A Summer Underway

Key West to Charleston to Bermuda to Boston to Nova Scotia to Quebec. Join us on our epic journey!

A Summer Underway

Key West to Charleston to Bermuda to Boston to Nova Scotia to Quebec. Join us on your journey!

Follow us around the Canadian Maritimes

With eight stops in Canada this Summer we can't wait to go exploring!

Email us to enquire about bunks between ports

or see our schedule here!

Follow us around the Canadian Maritimes

With eight stops in Canada this Summer we can't wait to go exploring!

Email us to enquire about bunks between ports

or see our schedule here!

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

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.