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.
16 results | All Key West Tours

Key West Sunset Cruise with Tropical Buffet Dinner
624
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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From
$88.95
From
$88.95

Key West Sunset Cruise with Live Island Music
619
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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From
$90.75
From
$90.75

Sunset Sail in Key West with Beverages Included
393
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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From
$79.00
From
$79.00

Key West Glass-Bottom Boat Tour with Sunset Option
280
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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From
$64.45
From
$64.45

Small-Group Key West Sunset Sail with Wine
613
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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From
$99.95
From
$99.95

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
1463
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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From
$79.95
From
$79.95

Key West Sunset Champagne Catamaran Cruise
389
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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From
$59.95
From
$59.95

Adults only Champagne Celebration Sunset Cruise from Key West
434
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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From
$81.40
From
$81.40

Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
301
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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From
$99.95
From
$99.95

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar
63
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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From
$65.00
From
$65.00

2-Hour Private Sunset Cruise around Key West
35
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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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
34
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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From
$456.88
per group
From
$456.88
per group

Key West Sunset Sail Aboard Schooner
364
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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From
$111.80
From
$111.80

Sunset Tiki Boat Tour in Key West
30
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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From
$80.58
From
$80.58

Key West Sushi Sunset Cruise
26
Key West is famed for its glorious sunsets but the most popular spots to take them in are usually crowded and noisy. Swap the bustling streets of Key West for the calm of the sea. This sunset cruise lets you see the sun dipping below the horizon while you relax on the deck while enjoying great food and drinks.
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From
$75.00
From
$75.00

Sunset Sail Cruise in Key West
19
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!
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From
$91.38
From
$91.38
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