WHICH SUNSET BOAT HAS THE BEST SAILORS? FIND OUT FEB. 9

a couple of people on a sailboat in the water
Teams from local watersports companies will compete Sunday, Feb. 9 in the inaugural Sunset Cruise Cup, sponsored by the Key West Community Sailing Center, 705 Palm Ave. CONTRIBUTED

There’s no shortage of sailboats in Key West Harbor each night at sunset. Captains and crews from dozens of local companies welcome passengers daily for snorkeling, sightseeing and sunset trips. Sleek schooners and cavernous catamarans hoist their sails, harness the wind and host Instagram moments.

But how honed, really, are those sailors’ skills when they’re challenged to go back to the basics and navigate a tight course in a simple boat? They’ll have no engine to overcome wind and current, and certainly no bow thrusters to bring them gracefully back to the dock.

Who are the best sailors among the captains and crew of local watersports companies?

The Key West Community Sailing Center will find out on Sunday, Feb. 9 when it hosts the inaugural Sunset Cruise Cup.

For 50 years, the nonprofit sailing center on Palm Avenue has taught generations of Key Westers essential sailing skills — and the practical science that makes it possible. Have the local pros kept those skills sharp?

“The Sunset Cruise Cup at the Key West Community Sailing Center aims to crown the best sailors amongst the captains and crews of local watersports companies each year,” said Ben Hermelin, executive director of the center. “Participating companies have nominated a team from their crew to represent their business and compete against other companies’ teams for bragging rights, a trophy and cash prize.

“Teams will race against each other on C420 sailboats inside Garrison Bight for all to see,” Hermelin said, encouraging spectators to watch the back-to-basics battle of the sailboats from the sailing center’s docks. 

Entry fees support the center’s sailing education programs, scholarships and financial assistance for students.

Participating companies include Fury Watersports, Danger Charters, America 2.0, Jolly II Rover, and more.

The Sunset Cruise Cup takes place from 9:30 a.m. to 2 p.m. at the Key West Community Sailing Center, 705 Palm Ave.

Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.