Winter 2019/20: When And If returns to Florida for Winter in Key West!
Book online now...or you can call us to book!
Winter in Key West!
Book online now...or call us for your ticket


Daysail in Key West, FL
Tropical Winter Sailing
Sunset Sails in Key West
Winter in the Keys!
Our Winter Hosts
Sunset Sail Key West
Sunset Sails. Day Sails. Private Charters. Regattas. Special Events.
General Patton's gorgeous 1939 wooden schooner is sailing out of Key West, FL every day.
Click here to call Captain Dylan or Captain Kayla and enquire about chartering When and If.
We know you'll have lots of questions so don't be shy!