New England: A Road Trip from Coast to Peaks

10 days From £11,400pp

ITINERARY HIGHLIGHTS

  • Embark on a leisurely New England road trip through rugged coastlines, forested mountains, historic towns and quintessential rural landscapes.
  • Discover Boston’s rich character, from historic neighbourhoods and riverside walks to the unmistakable energy of Fenway Park.
  • Follow Maine’s Atlantic coast through charming seaports, lobster boats, oyster farms and lighthouse-studded headlands.
  • Journey inland through New Hampshire’s White Mountains and Vermont’s Green Mountains, where covered bridges, local farms and tranquil lakes invite slow exploration.
  • Experience the Berkshires through a blend of culture and nature, with historic homes, contemporary art and memorable private experiences.
  • Stay in characterful boutique inns and embrace the journey itself, connecting with local communities, landscapes and the timeless rhythms of New England.

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
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ITINERARY IN DETAIL

Fenway Park, Boston, Massachusetts, USA

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.

Kennebunkport, Maine, USA

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.

Oysters, Maine, USA

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, New Hampshire, USA

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.

Vermont, USA

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, Vermont, USA

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.

Peregrine Falcon, Vermont, USA

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.

Little River watershed, the Berkshires, Massachusetts, USA

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.

Nothing but the best. On this suggested New England itinerary, these are our handpicked, tried-and-tested hotels + lodges.

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