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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Key West Sunset Cruise with Live Island Music
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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From
$69.82
From
$69.82
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
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Key West Sunset Sail Aboard Schooner
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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From
$103.20
From
$103.20
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More

Key West Sunset Dinner Cruise with Tropical Buffet
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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From
$67.65
From
$67.65
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Learn More

Key West Glass-Bottom Boat Tour with Sunset Option
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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From
$49.77
From
$49.77
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More

Small-Group Key West Sunset Sail with Wine
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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From
$91.38
From
$91.38
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
Transportation vehicles regularly sanitized
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Sunset Sail in Key West with Beverages Included
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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From
$61.46
From
$61.46
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Learn More

Key West Sunset and Cocktail Cruise
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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From
$60.00
From
$60.00

2-Hour Private Sunset Cruise around Key West
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!
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From
$200.00
Price varies by group size
From
$200.00
Price varies by group size

Private Sunset Boat Charter Key West
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!
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From
$208.34
Price varies by group size
From
$208.34
Price varies by group size

2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West
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.
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From
$456.88
per group
From
$456.88
per group
Face masks required for travelers in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More

Private Sunset Cruise Featuring Duck Key
Duck Key is known for having some of the bluest water in the Keys and we operate the only Sunset Cruise from the beautiful tropical island of Duck Key. Your US Coast Guard licensed captains have over 50 years combined commercial excursion experience in the Keys and look forward to sharing our paradise with you! We hold ourselves to a high standard and run a quality operation. With your enjoyment in mind, the private boats are clean, comfortable offering multiple seating options, and maintained regularly.
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From
$345.00
per group
From
$345.00
per group
Hand sanitizer available to travelers and staff
Social distancing enforced throughout experience
Regularly sanitized high-traffic areas
Learn More
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