Where to Stop on a New England Sailing Trip this Fall

New England is a glorious tourist destination year-round.

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New England is a glorious tourist destination year-round. It has abundant cultural treasures, unique culinary delights and spectacular landscapes, and each characterful area offers something different.

However, fall is when the region really comes into its own. The trees lining the waterways and horizon hills gleam gold, orange and scarlet and you are free to explore largely undisturbed. You can look for yachts for sale in the area or charter a vessel with an experienced crew. Whichever option you choose, prepare to be dazzled by New England this fall.

  1. Newport

Long-time host of the America’s Cup, the famous annual sailing regatta, the Rhode Island city of Newport is a haven for yachts of all shapes and sizes. Its pretty harbour hosts markets, food festivals and seasonal events such as pumpkin parties and Oktoberfest evenings in the fall.

Exploring beyond the harbour is made easy by the hop-on hop-off trolley which is free to ride. The streets are lined with enchanting colonial-era mansions, some of which are museums, charming parks and restaurants specialising in seafood. Further inland, scenic biking and hiking trails, farms and orchards and wineries and breweries await.

  1. Martha’s Vineyard

Just south of Cape Cod – which itself is a specular seaside destination – is the idyllic island of Martha’s Vineyard. Only accessible by boat or (or seaplane), this is a must-visit destination for sailors.

The weathered harbour towns have oodles of charm, colorful houses and an idyllic restful atmosphere. Wander the dramatic cliffs, relax on unspoiled windswept bays and stroll to the end of sandbanks overlooked by decades-old lighthouses.

Nearby is Nantucket, a beloved vacation spot for John F. Kennedy that is today an upmarket island with stylish boutiques and restaurants. The beaches are beautiful with golden sand and deep blue waters and will be almost deserted in October and November.

  1. Boston

No trip to New England would be complete without a stop at Boston, the capital of Massachusetts. This historic city has many cultural treasures to explore including the Freedom Trail, Boston Tea Party Ships & Museum and the Old State House, and is also a hotspot for wildlife with great hiking trails and whale watching just offshore. The fall color is especially beautiful at Harvard which you can tour independently or with a guide.

Sail north to Salem to experience the mystery of this famous community heavily associated with witchcraft. Enjoy some spookiness for Hallowe’en at the Witch House and Witch Dungeon Museum or explore the artefacts at the Peabody Essex Museum.

  1. Arcadia National Park

It’s worth going further north into Maine instead of stopping your sailing trip in Boston. You can sample the best lobster in the world and see spectacular fall foliage at the national parks.

Arguably the most beautiful national park is Arcadia, nicknamed the ‘crown jewel’ of the North Atlantic Coast. The landscape is a dramatic blend of striking, rocky cliffs, rugged tree-lined coastline and small pebbled beaches. Mornings are misty and ethereal but the sunsets are most magical.

Travel Begins at 40

Travel Begins at 40 Editor

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