Soak in the gorgeous Key West sunset with these sailboat tours

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Key West has a well-deserved reputation for being a great party island, and the nightlife and day-drinking) scene along Duval St. is fantastic. But there is another world beyond the bars and nightclubs of Key West, and it starts at the ocean.

Going to Key West and not enjoying the water is experiencing only half of the island’s true identity. Key West is a natural “deep-water port,” which means it is perfect for docking big, beautiful boats, even sailboats with tall masts and gorgeous white sails that catch trade winds that blow across the Florida Keys.

Evenings in Key West bring a flawless view of the setting sun and watching the kaleidoscope of colors as the sky meets the ocean. The sunset on the water is not something that people merely “see.”

It is an experience of all the senses: the smell of the ocean air, the feel of the rocking ship…and then there’s also the taste of the wine served on board.

Related: Bartender Mark ‘I wear as little as possible’ Watson gives you the inside scoop on Key West Pride

There are lots of friendly sailors with boats in Key West who bring visitors out for sails, for any sort of occasion. For an intro to life at sea, taking in a nice evening cruise, here are some of our favorites, where you can enjoy a ride on the ocean around the Florida Keys and toast the setting sun:

Danger Charters

Don’t let the name fool you. Danger Charters sail 65-foot schooners, which are small enough to sail shallower waters but still keep the ride smooth along the waves. Even when the boat leans, the keel (fin beneath the hull) will keep the boat upright, although you may have to hold onto your glass of wine in those big gusts of wind. That’s a nice boat, and it is just one of several in the Danger Charters fleet.

Jolly II Rover

The Jolly II Rover is one of the most famous sights in the Key West sunset. Setting sail on weekends, those trademark red sails cut a lovely profile against the horizon. The Jolly II Rover is big, an 80-foot schooner, built as a replica of pirate ships from years gone by, complete with cannons that passengers can fire just for fun. There will be no pillaging or plundering on this vessel, except for the treasure you bring aboard yourself in the form of drinks because this ship (as is the case with many tourist tour vessels) is BYOB. So don’t be shy with bringing aboard what you want, and leave the leftovers for the crew. They’ll drink it.

Blu Q

Captain Steve is known around Key West for sailing his beloved Blu Q, a small catamaran that zips through the reefs and mangroves around the island. Although it is a smaller boat than the other sailing charter vessels, catamarans are generally made stable in the water thanks to their double-hulled design. During the day, before his sunset sails, Captain Steve also takes out groups of friends on all-male, clothing-optional snorkeling tours.

And we have Instagram evidence of shenanigans on board:

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Hello, sailor.