Itinerary Highlights
- Experience historic Boston, exploring red-brick streets, harbourfront dining and the echoes of revolutionary history
- Journey along Maine’s rugged coast, feeling the sea mist in Camden and enjoying Acadia’s wild, granite splendour
- Venture inland through Vermont’s rolling countryside, discovering covered bridges, farm stands and the beauty of Woodstock and Stowe
- Uncover the islands of Martha’s Vineyard and Nantucket, where coastal elegance mixes with timeless New England character
- Best time to travel May - October
What's Included
- Accommodation Throughout
- Car Hire
- International Flights
18 nights from £6,899 per person
Nick
Travel Specialist
This all-encompassing suggested fly-drive holiday takes you to five US states. From bustling harbourfronts to windswept headlands, New England beckons with timeless charm and boundless discovery.
Begin in Boston, where red-brick streets and revolutionary history set the tone, and savour clam chowder harbourside before drifting along a coastline of cedar-shingled houses and quaint fishing towns. Feel the sea mist in Camden, take in the salty stillness of Rockland and see Bar Harbor’s granite shores unfurl into Acadia’s untamed splendour.
Inland, Vermont’s emerald countryside rolls into focus with farm stands, covered bridges and the postcard poise of Woodstock and Stowe. Additionally, hop to Martha’s Vineyard for gingerbread cottages and salt-blown beaches or roam Nantucket’s cobbled lanes steeped in seafaring charm.
Across six states, New England unfolds like a story well worth retelling.
Itinerary
Day 1 Fly UK to Boston
Begin your fly-drive holiday with a stay in Boston, a city with plenty of old-world charm and history.
Day 2 Boston, Massachusetts
Start your day with a walking tour along the Boston Freedom Trail, led by a knowledgeable 18th-century costumed guide. For a more in-depth version, upgrade to a private guided tour. The rest of the day is free for you to explore more of Boston, such as the antique shops of Beacon Hill, the shops of Newbury Street and the fashionable area of Back Bay. Perhaps go on a trolley or duck tour of the city and visit some of the great museums, many of which are also great for families.
Staying at
Fairmont Copley Plaza
Upgrade to
Mandarin Oriental Boston
Day 3 Boston to Kennebunkport, Maine (90 miles)
Kennebunkport, Maine
Collect your rental vehicle from the Boston downtown depot and drive north to Maine, stopping off in Kittery to go outlet shopping. Enjoy free time to explore the quaint coastal town of Kennebunkport with its gorgeous long sandy beaches, Seashore Trolley Museum and highly rated restaurants on Dock Square.
Day 4 Kennebunkport to Bar Harbor, Maine (203 miles)
Bar Harbor, Maine
Continue your drive north following the coast to Bar Harbor, the gateway to the mountains of Acadia National Park. There are several attractions along the way, such as Portland, with its attractive waterfront of converted warehouses and working fishing wharves. Rockport and Camden are quaint seaside towns with attractive "Main Streets" and interesting boutiques and eateries, making this an ideal lunch stop before reaching Bar Harbor.
Day 5 Bar Harbor, Maine
Bar Harbor, Maine
Why not start your day with a two-hour Lulu Lobster boat ride? Learn about the local lobster fishing industry and watch seals basking on the rocks at low tide or swimming and playing in the surf at high tide. Then, in the afternoon, you could spend some time exploring Acadia National Park. It’s an outdoor playground with miles of hiking and biking trails, wildlife viewing and fishing opportunities.
Staying at
Harborside Hotel, Spa & Marina
Day 6 Bar Harbor to Mt Washington, New Hampshire (250 miles)
Mt Washington, New Hampshire
Travelling from Bar Harbor to Mt Washington, you’ll pass forests, fields, lakes, rivers and beautiful scenery.
Day 7 White Mountains to Woodstock, Vermont (130 miles)
Woodstock, Vermont
Depart Mount Washington and cross the border into Vermont. For those who love ice cream, take a short diversion to Waterbury Village Historic District with its historically and architecturally distinctive structures. Waterbury is also the home of Ben & Jerry's Ice Cream Factory, where you can take a tour and even have a private VIP experience making ice cream with one of the flavour gurus.
Day 8 Woodstock, Vermont
Woodstock, Vermont
Visit a typical New England village (Stowe) and also if you wish, the Shelburne Museum with its side-wheeler, gardens and Americana feel.
Day 9 Woodstock to Stockbridge, Massachusetts (158 miles)
Stockbridge, Massachusetts
Depart Vermont and drive to Stockbridge, arriving at the Red Lion Inn for your overnight stay. You can explore the area by visiting the Norman Rockwell Museum, which hosts iconic illustrations that capture quintessential American life. There’s also time to wander the Berkshire Botanical Garden, where you can admire seasonal blooms, or enjoy a performance at the Tanglewood Festival.
Day 10 Stockbridge to Washington, Connecticut (53 miles)
Washington, Connecticut
Today, you’ll travel to the town of Washington. Settle into The Mayflower, an elegant retreat renowned for its tranquillity, and enjoy some well-earned relaxation. You could unwind in the luxury spa, enjoy a stroll through the hotel’s manicured grounds, or curl up with a book in the lounge.
Day 11 Washington to Newport, Rhode Island (134 miles)
Head from Washington to Newport. The journey takes you past villages, wooded hills and the serene Connecticut River Valley before reaching the coast. Pause in Old Saybrook or Mystic for a taste of seaside heritage, then continue along the shoreline into Rhode Island. Arrive in Newport, which is home to elegant yachts and grand mansions that line the waterfront.
Day 12 Newport, Rhode Island
The summer resort of America’s millionaires of the past, Newport is home to some beautiful summer mansions as well as stylish shops and restaurants. Several of Newport's Mansions are open to the public, such as The Breakers and Marble House, and can be visited on guided tours.
Staying at
Vanderbilt Auberge Resorts Collection
Day 13-14 Newport to Martha’s Vineyard, Massachusetts (87 miles)
Martha's Vineyard, Massachusetts
Take the ferry from Woods Hole to Martha’s Vineyard. Then check in at Harbor View Hotel, the perfect base for exploring this island for the next two nights. You could discover the dramatic Aquinnah Cliffs Overlook and the windswept beaches beyond. Or, wander the streets of Edgartown, admiring historic architecture and boutique shops. Speak with our Travel Specialists for more ideas.
Day 15-16 Martha's Vineyard to Nantucket, Massachusetts (38 miles)
Nantucket, Massachusetts
Catch the ferry back to the mainland and drive to Hyannis, where you leave your car to take the ferry to Nantucket and settle into White Elephant Hotel, ideally located so you can explore the island for the next two nights. Stroll the cobbled streets of the main town, admiring classic New England architecture. Or, you can rent a bicycle to discover quieter corners. Coskata-Coatue Wildlife Refuge is another excellent addition.
Day 17 Nantucket to Cape Cod, Massachusetts (30 miles)
Take the ferry to Hyannis and drive to Chatham Bars Inn for the final two nights of your journey. Cape Cod provides relaxation and exploration: lounge on pristine white-sand beaches, breathe in the salty sea air and experience a whale-watching cruise to witness magnificent marine life.
Day 18 Cape Cod, Massachusetts
Visit the pretty town of Chatham and the alternative Provincetown, also known as P-Town.
Staying at
Chatham Bars Inn
Day 19 Cape Cod to Boston (75 miles) & Departure
In the morning, drive to the Plimoth Plantation to learn about 16th century life in this living museum and then travel onwards to Boston for your flight home or extend your holiday further in Boston.
Nick
Travel Specialist
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18 nights from £6,899 per person
