Kick start your New England holiday in Boston, the leafy, walkable capital of Massachusetts. You’ll be staying at the grand dame that is the Fairmont Copley Plaza at the heart of historic Back Bay, overlooking Copley Square.

From here you can head over to nearby Beacon Hill. Enjoy a stroll around this historic, gas-lit neighbourhood before picking up the Freedom Trail. Winding from Boston Common to the Bunker Hill Monument, this 2.5-mile-long red-brick path will lead you past 16 of the main revolutionary sites – including meeting halls, cemeteries and the church steeple where Paul Revere hung lanterns to warn of the impending British invasion. Otherwise, you can enjoy a visit to the world-famous Harvard University, browse superb galleries and museums and immerse yourself in the city’s thriving culinary scene.

Stay: Three nights at Fairmont Copley Plaza

You’ll now drive south to Cape Cod, checking into Wequassett Resort – an upscale beachfront property overlooking Pleasant Bay and with access to the prestigious Cape Cod National Golf Club.

A hook-shaped peninsula of Massachusetts, Cape Cod is a sought-after summer retreat known for its beautiful sandy beaches and soothing ocean views, quaint villages, seafood shacks and pretty lighthouses. Whale watching (in season) is one of the Cape’s biggest draws, but you can also fill your days with sailing, kayaking, fishing and stand-up paddle boarding along the famed Cape Cod National Seashore. The John F. Kennedy Museum in Hyannis is always worth a visit, whilst the Cape Cod Rail Trail offers you 36 miles of paved bike paths to explore.

Stay: Three nights at Wequassett Resort

Today you’ll make the short ferry ride over to Martha’s Vineyard, transferring to your hotel in the 300-year-old fishing village of Menemsha.

A long-time New England summer colony, this is a place of soft sanded beaches and breezy beach grass, artisan coffee shops and quaint harbour towns, plentiful seafood and brightly painted cottages. Enjoy wandering the narrow streets and upmarket restaurants of Edgartown and marvelling at the glacier-carved cliffs at Aquinnah, making the most of the wonderful fishing, swimming and golfing opportunities on offer.

Stay: Two nights at Menemsha Inn

Today you’ll sail across to the tiny, isolated island of Nantucket, another picture-perfect summer getaway just 30 miles south of Cape Cod. Designated a National Historic Landmark, the main town is comprised of weathered cedar-shingled buildings dating back to before the Civil War, as well as high-end boutiques, cobblestone streets and steepled churches. Nantucket is also considered to be the setting for Herman Melville’s novel Moby Dick.

When not browsing antique shops, dining in outstanding seafood restaurants or lounging on picturesque beaches, be sure to pay a visit to the Whaling Museum to learn more about Nantucket’s fascinating past as a 19th-century whaling hub. The much-photographed Brant Point Lighthouse is another must-see.

Stay: Two nights at White Elephant

Leaving Massachusetts behind, you’ll now cross the border into Rhode Island and the upmarket seaside city of Newport whose yacht-filled harbour famously hosted the America’s Cup sailing regatta a dozen times between 1930 and 1983.

Staying in a landmark Victorian mansion on the waterfront, you’ll be able to head out to admire the glamorous, Gilded Age mansions (the former homes of America’s wealthiest vacationers) lining the streets of Bellevue Avenue. The most famous of these is known as The Breakers, a lavish 1895 mansion fashioned after a Renaissance palace. The Old Colony House, Trinity Church and Fort Adams – the largest coastal fortification in the USA – are also worth visiting. Otherwise, take to the water aboard a historic America’s Cup winning yacht.

Stay: Three nights at Castle Hill Inn, Newport