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Top Key West Sunset Cruises

Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

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Experience your destination with peace of mind. Learn what steps operators are taking to keep you safe and search for activities with increased health and safety measures. Before you go, check local regulations for the latest information.

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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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24 Key West Sunset Cruises | All Key West Tours

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Schooner Key West Day and Sunset Cruises with Full BarSailing

Schooner Key West Day and Sunset Cruises with Full Bar

star-4.5
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
  • Taking safety measures
From
$38.95
From
$38.95
Taking safety measures

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

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

star-5
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
$75.95
From
$75.95
Taking safety measures

Key West Sunset and Cocktail CruiseCity Packages

Key West Sunset and Cocktail Cruise

star-5
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

Key West Sunset Sail Aboard SchoonerDay Cruises

Key West Sunset Sail Aboard Schooner

star-5
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
$81.70
From
$81.70
Taking safety measures

Key West Sunset Cruise with Live Island MusicDay Cruises

Key West Sunset Cruise with Live Island Music

star-4.5
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
$58.72
From
$58.72
Taking safety measures

Key West Sunset Champagne Catamaran CruiseCity Packages

Key West Sunset Champagne Catamaran Cruise

star-5
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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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

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

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

star-5
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 60-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
$63.00
From
$63.00
Taking safety measures

Key West Sunset Dinner Cruise with Tropical BuffetCity Packages

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
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

Small-Group Key West Sunset Sail with WineDay Cruises

Small-Group Key West Sunset Sail with Wine

star-5
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 Day Cruises

Sunset Sail in Key West with Beverages Included

star-5
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 Snorkel Sail with Open Bar, Live Music, and Appetizers Sailing

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

star-5
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
  • Taking safety measures
From
$56.19
From
$56.19
Taking safety measures

Key West Sunset Sail with Premium Wine, Champagne and Tapas PairingsDay Cruises

Key West Sunset Sail with Premium Wine, Champagne and Tapas Pairings

star-5
Our Captain’s Choice Sunset Sail is limited to an intimate number of passengers for an awesome experience! It’s more like a private cruise than a tour and is one of the top things to do in Key West. A chef’s selection of Tapas is served during the sail, prepared fresh daily by Sebago’s own catering kitchen. Delectable shrimp cocktail and tuna poke are Sebago’s signature dishes. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour! As the sun sinks lower, your captain carefully positions the boat to capture a perfect view of the fiery sky. As we leave behind the Historic Seaport, look for Key West landmarks like Mallory Square’s Sunset Celebration with its jugglers, opulent Sunset Key and the historic Fort Zachary Taylor. On reaching open water, the sails are unfurled to provide you with an authentic sailing experience. A sunset cruise Key West style with Sebago will forever linger in your memories.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
From
$79.00
Taking safety measures

Key West Glass-Bottom Boat Tour with Sunset OptionDay Cruises

Key West Glass-Bottom Boat Tour with Sunset Option

star-4
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 Champagne and soft drinks 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

Champagne Celebration Sunset Cruise from Key WestWine Tasting

Champagne Celebration Sunset Cruise from Key West

star-5
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
$79.49
From
$79.49
Taking safety measures

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

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

star-5
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
$56.19
From
$56.19
Taking safety measures

Key West Snorkel and Sunset Sail: Rum n' ReggaeSnorkeling

Key West Snorkel and Sunset Sail: Rum n' Reggae

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

2-Hour Private Sunset Cruise around Key WestCity Packages

2-Hour Private Sunset Cruise around Key West

star-5
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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  • 2 hours
  • Free Cancellation
From
$400.00
From
$400.00

Private Key West Sunset SailDay Cruises

Private Key West Sunset Sail

star-4.5
Watch the sun set and the moon rise off the coast of Key West on this private, 2-hour sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a private sailing vessel with a captain and mate. Stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset. Soft drinks are included. A cooler with ice is available to store any beverages brought on board.
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  • 2 hours
  • Free Cancellation
From
$479.99
per group
From
$479.99
per group

Sunset Sail from Key WestCity Packages

Sunset Sail from Key West

star-5
Watch the sunset from the water on your own boat in Key West during a 2-hour private evening sailing tour. With a captain at the helm, you'll glide along the coast of the island with your group of friends or family (up to six guests total), enjoying the views and watching for birds and other sea life. Light refreshments are provided.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$85.00
From
$85.00
Taking safety measures

Key West Sunset Sail on Traditional SchoonerSailing

Key West Sunset Sail on Traditional Schooner

star-5
The Tall Ship Schooner Jolly II Rover offers an exciting, traditional sailing experience - with a hint of Piracy! Yes - there are cannons! You will actually be sailing on the most photographed ship in Key West! The Rover is a replica of an early 1800's American Coastal Schooner. It is the only square rigged, topsail, gaff rigged schooner in the Historic Seaport of Key West. It will actually take you back in time! Key Wests famous "Red Sails in the Sunset" schooner has plenty of room to move around and let you walk the decks! You can even help raise the sails and steer the ship! Or just simply sit back and relax. The Rover is the first legally sanctioned U.S, sailing vessel allowed to enter Havana Harbor in over 50 years!
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  • 2 hours
  • Free Cancellation
From
$65.00
From
$65.00

Private Sunset Boat Charter Key WestCity Packages

Private Sunset Boat Charter Key West

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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  • 2 hours
  • Free Cancellation
From
$400.00
per group
From
$400.00
per group

Key West Sunset Booze Cruise with Unlimited Draft Beer and WineCity Packages

Key West Sunset Booze Cruise with Unlimited Draft Beer and Wine

star-4
Celebrate the sunset in Key West with this cruise aboard a 65-foot (20-meter) custom-built Gold Coast yacht. Passengers can enjoy the air-conditioned main cabin or opt for outdoor seating on the upper deck. Live music and complimentary draft beer, wine, Champagne, and soft drinks accompany the setting sun.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.87
From
$45.87
Taking safety measures

Private Afternoon Snorkel with Sunset Sail in Key WestSailing

Private Afternoon Snorkel with Sunset Sail in Key West

star-5
Watch the sun set off the coast of Key West on this private, 4-hour snorkeling cruise. Enjoy the scenery and peaceful calm of a late afternoon sail. Pass some of Key West’s top attractions, then dive into the water to see more than 600 species of colorful fish, coral and other sea life. Then watch a legendary Key West sunset as the sun glistens off and gently settles into the water. This cruise includes a gourmet cheese platter with a variety of light refreshments to sample along the way.
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  • 4 hours
  • Free Cancellation
From
$723.96
per group
From
$723.96
per group

Sunset Sail on Historic Schooner in Key WestSailing

Sunset Sail on Historic Schooner in Key West

star-4.5
Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant When And If!, built for General Patton in the late 1930s. Cruise around the Florida coast with the boat’s crew looking after you the whole time, providing a complimentary cheeseboard and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.
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  • 2 hours
  • Free Cancellation
From
$89.48
From
$89.48

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