Sunset Sails. Day Sails. Private Charters.

Regattas. Special Events.

General Patton's gorgeous 1939 wooden schooner is sailing out of

Salem, MA every day this Summer!

Book your Salem sunset sail here

Private Charter

Cruise Massachusetts

Daysail in Salem

North Shore Sailing

Keep in touch!

Day-By-Day-Updates

Our Summer Hosts

Sunset Sail Salem

A truly unique opportunity

enjoy sailing salem sound

Daily Doings on FaceBook

Visit sunset sail salem

Book Your Perfect Salem Sailing Experience

Enjoy a day sail, or Salem'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!