KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular cruises & boat tours in Key West. What each trip costs, how long it runs, and who takes you out.
Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.
Most Popular“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.”
Key West sunset dinner cruise with a tropical buffet, unlimited drinks, and live music on a 65-foot yacht. See sunset from the water.
“It was a great ride out and back. Captain did an awesome job. Food was good but we didn't care for the music. Sunset was amazing”
Sail the 69-foot Marquesa to the Florida Reef for easy snorkeling, unlimited drinks after swimming, and the chance to spot dolphins.
“Very rude staff.. 10 mins of snorkeling in 30 feet water. They were in big rush.. just roamed around in the water to kill time. Very rude staff. Very bad experience. Over crowded too.”
Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.
“What an amazing experience! The wine was plentiful, the snacks were delicious, and the view of the water and sunset were unbeatable. Mary, James, and Connor were professional and friendly. All around absolutely worth doing this!”
Adults-only Key West sunset cruise on a small Echo catamaran with champagne-inspired drinks, gourmet cheeses, and Moët upgrades available.
“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!”
A 2-hour Key West catamaran sunset sail with live music, unlimited drinks, and appetizers—plus views of Mallory Square and more.
“Great trip!! Well organized, and a perfect amount of time with a beautiful sunset!’ we decided last minute to do it, and it all worked out perfectly”
Key West sunset sail with included drinks. Small-group 90 minutes from Hyatt Centric; champagne, wine, margaritas, craft beer.
“Amazing! Eric and Carlos are incredible hosts. The sunset was incredible! And seeing dolphins was an added bonus.”
Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.
“Captain Janet along with her crew of Heather, Jade, and Milo we're so friendly and accommodating and efficient. Good snacks, nice wine, and a beautiful sail into the sunset.”
A full-day Key West sailing, snorkeling, and kayaking trip to the wildlife refuge, with lunch and unlimited drinks included.
“Captain kid rock, James and Kylie did AMAZING!! It was so fun. Super knowledgible and friendly!! Cannot say enough great things. BOOK THIS TRIP!!”
Key West sunset sail with dolphin watching, premium wine, champagne and tapas on a luxury catamaran, small group max 50.
“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”
Key West dolphin cruise with included snorkeling gear and drinks on a 45-foot catamaran, plus sunset timing options.
“Our guides Lisa & Ivy were so friendly and informative, with great energy throughout the trip. We saw lots of dolphins and the snorkelling was a nice addition to other dolphin trips I’ve been on before. Would recommend to everyone!”
Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.
“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to the 2 hour sail with live music and hors d’oeuvres.…”
Glass-bottom boat over Key West’s living coral reef, with narrated marine life and optional sunset champagne cruise. Air-conditioned comfort.
“Fun to see the reef. The guide was very informative. We walked through the inside and out to the back and had a great view. When you get to the reef, sit in the side the interpreter is speaking from so when things are pointed out you can see it. We got lucky and saw…”
Small-group sail and snorkel from Key West’s only living coral reef. Sanitized gear and drinks included. About 3 hours.
“This trip was a 10/10!! It was peaceful, relaxing and also very fun and exciting!! We saw dolphins, sea turtles and felt very safe and supported while snorkeling. Which is optional of course!! The boat ride was dreamy. The captain was calm, capable, and kind, as was the first mate!”
A 3-hour Key West dolphin watching and snorkeling sunset cruise with snorkel gear, draft beer, and possible reef sightings at Cottrell Key.
Every way to get out on the water, and every reason to stay for the sunset.
