Best of New England
A classic New England trip through charming towns, rugged coastlines, mountain landscapes and vibrant cities from Boston to New York City.
Experience the very best of New England on this enchanting 16-night journey through coastal towns, forested mountains and historic cities. Begin in Boston, where revolutionary stories echo through cobbled streets and harbourfront markets, before discovering the beaches and lighthouses of Cape Cod, the maritime charm of Maine, and the dramatic beauty of Acadia National Park. As you travel inland, New England’s landscapes unfold in rich layers — covered bridges, crystal-clear lakes and sweeping mountain valleys that glow brilliantly during the autumn months.
Your adventure continues through the White Mountains and into Vermont’s peaceful Green Mountain region, where small villages, scenic byways and artisan producers capture the essence of rural New England. Crossing into New York State, you’ll spend three nights exploring the waterfalls, vineyards and glacial lakes that define the Finger Lakes before finishing with two unforgettable nights in New York City. This itinerary strikes a perfect balance of culture, scenery and adventure — a classic American road trip filled with spirit, beauty and timeless charm.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
16 night self drive holiday from £2,699pp including flights, accommodation & car rental
Highlights
Explore iconic regions: From Boston’s revolutionary landmarks to Cape Cod’s beaches and Acadia’s rugged shoreline.
Travel the Kancamagus Highway into the Green Mountains and through the scenic White Mountain National Forest.
Enjoy the charm of Stowe, Bar Harbor, Kennebunkport and other classic New England villages.
Savour the Finger Lakes: Waterfalls, gorges, wineries and peaceful lakeside scenery create a perfect three-night retreat.
Your itinerary
Days 1–3: Boston
Discover one of America’s most historic and walkable cities
Arrive in Boston and settle in for three unforgettable nights in this vibrant and historic coastal city. Wander the lively markets of Faneuil Hall and Quincy Market, follow the Freedom Trail past red-brick landmarks of the American Revolution, and explore the cobbled charm of Beacon Hill. Enjoy harbour views along the waterfront or take a short trip to Harvard University in Cambridge to stroll its atmospheric campus. For a deeper dive into history, the Boston Tea Party Ships & Museum offers a fully immersive, interactive experience that brings one of America’s defining moments to life.
3 Nights in
Boston, MA
Arrive &
Explore
Days 4–5: Cape Cod
Seafood shacks, sandy shores and quintessential coastal villages
Pick up your rental car and make the short journey to Cape Cod, a sun-drenched peninsula famous for its dunes, beaches and maritime heritage. Explore quaint towns like Hyannis and Chatham, visit historic lighthouses, and stroll boardwalks overlooking wide Atlantic bays. Enjoy fresh lobster rolls, wander art galleries, or cycle part of the scenic Cape Cod Rail Trail. If you’d like, we can arrange a Martha’s Vineyard ferry, offering a perfect day trip to one of New England’s most beloved islands, known for its clapboard houses, boutique shops and relaxed seaside charm.
2 Nights in
Cape Cod, MA
90 miles
Day 6: Kennebunkport
A picturesque harbour town with beaches and maritime history
Travel north along the coast and into Maine, arriving in postcard-perfect Kennebunkport, known for its charming streets, art galleries and long sandy beaches such as Goose Rocks Beach. Visit the scenic fishing village of Cape Porpoise, home to the 1833 Goat Island Lighthouse, still guarding the harbour. Wander Dock Square with its boutiques and cafés, try world-renowned Maine lobster, or enjoy a sunset walk along the shoreline. Kennebunkport’s timeless New England elegance makes it a delightful one-night stop.
1 Night in
Kennebunkport, ME
170 miles
Days 7–8: Acadia National Park
Explore the dramatic landscapes and wildlife of Mount Desert Island
Continue north through Maine’s beautiful coastline to Bar Harbor, gateway to Acadia National Park, one of America’s most beloved natural treasures. Spend two nights exploring this majestic landscape where granite peaks meet crashing Atlantic surf. Drive the famous Park Loop Road, walk the oceanfront Thunder Hole, or take in sweeping views from Cadillac Mountain, the highest summit on the eastern seaboard. Wildlife watching is exceptional here, with chances to spot moose, seals, whales and seabirds. In the evenings, Bar Harbor’s boutiques, seafood restaurants and coastal charm create a relaxing and welcoming atmosphere.
2 Nights in
Bar Harbor, ME
200 miles
Day 9: White Mountain National Forest
Covered bridges, mountain vistas and serene wilderness
Head west into New Hampshire’s White Mountain National Forest, known for its brilliant autumn foliage, pristine lakes and dramatic mountain peaks. Stop at scenic viewpoints, walk short forest trails, and discover historic covered bridges tucked among rivers and valleys. The region offers a wonderful mix of tranquillity and natural beauty, with highlights such as the Conway Scenic Railroad, the Mt. Washington Valley, and charming mountain towns that welcome travellers year-round.
1 Night in
N Conway, NH
220 miles
Days 10–11: Green Mountains
Rolling mountains, historic towns and the charm of Stowe
Drive the breathtaking Kancamagus Scenic Byway, one of America’s most celebrated autumn routes, before crossing into Vermont and the idyllic mountain town of Stowe. Spend two nights enjoying its alpine scenery, boutique shops and inviting cafés. Visit local farms and creameries, stroll through covered bridges, or explore trails winding through the Green Mountain National Forest. In autumn the region glows with fiery oranges and reds, while spring and summer offer wildflowers, waterfalls and warm mountain breezes.
2 Nights in
Stowe, VT
130 miles
Days 12–14: Finger Lakes
Waterfalls, Wineries & Lakeside Beauty
Travel southwest through New York State toward the serene Finger Lakes, with a scenic stop in Buffalo to view mighty Lake Erie. Base yourself in Ithaca, home to dramatic gorges, elegant waterfalls and a vibrant college-town atmosphere. Explore Watkins Glen State Park with its rainbow-lit cavern cascades, visit Taughannock Falls, one of the tallest waterfalls east of the Rockies, or enjoy wine tasting along lakeside vineyards renowned for Riesling and cool-climate varietals. With artisan markets, farm-to-table dining and peaceful lakeside views, the region offers a perfect blend of nature and relaxation.
3 Nights in
Ithaca, NY
310 miles
Days 15–16: New York City
The perfect finale in one of the world’s most exciting cities
Your final two nights bring you to New York City, a vibrant metropolis filled with world-famous landmarks and endless energy. Visit the Statue of Liberty, take in sweeping views from the Empire State Building, shop along Fifth Avenue, or stroll through Central Park. Explore neighbourhoods like Greenwich Village, SoHo or Chinatown, visit the Metropolitan Museum of Art, or experience the lights and life of Times Square. Broadway shows, world-class restaurants and atmospheric rooftop bars give you countless ways to spend your evenings. On your last morning, enjoy one final wander through Manhattan before boarding your overnight flight back to the UK — a fitting end to your New England adventure.
2 Nights in
New York City, NY
230 miles
June - mid Sept: Many lodgings and transport links are only open during the Summer. Amazing wildlife including bears, bald eagles, whales, sea otters and seals can be spotted.
Daytime temperatures are usually cool but very comfortabl, generally in the 15-20°C range and even into the high 20s. Days are long during the with July being the peak month.
You’ll need a connecting flght from the UK, probably via Seattle or Vancouver, we highly recommend a couple of days to explore the connecting city. Alaska is 8 or 9 hours behind the UK.
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