Key West

15 Best Key West Sunset Sails

Every boat in Key West claims the best sunset, so I sorted out the sails that deliver. Most depart 90 minutes to two hours before sundown from the Historic Seaport. Champagne cruises and quiet catamarans both made the list.

1.Key West Sunset Sail With Full Bar, Live Music & Hors Doeuvres

Experience the magic of a Key West sunset sail with a full bar, live music, and delicious hors d'oeuvres. Don't miss out on this unforgettable evening at sea!

Most Popular★ 4.5

“Super fun. Great crew and snacks. The musician played a little too much rap and no islandy music, but that being said still a great time!”

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3.Small-Group Key West Sunset Sail With Wine

Experience the ultimate Key West sunset sail with wine. Escape the crowds and enjoy a small-group adventure, sipping wine while taking in breathtaking views. Book now!

★ 5.0

“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”

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4.Adults Only Champagne Celebration Sunset Cruise From Key West

Experience an unforgettable adults-only sunset cruise in Key West, complete with champagne and celebration. Set sail on this luxurious adventure and make memories that will last a lifetime.

★ 5.0

“Have a good time and meet new friends. Staff and crew were helpful and kept your glasses full. Beautiful night”

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5.Key West Sunset Cruise With Live Music, Drinks and Appetizers

Experience the magic of a Key West sunset cruise featuring live music, refreshing drinks, and mouthwatering appetizers. Unwind, indulge, and create unforgettable memories. Book your ultimate sunset adventure now!

★ 4.5

“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”

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6.Sunset Sail in Key West With Beverages Included

Experience the beauty of a sunset sail in Key West, complete with refreshing beverages. Don't miss out on this unforgettable adventure. Book your spot now!

★ 5.0

“After days with chilly wind, we were able to book an evening sunset cruise for our last evening in Key West. Eric and Carlo took great care of all passengers. They were friendly, informative, and focused on safety for all. The 90 minutes on the…”

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7.Key West: Schooner America Sunset Sail With Bar & Hors Doeuvres

Experience the breathtaking beauty of Key West at sunset aboard the Schooner America. Sip on cocktails, indulge in delicious hors d'oeuvres, and make memories that will last a lifetime.

“Skies were a bit cloudy, but Capt Janet and crew sail the ship to the best sunset viewing spot as possible. Even had a few dolphins off the bow. What I enjoyed the most was the interaction with the crew ex: asking for volunteers to…”

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8.Key West Dolphin Watch Sunset Sail With Premium Wine, and Tapas Pairings

Experience the magic of Key West's dolphins while sipping premium wine and indulging in mouthwatering tapas. Join us for an unforgettable sunset sail like no other.

★ 4.5

“No guarantee of dolphins. We didn't see any. Boat was nice. The captain was a little "short" with some of the guests. He didn't want to tell any facts or history that didn't match his "script".”

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9.Key West Sunset Champagne Catamaran Cruise

Experience the ultimate luxury on a Key West Sunset Champagne Catamaran Cruise. Sip champagne, soak in stunning views, and create unforgettable memories. Book your adventure now!

★ 4.5

“Had a wonderful time on this sunset cruise. Loved that they limit amount of people so wasn’t crowded at all.”

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11.Key West: Dolphin Watching, Snorkeling, and Sunset Cruise

Lose yourself in the magical world of Key West as you embark on a journey filled with dolphins, snorkeling, and breathtaking sunsets.

★ 4.4

“I really loved how nice and inclusive everyone were even though I did not want to swim they still made sure I was comfortable and made sure my friends in the water were comfortable and safe as well Ron Sprinkles and Captain Maddison are the…”

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12.Key West Snorkel and Sunset Sail: Rum N Reggae

Discover the ultimate tropical adventure! Dive into crystal-clear waters, soak up the sun, and groove to reggae beats on a Key West Snorkel and Sunset Sail: Rum N Reggae tour.

“If it is to rough out there, you can get a full refund if you don’t want to go last minute before boarding. The rum punch was delicious the whole ride was an amazing experience. Just be mindful if you haven’t done research that this…”

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14.Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West

Experience the magic of Key West's stunning sunsets while sipping on cocktails, dancing to live music, and indulging in delicious appetizers. Don't miss out on this unforgettable sunset sail!

★ 4.5

“Fun live music and a sunset sail. The captain, crew, and live musician were great. Open bar and light snacks were provided”

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15.Key West: Sunset Sailing Trip With Open Bar, Food and Music

Immerse yourself in the magic of Key West's sunset sailing trip with a secret ingredient that transforms the ordinary into something extraordinary...

★ 4.5

“Fun activity and value for the price. The crew was outstanding from check in to completion. There is plenty of drinks and a nice selection of lite snacks. Live entertainment on board was a great addition to a nice evening.”

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5.0Sunset Sail Cruise in Key West2 hours (approx.)$95.00 5.0Key West Sunset Sail Aboard Legendary Schooner Appledore2 hours (approx.)$89.00 4.5Key West: Sunset Cruise With Buffet Dinner and Open Bar2 hours$92 5.0Classic Key West Schooner Sunset Sail With Full Open Bar2 hours (approx.)$109.00 5.0Key West Sushi Sunset Cruise With Complementary Drinks$75.00 5.0Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar2 hours (approx.)$65.00 4.7Key West: Sunset Party Cruise by Catamaran$80 4.5Key West Sunset Snorkel With Unlimited Draft Beer & Wine3 hours (approx.)$69.95 4.7Key West: 2-Hour Sunset Sail With Live Music2 hours$79 5.0Sunset Sail on Historic Schooner in Key West2 hours (approx.)$109.00 5.02-Hour Sunset Sailing With Wine In Stock Island2 hours (approx.)$125.00 5.0Private 2-Hour Wind and Wine Sunset Sail in Key West$4,000.00 4.52-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West2 hours (approx.)$456.88 5.0Private Sunset Cruise Around Key West2 hours (approx.)$400.00 5.0Tropical Sunset Cruise From Hawks Cay1 hour 30 minutes (approx.)$124.99 4.5Private Key West Sunset Sail2 hours (approx.)$695.00 4.7Key West: Sunset Snorkel Cruise With Draft Beer & Wine$70 4.5Captains Choice: Dolphin Watch Sunset Sail2.5 hours$89 4.5Sunset Sail & Dolphin Search With Honest Eco3 hours (approx.)$117.17 5.0Reef Snorkel & Sunset Sail With Honest Eco4 hours 30 minutes (approx.)$143.05 5.0Private Boat Tour to Sand Bar Snorkel Dolphins and Sunset3 hours 30 minutes (approx.)$600.00 5.0Key West: Windjammer Champagne Sunset Sail2 hours$89 4.0Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!2 to 3 hours (approx.)$139.00 5.0Key West Wind and Wine Sunset Sail Aboard Classic Schooner2 hours$133