Unique & Boutique Massachusetts

Days 1-2 Boston  
Arrive into welcoming Boston for a stay at The Boxer, a sophisticated and intimate hotel in the city's downtown. Walk the Freedom Trail as it winds past historic landmarks such as Faneuil Hall.  

Day 3 Boston to Gloucester      
Pick up your car and route via Salem, to visit the Salem Witch Museum, before arriving at Rockport. Base yourself at the Beauport Hotel to explore this lovely fishing village on the picturesque Cape Ann peninsula.            

Day 4 Gloucester to Stockbridge          
Journey west to the hills of The Berkshires, home to pastoral villages and white steeple 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 Nobnocket Boutique Inn, a charming little hotel hidden amongst two acres of beautiful gardens.    

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.