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Bar Harbor, Maine

Discover New England

16-day tailor-made self-drive from £1,610 pp incl. flights

Special offer: Save up to £475pp


Short description

A sight-filled road trip taking in the best of New England from Boston to Cape Cod


  • Discover the beaches and boutiques of Cape Cod and the colourful cottages of Martha’s Vineyard
  • Explore the Newport Mansions of Rhode Island and wander the campuses of Harvard and Yale
  • Travel to New England’s Green Mountains in September and October to see the changing colours of the New England ‘fall’

In Brief

  • 2 Nights Boston
  • 1 Night Kennebunkport
  • 2 Nights Bar Harbor
  • 2 Nights Bretton Woods
  • 1 Night Woodstock
  • 2 Nights Lenox
  • 1 Night Mystic or Westerly
  • 1 Night Newport
  • 2 Nights Cape Cod


Recommended for:
City | History & culture | Natural world | Self-drive

New England is the birthplace of America, filled with rich history, cultural attractions, fascinating cities, scenic villages and outdoor adventures – all within easy reach of Boston's Logan International Airport. On this tailor-made road trip, you'll discover the white-sand beaches and quaint antique shops of Cape Cod, the colourful cottages of Martha's Vineyard and the historic Newport Mansions of Rhode Island. See the town where the Pilgrim Fathers first settled in the winter of 1620, or stroll around the campuses of Harvard and Yale. Dine at dockside restaurants on delicious clam chowder, fresh from-the-sea lobster and blueberry pie. Ooh and aah at New England's breathtaking 'fall' foliage, when the leaves on the trees turn a tapestry of scarlet, gold, purple and orange. Bike, hike, zipline, ski or snowboard in the Green or White Mountains. Swim and sail at Lake Winnipesaukee. Or, watch out for whales on the New England coast.

Day by day itinerary

Days 1-2

From the comfort of your included VIP airport lounge, depart the UK for Boston where you'll transfer to your downtown hotel. The following morning you'll head out into the city to explore the Freedom Trail. Visit Cambridge and Harvard University, shop at Quincy Market or in the upscale boutiques of Newbury Street. Stroll through Beacon Hill with its narrow lanes and townhouses and head to the North End, an Italian neighbourhood full of tempting restaurants and traditional delis.

Stay: Courtyard Boston Downtown/Tremont Hotel (Standard) Fairmont Copley Plaza (Deluxe)

Day 3

Collect your hire car and travel through coastal New Hampshire to the villages of Kennebunk and Kennebunkport, one of Maine's prettiest seaport villages. It's also a favourite of the monied East Coast elite, showcased in elegant sea-facing mansions and residents that include the United States' 41st President, George Bush.

Stay: Nonantum Resort (Standard) The Boathouse Waterfront Hotel (Superior)

Days 4-5
Bar Harbor

Spectacular scenery awaits as you head to Bar Harbor on Mount Desert Island. Home to Acadia National Park, its a region of sparkling lakes and old-growth forest that forms the backdrop to a stunning coastline. The following morning, consider a sunrise hike or drive to the top of Cadillac Mountain, one of the highest points on the eastern seaboard. Explore Bar Harbor with its sidewalk cafes, shops and the 19th century mansions that look out over Frenchman's Bay.

Stay: Bayview Hotel (Standard) Harborside Hotel, Spa & Marina (Superior)

Days 6-7
Bretton Woods

Drive through gorgeous scenery from forests to fields, interspersed with lakes and rivers to the White Mountains. Enter the picture postcard village of Jackson through one of New England's famous covered bridges. On the deluxe option you will stay in nearby Bretton Woods at the fabulous Omni Mount Washington Resort – famed for its history of accommodating, presidents, literary greats and renowned celebrities. For spectacular views, drive to the top of Mount Washington or follow The White Mountains Trail, a designated Scenic Byway that passes many of the areas main attractions.

Stay: North Conway Grand Hotel (Standard) Omni Mount Washington Resort (Deluxe)

Day 8

Travel along the scenic Kancamagus Highway, a former Indian trail that cuts through the White Mountains National Forest. Then, tour the idyllic Lakes District before driving to the Green Mountain State of Vermont. Head to the pretty village of Woodstock where you'll spend the night.

Stay: 506 on the River (Superior) or Woodstock Inn & Resort (Superior)

Days 9-10

Visit the Quechee Gorge, a huge glacial ravine, before driving to the Berkshire Hills in Massachusetts. Perhaps visit the Hancock Shaker Village, near Pittsfield and Lenox, the summer home of the Boston Symphony. The next day is free to explore the area at your own pace – the Pleasant Valley Sanctuary is excellent for hiking, or perhaps recharge your batteries with a picnic at nearby Tanglewood.

Stay: Briarcliff Motel (Standard) Cranwell Spa & Golf Resort (Superior)

Day 11

Travel south to Mystic Seaport, America's largest maritime living history museum and the setting for our Standard-option hotel. Alternatively, continue on to Westerly on the border of Rhode Island and Connecticut. Our Superior hotel, Weekapaug Inn, is situated right on the coast with fabulous cove views.

Stay: Hilton Mystic (Standard) Weekapaug Inn (Superior) 

Day 12

Drive to historic Newport, the summer resort of America's first millionaires. Stroll along Newport's restored waterfront with its many shops and restaurants. Stop for refreshing drink in what is believed to be America's oldest pub, the White Horse Tavern. A tour of the famous Cliff Walk & Ten Mile Drive are other options worth considering, taking in the region's impressive mansions. Several mansions are open daily for tours (except public holidays). See The Breakers, Marble House or Rough Point, the incredible ocean estate of heiress and art collector, Doris Duke.

Stay: Newport Beach Hotel & Suites (Standard) Hotel Viking (Superior)

Days 13-14
Cape Cod

It's a short drive to the sandy beaches and quaint villages of 'the Cape'. Sandwich is the oldest town on Cape Cod and is well worth exploring. Spend the next day at leisure, perhaps visiting Chatham or colourful and artistic Provincetown. Optional whale-watching cruises showcase the region's marine wildlife or simply spend the day relaxing on one of the island's dune-fringed beaches. Be sure to indulge in a seafood dinner – fresh-from-the-pot lobster is an absolute must.

Stay: Ocean Edge Resort & Golf Club (Superior) Chatham Bars Inn (Superior)

Days 15-16

Return to Boston stopping en route at Plymouth, the town where the Pilgrim Fathers first settled in the winter of 1620. Then return your rental car and check-in for your flight back to the UK, arriving on day 16.



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Standard Superior Deluxe

16-day tailor-made self-drive from £1,610 incl. flights


Special Offer

Save up to £475 pp.

Book by: 30 November 2017

Low Season

from £1,610 pp. incl. flights

High Season

from £3,070 pp. incl. flights


  • Complimentary UK airport lounge access
  • Return flights between the UK and Boston
  • 13 days Economy car hire including personalised road book
  • 14 nights accommodation in typically 3-4* (Standard) hotels on a room only basis

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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