Sunset Sails. Day Sails. Private Charters.

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.

reservations

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.

reservations

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!

An Historic Vessel

Welcome Aboard!

Sailing Schedule

Tall Ships New Orleans

20th - 22nd April 2018

Book your Lake Pontchartrain Sail Here

Private charter on When and If in NYC

WHEN AND IF, NYC from Caleb Seppala on Vimeo.

Private charter on When and If in NYC

WHEN AND IF, NYC from Caleb Seppala on Vimeo.

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

Key West to Cuba from Caleb Seppala on Vimeo.

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

Key West to Cuba from Caleb Seppala on Vimeo.

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

When And If from Caleb Seppala on Vimeo.

OFF THE BEATEN PATH

Dine and stay with our friends on Stock Island!