A Summer Underway

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

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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 uto 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 uto 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!

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