SUNSET SAILING CRUISES IN KEY WEST

15 Sunset Sailing Cruises in Key West, Best Day First

30 sailings  ·  from $60 a head

The 15 best sunset sailing cruises in Key West you can get aboard today, with what each costs, how long it stays out and who it suits. Number one is first for a reason; start there.

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 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

2.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

3.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

4.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

5.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 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

6.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 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

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

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

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

8.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

9.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

10.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

11.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

12.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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Classic Key West Schooner Sunset Sail with Full Open Bar - Leaving the Historic Seaport
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Classic Key West Schooner Sunset Sail with Full Open Bar

13.Classic Key West Schooner Sunset Sail with Full Open Bar

★★★★★★★★★★5.0 · 213 reviews · 2 hours (approx.)

Sail from Key West’s Historic Seaport aboard a classic schooner for about two hours, with a maximum of 22 people. Captain Joe, Josh, and crew members such as Christina, Michael, Molly, and Vitali have hosted recent trips. Expect cocktails, wine, beer, champagne, soft drinks, water, hors d’oeuvres, and sunset views, with no shore stops.

“We had a great time on the Schooner Sunset Cruise. The three young gentlemen running the show did a phenomenal job on all fronts. I highly recommend this excursion. We will definitely be making this a tradition! Thank you for the memories!!”

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Key West: Sunset Sail with Live Band, Drinks, and Appetizers - What the 65-foot catamaran feels like
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Key West: Sunset Sail with Live Band, Drinks, and Appetizers

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

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

You’ll spend about two hours aboard Fury’s 65-foot Commotion on the Ocean, cruising off Key West as local musicians play. Beer, wine, champagne, margaritas, sodas, lemonade, water, and seasonal appetizers are included. Choose the shaded lounge or open sundeck, and book July 4 for sunset views plus fireworks.

“Nice drinks and great music, just good could be better! Leeet‘s rock 🤟”

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Key West: 2-Hour Sunset Sail with Live Music - What the two hours feel like
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Key West: 2-Hour Sunset Sail with Live Music

15.2-Hour Sunset Sail with Live Music

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

Spend two hours aboard Sebago Watersports’ spacious Marquesa catamaran, sailing past Key West’s Historic Seaport, Mallory Square, and Fort Zachary Taylor. Your captain positions the boat for sunset while live music, unlimited drinks, and passed appetizers keep the evening moving. Premium drinks cost extra, and you should arrive 30 minutes early.

“Really good service and boat trip! Tips were pushed a bit too much, the service was good enough that I think everyone would’ve tipped anyway”

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