15 Sunset Sailing Cruises in Key West Worth Booking

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Sail from Key West for about two hours aboard a spacious catamaran with sunset views, live local music, an open bar, shrimp, antipasti, mini tarts, and soft drinks. Arrive 30 minutes early, claim a good bow seat, and bring a sweater for breezy evenings.

“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”

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2.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Top rated

Board Danger Charters at 255 Front Street for a two-hour sunset sail limited to 26 people. Crew members such as Mary, Connor, Lexi, Tony, and Molly have served wines, beer, small bites, stories, and blankets while the boat heads offshore for sunset.

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

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3.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Board Fury’s 65-foot catamaran at Greene and Elizabeth Streets for two hours of live cover music, unlimited margaritas, beer, wine, Champagne, and seasonal appetizers. Sail past Mallory Square and possibly Fort Zachary Taylor while the crew picks the best route for sunset. Arrive early for seating.

“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our last night in town.”

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4.Sunset Sail in Key West with Beverages Included

★★★★★★★★★★5.0 · 907 reviews · 1 hour 30 minutes (approx.) · from $79

Board Floridays at Hyatt Centric Key West for a relaxed 90-minute sail with up to 24 people. Eric, Carlo, Hunter, Janet, Chuck, Lori, and other crew members may handle the evening. Enjoy champagne, wine, margaritas, beer, and soft drinks while watching the sunset and Sunset Celebration from the water.

“There are bigger boats and longer trips and options out there for dinner cruises, etc. But we just wanted a nice 90 minute trek around the port with a small number of people on a sailboat. The bar service was a bonus to me. Captain Chuck and Lori were great hosts and were glad to let people drive the boat, take pictures of us and play tunes. We had very good weather and wind so we sailed most of the trip which is much better that motoring around IMO.”

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5.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122

Spend two hours sailing Key West aboard the replica schooner America 2.0. Captain Janet, Captain Rae, or Captain Dan may lead the trip, with crew serving plated hors d’oeuvres, beer, wine, Champagne, and soda while you pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse.

“Fun and good information! Fun to learn how the boat worked! The the Keys are beautiful and the water was great.”

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6.Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Set out from Key West Historic Seaport for a 2.5-hour catamaran cruise with dolphin watching, wine, beer, champagne, and chef-selected tapas. Expect views of Mallory Square, Fort Zachary Taylor, and Sunset Key. Crew members such as Captain Daniel, John, Gracie, Jordan, and Brandon have been praised for friendly service, though dolphin sightings depend on nature.

“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”

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7.Key West Champagne Sunset Catamaran Cruise

★★★★★★★★★★4.5 · 586 reviews · 1 hour 30 minutes (approx.) · from $59Best value

Sail from Key West’s Historic Harbor for about 90 minutes aboard a spacious catamaran. Enjoy included champagne, wine, beer, sangria, soft drinks, and water while the captain points out sunset views, marine life, Mallory Square, and Fort Zachary Taylor. Bring a light jacket, camera, and photo ID if you drink.

“activity for a mid-sized bachelorette party: captain and crew were awesome, boat was gorgeous, bottomless cocktails, and the perfect length of time on board. event was a hit for the group and the peak of the trip!”

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8.Reef Snorkel Adventure and Sunset Sail

★★★★★★★★★★4.5 · 370 reviews · 3 hours (approx.) · from $59

Join Fury Water Adventures from 241 Front Street for a three-hour Key West catamaran outing with Captain Ron and crew. Learn to snorkel over the living coral reef, then relax with rum punch, beer, wine, sparkling wine, reggae, and a sunset at sea.

“I would’ve loved to appetizers. The staff energetic was great. Your out there for 3 hours with nothing to eat”

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9.Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Board the America 2.0 behind Schooner Wharf Bar for a two-hour sunset sail with Captain Janet or another experienced captain. Enjoy drinks, a personal plate of hors d’oeuvres, open-water views, and possible sightings of dolphins, turtles, and the Green Flash.

“everything the captain and crew the boat is beautiful the food and drinks are great and the scenery beautiful well worth every penny 😀”

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10.Sunset Sailing Trip with Open Bar, Food and Music

★★★★★★★★★★4.5 · 310 reviews · from $80

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat. You get two hours of open-bar drinks, light appetizers, live music, and a clear sunset view offshore. The crew may let you help raise the sails or pose at the wheel. Bring your driver’s license.

“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”

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11.Sunset Sail with Live Band, Drinks, and Appetizers

★★★★★★★★★★4.7 · 171 reviews · 2 hours - 150 minutes · from $79

Board Fury’s 65-foot Commotion on the Ocean for about two hours of sunset views, live local music, open beer, wine, champagne, margaritas, and light appetizers. Choose the sundeck or shaded lounge, but plan ahead if you get seasick or need dietary accommodations.

“Staff was not only friendly they were safety conscious The band was very good the busy was clean. Food was good. This was our second time on this cruise. Would def recommend”

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12.2-Hour Sunset Sail with Live Music

★★★★★★★★★★4.7 · 130 reviews · 2 hours · from $79

Spend two hours aboard Sebago Watersports’ catamaran, sailing past Key West’s Historic Seaport, Mallory Square, and Fort Zachary Taylor. Enjoy live music, unlimited drinks and appetizers, and open-water sunset views. Meet at Lazy Way Lane 30 minutes before departure.

“Had an amazing time, weather was not the greatest but the crew and music kept the adventure fun and engaging!! Food was excellent, whoever Maria is, god bless her!!”

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13.Dolphin Watch Sunset Sail

★★★★★★★★★★4.5 · 34 reviews · 2h 30m · from $89

Spend 150 minutes aboard a small Sebago catamaran, tracking dolphins off Key West before settling in for sunset. Your captain points out Mallory Square, Sunset Key, and Fort Zachary Taylor. Unlimited wine, champagne, sangria, soft drinks, shrimp cocktail, tuna poke, and tapas are included.

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14.Windjammer Champagne Sunset Sail

★★★★★★★★★★5.0 · 18 reviews · 2 hours · from $89

Spend two hours aboard the two-masted Appledore II, helping raise the sails before cruising past Key West landmarks and settling in for sunset. Champagne, wine, sangria, beer, spirits, soft drinks, and water are included. Captain Pedro and the English-speaking crew add sailing tips and local context.

“Beautiful sunset sail. The crew were extremely friendly and shared tons of information about the ship and gave us an unforgettable experience!”

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15.Key West Wind and Wine Sunset Sail aboard classic Schooner

★★★★★★★★★★5.0 · 16 reviews · 2 hours · from $133

Spend two hours aboard a historic Key West schooner as the crew hoists the sails and the sun drops over the water. Sip eight wines, five beers, soda, and bottled water while enjoying charcuterie, fruit, vegetables, crackers, and chocolate. Depart from Opal Key Resort and Marina in Old Town.

“Loved it all. very fun, knowledgeable, and skilled crew. Would go back every evening if I could.”

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