Sunset Sail Salem


Salem and the North Shore are home to some of loveliest sailing in New England. England sailing experience. We offer daily sailing and private charters on the beautiful Salem Sound.

Come sail on our unique historic yacht and take in the views of Boston’s North Shore, the scenic islands, and abundant wildlife as wind fills the sails.

With per-head sails and private charters available When And If is perfect for a variety of occasions and will fit your every need. Contact us to make arrangements for a personalized trip.

A Beautiful Classic

When and If Flying the Fisherman in Salem

The Historic Schooner When And If, built in 1939 for General George S Patton to sail around the world “When the war is over, and If I live through it” takes up residence with Sunset Sail Salem under the care of Captain Dylan this summer. This vessel is your chance to enjoy truly glorious sailing with room for up to 32 guests on day sails or private charters.

See When And If’s Sailing Trips Here:

Perfect Sailing


No matter what type of trip you are looking for, we’ve got you covered.

Book a seat on a day sail or sunset sail aboard the gorgeous When and If. Schooner When and If is perfect for larger private groups, accommodating up to 32 guests.

For something more tailor-made, ask about a private charter. From Gloucester to Newport, round the Islands and the Cape, When And If can travel to meet your needs for the sailing trip of a lifetime.

Most Popular Sailing Trips


Sunset Sails on When And If

Lazy, hazy Summer sunsets on the lovely When And If – the 1939 schooner built for General George Patton.

Whif in Havanasqlg

3hr Daysail

Time to catch that Summer breeze and take an afternoon to sail the North Shore – who’s up for some lighthouse-spotting?


Morning Mimosas

It’s the Summer holiday, and what better way to celebrate than with fresh morning mimosas and a chance to blow away those cobwebs?