Best Boat Tours in Key West: 15 Worth Booking

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 Afternoon Snorkel Sail with Unlimited Cocktails!

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

Sail from Key West’s historic seaport aboard the 69-foot catamaran Marquesa to the Florida Reef. You’ll receive gear and a safety briefing, snorkel in shallow reef water, then enjoy beer, wine, cocktails, and soft drinks on the ride back. Captain Brett and the crew may spot dolphins, fish, turtles, or nurse sharks, but marine life and water clarity vary.

“Too many people and not enough snorkeling. It took an hour to get to the spot,15 minutes to park. Only 45 minutes of snorkeling and they don’t serve drinks until the ride back.”

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4.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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5.Key Largo Coral Reef Glass Bottom Boat Adventure

★★★★★★★★★★4.0 · 1,048 reviews · 2 hours (approx.) · from $45Best value

Board the M. V. Key Largo Princess for a 2-hour cruise from Key Largo to John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary. You’ll have indoor and outdoor seating, a glass viewing area, a restroom, and a guide explaining the reef and its fish. Drinks are sold onboard.

“We stayed at the Holiday Inn Key Largo and the dock was right next to our building. Boarding was easy and the ride was smooth. We saw 2 green sea turtles and a beautiful sunset, but would enjoy more if we could see more fish at the coral reefs.”

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6.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

★★★★★★★★★★5.0 · 954 reviews · 2 hours (approx.) · from $108

Sail from Key West Bight Marina aboard Catamaran Echo for a two-hour adults-only sunset cruise limited to 14 passengers. Your crew serves bottomless Domain Chandon Brut Classic, wine, beer, and a cheese buffet with berries, smoked fish dip, crisps, and fresh bread. Moët and Chandon upgrades are available at wholesale prices.

“It was so well worth it. We had such a a wonderful time. Cannot say enough as to how wonderful the captain and crew were.”

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7.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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8.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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9.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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10.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

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

Spend 6.5 hours aboard a 65-foot schooner with Danger Charters, sailing through Key West National Wildlife Refuge, snorkeling in Florida Keys waters, and kayaking among mangroves. Your crew, which may include guides such as Daniel, Brian, or Captain Joe, provides lunch, snacks, unlimited beer, wine, and soft drinks.

“They were so sweet and very kind. Would love to take a trip with them again when I come back. 10/10 will come again.”

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11.Dolphin Watching and Snorkeling Eco Cruise Tour

★★★★★★★★★★4.6 · 757 reviews · 3 hours · from $79

Join Fury Water Adventures for a three-hour catamaran trip from Key West. You’ll watch for wild bottlenose dolphins, snorkel in shallow refuge waters, and ride back with beer, wine, sodas, or seasonal champagne. Guides such as Lisa, Alli, Nicole, Liv, and Penny have been praised for calm, friendly help, especially with nervous snorkelers.

“Great trip. Informative, friendly, helpful and attentive staff. We thoroughly enjoyed the trip.”

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12.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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13.Key West Champagne Sunset Catamaran Cruise

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

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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14.Key West Glass-Bottom Boat Tour with Sunset Option

★★★★★★★★★★4.0 · 576 reviews · 1 hour 45 minutes to 2 hours (approx.) · from $69

Cruise seven miles from Key West aboard a 65-foot glass-bottom catamaran, spending about 25 to 30 minutes over the Florida Reef. Crew members point out coral, fish, rays, turtles, and other sea life. Choose a daytime sailing or sunset trip with Champagne, and enjoy a shaded cabin, sundeck, restrooms, and snack bar.

“We learned a lot and saw lots of fish. The trip was fun. I didn't get sea sick which is unusual for me.”

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15.Key West Reef Snorkel & Sail Adventure

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

Sail from Hyatt Centric Key West aboard a 54-foot yacht for a roughly three-hour reef trip. The crew provides instruction, sanitized gear, flotation vests, and drinks. Most time is spent sailing, with about 45 minutes snorkeling. Groups can be as small as a few people, though the maximum is 24.

“The captain and deck hand were wonderful! We had a wonderful boat ride and saw a lot of marine life.”

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