North Shore Sailing for Summer 2022!


Our 2022 Salem season features all your favourite Daysails, Sunset Sails, Private Charters and Race Days

Check out our schedule online to book or call us any time!

Our full on-board bar is up and running! Take a look at our bar menu here, or see our selection of Special Drinks Sails for Summer 2022.

Early Bird Discounts for 2023

We're freezing our 2022 Private Charter prices until Christmas for the early birds! Book yourself a sunny summer sailing trip to get you through those long winter months - with flexible booking up to 7 days out it's time to start filling in your 2023 diary!

Sunset Sail Salem


Salem and the North Shore are home to some of loveliest sailing in New England.  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.

This Summer we are starting out with private charters only, to comply with social distancing advice and to keep our guests and crew safe and well. See our scheduled availabilities here or  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 Joseph this summer. This vessel is your chance to enjoy truly glorious sailing with room for up to 32 guests on private charters.

See When And If's Sailing Trips Here:

Perfect Sailing


Get away from the crowds in these strange times and take a private sail with your family and friends during one of our scheduled sailing slots this Summer. Our bar is still available on board and we look forward to welcoming you for a break from Land Life before too long!

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

2hr 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?