This 7- to 10-day loop tour starts in Boston and takes you to the highlights of southern New England: Massachusetts, Connecticut and Rhode Island.
(For northern New England—Vermont, New Hampshire and Maine—see my 6- to 10-day Northern New England Tour.)
Day 1- Pioneer Valley
Drive west from Boston on the Massachusetts Turnpike (I-90) for 90 minutes to Sturbridge for a visit to Old Sturbridge Village. Stay in the area, or continue westward to Amherst or Northampton. Visit Old Deerfield if you have extra time.
Day 2 - Berkshire Hills
Head for the Berkshire Hills. Enjoy a picnic, visit the Norman Rockwell Museum in Stockbridge, and Chesterwood, the studio of sculptor Daniel Chester French, or perhaps the Hancock Shaker Village, and take in an evening performance at Tanglewood, Jacob's Pillow Dance Festival, the Berkshire Theater Festival, or some other cultural venue.
Day 3 - Connecticut Hills
Drive south to Connecticut's Lake Waramaug and Litchfield for a look at this pristine 18th-century town and nearby vineyards. Continue south down the Naugatuck River Valley along CT Route 8 to Derby, then east on CT Route 34 to New Haven for dinner.
Day 4 - Connecticut Shoreline
Explore Yale University and its excellent museums in the morning, and drive east along I-95 to the delightful towns at the mouth of the Connecticut River: Essex, Ivoryton, and Old Lyme. Choose a place for lunch. Continue to New London or Mystic for the night. (If you're starting your tour from New York City, this would be Day 1).
Day 5 - Mystic Seaport
Day 6 - Newport Mansions
If time is short, head for Plymouth to view Plymouth Rock and visit Plimoth Patuxet Museums before heading back to Boston.
If you have a few more days, head for Cape Cod. It's best not to attempt to drive all the way to Provincetown at the tip of the cape today. Choose a town on the "lower cape" or "mid-cape" such as Falmouth or Hyannis for the night.
Day 8 - Cape Cod
Enjoy Cape Cod: tour the Cape Cod National Seashore, lunch on fried clams and french fries, take a swim. If you're in the mood for a circus atmosphere, drive out to the tip for a look at Provincetown. Or, from Wood's Hole or Hyannis, take a day-trip or an overnight excursion to Martha's Vineyard or Nantucket (going by plane will save time).
Day 9 - Nantucket & Martha's Vineyard
Day 10 - South Shore
Head back to Boston along the South Shore of Massachusetts Bay, stopping at Plymouth for a look at Plymouth Rock, the Mayflower II, and a few hours at Plimoth Patuxet Museums.