We're in Downtown Key West!

Winter in Key West!

Book online now...or call us for your ticket

Check out our online store...

...and order before 12/18 for shipping in time for Christmas! Our star products are our new buff/face coverings and gorgeous 2021 When And If calendars but have a look at all our fab swag and get shopping!

COMING SOON:

Wreckers Race Sailing 2021!

Daysail in Key West, FL

Tropical Winter Sailing

Sunset Sails in Key West

Winter in the Keys!

Our Winter Hosts

Sunset Sail Key West

Book online or call to enquire

Winter sailing in Key West

book sunset tickets here

Visit 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.

Book your Key West sunset sail here

Book Your Perfect Florida Keys Sailing Experience

Enjoy a day sail, or Key West's most elegant and exclusive Sunset Sail on this historic classic yacht!

Built for General George Patton in 1939, When And If is open to the public for the first time in her history.

Help raise sail, take the helm or sit back and relax with our complimentary Schooner Wine and select beers - don't forget to ask about our Beverage Upgrade!

reservations