Florida

The Best Key West Sunset Cruises

by Cedric Pentonville  |  Updated December 11, 2023

Sail into the sunset with food, bubbly, wilderness and a little culture all thrown in together on these five elegant Key West cruises.

(Photo: Viator.com)

Key West conjures up images of Caribbean culture, taking a catamaran cruise through the balmy Gulf of Mexico, magnificent marine life and Ernest Hemingway fishing with a cold beer in hand. Located at the tip of the Florida Keys, 165 miles from Miami, it is the perfect place to find a private sunset cruise or shared boat trip. You’ll see boats wherever you go in these parts, so there’s little enticement needed to get out onto the open sea, especially for romantic sunset dinner cruises, where you can look back across the water towards Key West with a glass of Champagne.

Key West Sunset Champagne Catamaran Cruise

Champagne and sailing might not be the best mix if you’re in charge of navigating. But that’s why catamaran tours were invented. Departing an hour before sunset from Key West, this cruise aboard a 69-foot catamaran gives the perfect view of the string of Florida Keys islands across the turquoise water. Wine, beer and sangria are also provided as part of the price and cocktails can be bought for a little extra. If you’re lucky, there may also be a chance to spot marine life, such as dolphins. An hour after sunset, the cruise returns to the same departure point in Key West. From $60 per person.

Book at Viator.com

(Photo: Viator.com)

Schooner Key West Sunset Cruise with Full Bar

For one of the most memorable, popular and romantic sunset cruises, hop aboard this two-masted, wooden schooner for a two-hour sunset voyage. Watch as the sails are raised (only if the weather conditions allow), catching the wind and propelling you out onto the Gulf of Mexico as the sun sinks below the horizon. You can even take your turn at the wheel. Then grab a cocktail, glass of wine or a cold beer, all included in your ticket, and enjoy the ride. It’s best to reserve your tickets on this schooner sunset tour as early as possible. Cruises are only available from November until early June, during which time they depart daily. From $60 per person.

Book at Viator.com

Key West Sunset Sailing Trip with Open Bar, Food and Music

For a sunset sailing cruise from Key West that runs throughout the year, there’s the Sandie Cat, a modern, three-deck catamaran with space for up to 150 people. The sails are often raised on this catamaran cruise, while the ambience is set by the live music on board. And helping set the mood even further, as you sail into a romantic sunset, is the open bar offering unlimited drinks during the two-hour trip, tempered by the snacks provided on-board, such as meat and veggie platters. From $70 per person.

Book at Getyourguide.com

(Photo: Getyourguide.com)

Key West Sunset Party Cruise by Catamaran

For a more upbeat version of a sunset cruise, there’s a party catamaran with part of its deck converted into a dancing space, so that you can make the most of the live music on board. Head out onto the open water as the skies warm up between the blue and black of day and night. Make the most of the complimentary drinks, including beer and margaritas, to get those feet moving. Whenever you want to take a break, you’ll have the spectacular sunset views over Key West, or the snack table to keep you occupied. From $86 per person.

Book at Getyourguide.com

Key West Dolphin-watch Sunset Sail with Wine and Light Bites

Snack on tuna poke or a shrimp cocktail while trying a perfect wine pairing or glass of Champagne as you sail into a Gulf of Mexico sunset from Key West. In the right conditions, once out on the open sea, the sails are unfurled to create the most romantic sunset experience possible. If you’re lucky, you’ll even be able to spot dolphins cavorting around the boat; your catamaran captain will head to areas of open water that are known hangout spots for these enigmatic creatures, although sightings can’t ever be guaranteed. From $90 per person.

Book at Viator.com