Best Key West Sunset Cruises

Discover the magic of Key West, a place where vibrant sunsets paint the sky each evening, marine life dances beneath crystal-clear waters, and Caribbean charm infuses every corner of the city. Ready to immerse yourself in this enchanting paradise? Step aboard a Key West sunset cruise!

With an array of options, each promising a distinctive adventure, you can witness the sun’s descent in style. Whether you opt for a lavish dinner cruise, set sail on a classic sailboat, or indulge in champagne aboard a sleek catamaran, prepare for an unforgettable journey into the heart of Key West’s enchanting twilight. Here are some of the best sunset cruises in Key West, Florida.

Danger Charter’s Wind and Wine Sunset Sail

Check Availability

A favorite amongst locals, Danger Charter’s Wind and Wine Sunset Sail is one of the best sunset cruises in Key West, Florida. Throughout the evening, you’ll be spoiled with high end wine and beer selections, plus some hors-d’oeuvres as you sail along the island’s west coast. 

The sailboat you’ll board is a historic Key West schooner, adding to the charm of this luxe cruise. This is a smaller boat, which means fewer people will be onboard! Prices start at $109, and the tour lasts about two hours. 

Argo Navis All Inclusive Sunset Sail

Check Availability

Sail along the aqua green waters where the Atlantic Ocean meets the Gulf of Mexico on a sunset cruise with Argo Navis. This tour takes place on a 75’ luxury catamaran sailboat with space for about 40-45 people. 

Wine, beer, cocktails, and non-alcoholic beverages are included in the price, plus several rounds of appetizers. Rates start at $111, and the tour is around two hours long. In the summer, you can book a Tuesday evening sail that includes an extra hour for swimming before the sun goes down ($149).

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

Check Availability

Interested in seeing some of the marine life that lives below the surface during your excursion? This is one of the best sunset cruises in Key West, as you’ll likely be able to see dolphins as you glide along the beautiful waters. 

In addition to dolphins, experienced guides will point out noteworthy landmarks along the way, including Mallory Square, Sunset Key, and historic Fort Zachary Taylor. Drinks and snacks are also included in your trip. The cruise lasts about two and a half hours, and prices start at $90.

Sunset Dinner Cruise With Sunset Watersports

Check Availability

Treat yourself to a dinner and a sunset show aboard Sunset Watersports Sunset Dinner Cruise. Sail along Key West’s picturesque coastline while savoring freshly prepared dishes and refreshing beverages. The menu changes with the season, but you can expect to find staples like Blackened Mahi, Smoked Mojo Pulled Pork, fresh side dishes and enticing dessert options on the menu no matter when you sail. Did we mention that an open bar is included?

The cruise lasts around two hours, and prices start at $90 for adults. Premium liquor upgrades are available for $20.

Champagne Sunset Sail With Sebago Watersports

Check Availability

Raise a toast to the day’s end aboard Sebago Watersports’ Champagne Sunset Sail. Relax on a spacious catamaran deck, champagne flute in hand, as you watch the sky transform into vibrant shades of oranges, pinks, and purples.

If champagne isn’t your thing, you can choose from a selection of wines, beers, and non-alcoholic beverages. This is one of the best sunset cruises in Key West, Florida, for those looking for a more affordable way to watch the sun go down. Prices start at $50, and you’ll have about one and a half hours to enjoy the sunset and unlimited champagne.

Private Sunset Charter With Sunset Sail Key West

Check Availability

For a truly intimate experience, consider a private sunset charter with Sunset Sail Key West. With a customizable itinerary and personalized service, you can tailor your sunset cruise to suit your preferences, whether it’s a romantic evening for two or a celebration with friends and family.

You’ll cruise along the waters on a small sailboat, with just enough space for groups up to 12. Soft drinks and water are provided, and guests can bring their own adult beverages if they’d like. Trips last two hours and prices start at $595 for this private charter.

Commotion On The Ocean Sunset Cruise With Fury Watersports

Check Availability

Brace yourself for an unforgettable evening of entertainment aboard Fury Water Adventures’ Commotion on the Ocean sunset cruise. This is one of the best sunset cruises in Key West, Florida, with live music and a variety of appetizers and drinks. 

This cruise sails for about two hours, and prices start at $80. Fury is one of the most popular companies in Key West offering many fun things to do including lots of water experiences.