15 Boat Tours in Key West 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

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.”

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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 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.”

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3.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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

Board the 69-foot catamaran Marquesa at Key West’s seaport for a three-hour sail to the Florida Reef. The crew supplies gear, safety guidance, and snorkeling tips. After you leave the water, enjoy included beer, wine, soft drinks, and open-bar cocktails on the return trip.

“The boat is nice. The snorkel experience is meh…. There are definitely much better options outside of Florida. You should know that drinks are limited for the first half and open up to more options after the snorkel. The crew was fine other than the begging for tips. I was fully prepared to tip via Venmo as I did not have any cash until the one crew member started saying “ouch” to anyone not throwing cash in the jar. That type of entitlement is a real turnoff.”

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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

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.”

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5.Key Largo Coral Reef Glass Bottom Boat Adventure

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

Set out from Key Largo aboard the M. V. Key Largo Princess for a two-hour glass-bottom boat trip to John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary. Enjoy indoor or outdoor seating, a full-service bar, reef commentary, and views of fish, coral, turtles, and other sea life without getting wet.

“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

Board Catamaran Echo at Key West Bight Marina for a two-hour adults-only sunset sail. With only 14 seats, you get calm water views, bottomless Domain Chandon Brut, premium wines, beer, smoked fish dip, cheeses, berries, and fresh bread. Moët Imperial and Rosé Imperial are available at wholesale prices.

“This was such a wonderful experience. Having a small group made it even more special. The sunset was beautiful. The captain and crew were knowledgeable and hospitable. If you’re wondering if you should book this trip- you definitely should!”

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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 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”

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8.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!”

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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 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…”

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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 sailing from Key West to the National Wildlife Refuge and Florida Keys sanctuary. Snorkel, kayak through mangroves, swim, and eat a buffet lunch with unlimited beer, wine, and soft drinks. Guides such as Daniel, Joe, Brian, and James add local history and ecology.

“Great Day! The crew Tony, Anthony & Conner were personable and ensured that everything worked without a hitch. Felt taken care of the entire day. Highly recommend this tour!!”

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11.Dolphin Watching and Snorkeling Eco Cruise Tour

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

Cruise from Captain's Corner on Fury's 45-foot power catamaran to watch wild bottlenose dolphins, snorkel in Key West's backcountry, and enjoy drinks on the ride home. Guides such as Lisa, Ivy, Nicole, and Liv are praised for calm instruction and friendly care. Sunset departures add champagne and evening views.

“The excursion was fanaminal our tour guides where fantastic. We got to see dolphins. We saw plenty of fish and a few lobster's while snorkeling. The tour provides plenty of beverages for all. My girl's had a blast we will definitely do it again the next time we return to the key's.”

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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

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.”

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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 aboard a spacious catamaran for 90 minutes of sunset views, open drinks, and easygoing island scenery. The crew points out prime viewing spots, and you may see birds, fish, dolphins, or other marine life. Bring a light jacket for the cooler ride home.

“It was amazing. Beautiful sunset we had and awesome 👌 time. Beautiful views. It was the best experience in key west the highlight of out vacation.”

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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

Ride a 65-foot glass-bottom catamaran seven miles from Key West to the Florida Reef. Crew members point out coral and marine life during about 25 minutes over the reef. Choose a daytime trip or a seasonal sunset cruise with champagne, air conditioning, restrooms, and a 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

Join Floridays aboard a 54-foot sailing yacht from the Hyatt Centric Key West for about three hours on the water. You’ll receive sanitized gear, safety instruction, flotation support, and drinks. Expect roughly 45 minutes snorkeling, with guides such as Captain Owen, Chuck, Jared, or Hunter helping guests of mixed abilities.

“Great crew. Very attentive and had lots of knowledge. It was pretty rough when we went out, but we still managed to see nurse shark, rays, and an abundance of fish.”

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