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“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.…”
★★★★★★★★★★
3,559 reviews2 hours (approx.)From $79.00by Sebago Key West
Check Availability →Read our full review →
Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.
★ 4.5“Beautiful weather calm seas. Entertaining & knowledgeable captain & crew. Great experience on board. All equipment needed available & in great condition. Enjoyed hour at reef snorkeling. Bartenders make a great Rum punch & full bar. We will do again when we return to visit…”
★★★★★★★★★★
1,572 reviews3 hours (approx.)From $59.00by Sebago Key West
Check Availability →Read our full review →
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“Friendly, knowledgable staff, excellent wine, plenty of options to drink aside from their wine. Ample amount food”
★★★★★★★★★★
1,366 reviews2 hours (approx.)From $125.00by Danger Charters
Check Availability →Read our full review →
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
★ 4.5“Great time well organized fun way to see sunset… good music with Killer Dudes excellent service very fun”
★★★★★★★★★★
952 reviews2 hours (approx.)From $79.95by Fury Water Adventures
Check Availability →Read our full review →
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“Amazing! Eric and Carlos are incredible hosts. The sunset was incredible! And seeing dolphins was an added bonus.”
★★★★★★★★★★
907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays
Check Availability →Read our full review →
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“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…”
★★★★★★★★★★
804 reviews2 hours (approx.)From $122.59by Classic Harbor Line
Check Availability →Read our full review →
Experience a full day of sailing, snorkeling, and kayaking in Key West with all-inclusive food, drinks, and expert guides. Perfect for active water lovers.
★ 5.0“Great fun! Would do again on next trip. Crew was nice and helpful! Water was clean and perfect temp.”
★★★★★★★★★★
767 reviews6 hours 30 minutes (approx.)From $152.00by Danger Charters
Check Availability →Read our full review →
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“This was the BEST dolphin cruise ever! Well worth the money. Sebago is the bomb!!🤗🥰 Will definitely do this cruise again!”
★★★★★★★★★★
699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West
Check Availability →Read our full review →
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“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…”
★★★★★★★★★★
586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West
Check Availability →Read our full review →
Discover the Key West Reef Snorkel & Sail Adventure, a small-group cruise offering stunning reef views, friendly guides, and great value for memorable water fun.
★ 4.5“This was an awesome snorkeling experience!! The boat was small - about 12 passengers, and the crew, Chuck and Jared, were very friendly, welcoming and helpful! Compared to the mega boats, this was excellent for our first time snorkeling. We had a variety of ages…”
★★★★★★★★★★
540 reviews3 hours (approx.)From $79.00by Floridays
Check Availability →Read our full review →
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
★ 4.5“We had a wonderful time. Mostly we enjoyed the walking tour with Dan. We learn the history and also all of past and present. A few stories also. Great job Dan! The ship’s crew out of their way to serve us and make sure we…”
★★★★★★★★★★
433 reviewsFrom $220.00by Historic Tours Of America - Dry Tortugas
Check Availability →Read our full review →
Experience soaring above Key West’s turquoise waters with a safe, fun parasailing trip—breathtaking views, friendly staff, and photos to remember.
★ 5.0“Great fun for everyone.. very friendly crew. Enjoyed very much!!! Definitely a must do for anyone visiting the Keys.”
★★★★★★★★★★
387 reviews50 minutes (approx.)From $53.70by Fury Water Adventures
Check Availability →Read our full review →
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“I would’ve loved to appetizers. The staff energetic was great. Your out there for 3 hours with nothing to eat”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
Check Availability →Read our full review →
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
★ 4.9“So beautiful to travel on this wooden Schooner!! Brilliant work and excellent crew”
★★★★★★★★★★
318 reviews2 hoursFrom $122by Classic Harbor Line - Key West
Check Availability →Read our full review →
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
★ 4.5“Great cruise. The food is meager so you are not going to make a meal of it. However the drinks were flowing good!!”
★★★★★★★★★★
314 reviews2 hours (approx.)From $72.00by Sunset Watersports
Check Availability →Read our full review →
More Key West Sailing & Catamaran Tours