Key West Sunset Cruises
Enjoy an evening you won’t soon forget while onboard a sunset cruise in Key West. These cruises offer a magical experience that is ideal for families, couples, and groups alike. As you cruise the waterways, keep your eyes open for dolphins and other ocean creatures. Not only will you see a beautiful sunset with your loved ones by your side, but you will also see popular landmarks such as Fort Zachary Taylor and Sunset Key. With spectacular sunsets, a tranquil atmosphere, and beautiful sites, Key West sunset cruises make for the perfect evening on the water that everyone in your group is sure to enjoy.
Featured Sunset Cruises in Key West
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Dec 25 - Dec 31
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Private Trip
Swim Friendly
Cruise Only
Restroom
Captain Included
1-6 passenger
21-40 passenger
75+ passenger
Half Day Trip (if duration 3-6 hour)
All Day Trip (if duration 7-12 hour)
Kid Friendly
Water Toys Available
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
Hourly Rental
Southernmost Sunset Sail with Bar and Hors d’Oeuvres
211 ratings
2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
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Key West Sunset Dinner Cruise
289 ratings
2 Hrs.
Enjoy a memorable evening on the water with the Key West Sunset Dinner Cruise. Savor a fresh, tropical-inspired dinner, including roast pork with Cuban bread and fried plantains, all prepared onboard. Relax with drinks from the fully stocked bar and take in the stunning sunset views. The friendly crew ensures a comfortable experience, with indoor seating in a climate-controlled cabin. This is the perfect way to dine, drink, and dance while making unforgettable memories. Reserve your spot today for an unforgettable Key West sunset experience!
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Live Music Sunset Cruise with Cocktails Included
85 ratings
2 Hrs.
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!
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Wind and Wine Sunset Sail
71 ratings
2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!
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Key West Sunset Sail on America 2.0
45 ratings
2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!
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Sunset Sip and Sail with Open Bar and Live Music
53 ratings
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!
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Seabreeze Sunset Harbor Cruise with Wine and Beer
19 ratings
2 Hrs.
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!
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Schooner Champagne Sunset Sail
11 ratings
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!
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Sunset Sail Aboard the Historic When and If
20 ratings
2 Hrs.
Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea. Book your Sunset Sail today!
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Sunset Snorkel & Sail with Rum & Reggae Included
8 ratings
3 Hrs.
Leave the land behind for an evening of snorkeling and Reggae music on this Sunset Snorkel & Sail with Rum & Reggae included. The rhythmic sounds of Reggae fuse brilliantly with the vitality of your surroundings as you sail to North America’s only living reef. Scope out the brightly colored tropical fish and corals on an underwater snorkel exploration excursion before eventually heading back to the boat to enjoy some tasty tropical rum drinks. This trip includes many exciting activities all in one trip, so embark on the Rum & Reggae Sunset Snorkel & Sail today.
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Windjammer Champagne Sunset Sail
1 rating
2 Hrs.
Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this cruise. Book today!
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2 Hour Sunset Tiki Boat Cruise
5 ratings
2 Hrs.
If you are looking for a way to float away the day, then this Sunset Cruise on a Tiki Bar Boat is the right choice for you. Key West is famous for its glorious sunsets and this tiki cruise does not disappoint. This custom 20 foot tiki bar catamaran features a private bathroom, Bluetooth stereo, and flatscreen TV. Toast the sunset with your closest companions and favorite libation while experiencing the gorgeous scenery, cotton candy skies, turquoise water, and pure relaxation on this Sunset Cruise on a Tiki Bar Boat. Book today!
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Key West Sunset Sail on Schooner Jolly II Rover
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2 Hrs.
End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover. Witness the beauty of Key West, Florida as you admire the sunset from the decks of a schooner. Watch for Florida wildlife, dolphins, turtles, flying fish, pelicans, and more as you coast through the ocean. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic sailing experience. Enjoy an exciting sailing experience and take in the amazing views. Book your tickets today!
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Private Chill Out Lily-Pad Sail
2 ratings
3 Hrs.
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.
Read moreFrequently Asked Questions
1. Can you watch the sunset in Key West from a boat?
Yes, sunset cruises and sunset sailing are a great way to enjoy the sunset in Key West, FL. There are also snorkeling trips that you can take and enjoy the sunset.
2. What other ways can you enjoy the sunset in Key West, FL?
You can stroll to the Southernmost point. You can rent a bike and ride to Mallory Square. You can rent a hydrobike and view it on the water!
3. What is a peaceful way to enjoy the sunset in Key West, FL?
A sunset sail is one of the most peaceful ways to enjoy the sunset on the water. It's quiet and natural.
4. Where are some places to view the sunset in Key West, FL?
The Mallory Square Sunset Celebration happens nightly and is alot of fun! Anywhere with a view of the water makes the sunset enjoyable.