The 11 Sunset Cruises in Key West That Earn Their Price

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

Spend about two hours sailing from Key West with local musicians, a full liquor bar, champagne, wine, sangria, beer, soft drinks, and hearty hors d’oeuvres. You’ll pass Mallory Square, Fort Zachary Taylor, and Sunset Key before returning to the harbor.

“The staff was excellent as well as the entertainment! They made sure you had a great time and the appetizers were perfect. The captain was skilled and made sure everyone was safe and comfortable.”

Check availability →Read our full review

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 with crew-served Caribbean buffet, unlimited well drinks, beer, wine, soft drinks, and live music. You’ll pass Mallory Square and the Florida Keys National Marine Sanctuary before returning to the harbor.

“Was very relaxing. If you wanted to be alone by yourself, you could. if you wanted to party with others you could. Good mix.”

Check availability →Read our full review

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

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

Sail from 255 Front Street for about two hours with a maximum of 26 people. The crew serves up to eight wines, five beers, soft drinks, and small plates while sharing stories and helping you enjoy the sunset.

“It was wonderful. At first your like where are we going to sit but they have it all figured out. It was perfect.”

Check availability →Read our full review

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

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

Spend two hours aboard Fury’s 65-foot catamaran with live local music, unlimited beer, wine, champagne, margaritas, soda, and seasonal appetizers. Sail past Mallory Square and possibly Fort Zachary Taylor as the sun sets. Arrive 45 minutes early, bring photo ID, and expect a lively, family-friendly party boat.

“Great time well organized fun way to see sunset… good music with Killer Dudes excellent service very fun”

Check availability →Read our full review

5.Sunset Sail in Key West with Beverages Included

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

Board the Floridays at Hyatt Centric Key West for a 90-minute sunset sail limited to 24 people. Crew members such as Eric, Carlo, Hunter, and Janet serve champagne, wine, beer, margaritas, and soft drinks while you cruise Key West Harbor and watch the sunset celebration from the water.

“It was absolutely wonderful! The crew was amazing, the boat was beautiful and the views were incredible!”

Check availability →Read our full review

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

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

Spend about two hours aboard America 2.0, a replica of the 1851 Schooner America. From Key West Bight Marina, sail past Fort Zachary, Sunset Pier, Mallory Square, and Sand Key Lighthouse while the crew serves plated hors d'oeuvres, beer, wine, Champagne, and soda.

“We went out on a cool day with a low cloud bank, so not a great sunset… but they can’t control the weather! The staff did a nice job keeping everything moving smoothly and distributing the hors d’oeuvres, which consisted of vegetable plate with wrench dip, shrimp with cocktail sauce, cheese, and crackers, and a brownie bite for dessert. They had a good offering of different wines and beers and sodas. Sadly, we did not see any wildlife to speak of except birds. It was fun to visit with the people around us, of which there were a lot! It was impressive to see the crew of Milo, Mary, Dan…”

Check availability →Read our full review

7.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, Captain Dan, Jordan, Gracie, and other attentive crew members. Look for wild dolphins, pass Mallory Square, Sunset Key, and Fort Zachary Taylor, then enjoy wine, champagne, beer, shrimp cocktail, and small bites at sunset.

“The captain and mate were a great match in making sure that we had a great time. Drinks, food and sights were top notch.”

Check availability →Read our full review

8.Dolphin Watching and Snorkeling Sunset Cruise

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

Cruise aboard Sunset One with an English-speaking guide, look for wild dolphins, snorkel near Cottrell Key, and watch the sun set over turquoise water. The crew, including guides such as Kevin, Kylie, Madison, and John, helps swimmers of different experience levels feel at ease.

“It was a wonderful experience. Not only did we get to see a lot of dolphins, but also learn about them. All in all a very fun experience.”

Check availability →Read our full review

9.Key Largo Sunset Cruise

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

Set out from 103800 Overseas Hwy at 6:00 pm for a 90-minute cruise across Florida Bay and Blackwater Sound. Captains and guides such as Jeff, Katie, Scuba Joe, and Bobby share local facts, play music, and watch for dolphins, birds, and sunset color. Water is provided, and you may bring food and drinks.

“It was a peaceful sunset trip with right amount of fun. The atmosphere was great and the sunset was beautiful. I recommend it for anyone.”

Check availability →Read our full review

10.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 two hours of sunset views, an open bar, light appetizers, and live music. You can help raise the sails and ask the crew for a photo at the helm. Captain Matthew and crew have earned praise for their friendly service.

“great... would have been better with more people though”

Check availability →Read our full review

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

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

Set out from 241 Front Street with Fury Water Adventures for a reef snorkel at a site chosen by the captain, followed by rum punch, beer, wine, sparkling wine, reggae, and a Key West sunset. Captain Ron and the crew provide instruction, gear, flotation devices, and reef-safe sunscreen.

“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.”

Check availability →Read our full review