The 8 Best Sunset Cruises in Key West (2024)

What better way to experience the majestic beauty of the Florida keys than by enjoying some of the best sunset cruises in Key West. Enjoy a fantastic Key West sunset with live music and bottomless booze with several different sunset cruise operators to choose from.

Photo by Jonathan Wheeler on Unsplash

There are plenty of options for the best sunset cruise in Key West, with many providing drinks, snacks, or dinner as you take in the sunset. The most popular options are watching the sunset on a catamaran, listening to a live band, hoisting the sail and enjoying the best of Key West. 

Top Pick: Key West Sunset Cruise

Don’t miss one of the highest-rated Sunset Cruises in Key West with over 2000 positive reviews and our top choice of the best sunset cruise in Key West!

Meeting Points & Information

  • Most of the Key West sunset cruise meeting points are Key West Historic Harbor or near Conch Republic
  • The minimum drinking age is 21 years old
  • The time of sunset in Key West varies throughout the year, but you can expect boat departures between 6 pm and  8 pm. 

1. Key West Sunset Champagne Catamaran Cruise

4.5 Stars (449 Reviews)

Sebago has operated its Key West Sunset Champagne Catamaran Cruise for a number of years and is one of the top-rated Key West sunset cruises. Experience a 69-foot catamaran with an open bar that includes views across the Gulf of Mexico & Atlantic Ocean. 

The hugely popular tour offers a hugely enjoyable Key West cruise experience, with a fantastic crew and captain who are eager to answer questions and point out sights of interest. Savor the spectacular sunset with either a beer, glass of champagne, wine or sangria. 

A catamaran at sunset

Included in the tour: 

  • Unlimited wine, beer, soft drinks
  • A modern catamaran
  • Tour length: 1 Hour & 30 Minutes – 2 hours. 

What Guests Said:

“I had an absolutely amazing time! The views were breathtaking, the crew was exceptional, and the overall ambiance was magical. The sunset was a sight I will cherish forever. I highly recommend this cruise to anyone visiting Key West. Thank you for providing such a remarkable experience!”


2. Key West Dolphin Watch Sunset Sail with Premium Wine, and Tapas Pairings

4.5 Stars (372 Reviews)

Relax on a catamaran and enjoy some of the best sunset cruises in Key West.

Enjoy a cruise on a spectacular Key West catamaran with departures either in the morning or late in the evening for a sunset cruise.

The Key West Dolphin Watch Sunset Sail is an intimate sunset cruise that sails past the landmarks of Key West and takes in stunning views of Fort Zachary Taylor, as well as spotting wild dolphins in the Gulf of Mexico. 

Enjoy the Key West sunset from the catamaran as you enjoy freshly prepared tapas and snacks. This Key West sunset cruise is perfect for anyone looking to sit back and relax, perhaps even spot dolphins and enjoy conversation with fellow passengers. 

Included in the tour:

  • Snacks
  • Soda
  • Open bar
  • Small Groups
  • Departures from Key West Historic Harbor
  • Tour length 2 Hours 30 Minutes

Price of Cruise: $92 per person. 

What Guests Said:

Aside from the amazing sail, the chats with the crew and other passengers was really an added highlight. We love being on the water and sunset did not disappoint – we also got to see some dolphins, but, being able to talk to the entire crew and some passengers really did add to the overall experience. Highly recommend this experience. Captain Rachel was phenomenal and we thoroughly enjoyed it.”

3. Key West Premium Sunset Sail aboard Schooner with Hors D’oeuvres and Full Bar

5 Stars (442 Reviews)

Unlike several of the other Key West sunset cruises which take place aboard a catamaran, sailing on a classic schooner is a completely different experience

Photo by Braden Egli on Unsplash

The classic schooner offers visitors a romantic vessel to enjoy watching the spectacular Key West sunset. With gorgeous hors d’oeuvres provided as you sail around iconic Key West landmarks such as Mallory Square which also happens to be the birthplace of watching sunsets in Key West. 

Take in the sights and even help the crew hoist the sails on this classic Key West Schooner.  The romantic sunset cruise on Appledore Star is one of the best sunset sail Key West tours.

Included in the Key West Sunset Cruise:

  • Open Bar
  • Tasty finger food
  • Hoist the sails with the crew
  • Tour length: 2 hours

What Guests Said: 

“Great crew, just the right amount of time and beautiful sunset. The hors’d ‘oeuvres were tasty and lots of drink options. Champagne at sunset was my guilty pleasure! We’ll book again next time we visit!”

4. Key West Sunset Cruise with Tropical Buffet Dinner

4 Stars (961 Reviews)

Spend your late afternoon enjoying the infamous Key West Sunset with a tropical buffet dinner. The menu changes regularly but can expect to find typical dishes that are influenced by the region, such as black beans and rice, or Caribbean roast pork. Don’t miss trying the plantains!

With the weather in Florida sometimes being overwhelmingly hot, you can relax in the large open cabin that is able to fit 60 people comfortably with AC. When you’ve finished dining on the scrumptious buffet dinner, head to the deck, listen to the live music and enjoy the incredible sunset. 

With an open bar that includes mojitos, what better way to enjoy one of the best sunset cruises in Key West than by sitting on a 65-foot yacht and making new memories. 

Photo by Chase Baker on Unsplash

Included in the tour:

  • Tropical buffet dinner
  • Open bar
  • Live music
  • Air Conditioning
  • Spectacular Key West sunset views

Price of Cruise: $88

What Guests Said: 

“The food was amazing!! The service outstanding! Entertainment was great and funny! The performer engaged the crowd and was family friendly.”

5. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

4.5 Stars (2229 Reviews)

One of the top-rated and best sunset cruises in Key West is the Key West Sunset Sail with Full Bar and Live Music. Set sail in the late afternoon and enjoy terrific live music, a full open bar, and plenty of delicious hors d’oeuvres. 

Photo by Jim Davis on Unsplash

It also happens to be one of the busiest booze cruises in Key West that has a solid reputation for its energetic crew and entertainment. Dance the evening away while enjoying a full open bar that includes beer, sodas, wine and sparkling wine. 

The hors d’oeuvres are tasty finger food staples such as egg rolls, shrimp and other great food for soaking up all the booze!

With live commentary and information about the island of Key West, the Key West cruise takes in the landmarks of Key West and one of the most spectacular sunsets in the Florida Keys. 

Included in the tour:

  • Live music
  • Hearty snacks
  • Open bar
  • Departures from Key West Historic Harbor

Price of Cruise: $80

What Guests Said: 

“Live music, good appetizers and great crew! We had a blast! We’d do it again and recommend to anyone especially couples.”

6. 2-Hour Private Sunset Cruise around Key West

4.5 Stars (46 Reviews)

Want to escape the crowds and charter your own private sunset cruise in Key West? Then Blue Chi Charters offers an incredible and intimate experience. Experience the incredible Key West sunset with just your loved ones, as you spend 2 hours passing by the iconic Key West landmarks. 

Savour the privacy and experience Key West without the crowds, as you head to points of interest like the Southernmost Point in the USA, or uninterrupted views of Fort Zachary Taylor State Park & Mallory Square. 

You can enjoy your private sunset cruise in Key West with complimentary beverages. You can also bring your own bottles of wine and beer on board as they have an ice cooler. 

Included in the tour: 

  • Private Charter Boat
  • Bottled Water
  • Soda
  • Ice Cooler

What Guests Said: 

“I took my significant other for a private, romantic cruise into the sunset and we had a wonderful time on this two hour ride around Key West. Our Skipper was very knowledgeable and kind, he provided interesting insights at just the right moments without being intrusive. It was a truly romantic and memorable experience that ended with a spectacular sunset.”

7. Key West Sunset Snorkel with Unlimited Draft Beer & Wine

4.5 Stars (76 Reviews)

Set sail and explore the incredible crystal clear waters of Key West, stopping off for snorkeling and swimming in the waters of the Atlantic Ocean. Experience the magic of the coral reefs that are abundant with marine life. 

Spend the hours before sunset swimming the 3rd largest natural reef in the world, the Florida Marine Sanctuary. Keep your eyes peeled for turtles, reef fish and you may even spot a wild dolphin!

Back on board, enjoy the amazing Key West sunset with a nice cold beer or glass of wine as your dry off. This is one of the best sunset cruises in Key West for visitors looking to swim and enjoy a spectacular sunset.

Included in the private catamaran:

  • Snorkeling equipment
  • Open water snorkeling in a coral reef
  • Open Bar

Price of Cruise: $60

What Guests Said: 

“The crew made the experience easy and super enjoyable. The tour isn’t crowded and comfortable. Definitely recommend this one out of all the tours in Key west!”

8. Sunset Tiki Boat Tour in Key West

5 Stars (93 Reviews)

If you are in Key West with a group of friends, what better way to enjoy the amazing sunset in Key West than by renting your very own Tiki Boat

Bring your own booze as you and your friends set sail on a tiki boat complete with a tiki bar! 

Price of Cruise: $60

What Guests Said:

“What a great night! Very fun to be on the water on this boat! Nick the captain was personable and fun! We brought our white claw and snacks! We will book this again!!”

A Key West Sunset Cruise You Won’t Forget

Why not take the hassle and claustrophobia out of watching the Key West sunset by taking a splendid and squish-less experience of a fabulous Key West sunset cruise?

Drop a comment below and let me know which of the best sunset cruises in Key West you ended up choosing and how it was! Continuing on your Florida adventure? Make sure to check out my post on the best rooftop bars in Tampa.

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