Island-hopping by yacht in New England

Fair winds, cool culture and untold idiosyncrasies, a New England yacht charter delivers an great opportunity to holiday in style. From tranquil spots on secluded beaches to mouth-watering cuisine in lively townships, this is the trip of a lifetime, wherever you choose you cannot go wrong. The greatest time to visit these coastal isles is between late summer and early autumn, when temperatures mean beach crowds are reduced and dock space for yachts comes easy. With a variety of fantastic yachts cruising this area, a yachting getaway in New England during Covid additionally offers a safe and secure environment to island hop at your leisure.

Chebeague Island

One of Maine’s most attractive islands, the name Chebeague means “isle of many springs” and it is certainly where the crowds aren’t. An invigorating stop on a New England yacht charter, there is no shortage of choices for beach fans, from popular Hamilton to the peacefully isolated Sunset Beach. At low tide explorers can walk the sandbar to uninhabited Little Chebeague where the feeling of detachment at Indian Point is exhilarating. This is an island that inspires relaxation, so breathe the ocean air and enter a little world of paradise.

Peaks Island

Originally residence to Abenaki Indians, pedestrian-only Peaks Island in Casco Bay offers an active stop on a yacht charter, with hiking trails, interesting history and plenty of local colour. Individual to a fault, stroll along Island Avenue where eccentric boutiques are the norm and, it’s true, the Umbrella Cover Museum does what it says on the tin. Conduct a personal all-terrain tour on bikes or golf carts, grab flashlights for WW2 bastion Battery Steele’s dark tunnels and delight in retail therapy, where local honey and oysters top the bill. No wonder yacht enthusiasts gather in Peaks for its relaxed mood and modish style.

Cruising New England on 46m AVALON delivers an excellent opportunity to island-hop at ease. With her ideal layout for the young and young at heart, she has spacious accommodation for 10 adults or 12 with children. Her endless list of water toys and a crew eager to assist, allow guests to enjoy all the fabulous amenities from sun up to sun down whilst visiting fascinating towns along the way.

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 yachts’ bow and try surf casting at Sandy Point. The Parker River zone, complete with fun wildlife refuge, cycle trails and enough peace and quiet to satisfy the most demanding escapee will not disappoint. 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 stalwart summer destination, where elegant 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 fashion a divers’ nirvana. Close to the friendly Gulf Stream, Nantucket gains an extra 10 degrees of winter warmth and boasts 10 degrees less in summer, when compared with mainland barometers.

With her Bohemian chic styling and large scale windows throughout, 33m COOL BREEZE exudes the feel of being aboard a much larger yacht. Cruising at leisure with her professional crew delivering top level service, relish the huge sunpad on the bow, or soak up the sun from the popular top deck. Guests have 3 al fresco dining areas to choose from while your dedicated chef can incorporate the sensational New England produce in an array of bespoke menus during your charter.

Martha’s Vineyard

Martha’s Vineyard, simply put, is idyllic. Notorious by default as the set for epic 1975 movie Jaws, this quaint summer resort is anything but scary. Oozing a stylish laid-back vibe, it is a hub for Insta-worthy snaps framing the famous clay cliffs in Aquinnah. One of 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 to discover the heavenly Long Point Wildlife Refuge or lounge on tranquil shores at Lobsterville Beach, where Vineyard Sound’s calm waters offer floating, snorkelling and fishing.

Block Island

Feeling like a world away, Block Island is New England’s southern belle – compact in size but big on character. Renowned for the robust Southeastern Lighthouse topping the magnificent 250-foot Mohegan Bluffs, choose from a staggering 17 miles of pristine sands to languish on island time. Tiki bars emanate a cool vibe at Ballards, while solitude 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.

Nicholas Dean is Managing Partner of Ocean Independence. Ocean Independence is a global leader in luxury yachting, providing a bespoke experience across yacht charter, sales and management.

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Comments (11)

  1. Jeff G says:

    Vaccinations are going on at a pace in both USA and U.K. I can see some sort of air corridor opening up between the two countries fairly soon. Being on a yacht and island-hopping off the New England coast would be some way to return to international travel.

    • Nicholas Dean says:

      We are definitely finding that travel by yacht has become a very popular holiday thanks to the safety and seclusion on offer. This spectacular area is perfect to explore from the water.

  2. Sally Arnold says:

    I didn’t even know that there were islands off the New England coast. They look really appealing. I always learn something from A Luxury Travel Blog.

    • Nicholas Dean says:

      Pleased you enjoyed this feature. It is just a small snippet of detail about a lovely part of the world, well worth exploring by yacht!

  3. Maggie says:

    Nantucket is the place where I would moor up. I’m no good with extremes of temperature. In summer heat I frazzle and in winter cold I freeze.

    • Nicholas Dean says:

      Definitely sounds like you can time a holiday perfectly in this area to suit the temperature you enjoy. On board a yacht you can relish the breeze – when on land it can get a little warm!

  4. Peter Ryan says:

    Now that we are finally free of children and mortgages my friends and I often indulge in talk of chartering a yacht between us and sailing the seven seas. Strangely, the Atlantic off New England has never cropped up in our discussions. After reading this I’ll put it on the agenda for our next blue skies / blue seas discussion.

    • Nicholas Dean says:

      There are so many fantastic destinations to choose from it is a difficult selection! These islands are certainly full of beauty and character.
      We would be happy to help with any yachting plans or supply of information to assist you when the time comes.

  5. Giles says:

    We’ve driven along the New England coast. Everyone raves about doing the California coastline from LA to San Francisco, the New England drive isn’t quite that good. I’d be interested in seeing it from out at sea.

  6. Will Stewart says:

    AVALON looks very smart and a nice size. This sounds like a dream trip!

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