Key West

15 Best Key West Sunset Sails

The sunset sails: champagne decks, live music boats and the old wooden schooners, all facing the same direction at seven. Sunset is a scheduled event in Key West, and the boats beat the Mallory Square crowds to it.

1.Key West Sunset Sail with Full Bar, Live Music and Hors D’oeuvres

Experience a memorable Key West sunset aboard a spacious catamaran with live music, premium drinks, and delicious hors d'oeuvres for a relaxing evening on the water.

Most Popular★ 4.5

“Great time!!! Awesome crew and entertainment!! Snacks were excellent 😊 Drinks, drinks and more drinks! Awesome sunset.”

Check Availability →Read our full review →

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

Experience a relaxing sunset cruise in Key West with dinner, live music, and drinks included. Perfect for romantic evenings or lively gatherings.

★ 4.5

“Captain and all the crew members were great. Bartenders were outstanding. I was invited into the wheelhouse and talked to Capt Mike for almost 20 minutes. Great night overall.”

Check Availability →Read our full review →

4.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.

★ 5.0

“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”

Check Availability →Read our full review →

5.Adults only Sunset Cruise from Key West with Champagne

Experience a romantic adults-only sunset cruise from Key West with champagne, gourmet cheese, and stunning water views—perfect for a relaxed, intimate evening.

★ 5.0

“It's a fun way to enjoy the sunset. They had many selections besides Champagne and the crew was fabulous. I highly recommend this activity. The boat only seats a small group, and it was delightful.”

Check Availability →Read our full review →

6.Key West Sunset Sail with Live Music, Drinks and Appetizers

Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.

★ 4.5

“This cruise was so much fun! The band was phenomenal! The crew worked non-stop serving drinks and making sure there was always plenty of appetizers available.”

Check Availability →Read our full review →

7.Sunset Sail in Key West with Beverages Included

Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.

★ 5.0

“Wear comfortable shoes, it may get chilly in winter weather but a light sweatshirt is plenty to keep warm. The captain and fist Kate are very kind and well informed about sailing and Key West history.”

Check Availability →Read our full review →

8.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

Experience a relaxing sunset sail in Key West aboard a classic schooner with complimentary drinks and hors d'oeuvres. Perfect for a romantic or scenic evening.

★ 5.0

“Great experience! Crew was very attentive and food and drinks hit the spot. Weather was a little iffy but cleared for a spectacular sunset.”

Check Availability →Read our full review →

9.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

Experience a relaxing sunset sail in Key West with dolphin sightings, tapas, and premium wine. A cozy, scenic cruise perfect for nature lovers and foodies alike.

★ 4.5

“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”

Check Availability →Read our full review →

10.Champagne Sunset Catamaran Cruise in Key West

Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.

★ 4.5

“We didn't get to go on this cruise. It got canceled. We got put on a different cruise with appetizers, open bar, and live music. It was fine. But, not what we signed up for. However at least we still got to go on a…”

Check Availability →Read our full review →

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

Experience Key West’s vibrant coral reef from a glass-bottom boat, with options for daytime or sunset cruises, perfect for non-swimmers and reef lovers alike.

★ 4.0

“It was a great experience - have seen something very similar in Puerto Rico during my visit. Wanted to take my family along for a ride and they loved it!”

Check Availability →Read our full review →

12.Key West: Dolphin Watching and Snorkeling Sunset Cruise

Experience dolphin sightings, snorkeling in protected waters, and stunning sunsets on this 3-hour Key West cruise for $72. Perfect for nature lovers and sunset seekers.

★ 4.4

“The trip was amazing! We saw so many dolphins, they even came right up to the boat. The snorkeling was great too, and the crew was super fun and friendly! The sunset was incredible, and we saw dolphins again! Highly recommend! 😍”

Check Availability →Read our full review →

13.Key West: Reef Snorkeling with Drinks and Sunset Option

Experience snorkeling at North America's only living coral reef in Key West, with drinks and sunset options, on a spacious catamaran with friendly crew.

★ 4.4

“Really nice cruise. snorkeling spot wasn't exceptionnal but best in the area. The bar was great, boat was a big catamaran and crew really knew what they were doing.”

Check Availability →Read our full review →

15.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

Experience snorkeling over Key West’s only living coral reef, followed by a sunset sail with reggae music and drinks, all for about $59 per person.

★ 4.5

“Great trip, as advertised. Crew was great, the reef was awesome, saw beautiful 🐠 . We enjoyed chatting with other passengers and ended with a gorgeous sunset.”

Check Availability →Read our full review →

More Key West Sunset Sails

4.9Key West: Schooner Sunset Sail with Food & Drinks2 hours$122 4.5Sunset Sip and Sail Key West with Open Bar and Live Music2 hours (approx.)$72.00 5.0Sunset Sail Cruise in Key West2 hours (approx.)$95.00 5.0Key West Sunset Sail Aboard Legendary Schooner Appledore2 hours (approx.)$89.00 4.5Key West: Sunset Dinner Cruise with Open Bar & Live Music2 hours$92 5.0Classic Key West Schooner Sunset Sail with Full Open Bar2 hours (approx.)$109.00 5.0Key West Sushi Sunset Cruise with Complementary Drinks$75.00 4.7Key West: Sunset Sail with Live Band, Drinks, and Appetizers2 hours - 150 minutes$79 5.0Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar2 hours (approx.)$65.00 5.0Key West Tiki Bar Sunset Cruise (by the seat)2 hours (approx.)$80.58 4.5Key West Sunset Snorkel with Unlimited Draft Beer & Wine3 hours (approx.)$69.95 4.7Key West: 2-Hour Sunset Sail with Live Music2 hours$79 5.0Sunset Sail on Historic Schooner in Key West2 hours (approx.)$109.00 4.2Key West: Glass Bottom Boat Reef Tour with Sunset Option1.8 hours$69 5.02-Hour Sunset Sailing With Wine In Stock Island2 hours (approx.)$125.00 4.5Key West: Dolphin & Reef Snorkel Trip with Sunset Option3 hours$75 4.6Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks3 hours$69 4.5Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat2 hours (approx.)$456.88 5.0Private Sunset Cruise around Key West2 hours (approx.)$400.00 5.0Historic 7-Mile Bridge Sunset Cruise in Marathon1 hour 30 minutes (approx.)$124.99 4.5Private Key West Sunset Sail2 hours (approx.)$695.00 4.5Captain’s Choice: Dolphin Watch Sunset Sail2.5 hours$89 4.5Dolphin Watch + Sunset Sail with Honest Eco3 hours (approx.)$117.17 5.0Reef Snorkel + Sandbar & Sunset Sail-Small Groups with Honest Eco4 hours 30 minutes (approx.)$143.05