Key West
Every boat in Key West claims the best sunset, so I sorted out the sails that deliver. Most depart 90 minutes to two hours before sundown from the Historic Seaport. Champagne cruises and quiet catamarans both made the list.
Experience the magic of a Key West sunset sail with a full bar, live music, and delicious hors d'oeuvres. Don't miss out on this unforgettable evening at sea!
Most Popular★ 4.5“Great time!!! Awesome crew and entertainment!! Snacks were excellent 😊 Drinks, drinks and more drinks! Awesome sunset.”
★★★★★★★★★★
3,559 reviews2 hours (approx.)From $79.00by Sebago Key West
Experience a breathtaking Key West sunset on a dinner cruise! Indulge in a tropical buffet, sip cocktails, and create memories that will last a lifetime. Book now!
★ 4.5“Wonderful trip Good food DJ was great Got everyone dancing and even took requests for the kids Great captain”
★★★★★★★★★★
1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports
Experience the ultimate Key West sunset sail with wine. Escape the crowds and enjoy a small-group adventure, sipping wine while taking in breathtaking views. Book now!
★ 5.0“A little late in posting as our sailing was back in December. This was the best sailing ever. Molly and team were stupendous. The level of detail was beyond what we had expected. Plenty of d'oeuvres and wine/bubblies to go around. Crowd was small and…”
★★★★★★★★★★
1,366 reviews2 hours (approx.)From $125.00by Danger Charters
Experience an unforgettable adults-only sunset cruise in Key West, complete with champagne and celebration. Set sail on this luxurious adventure and make memories that will last a lifetime.
★ 5.0“It was so well worth it. We had such a a wonderful time. Cannot say enough as to how wonderful the captain and crew were.”
★★★★★★★★★★
954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)
Experience the magic of a Key West sunset cruise featuring live music, refreshing drinks, and mouthwatering appetizers. Unwind, indulge, and create unforgettable memories. Book your ultimate sunset adventure now!
★ 4.5“You will have a great time on this sunset cruise. The band was great and played all our favorite songs. People were happy and dancing. Seeing the Christmas lights from the water was a wonderful experience!”
★★★★★★★★★★
952 reviews2 hours (approx.)From $79.95by Fury Water Adventures
Experience the beauty of a sunset sail in Key West, complete with refreshing beverages. Don't miss out on this unforgettable adventure. Book your spot now!
★ 5.0“Eric and Carlo were great. Friendly, professional and considerate of all on board. Very relaxing and enjoyable cruise.”
★★★★★★★★★★
907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays
Experience the breathtaking beauty of Key West at sunset aboard the Schooner America. Sip on cocktails, indulge in delicious hors d'oeuvres, and make memories that will last a lifetime.
“Fun experience! Crew members were the best and took care of everyone on board. The food and drink were great too!”
★★★★★★★★★★
804 reviews2 hours (approx.)From $122.59by Classic Harbor Line
Experience the magic of Key West's dolphins while sipping premium wine and indulging in mouthwatering tapas. Join us for an unforgettable sunset sail like no other.
★ 4.5“Great seeing the dolphins in their natural habitat. The boat crew were great and no point we didn't feel unsafe.”
★★★★★★★★★★
699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West
Experience the ultimate luxury on a Key West Sunset Champagne Catamaran Cruise. Sip champagne, soak in stunning views, and create unforgettable memories. Book your adventure now!
★ 4.5“Perfect sunset and so much fun. Crew was friendly and fun. Music and drinks were great. We had a great time.”
★★★★★★★★★★
586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West
Experience the stunning beauty of Key West with our glass-bottom boat tour. Don't miss the unforgettable sunset option. Book now!
★ 4.0“Very relaxing trip out to the reef. Staff was professional and knowledgeable. I highly recommend this trip.”
★★★★★★★★★★
576 reviews1 hour 45 minutes to 2 hours (approx.)From $69.95by Fury Water Adventures
Lose yourself in the magical world of Key West as you embark on a journey filled with dolphins, snorkeling, and breathtaking sunsets.
★ 4.4“The crew was fantastic! Madeline, Caroline and Kathy were phenomenal! The customer service exceptional! They made the snorkeling feel incredibly easy and super attentive to all experience levels!”
★★★★★★★★★★
493 reviews3 hoursFrom $79by Sunset Watersports Key West
Discover the ultimate tropical adventure! Dive into crystal-clear waters, soak up the sun, and groove to reggae beats on a Key West Snorkel and Sunset Sail: Rum N Reggae tour.
“Fantastic experience, the captain and the crew are fantastic and professional. We will do again for sure”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
Experience a breathtaking sunset sail in Key West aboard the Schooner America 2.0. Enjoy a 2-hour cruise, beautiful views, and create memories that will last a lifetime.
★ 4.9“Amber was a great Captain and her crew couldn’t have been nicer. They very knowledgeable and answered many questions, served snacks and drinks with a smile and the sunset was spectacular! 💯 will do it again.”
★★★★★★★★★★
318 reviews2 hoursFrom $122by Classic Harbor Line - Key West
Experience the magic of Key West's stunning sunsets while sipping on cocktails, dancing to live music, and indulging in delicious appetizers. Don't miss out on this unforgettable sunset sail!
★ 4.5“I’m not really sure if the vibe was supposed to be a fun party or a romantic sunset experience. The entertainment was a guitarist on the upper deck and his choice of music was something you’d find in a pub. This was not as fun…”
★★★★★★★★★★
314 reviews2 hours (approx.)From $72.00by Sunset Watersports
Immerse yourself in the magic of Key West's sunset sailing trip with a secret ingredient that transforms the ordinary into something extraordinary...
★ 4.5“Unfortunately it was cloudy when the sun was setting. The musician was great and friendly staff. Got some great pics. Worth the price.”
★★★★★★★★★★
310 reviewsFrom $80by Sunset Watersports Key West
Four square miles, water on every side, and a sunset party every single night; Key West never lets me stay on shore.