7 Dinner and Sunset Cruises in Key West to Build a Day Around

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 aboard Sebago’s spacious Key West catamaran, passing Mallory Square, Fort Zachary Taylor, and Sunset Key as daylight fades. Enjoy champagne, wine, sangria, premium beer, cocktails, soft drinks, shrimp, small bites, and live music from local performers. Arrive 30 minutes early at 205 Elizabeth Street.

“Sunset was beautiful. Music and food were good. Dancing was fun. Would recommend to a friend. The time of the excursion was perfect.”

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

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

Set out from Key West’s historic seaport aboard a 65-foot yacht for a tropical buffet, unlimited well drinks, beer, wine, and soft drinks. You’ll pass Mallory Square and the Florida Keys National Marine Sanctuary, then head upstairs for sunset and live music. Arrive 60 minutes early, and bring a light jacket for the open deck.

“Love it and it's candid experience!!! We didn't have experience the sunset but the majestic sights are awesome. The dancing bonding was fun. I love the music that was played by the dj. The crews are awesome especially the captain and the dj.”

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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

Meet the Danger Charters crew at 255 Front St, then spend about two hours sailing Key West waters with up to 26 passengers. You’ll taste as many as eight wines, sample beer and soft drinks, and enjoy small bites such as cheese, fruit, and skewers while crew members including Mary, Connor, Lexi, Tony, and Molly may share stories and handle the pours.

“This was such a wonderful experience! We are eloping in Key West and opted to do this sunset sail with family in lieu of a traditional rehearsal dinner. It was so so enjoyable. The staff was so friendly, attentive and warm. One of them serving wine even memorized everyone’s name aboard. The nibbles were so perfect for a boat experience and easy to eat as well as a great wine selection + beer options, sodas and waters. We would absolutely book this again. I highly recommend Danger Charters and will use them the next trip down here!”

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4.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 631 Greene Street for a two-hour sunset sail with live local musicians, unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. Choose the sundeck or shaded lounge, watch the sun set near Mallory Square and Fort Zachary Taylor, and return to the dock in time for dinner.

“You will have a great time on this sunset cruise. The band was great and played all our favorite songs. People were happy and dancing. Seeing the Christmas lights from the water was a wonderful experience!”

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5.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 Historic Seaport for a 2.5-hour catamaran cruise past Mallory Square, Fort Zachary Taylor, and Sunset Key. You’ll look for wild dolphins, then settle in with wine, beer, champagne, and small plates including shrimp cocktail. Crew members such as Captain Daniel, John, Gracie, Jordan, and Brandon are praised for warm service.

“Very enjoyable sailing and ocean experience with personalized service and attention to detail on behalf of captain & assistant”

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6.Dolphin Watching and Snorkeling Sunset Cruise

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

Spend three hours aboard Sunset One searching for wild dolphins, snorkeling near Cottrell Key in the Key West National Wildlife Refuge, and watching the sunset from the water. English-speaking guides such as Kevin, Kylie, Madison, and John explain the wildlife and keep an eye on swimmers. Snorkel gear, safety equipment, and draft beer are included.

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

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7.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 have unlimited basic drinks, appetizers, live music, and room to dance on the upper deck. The crew may let you help raise the sails or pose at the helm. Bring your driver’s license and arrange your own transport.

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

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