KEY WEST SAILING TOURS

15 Key West Sails, Sunset First

52 sailings  ·  from $11 a head

Sunset is an institution here and the schooners are the good way to see it. These 15 are compared on the rig, the bar, the hors d’oeuvres and how far past Mallory Square the boat actually gets.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Fort Zachary Taylor and the open-water turn
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Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

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 an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy 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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Key West Afternoon Snorkel Sail with Unlimited Cocktails! - Snorkeling over shallow coral reef
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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Best value

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies masks, fins, instruction, and safety guidance. Expect roughly 45 to 60 minutes in the water, then beer, wine, soft drinks, and cocktails on the ride home. Captain Brett has led some departures.

“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Setting sail with wine and small plates
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Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

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

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

Spend about two hours sailing from 255 Front Street with a group capped at 26 people. The crew serves up to eight wines, five beers, soft drinks, and easy-to-eat hors d’oeuvres while sharing stories and tending to the boat. Recent sailings have featured crew members including Mary, James, Connor, Lexi, Tony, and Molly.

“Our sunset sail was perfect from start to finish. We absolutely loved the wine tasting and appetizers — you never know what you’re going to get on these types of excursions, and sometimes you brace yourself for cheap wine and sad snacks… but this was the total opposite. The wines were genuinely great bottles, and the cheese apps were delicious and beautifully done. We also adored our all-women crew. They were fun, warm, and made the whole experience feel extra special — the perfect vibe for a girls trip celebrating our 40ths. Would 100% recommend this sail to anyone looking for something elevated, relaxing, and unforgettable.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - A 65-foot catamaran with room to move
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Key West Sunset Sail with Live Music, Drinks and Appetizers

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

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

Spend about two hours aboard Fury’s 65-foot catamaran, with live local musicians, unlimited margaritas, champagne, beer, wine, soda, and seasonal appetizers. You can dance, sit on the sundeck, or watch the sunset from shaded decks. The cruise returns to Greene Street in time for dinner.

“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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Sunset Sail in Key West with Beverages Included - Watching Key West’s Sunset Celebration from offshore
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Sunset Sail in Key West with Beverages Included

5.Sunset Sail in Key West with Beverages Included

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

Sail from the Hyatt Centric Key West Resort aboard Floridays for about 90 minutes, with champagne, wine, margaritas, beer, and soft drinks included. The crew, including Eric, Carlo, Hunter, Chuck, Lori, and Janet on various departures, keeps the mood relaxed while you watch the sunset and the nightly waterfront celebration from the water.

“This is a great cruise. We did not want a loud and loaded up party boat. Instead we wanted a nice and quiet cruise. Our boat was a 54 ft sailboat and we had about a dozen people on the boat (I think it holds twice that). The captain and mate were very nice and informative. Plenty of wine, prosecco and beer on board. If you want a peaceful and pleasurable sunset cruise, this is the one.”

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Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - The marina meeting point and boarding routine
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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

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

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

Board America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail - Sailing through the Key West National Wildlife Refuge
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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

7.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152

Join Danger Charters at Opal Key Resort for a 6.5-hour sail aboard a 65-foot schooner. You’ll snorkel in the Florida Keys National Marine Sanctuary, kayak through mangroves, and explore Key West National Wildlife Refuge. Guides such as Daniel, Brian, Joe, and Captain Janet have helped make the trip friendly, informative, and easygoing.

“We had great experience! The crew was amazing:the capital Evan and his crew was very friendly, helpful and made our trip comfortable and so many ways”

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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Passing Mallory Square and Key West’s western shore
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Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

8.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

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

Sail from Key West’s Historic Seaport on a catamaran with Captain Daniel, John, Jordan, Gracie, and other rotating crew members. Look for wild dolphins, pass Mallory Square, Fort Zachary Taylor, and Sunset Key, then settle in for sunset with wine, champagne, beer, and tapas including shrimp cocktail. Dolphin sightings and sailing under wind are not guaranteed.

“Best couple hours during our entire vacation. Sunset, dolphin, drinks, snacks, romantic,, picture perfect.”

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Key West Reef Snorkel & Sail Adventure - What you may see below the surface
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Key West Reef Snorkel & Sail Adventure

9.Key West Reef Snorkel & Sail Adventure

★★★★★★★★★★4.5 · 540 reviews · 3 hours (approx.) · from $79

Sail from Key West on the 54-foot Floridays, then snorkel a living coral reef with crew guidance and sanitized gear. Captain names vary, with Owen, Chuck, Eric, Alexis, Janet, and others praised for calm, friendly service. Expect roughly 45 minutes in the water, marine life sightings, and included water, soda, wine, and craft beer.

“We had a group of 12 with ages varying from 16 to 63! Everyone enjoyed the sail and snorkel experience! The hosts are helpful, patient, and a ton of fun! Highly recommend this adventure!!”

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Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail - The boat ride to Key West’s living reef
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Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

10.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

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

Sail from 241 Front Street to a reef selected for the day’s sea conditions. Fury provides instruction, mask, fins, flotation gear, and reef-safe sunscreen. After 30 to 40 minutes in the water, enjoy rum punch, beer, wine, sparkling wine, reggae, and a Key West sunset. You must know how to swim.

“The trip was great, but we expected to see more corals and fish. But it’s not connected to the team.”

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Key West: Schooner Sunset Sail with Food & Drinks - Checking in behind Schooner Wharf Bar
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Key West: Schooner Sunset Sail with Food & Drinks

11.Schooner Sunset Sail with Food & Drinks

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

Sail for two hours aboard the America 2.0, a polished wooden schooner with teak decks and 3,600 square feet of canvas. Enjoy drinks and a personal hors d’oeuvres plate while the crew sails past Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Captain Janet is a favorite on many departures.

“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”

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Key West Signature Sunset Sail with Live Music, Open Bar & Food - Live music, from gentle strings to a party mood
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Key West Signature Sunset Sail with Live Music, Open Bar & Food

12.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Board the Sandie Cat at 201 William Street for a two-hour Key West sunset sail with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The three-deck catamaran offers broad sunset views, though the food is snack-sized and the mood can range from calm to lively. Captain Anna has earned praise for her friendly, confident handling of the boat.

“Great drinks and fun crew! We had a great time on the boat and enjoyed the music and the other guests.”

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Key West: Sunset Sailing Trip with Open Bar, Food and Music - The first hour: drinks, snacks, and open water
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Key West: Sunset Sailing Trip with Open Bar, Food and Music

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

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

Set sail from Key West’s historic seaport aboard the three-deck Sandie Cat. You’ll get two hours of sunset views, unlimited basic drinks, light appetizers, and live music, with time to dance or help raise the sails. Captain Matthew and the crew may even let you take a turn at the wheel for a photo.

“This cruise was over the top. The food the drinks the entertainment and the sunset a very memorable trip!”

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Sunset Sail Cruise in Key West - The route from Historic Seaport to open Atlantic
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Sunset Sail Cruise in Key West

14.Sunset Sail Cruise in Key West

★★★★★★★★★★5.0 · 260 reviews · 2 hours (approx.)

Spend about two hours sailing Key West aboard the vintage, red-sailed Schooner Jolly II Rover. Captain Rachel, Captain Harley, Bill, Carl, Jeremy, Simone, Chris, and other crew members have made this a friendly, hands-on trip, with harbor views, sailing tips, light snacks, bottled water, and the chance to see a cannon fired at passing boats.

“Great sunset sail with good food, friendly crew, and an overall wonderful experience! Highly recommend, you will enjoy!”

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Key West Sunset Sail Aboard Legendary Schooner Appledore - Leaving the Historic Seaport on William Street
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Key West Sunset Sail Aboard Legendary Schooner Appledore

15.Key West Sunset Sail Aboard Legendary Schooner Appledore

★★★★★★★★★★5.0 · 251 reviews · 2 hours (approx.)

Spend two hours aboard the Appledore, a globe-circling wooden schooner, sailing from Key West’s Historic Seaport toward Mallory Square and Sunset Key. You can help raise the sails, watch the sun fall over the Gulf, and enjoy beer, wine, champagne, cocktails, soda, and hors d’oeuvres. Arrive early for the boarding pass.

“Wonderful crew and hospitality. Appetizers were wonderful surprise and variety of drinks very good. Loved the Maine connection.”

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