Cool Cat Charters

New England Yacht Charter Itinerary

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Along the coast, yacht charter guests will find classic New England elements: quaint homes with gray shingles, towering lighthouses, families having clam bakes, cobblestone streets and more. From Nantucket and Cape Cod, to Martha’s Vineyard and beyond, New England is where America’s yachting tradition began many years ago.

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Day 1: Newport

Start your yacht charter in Newport, which is known as New England’s sailing hub. Take a local harbor tour, and let yourself be dazzled by the island’s historic waterfront and its beautiful views, or get a taste of New England’s delicious cuisine at a restaurant on Bannister’s Wharf. Everywhere you turn, yachts dot the sea – all amidst a stunning backdrop of Newport mansions, shops and landscapes.

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Day 2: Block Island

Cruise about two hours, and you’ll end up at Block Island. While there, take in the area’s laid-back vibes and white-sand beaches, or hop on bike and ride along stone walls that have been erected for centuries. 

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Day 3: Cuttyhunk Island

Sail on to Cuttyhunk Island, on the south end of Cape Cod. There is wonderful hiking, lots of photo ops, and remote locations where you can relax, unwind and even nap.

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Day 4: Martha’s Vineyard

Of course, you can’t go to New England without making a stop at Martha’s Vineyard. This is a popular place where many U.S. presidents go on vacations and, as such, is also where you’ll find some of the world’s most raved-about yachts. Grab a bike and spend your day shopping, at the beach, or eating at one of Edgartown’s delicious restaurants. Whatever you choose, you won’t be disappointed.

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Day 5: Nantucket

Nantucket gives visitors a quintessential “New England” feel. It’s filled with cobblestone streets, charming, sea-weathered buildings, plenty of quirky shops and haunts, and popular local museums like The Whaling Museum and the Toy Boat – the latter of which boasts a stellar collection of classic wooden floatables. Get the best sunset views you’ve ever seen at White Elephant Hotel’s Brant Point Grill, a popular restaurant in the area.

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Day 6: Provincetown, Cape Cod

Wake up early and make your way to Provincetown, in Massachusetts. As you drink your morning coffee, you can take in the beautiful views you’ll see on your journey. When you anchor, explore this historic New England town known for its flamboyant street scenes, art galleries, nightlife and vast beaches. While you’re there, go for a whale watch – it’s one of New England’s best activities.

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Day 7: Hadley’s Harbour, Elizabeth Islands

The Elizabeth Islands are a small group of islands that extend southwest from Cape Cod and sit just north of Martha’s Vineyard. Hadley’s Harbour is considered one of the best protected and attractive anchorages in the cruising ground south of Cape Cod, making it a great stop on your New England yacht charter.

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Day 8: End charter in Newport

Head back to Newport – your starting point. Take in the idyllic New England views and weather along the way.  After disembarkation, enjoy another great meal along Bannisters Wharf. Want to change it up? Head to a historic restaurant on Thames Street; wherever you go in Newport, the food will be delicious.

Over lunch, don’t forget to start planning your next adventure aboard Catatonic 500!