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.
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Featured Sunset Cruises in Key West

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Jun 23 - Jun 29
Captains-Choice-Sunset-Sail-with-Wine-and-Tapas-Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

114 ratings
2.5 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!
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Triple Combo Snorkeling, Dolphin, and Sunset Cruise

76 ratings
3 Hrs.
This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their natural habitat, snorkel at a tropical reef, and last but not least witness the famous Key West sunset! This action-packed, three-for-one adventure is sure to yield magic and memories to last a lifetime. Book now!
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Key West Sunset Dinner Cruise

289 ratings
2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So, get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise. Reserve your spot today!
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Champagne Sunset Catamaran Cruise

100 ratings
1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!
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Land-s-End-Sunset-Sail-with-Hors-d-Oeuvres-by-Sebago-Watersports

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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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 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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Seabreeze Sunset Harbor Cruise with Wine and Beer

18 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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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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Sunset-Snorkel-Sip-and-Sail-Cruise-with-Live-Music-by-Sunset-Watersports

Key West Sunset Snorkel Cruise

60 ratings
3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot 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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Schooner-Champagne-Sunset-Sail

Schooner Champagne Sunset Sail

11 ratings
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline waters 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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Rum-and-Reggae-Sunset-Snorkel-Combo

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 now!
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Barebones-Sandbar-Boat-Rental

Key West Sandbar Boat Charter

1 rating
4 - 8 Hrs.
Hit the water around tropical Key West with this carefree Barebones Sandbar Boat Charter. Experience the sights and sounds of a beautiful area as you enjoy ample and comfortable seating, expert navigation, and so much more! The sky's the limit with this boat rental unlike any other, but be sure to book early so you don't miss out!
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Rum-Runner-Sunset-Downtown-Tour

Rum Runner Sunset Downtown Tour

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1.5 Hrs.
Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheer for every gorgeous sight. Perfect for you and up to 15 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100-year-old shipwreck, and more. You can BYOB or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. So, don't miss the boat! Book your Rum Runner Sunset Downtown Tour now!
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Private Snorkel and Sunset Sail Excursion

1 rating
4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across the water in classic sailboat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.
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Private-Chill-Out-Lily-Pad-Sail-with-Sunset-Sail-Key-West

Private Chill Out Lily-Pad Sail - Up to Six Guests

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.
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Rum-Runner-Bar-Boat-Sunset-Cruise

Rum Runner Bar Boat Sunset Cruise

7 ratings
1.5 Hrs.
Enjoy a sunset cruise on the water on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheers for every gorgeous sight. Perfect for you and up to 5 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100 year old shipwreck, and more. You can BYOB or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. So, don't miss the boat! Book your Rum Runner Bar Boat Sunset Cruise today!
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Private-Sandbar-Experience

Private Sandbar Experience

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2 - 4 Hrs.
There's no better way to spend your day than with this Private Sandbar Experience. Travel the crystal clear water of Key West with family and friends to the backcountry sandbars. Feel the sun and the salty breeze on your skin. Take in the moment and admire the natural beauty this part of Florida has to offer. Your captain knows the best spots to make your experience one to remember. Once at the sandbar, get out in the water to splash and play! Swim, relax on floats, or dive down under the water and snorkel. Make lifelong memories, book this experience now!
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Frequently 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.

Destinations

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