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 this Winter!

Book your Key West sunset sail here

Private Charter

Cruise The Keys

Daysail in Key West

Tropical Winter Sailing

Wreckers Races 2019

What's it all about?

Our Winter Hosts

Sunset Sail Key West

A truly unique opportunity

Sunny sailing in Florida

Book your WR ticket here!

Visit sunset sail Key West

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.

reservations

Click here to call Captain Dylan 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

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!