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.)
If you're starting this tour from New York City, begin at Day 4, heading east along the Connecticut shoreline, and end on Day 3, heading south back to New York.
Here are tips on renting a car in New England.
Day 1- Pioneer Valley
Drive west from Boston on the Massachusetts Turnpike (I-90) for 90 minutes to reach the Connecticut River Valley, noted for its early settlers (pioneers), including the birthplace of renowned nurseryman Johnny Appleseed. Visit Old Sturbridge Village. Stay in the area, or continue westward to Amherst or Northampton to visit any of the five colleges and universities, Springfield and its museums, and/or historic Old Deerfield.
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 of the Boston Symphony Orchestra at Tanglewood, Jacob's Pillow Dance Festival, the Berkshire Theatre 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—New Haven pizza is famous!—and overnight.
Day 4 - Connecticut Shoreline
In New Haven, 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: Guilford, 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
Visit Mystic Seaport Museum or, if you prefer, the US Coast Guard Academy and Navy Submarine Base. Spend the night in Mystic, Stonington, or the casinos (Foxwoods and Mohegan Sun).
Day 6 - Newport Mansions
Drive to Newport RI to tour the fabulous mansions along Bellevue Avenue, ride bicycles along Ocean Drive, amble along Cliff Walk, do some shopping, and enjoy an excellent seafood dinner.
Day 7 - Plymouth & Cape Cod
If time is short, head for Plymouth to view Plymouth Rock and visit Plimoth Patuxet Museumsbefore 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 active, artsy 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).
Village Green & statue of Iyannough, Hyannis, Cape Cod MA.
Day 9 - Nantucket & Martha's Vineyard
Continue your explorations of Cape Cod, Martha's Vineyard or Nantucket.
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.
