Salem: Historic Schooner Yacht Sail & Salem Sound Islands

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Free cancellationTravelers' pick

1/12

Duration2h

GroupUp to 28

LanguagesEN

Mobile ticketAccepted

Sail salem harbor on a storied yacht with island views and local stories

You’ll feel history under your feet as you sail Salem Harbor aboard a classic schooner yacht. Watch Marblehead’s shoreline drift by, explore stories behind local islands like Misery Island, and share laughs with crew over craft drinks. It’s two hours of real sailing — salty air included — with space to relax or try your hand at pulling lines if you want.

Step-by-step itinerary

Historic schooner sailing in Salem

Board the schooner at 10 Blaney St
Set sails on Salem Sound
Enjoy craft beverage bar onboard
Sail around Marblehead historic homes
Explore islands of Salem Sound

The Experience

The sails were already snapping overhead by the time I found my spot near the rail — honestly, I was still catching my breath from the walk down the gangway (steeper than it looked, so heads up). The Malabar X looked almost too perfect against the water, all polished wood and ropes that smelled faintly of salt and something older. Our captain — I think his name was Dave? — gave this quick nod as if to say, “You’re in good hands.” And then we were off into Salem Harbor before I’d even figured out where to stash my bag.

I kept glancing back at Salem’s shoreline, those old brick buildings getting smaller while the crew moved around like they’d done this forever. Someone pointed out Marblehead’s big houses stacked along the neck — apparently some are from the 1700s, but honestly I was more distracted by the way sunlight hit the water in weird patches. There was this moment when we passed Children’s Island and you could hear gulls fighting over something (probably not worth fighting for), and one of the deckhands told me about Misery Island’s odd name. I half-listened while trying not to spill my canned cocktail — which, by the way, is much better cold with sea air in your face.

It wasn’t all smooth; there was a gust that nearly sent my hat flying (caught it just in time), and at one point I tried helping with a line but mostly got tangled up. The crew didn’t mind — actually laughed with me instead of at me. There’s something about being on an old schooner that makes you forget your phone for a bit. Kids were sprawled out on deck, parents sipping wine, everyone sort of lost in their own little day trip machu picchu cusco kind of headspace, if that makes sense. Two hours went weirdly fast.

On the way back toward Salem, I just watched the light change over the islands and thought about how many people had sailed these waters before us. It’s not dramatic or flashy — just honest wind, creaking wood, and a bunch of strangers who felt like shipmates by the end. Still think about that view sometimes when things get noisy back home.

What’s included

Your two-hour day includes bottled water and soft drinks onboard as you sail from Salem Harbor past Marblehead Neck and several historic islands; craft cocktails, beer, cider, and wine are available for purchase throughout most of your journey before returning to shore.

Good to know

Easy physical levelStroller friendlyPets welcomeInfants must sit on laps

Operated by Sunset Sail Key West