A Key West Winter

Sunset Sails, Day Sails, Private Charters, Corporate Events, Classic Regattas, Photo Shoots

A Key West Winter

Sunset Sails, Private Charters,

Day Sails, Corporate Events,

Classic Regattas,

Photo Shoots

Book Your Perfect Key West 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 any adult beverages that you care to bring. Free shuttle service to and from your doorstep.

Book Your Perfect Key West 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 any adult beverages that you care to bring. Free shuttle service to and from your doorstep.

FREE SHUTTLE

right to your door!

FREE PARKING

At our lovely home in Stock Island Marina Village

FREE ICE! 🙂

bottled water and La Croix

BYOB!

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

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

Click here to call Captain Seth 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