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New England Yacht Charter Itinerary

Few sailing destinations in North America are as varied, fun and captivating as New England. Combining history, culture nature, and elegance, a New England yacht charter offers the avid sailor a multitude of experiences. This 10-day itinerary offers a taste of all that is on show along this attractive stretch of sea, and can easily be tweaked to personal preference. It is best suited for motor yachts as sailing yachts would need a bit more time to cover the distance. For Americans, New England is that ‘close to home’ yachting destination no avid sea-lover should miss.


  • Day 1 Newport, RI to Block Island, RI

    From the vibrant and historic ‘sailing capital of the world’ to the chilled-out vibe of Block Island, just 23 miles away, the first day of your New England Yacht Charter itinerary will be anything but bland. Settle into your new home at sea, meet the crew who’ll be your guiding family for the next 10 days and set your sights on Block Island. Beautifully preserved Victorian architecture sets the romantic mood on this island, one you can explore with a rental bike, or on foot, in the afternoon. With hiking trails aplenty, Block Island is a wonderful place to start your land-hopping adventure.

  • Day 2 Nantucket, MA

    Beloved by the rich and famous and renowned as a former whaling hub, Nantucket is a picturesque destination with plenty of cultural and historical sites to explore. Visit the Whaling Museum, meander through the cobblestone lanes of the historic center and cap off the day with a delectable cocktail at Club Car.

  • Day 3 Martha’s Vineyard

    Retrace the steps of former Presidents, actors and celebrities with a stopover at charming Martha’s Vineyard. Check out the brick-lined streets of Edgartown with its boutique shops and exquisite art galleries, ride the world’s oldest platform carousel in Oak Bluffs, bike or hike along the coastline, play a round of golf, paddle a dune lined cove, or simply stroll along one of the many beautiful beaches.

  • Day 4 Provincetown, MA

    Eclectic, artsy and ever-so-trendy, Provincetown is a charming village right at the northernmost tip of Cape Cod. Head down Commercial Street for a spot of shopping and a bite to eat (the blueberry muffins at the Lighthouse spring to mind!) and explore the sandy dunes on an afternoon guided tour.

  • Day 5 Boston, MA

    Surrounded by a bevy of striking islands and offering a wealth of alluring attractions, Boston is the ideal mid-way point of any New England Yacht Charter. With a mind-boggling 40-mile-long continuous waterfront – fantastic for strolling, jogging or bicycle riding – Boston Harbor is, in itself, a great place to explore. Revered for its high concentration of gourmet food trucks (let this be a primary reason you stop!), the harbor front stretch is home to the USS Constitution Museum, the New England Aquarium and wonderful boutiques and excellent bakeries. Barking Crab for lunch will surely delight everyone!.

  • Day 6 Portsmouth, NH

    Overlooking the mouth of the Piscataqua River in New Hampshire, Portsmouth is as attractive as it is interesting. What we (and all guests aboard New England yacht charters) love about this place is the sheer variety of attractions and activities on offer. Even a broody teenager will find SOMETHING fun to do here! From kayaking adventures to whale-watching, golfing, beach-bumming and hiking, to boutique brewery tours, fabulous shopping and even lobster in the rough. Chauncey Creek is our favorite! The Strawbery Banke outdoor museum is certainly worth a visit and younger kids will love the interactive displays at the Children’s Museum.

  • Day 7 Boothbay Harbor, Maine

    With over 500 years of boatbuilding history on its shores, Boothbay is a fascinating place to explore. Not to mention the fact that it is an absolute stunner! Kayak the harbor with seals following in your wake, pay a visit to the 140-year-old Boothbay Shipyard, delight the kids with a visit to the Maine State Aquarium, pop into the gorgeous Abacus Gallery and feast away at Downeast Ice Cream before returning onboard.

  • Day 8 Camden

    Camden is the quintessential northern New England village on your New England yacht charter - home to most of Maine’s windjammer sailing fleet which presents some spectacular Kodak moments. If you’re feeling energetic, hike to the top of Mt Battie for sensational views. If you prefer a more modest stroll, then check out the boutiques, cafés, bars and souvenir shops along Bayview St instead.

  • Day 9 Bar Harbor, Mane

    Often dubbed the prettiest town on the cost of Maine, Bar Harbor is, indeed, a bit of a stunner. As a springboard for tours of the Acadia National Park, Bar Harbor attracts many visitors. Yet you need not venture far from the harbor to thoroughly enjoy it. The seaside shopfronts are pretty as a picture and the whole waterfront promenade is simply wonderful, especially in the evening. Museums, shops, art galleries and restaurants are sure to be vying for your attention. Acadia National Park offers superb hiking and biking as well as horse carriage rides.

  • Day 10 Disembark

    Time to disembark your luxury yacht today…and start planning your next New England yacht charter.

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