrier reef.

Cocktail Cruises
Key West is a town that knows how to party, and no cruise would be complete without a drink in hand. Set sail on a catamaran while sipping a glass of Champagne, cruise into the sunset while sampling wines from around the world, or dance to Key West island beats on a party cruise, complete with unlimited drinks.

Dinner Cruises
Enjoy an island-style dinner with stunning views of the Key West coast on a dinner cruise aboard a yacht. Many tours include a buffet dinner, as well as a cash bar serving draft beer, wine, and cocktails. Often there’s live music on deck after dinner.
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14 results | All Key West Tours

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Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

star-4.5
492
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
From
$73.75
From
$73.75

Sunset Sail in Key West with Beverages Included

Sunset Sail in Key West with Beverages Included

star-5
287
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 Sunset Dinner Cruise with Tropical Buffet

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
430
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

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
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

Key West Sunset and Cocktail Cruise with Open Bar

Key West Sunset and Cocktail Cruise with Open Bar

star-5
52
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
From
$75.00
From
$75.00

Key West Glass-Bottom Boat Tour with Sunset Option

Key West Glass-Bottom Boat Tour with Sunset Option

star-3.5
221
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
From
$53.70
From
$53.70

2-Hour Private Sunset Cruise around Key West
Likely to Sell OutLikely to Sell Out

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

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
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

Skip the Line: Mel Fisher Maritime Museum Admission Ticket and Audio Tour

Skip the Line: Mel Fisher Maritime Museum Admission Ticket and Audio Tour

star-4.5
11
Naval history buffs and aspiring pirates alike are guaranteed to have a whale of a time at the Mel Fisher Maritime Museum. Your admission also includes an audio guide, which offers in depth commentary on the museum’s many artifacts. Highlights include the Spanish Treasure Galleons galleries, Slave Ship and Key West African Cemetery exhibits, and relics from the Henrietta Marie. You can even tour the museum's laboratory and see conservation firsthand.
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  • 1 to 4 hours
  • Free Cancellation
From
$19.50
From
$19.50

Mel Fisher Maritime Museum Admission Ticket

Mel Fisher Maritime Museum Admission Ticket

star-4
54
Relive the life of one of history’s most famous treasure hunters along with a wealth of exhibits on shipwreck archaeology with this admission to the Mel Fisher Maritime Museum. This Key West institution showcases a variety of treasures, both cultural and monetary, recovered from the treasure and slave ships that once plied the waters near the Florida coast. Check out the thought-provoking Slave Ship and Key West African Cemetery exhibits, then gaze in wonder at the magnificent gold, silver and jewels of the Spanish Treasure Galleons galleries.
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  • 1 to 2 hours
  • Free Cancellation
From
$17.50
From
$17.50

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
41
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

Double-Dip: Two Stop Snorkel Adventure in Key West

Double-Dip: Two Stop Snorkel Adventure in Key West

star-5
29
Take advantage of Key West’s paradisiacal scenery, and get up close and personal with its coral reefs and aquatic attractions, on this multi-stop snorkeling trip. Pick between daytime and sunset tour times (available seasonally), and hop aboard a speedy catamaran. Then, following professional instruction on board, grab your gear and snorkel around two different reef locations where you can see marine life before relaxing with beer and wine.
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  • 3 hours
  • Free Cancellation
From
$61.22
From
$61.22

Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

star-5
239
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

Sunset Tiki Boat Tour in Key West

Sunset Tiki Boat Tour in Key West

star-5
10
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
$80.57
From
$80.57

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