Summer Sailing on the North Shore


When And If returns to our Summer hosts at Sunset Sail Salem for Summer Sailing on the North Shore!

We are beginning the season with a limited schedule of private charters on When And If to keep all our guests and crew safe and happy. With unbelievable Summer 2020 special prices and a wide variety of scheduled slots available we’re excited to extend the opportunity for an exclusive private charter to all our guests! More sailing opportunities will open up in compliance with MA state law as the season progresses.

Book online now with Sunset Sail Salem…or you can call us to book!

When and If is the gorgeous 1939 wooden schooner yacht built for General George S. Patton to sail around the world “When the war is over and If I live through it.” Her history is long, illustrious and varied – there’s much more to explore on our history page. Come and be part of her story this Summer sailing on Boston’s North Shore out of Salem, MA with Sunset Sail Salem. Take a trick at the helm, help raise sail or simply relax and enjoy the ride!

Take a look at our scheduled daily trips out of Salem, MA


Photoshoots and Media

When And If has a fantastic portfolio as a stunning backdrop to upmarket print photoshoots, movie gigs and advertising campaigns. Her gorgeous joinery and original bronze hardware lend themselves perfectly as a contrast or a compliment to any creative vision.

Take advantage of our position in the North East this Summer to book your photoshoot opportunity!

Take a look at our portfolio or call Owner Operator Captain Seth for more information on chartering When And If as a media asset.


Planning Ahead?

When And If will rejoin her Winter hosts at Sunset Sail Key West from Thanksgiving. Start planning your Winter break with one of our exclusive small boat private charters, or a shared experience on When And If for a classic Key West Sunset Sail.