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

COMING SOON:

 

Wreckers Race Sailing 2020!

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 wheel or sit back and relax as the crew serves you a selection gourmet cheeses and still or sparkling water - BYOB!

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