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The road leads finally to the Berkshires, where cultural treasures, historic homes, and wooded landscapes form a contemplative finale. Private experiences, from falconry to contemporary art at Mass MoCA, bring the region vividly to life. Traveling by car and staying in boutique inns along the way, the focus is as much on the journey and local encounters as on the destinations, a thoughtful, grounding close to a road trip defined by discovery, connection, and the timeless rhythms of New England.
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Luxury New England Itinerary
New England: A Road Trip from Coast to Peaks
Shaped by rugged coastlines, forested mountains, and historic towns, this New England road trip unfolds at an easy pace. The route leads from Boston along Maine’s seaports, then inland to the White Mountains of New Hampshire. It continues through Vermont’s Green Mountains and ends in the Berkshires, where culture and nature sit side by side.
Time in Boston provides a dynamic start, with historic neighbourhoods, riverside strolls, and the energy of Fenway Park. From here, the journey unfolds along Maine’s Atlantic coast, visiting lobster boats, oyster farms, quaint towns, and lighthouse-studded headlands. Inland drives through the White Mountains and Vermont’s valleys slow the pace, offering rolling hills, covered bridges, and local farms to explore on foot or by car. Days are shaped by simple pleasures, farm-fresh meals, quiet woodland walks, and moments beside rivers and lakes.
READ MORE +KEY FACTS
PEAK TIME
May to September
PRICE
From GBP £12,690.48 USD $15,990 pp excl. international flights based on 2 adults
IDEAL LENGTH
14 days
FLIGHT TIME
8 hours from London
1 hour and 30 mins from NYC
CURRENCY
US Dollars
LANGUAGE
English
Where you'll go
When to go
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Best time to visit
Good time to visit
Average time to visit
Fenway Park
Fenway Park is the oldest ballpark in Major League Baseball, opening in 1912. One of its most famous features is the “Green Monster,” a 37-foot-high wall in left field that turns routine hits into exciting plays. The stadium is known for its close seating and lively atmosphere, making every game feel personal and full of energy.
Itinerary Highlights
Red Sox Game at Fenway Park
Spend an evening at Fenway Park, one of baseball’s most iconic stadiums. Join the crowd as the Boston Red Sox take to the field in a place full of history and character. The atmosphere is lively and full of local pride. Even if you’re new to the sport, it’s easy to enjoy.
Lobster Boat Experience, Kennebunkport
Head out onto the water with a local lobsterman and see how the trade works up close. Watch traps being hauled from the sea and learn how Maine’s most famous catch is handled. The pace is slow and relaxed, with time to take in the harbour views. It’s a simple, hands-on way to connect with coastal life.
Oyster Farm Visit
Take a short boat ride into the calm waters of Maquoit Bay. Meet a local farmer and learn how oysters are grown and harvested. You’ll try shucking your own and taste them fresh from the sea. Paired with a drink, it’s a laid-back and memorable food experience.
Kancamagus Highway Drive, White Mountains
Spend the day driving one of New England’s most scenic roads. The route winds through forests, over rivers, and past mountain views. Stop often for short walks and hidden waterfalls. It’s a day shaped by nature, with no need to rush.
Farm Lunch in the Mad River Valley
Visit a working organic farm set in rolling green hills. Walk the grounds with the owner and learn how the farm runs. Then sit down to a fresh, seasonal lunch made from local produce. The views stretch across the valley, making it a calm and grounding stop.
Sunset Sail on Lake Champlain
Step aboard a classic schooner and head out as the day winds down. The light softens as you sail across the water, with views of the Adirondack Mountains in the distance. It’s quiet, slow, and peaceful. A perfect way to end the day.
Falconry Experience, Vermont
Meet expert handlers and learn about birds of prey. Then take part in a hands-on session with a trained hawk. Feel the bird land on your arm and watch it fly through the trees. It’s a rare and memorable way to connect with wildlife.
The Berkshires
Spend your time in the Berkshires exploring a mix of art, history, and open landscapes. Visit the Massachusetts Museum of Contemporary Art with a private guide, then take time to explore at your own pace. You can also visit nearby museums, historic homes, or take a walk in the countryside. It’s an easy balance of culture and nature, with plenty of space to slow down.
Itinerary Highlights
Our tailor-made journeys include
- A dedicated Destination Expert who will curate your itinerary from scratch, tailoring it to your preferences + interests
- Private + extraordinary under-the-radar experiences
- Access to the very best guides + experts to bring the destination to life
- Private international airport transfers in destination
- The MyCazLoyd app to view your itinerary offline anywhere, anytime
- 24/7 support whilst travelling
- ATOL protection to give you total peace of mind
Where to stay
Nothing but the best. On this suggested New England itinerary, these are our handpicked, tried-and-tested hotels + lodges.
Boutique Hotel Gallery
Let us plan your perfect trip to the United States
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VIEW ITINERARY +Chat to an expert to start planning your trip
Get in touch with us and one of our travel experts will answer any questions you may have and help create your dream trip.
