We're in Downtown Key West!

Call to book or book online now

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

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 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!

Click here to call and enquire about chartering When and If.

We know you'll have lots of questions so don't be shy!

Private charter on When and If in NYC

Private charter on When and If in NYC

When and If sailing from Key West, FL to Havana, Cuba

When and If sailing from Key West, FL to Havana, Cuba

When and If at the Great Chesapeake Bay Schooner Race, 2015