KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular sunset sails & cruises 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“Sunset was beautiful. Music and food were good. Dancing was fun. Would recommend to a friend. The time of the excursion was perfect.”
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”
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!”
A 2-hour Key West catamaran sunset sail with live music, unlimited drinks, and appetizers—plus views of Mallory Square and more.
“Sunset was amazing. Staff were great and very engaging. Service was great. Lots to eat & drink. It was a beautiful night.”
Key West sunset sail with included drinks. Small-group 90 minutes from Hyatt Centric; champagne, wine, margaritas, craft beer.
“I do not have a rating on this. Unfortunately, our trip was cancelled due to high winds. I can say that the cancelation was done early enough that we could make other plans. Maybe next time.”
Sail on a replica Key West schooner at sunset with open bar and plated hors d’oeuvres, passing Fort Zachary and classic waterfront views.
“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for the great experience!🌞⛵️”
Key West sunset sail with dolphin watching, premium wine, champagne and tapas on a luxury catamaran, small group max 50.
“Wonderful trip! Saw dolphins, beautiful sunsets and great crew! Tapas and beverages to suit all. Highly recommend!”
Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.
“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”
A 3-hour Key West dolphin watching and snorkeling sunset cruise with snorkel gear, draft beer, and possible reef sightings at Cottrell Key.
Snorkel Key West’s living coral reef, then sail into sunset with reggae, rum punch, and free sunscreen on a spacious catamaran.
“Saw many fish, small but beautiful! A group of over 50 fish right in front of me, they were not scared at all. A very exciting experience. Will come back to do it again, but probably not in January again. The water was not cold but it was cold after coming out of water.”
Sail Key West at sunset on the America 2.0 schooner. Drinks and hors d'oeuvres included, wildlife sightings, and a shot at the green flash.
Sail Key West at sunset on a modern 3-deck catamaran with live music, unlimited open bar, and light appetizers for about 2 hours.
“The sunset, the drinks and the music were all great! Snacks were nothing special, but we planned ahead ate dinner. We have done a cruise like this before and it is usually a couple of veggies and maybe rolls or some kind of bite size snack.”
A 2-hour Key West sunset sail on the Sandie Cat with an open bar, finger foods, and live music on the upper deck.
“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”
Sail Key West at sunset on a vintage topsail schooner with red sails, classic sights from the water, plus snacks and bottled water.
“This was the best boat tour we’ve been on down here! The crew was super fun and kept us entertained. Capt Harley, Carl, Jeremy and Simone were very friendly and knowledgeable. Carl set off several cannon shots at other boats after some good natured taunting between us. Gorgeous sunset also! Will do this again when…”
Sail Key West at sunset on a classic wooden schooner with real sail work, small-group calm, and included drinks and hors d’oeuvres.
“Our experience aboard the Schooner Appledore was fantastic! Crew members Joe, Mary, and Christina were AMAZING; they were prepared with stories and anecdotes of their time at sea, and it was so fun to learn about their adventures. Drinks were great, apps were yummy, and they were appropriately careful of my spouse’s shellfish allergy. We…”
Every way to get out on the water, and every reason to stay for the sunset.
