New England Yacht Charter

7 Must-See Islands in New England & Canada

Fair winds, culture and quirks, a New England yacht charter delivers an access-all-areas opportunity to vacation in style. From relaxed seclusion on sheltered beaches to delicious cuisine in vibrant townships, this will be the trip of a lifetime. The greatest time to cruise these coastal isles is between late summer and early fall. This is when temperatures mean beach crowds are diminished, and dock space is easy. A yachting getaway in New England during Covid offers a safe and secure environment to island-hop at leisure.

7 breathtaking islands to visit on a private yacht charter in New England and Canada

Exploring New England on a Luxury Yacht Charter:

Chebeague Island

Meaning “isle of many springs,” Chebeague Island is considered one of Maine’s most beautiful islands. This is the ideal destination for those who wish to travel far from the madding crowds.

A restorative stop on a New England yacht charter, there is no shortage of options for beachgoers, from popular Hamilton to the peacefully secluded Sunset Beach. At low tide, adventurers can walk the sandbar to uninhabited Little Chebeague, where the remoteness of Indian Point is exhilarating. This is an island that inspires relaxation, so breathe in the ocean air and step into a little world of paradise.

Peaks Island

Originally home to Abenaki Indians, pedestrian-only Peaks Island in Casco Bay offers a leg stretching stop on a yacht charter, with hiking trails, history and plenty of local colour. Idiosyncratic to a fault, stroll Island Avenue where eccentric boutiques are the norm or explore the quirky Umbrella Cover Museum. Enjoy a personal all-terrain tour on bikes or golf carts, grab flashlights for WW2 bastion Battery Steele’s dark tunnels, or retail therapy where local honey and oysters top the bill. No wonder yacht enthusiasts gather in Peaks for its chilled out mood and celeb-worthy style.

Plum Island

Named after the delicious wild beach plums growing amongst the undulating dunes, Plum Island is a peach. Soak up far-reaching views over ribbons of velvet sand, set alarms to watch sunrise or sunset over the yacht’s bow or try surf casting at Sandy Point. The Parker River zone will not disappoint. It’s complete with wildlife refuge, cycle trails and enough peace and quiet to satisfy the most demanding escapee. Binoculars at the ready, birders will love the Hellcat Marsh Loop trail for insight into the migratory route and nesting habits of esteemed bird life that visits Plum.


A firm favourite, the National Historic Landmark of Nantucket is a classic summer destination. Its gorgeous architecture and cobblestone streets makes for a charming stop during a yacht charter getaway. It is no wonder Nantucket attracts its fair share of famous faces with picture-perfect lighthouses, miles of dreamy sand dunes and around 700 shipwrecks that make for a divers’ nirvana. Close to the friendly Gulf Stream, Nantucket gains an extra 10 degrees of winter warmth, while summer is 10 degrees cooler when compared with mainland barometers.

New England Yacht Charter

Martha’s Vineyard

Martha’s Vineyard, simply put, is idyllic. Famous as the set for epic 1975 movie Jaws, in reality this quaint summer resort is anything but scary. Oozing a stylish laid-back vibe, it is a hub for Insta-worthy snaps framing the eminent clay cliffs in Aquinnah. One of the few organic golf courses in the US, the private Vineyard Club, takes no prisoners across 235 challenging acres. Launch kayaks and paddleboards from your yacht’s garage at Long Cove Bay and discover the heavenly Long Point Wildlife Refuge. Or, lounge on tranquil shores at Lobsterville Beach, where Vineyard Sound’s calm waters offer floating, snorkeling and fishing. Martha’s Vineyard is a must-visit during a private yacht charter off the coast of New England.

New England Yacht Charter

Block Island

Feeling like a world away, Block Island is New England’s southern belle – compact in size but big on character. It’s famous for the robust Southeastern Lighthouse topping the magnificent 250-foot Mohegan Bluffs. You can choose from a staggering 17 miles of pristine sands to languish on island time. Tiki bars emit a cool vibe at Ballards, while seclusion with toe-tingling views at Mansion or family friendly Baby Beach may fit the bill. Don’t leave Block without trying a Mudslide cocktail and a lobster roll – you won’t regret it.

New England Yacht Charter

Thousand Islands

Straddling the US-Canada border, Thousand Islands includes some 1,864 mystical islands. The Thousand Islands in the Saint Lawrence River, Ontario, are home to lighthouses, castles and secluded beaches. Boasting beautiful landscapes, Thousand Islands is a veritable yacht charter haven. Vibrant waterfront stopovers at Brockville and Gananoque are recommended. Delivering activities, a-plenty, try your hand at pike fishing in Eel Bay, an action-packed national park white-water rafting experience or absorb tales of the region’s pirate and bootlegger history regaled by locals.

New England Yacht Charter

Whether you are looking for a family-fun adventure or a delightful escape, New England yacht charter services to these 7 unique islands can make for an ideal summer getaway.


Sarah Clayton-Lea

Co-founder of Big 7 Travel, Sarah created the company through her passion for championing the world's best food and travel experiences. Before her career in digital media, where she previously held roles such as Editor of Food&Wine Ireland, Sarah worked in the hospitality industry in Dublin and New York.

Contact [email protected]

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