• Day 1

    ​Outbound international flight to Boston

    Stay: Four Seasons Hotel Boston (3 nights)​​

    Your Stay

    Four Seasons Hotel Boston

    As beautiful and stylish as historic Boston itself, in a fabulous location overlooking this colonial city’s Back Bay and Public Gardens, the Four Seasons puts the city on a hill easily within in your reach.

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  • Days 2-3


    Possibly the prettiest city in North America, today you'll be met by your guide who'll take you to visit Boston's most legendary sites, including the highlights along the Freedom Trail.

  • Day 4

    Boston to Warren, Vermont

    Drive Time: 3 hours | Distance: 186 miles

    If you'd like to break up the drive, a nice little detour is Canterbury Shaker Village (adding an extra 40 minutes to your journey) – a living history museum in one of northern New England's most picturesque settings where you'll get a sneak peek into the life, times and values of this unique community, as well as their extraordinary craftsmanship through a range of tours, programmes and exhibits.

    Stay: The Pitcher Inn (2 nights)

    Your Stay

    Pitcher Inn

    The belle of Main Street and the epitome of Vermont: Pitcher Inn is peaceful, simple and sumptuously beautiful (particularly in Autumn), with eclectically-themed accommodation that weaves together tales of Vermont's history.

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  • Day 5


    Get ready to explore the charming village of Warren, and one of the most beautiful parts of Vermont, with 350,000 acres of wilderness on its doorstep. It's location – the incredible Mad River Valley – is well-known for some of the best skiing in the East come winter, and come summer reveals and a host of history, culture and a hyperlocal food scene.

  • Day 6

    Warren to Lenox, Massachusetts

    Drive Time: 3 hours, 10 minutes | Distance: 155 miles

    The drive from Warren to Lenox is one of the most beautiful in North America, and if you have time to spare, we highly recommend a visit to Hildene, The Lincoln Family Home and a little-known yet well-preserved piece of American history in the scenic village of Manchester (well worth the additional 30 minutes' journey time).

    Stay: Wheatleigh, Lenox (2 nights)​

    Your Stay


    An Italian palazzo–style mansion nestled on 22-acres, close to the charming neighbouring towns’ unique galleries, shops and museums. And come autumn, it's the most spectacular base for enjoying the region's world-famous fall foliage.

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  • Day 7


    The cultural heart of the Berkshires and famed for its rural beauty, and major cultural attractions (Tanglewood – the summer home of the Boston Symphony Orchestra; the international campus of Shakespeare and Company; The Berkshire Scenic Railway Museum; and Pulitzer Prize-winning novelist Edith Warton's gorgeous home, The Mount) – all of which draw visitors from New York, Boston and beyond each year.​​

  • Day 8

    Lenox to Morris, Connecticut

    Drive Time: 1 hour, 15 minutes | Distance: 51 miles

    Today's drive is just a short one, from Lenox to Winvian Farm in Morris Connecticut, surrounded by the largest nature and wildlife sanctuary in the state.

    Stay: Winvian (2 nights)​​

    Your Stay


    One hundred and thirteen acres of heaven on earth, with days as active, or as idle, as you wish. Each ultra-comfortable cottage has its own playful story to tell… but the best part? The unique seed-to-table cuisine.

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  • Day 9


    Winvian is a great place to relax, catch your breath, and recharge. Walking straight from your cottage, you'll find miles of trails for hiking, biking, horse-riding, snowshoeing and cross country skiing.

  • Day 10

    Morris to Newport, Rhode Island

    Drive Time: 1 hour, 55 minutes | Distance: 105 miles

    Rhode Island awaits today, but to see a little more of this stunning area why not stop off in Hartford and visit Mark Twain’s House and Museum, or Wadsworth Atheneum – the nation’s oldest art museum housing over 50,000 extraordinary pieces.

    Stay: Ocean House (2 nights)​

    Your Stay

    Ocean House

    Perched high on the bluffs of Watch Hill, this landmark seaside resort is one of New England's last remaining oceanfront hotels, with an astonishing selection of rooms and suites.

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  • Day 11


    Newport, with its grand Gilded Age mansions, Cliff Walk and other spectacular seaside lookouts was also home to The America's Cup up to 1983, so there's all sorts to see and do. A visit to Fort Adam's State Park – America's largest coastal fortification, best known for its annual summer jazz and folk festivals – is a must.​​

  • Day 12

    ​Newport to Nantucket

    Journey Time: 4 hours, 35 minutes | Distance: 159 miles

    The journey to Nantucket includes a trip on the Hyannis-Nantucket ferry before the short drive to The Wauwinet, your home for the next three nights.

    Stay: The Wauwinet (3 nights)​

    Your Stay

    The Wauwinet

    Escape to this coastal retreat with bay- and ocean-side beaches. Set out on the water aboard a kayak, or explore the island by bike; and in spring and autumn enjoy lobster outings, surfcasting, and cooking demonstrations.

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  • Days 13-14


    Now a fashionable summer resort, with picture-perfect beaches, trendy boutiques, the town of Nantucket was once the whaling capital of the world (albeit for a relatively short period) and boasts the nation's largest concentration of houses built prior to 1850. It’s the only place in the US where the entire town is a National Historic Landmark, so there’s a host of sights and activities to explore, from the Old Gaol (one of America’s oldest surviving jails), to Jethro Coffin House (the town’s oldest building and the sole surviving structure from the island's original seventeenth-century English settlement).​​

  • Day 15


    Depart Boston on your international flight back to London Heathrow​​

Speak to someone who has been there

Zoe has been here. Find out more and begin to plan your trip by getting in touch directly. You can speak to Zoe by calling the number below or by sending a direct online enquiry.

01565 656 000

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