10 Sunset Cruises in Key West – Which is Best for You?

Going on a sunset cruise in Key West is a must-do and is considered by many to be a rite of passage. After all, there’s probably no better place in the lower 48 to get out on the water and enjoy the golden hour than in the Conch Republic. However, not all cruises are the same, and some are definitely better than others—you don’t want to get stuck on an uncomfortable jam-packed boat with warm drinks, that doesn’t have anywhere to sit.

Key West is one of the most uniquely fascinating places to see in the country. With its laidback atmosphere and Caribbean vibes it’s the perfect place to escape the busyness of life for a while. However, if you’re looking to make your stay extra memorable then you should explore taking one of the 10 sunset cruises in Key West below.

Time to Relax

Use the chart below to assist in finding the perfect cruise.

Sure, you could save a few bucks and watch the sunset from Mallory Square, which is always a nice experience. Alternatively, you could sail past Mallory Square and Sunset Key and have an uninterrupted sunset experience out on the Florida Keys that you’ll remember forever.

10 Best Sunset Cruises in Key West

Below are the 10 best sunset cruises in Key West. Most cruises last about two hours and depart from either Opal Key Resort & Marina, Key West Bight Marina, or Garrison Bight Marina.

1. Snorkel and Sunset Sail

Jam to reggae beats and snorkel at North America’s only living coral reef, and enjoy a sunset sail tour. Unlimited rum punch, beer, wine, and sparking wine are provided, after snorkeling of course. At three hours long, this is the lengthiest tour on the list.

🥤🤿 Snorkel and Sunset Sail > Check Availability

2. Sushi Cruise

Sushi lovers will have a blast tasting fresh sushi while sipping on a refreshing drink as they watch the big orange ball sink into the Gulf of Mexico. This large pontoon-style boat provides a more intimate experience than some of the larger tour boats, which we like!

🍥⛴ Sushi Cruise > Check Availability

3. Cocktail Cruise With Open Bar

This cocktail cruise with an open bar is one of the most affordable ways to enjoy unlimited drinks on a sunset cruise in Key West. Visitors looking for a small group experience, a fun atmosphere, and comfortable seating are sure to enjoy the voyage! Light snacks including breads and spreads are also provided.

🍹🛥️ Cocktail Cruise With Open Bar > Check Availability

4. Classic Sunset Cruise With Live Music

When you think of a Key West sunset cruise this tour is most likely what you envision. This large catamaran has plenty of space to stretch your legs while you jam to live music. Moreover, with an open bar and a nice assortment of appetizers, this is the perfect tour for anyone looking to party!

🥳⛵ Classic Sunset Cruise With Live Music > Check Availability

5. Tiki Bar Tour

It doesn’t get more laidback than a Tiki Bar Tour in Key West. With only six passengers allowed, you won’t find a more intimate experience unless you charter a boat. Only water and ice are provided. However, passengers are allowed to bring their favorite adult beverages onto the boat. Check out these custom Key West koozies/party huggers to bring on board.

🗿⚓ Tiki Bar Tour > Check Availability

6. Premium Wine and Tapas

There’s no better sunset cruise in Key West for foodies and wine lovers than this one. Departing conveniently from Key West Bight Marina, the Premium Wine and Tapas Tour is 2.5 hours long and provides passengers with a plethora of scrumptious tapas and wine. Furthermore, the spacious and luxurious catamaran allows you to take in all of the sites and the sunset comfortably—also, the captain is obsessed with spotting dolphins!

🐬🍷 Premium Wine and Tapas > Check Availability

7. Pirate Cruise

Kids, and the kid in all of us, will feel like one of the Goonies aboard a vintage schooner—they even shoot a cannon! Water and snacks are provided, along with ice for anyone who would like to bring their own drinks.

🏴‍☠🦜 Pirate Cruise > Check Availability

Is it Your First Time in Florida? > Read This

8. Schooner for Adults

Those passengers without kids, and looking to sail aboard a schooner will find this tour as a fantastic alternative to the one listed above (#7). Complimentary beer, wine, cocktails, and sangria are provided, along with some tasty appetizers.

⛵🍸 Schooner for Adults > Check Availability

9. Private Pontoon

Whether you’re celebrating a special event or you’re just looking for a bit of privacy, this private pontoon tour is the way to go if you’re on a tight budget. Your captain will guide you to all of the significant landmarks and get you in the best position to take in the sunset. Also, water and ice are provided—bring your own snacks and drinks to make it a party!

👨🏻‍✈️🚤 Private Pontoon > Check Availability

Looking to Rent a Boat For the Entire Day? > Check Out These Low Prices!

10. Private Classic Sailboat

If money is no object, this private classic sailboat tour is one of the best sunset cruises in Key West. Your group, of up to six people, can relax as your captain and their first mate navigate through the waters around Key West.

Of course, you’ll pass by all of the must-see landmarks, and the crew will spot marine life, and position the classic sailboat in the perfect spot for sunset. Finally, snacks and refreshments are provided, and of course, you can bring your favorite drinks along with you as well.

😎⛵ Private Classic Sailboat > Check Availability

There are dozens of sunset cruises in Key West but only the ones listed above are the best. Whether you’re looking to have a Goonies moment aboard a vintage schooner or nibble on sushi as you watch the sunset you can’t go wrong with any of the cruises listed above. Welcome aboard!

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