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Unique & Boutique Massachusetts
From the rolling hills and villages of The Berkshires to the sand dunes and lighthouses of Cape Cod, explore this magical state whilst staying in the region’s most atmospheric hotels and unique inns.
- Style: Fly Drive Holiday
- Duration: 12 days/11 nights
- Starts in: Boston
- The Berkshires
- Martha's Vineyard
Days 1-2 Boston
Arrive into welcoming Boston for a stay at the luxurious XV Beacon, an opulent boutique hotel in the heart of the city. Walk the Freedom Trail as it winds past historic landmarks such as Faneuil Hall.
Day 3 Boston to Rockport
Pick up your car and route via Salem, to visit the Salem Witch Museum, before arriving at Rockport. Base yourself at the historic Emerson Inn to explore this lovely fishing village on the picturesque Cape Ann peninsula.
Day 4 Rockport to Stockbridge
Journey west to the hills of The Berkshires, home to pastoral villages and white steepled churches.
Day 5 Stockbridge
Nestled in the Berkshire Hills, Stockbridge is renowned for its quaint Main Street, antique shops and the Norman Rockwell Museum. It’s also home to the 18th Century Red Lion Inn, a charismatic hotel in the heart of town.
Day 6 Stockbridge to Sturbridge
Drive through Pioneer Valley to the town of Sturbridge where your home for the night is the Publick House Historic Inn, which offers simple but quintessentially quaint New England accommodation. Visit Old Sturbridge Village, the town’s excellent living museum recreates life in the 1800s.
Day 7 Sturbridge to Sandwich
Today head to Cape Cod. This famous peninsula boasts glorious beaches and bags of charm. Founded in 1637, Sandwich is the oldest village on the Cape and is where you’ll find the Belfry Inne. Comprised of a former church and its adjacent buildings, this B&B is as unusual as it is charming and we recommend a stay in one of the rooms in the Abbey.
Day 8 Sandwich to Martha’s Vineyard
Take the car or passenger ferry over to the endearing island of Martha’s Vineyard. It’s just a short walk from the port to Mansion House, a lovely little hotel with a roof top terrace overlooking the harbour.
Day 9 Martha’s Vineyard
Discover the island’s beaches, lighthouses and idyllic villages by car, bicycle or local bus. Dine on the fresh lobsters, oysters and clams that the region is famed for.
Day 10 Martha’s Vineyard to Chatham
Catch the ferry back to the mainland and drive to Chatham, arguably the Cape’s prettiest village. Enjoy a stay at the friendly Queen Anne Inn which is decorated with Victorian furnishings.
Day 11 Cape Cod
Unwind on one of Chatham’s beaches or head north to the magnificent sand dunes of the Cape Cod National Seashore.
Day 12 Chatham to Boston
Enjoy one last tasty lobster roll before heading to Boston for your flight home.
per person (based on 2 adults sharing a room)
- 10 days Alamo Inclusive Compact car hire including 24 hour Roadside Assistance and no surprise compulsory charges on pick-up
- Ferry between Woods Hole & Martha’s Vineyard
- 11 nights 3★ boutique to 5★ boutique accommodation
- 5 breakfasts
- International flights
Please Note:Due to the seasonal nature of tourism in the coastal regions of Massachusetts, we recommend this itinerary for travel between late May - mid Sep. Outside of these months attractions and restaurants may be closed or operating a reduced service.
New offers every day
As we can offer you such a flexible choice of flights, we don't include international airfares with our tour prices. The price you pay will be determined by the time of year you travel, your departure airport, airline and availability.
However, to give you a general idea of prices, flights to Boston currently cost from £382 in Economy, £662 in Premium Economy and £1,406 in Business Class
Your Trailfinders travel consultant will be able to find the best flights to suit you and your choice of tour. Please call for our latest offers.
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