12 Sunset Cruises in Key West, Ranked by What You Get

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 toward Mallory Square, Fort Zachary Taylor, and Sunset Key. Your ticket includes an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, hors d’oeuvres, and live music from local performers. Bring a photo ID if you plan to drink.

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked. This was a highlight of our time at Key West!!”

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2.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92

Board a 65-foot yacht at Key West’s historic seaport for a two-hour sunset cruise. Enjoy a crew-served tropical buffet, unlimited well drinks, beer, wine, and soft drinks, then head upstairs for sunset views, live music, and a pass by Mallory Square.

“Was cold, but captain made it fun and the drinks were flowing! The SUN came out just in time! Great time.”

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

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

Set sail from 255 Front Street for about two hours with a maximum of 26 passengers. The Danger Charters crew serves up to eight wines, five beers, soft drinks, and small hors d’oeuvres while you watch the Key West sunset. Mary, James, Connor, Tony, and other crew members have been praised for warm service and helpful local stories.

“The crew were helpful and friendly. It was a small group. I highly recommend. It is a mini wine tasting with an amazing view. We met new friends on the boat. Will definitely book again.”

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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 beer, wine, champagne, margaritas, soda, and seasonal appetizers. Sail past Key West views such as Mallory Square and Fort Zachary Taylor State Park, then watch the sunset from three viewing decks. The cruise returns to 631 Greene Street.

“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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5.Sunset Sail in Key West with Beverages Included

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

Spend about 90 minutes aboard Floridays, a 54-foot sailboat limited to 24 passengers. Sail through Key West Harbor, watch the sunset from the water, and enjoy champagne, wine, margaritas, craft beer, and soft drinks. Crew members such as Eric, Carlo, Hunter, Janet, Chuck, and Lori are praised for friendly service and helpful photo tips.

“This sailing was absolutely amazing!!! We sailed with about 20 people and it was wonderful!! The cruise was intimate yet engaging!!”

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

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

Spend about two hours sailing Key West aboard the replica schooner America 2.0. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, sailing tips, and help raising the sails. You’ll pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse while enjoying beer, wine, Champagne, soda, and small plated appetizers.

“We had such a great time and are so glad we did this! The crew was great, the sail unforgettable. So peaceful and beautiful out on the ocean and watching the sails go up and down was really fun!”

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

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

Set out from Key West’s Historic Seaport for a 2.5-hour sunset cruise aboard a luxury catamaran. The crew looks for wild dolphins before serving wine, beer, champagne, and chef-prepared bites such as shrimp cocktail, smoked fish dip, caprese skewers, and key lime pie. You’ll pass Mallory Square, Fort Zachary Taylor, and Sunset Key, with guides such as Captain Daniel, John, Jordan, and Gracie helping set the mood.

“Wonderful trip! Saw dolphins, beautiful sunsets and great crew! Tapas and beverages to suit all. Highly recommend!”

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8.Key West Champagne Sunset Catamaran Cruise

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

Sail from Key West Historic Harbor on a 90-minute catamaran cruise timed for sunset. Sip champagne, wine, beer, sangria, margaritas, soft drinks, or water while watching the island from offshore. The crew shares the best sunset viewpoints, and you may spot birds, fish, dolphins, or other marine life.

“This was an awesome cruise! The crew were attentive and very polite. The view was incredible and the food was great! Not dinner but light appetizers. A must do for any Key West visit!”

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9.Dolphin Watching and Snorkeling Sunset Cruise

★★★★★★★★★★4.4 · 493 reviews · 3 hours · from $79

Join the Sunset One for a three-hour Key West cruise with an English-speaking guide, wild dolphin watching, snorkeling near Cottrell Key, and a sunset sail back to the dock. The crew, including guides such as Kevin, Kylie, Madison, and John on different departures, provides gear, safety help, and a draft beer.

“Great crew, we were lucky not even to see the dolphins but also to swim nearby”

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10.Key Largo Sunset Cruise

★★★★★★★★★★5.0 · 469 reviews · 1 hour 30 minutes (approx.) · from $60

Cruise Florida Bay and Blackwater Sound from Key Largo for 90 minutes of sunset views, wildlife spotting, and lively local commentary. Captains and guides such as Jeff, Katie, Bobby, and Scuba Joe share stories about the Keys and ecosystem. Water is provided, and you may bring your own food, drinks, or cooler.

“Scuba Joe and Captain Steve were the best!!!! Treated us so good top tier experience!!! It was our honeymoon and my wife’s birthday and they made it super special. She said it was the best part of her day!”

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11.Key West Signature Sunset Cruise with Open Bar, Food & Music

★★★★★★★★★★4.5 · 418 reviews · 2 hours · from $79

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You’ll get an open bar with rum runners, Champagne, margaritas, and draft beer, plus light appetizers and live music. The crew may invite you to help raise the sails or pose at the helm.

“It was fun, we had live music, light appetizers, libations ( you paid a small feel for the better quality). The view was awesome and we would definitely recommend.”

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

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

Join Fury Water Adventures at 241 Front St. for a three-hour Key West catamaran trip to the living coral reef. The crew provides instruction, flotation gear, fins, masks, snorkels, and reef-safe sunscreen. After 30 to 40 minutes in the water, enjoy rum punch, beer, wine, sparkling wine, reggae music, and a seasonal sunset sail back to the marina.

“The crew were all super! Had a blast snorkeling. Very friendly and knowledgeable staff. The rum punch was excellent. We had a storm come out so we were not able to do sunset cruise.”

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