A sample itinerary from the Andrew Harper Travel Office: 8 Days in Boston and Cape Cod, with day excursions to Martha’s Vineyard and Nantucket.
After you settle into your Boston hotel, start your explorations in the Back Bay neighborhood, a sensibly laid-out neighborhood created in the 19th century. Newbury Street has some of the most interesting shopping. Walk two blocks south to tour Trinity Church, a Romanesque-style masterpiece overlooking Copely Square. At dusk, have a pre-dinner cocktail at Top of the Hub, a bar/restaurant that affords panoramic views over the city.
Focus today on colonial-era Boston, starting in the North End, one of Boston’s oldest and most atmospheric neighborhoods. After a cappuccino at Caffé Vittoria on Hanover Street, walk to nearby Old North Church, where two lanterns in the steeple signaled to Paul Revere that the British were coming by sea. His 18th-century house stands a couple of blocks away on North Square, and it features period furnishings and a gorgeous collection of Paul Revere silver.
Continue on to historic Faneuil Hall, a hotbed of revolutionary activity. The nearby Faneuil Hall Marketplace boasts an impressive food market where you can grab a gourmet snack to enjoy in Christopher Columbus Park, surrounded by beautiful views over the marina.
The Freedom Trail leads from Faneuil Hall along streets lined with 18th- and 19th-century architecture to Boston Common, the country’s first public park. If the weather is good, go for a paddle in the lagoon in one of the famous swan boats.
Start this morning with highlights of the Museum of Fine Arts, which recently added a dramatic new “Art of the Americas” wing, designed by Sir Norman Foster. Also be sure to wander through the museum’s impressionist collection. Later, explore the picturesque Beacon Hill neighborhood, with its red-brick buildings and cobbled streets. Shop along eclectic Charles Street, generally unmarred by chain stores, and ascend the hill to Park and Beacon streets, where you can view Charles Bulfinch’s imposing State House. After lunching in Beacon Hill, visit Harvard University. After spending some time in Harvard Square, relax at Garden at the Cellar, a popular gastropub. Or if you just need a little snack, indulge in a top-notch ice cream cone at Lizzy’s. You can visit one of Harvard University’s fine museums, such as the Peabody Museum of Archaeology and Ethnology, or head southwest to the Mount Auburn Cemetery, a national historic landmark where you can visit the graves of Winslow Homer, Henry Wadsworth Longfellow and Oliver Wendell Holmes.
Depart Boston by car and drive south toward Cape Cod. Make a stop in Plymouth, home of the famous (if rather unimpressive) Plymouth Rock, where the Mayflower first landed. Nearby, view a full-scale reproduction of the ship.
Farther south you’ll reach Sandwich, the first town on the Cape. Walk along the quaint, oak-lined Main Street and tour the fascinating Sandwich Glass Museum, which traces the history of what was once a vital town industry.
Check into the gracious Wequassett Resort and Golf Club, set on Pleasant Bay in Chatham.
Enjoy a day of pure relaxation back at the resort. Play a round of golf, swim, hit the croquet lawn, stroll on the beach or kayak. Kids can take advantage of a full range of activities in the Children’s Center. For couples, a romantic sunset cruise is in order.
Explore the Cape Cod National Seashore, a gorgeous stretch of beaches and wetlands with a wealth of historic attractions, including picturesque lighthouses and grand 19th-century mansions.
Take the 45-minute ferry from Woods Hole in the nearby town of Falmouth to the delightful island of Martha’s Vineyard. If you’re feeling active, a bicycle ride along the coast is a magnificent way to spend the day. Hikers will want to walk the nature trails in the Felix Neck Wildlife Sanctuary and the Long Point Wildlife Refuge. Also be sure to stop by the tranquil Japanese gardens of Mytoi.
After working up an appetite, have a sophisticated lunch at Alchmey in Edgartown, one of only two communities on Martha’s Vineyard that aren’t dry (Oak Bluffs is the other). Pop into some of the colorful shops in Edgartown. The galleries in artsy Oak Bluffs are also well worth a visit.
Take a ferry back before dusk and return to Wequassett.
Alternatively, take the passenger ferry from Hyannis to Nantucket, an island that grew rich from whaling in the early 19th century (the high-speed ferry takes just an hour and is available April 24 through Oct. 15). The wonderfully preserved Nantucket Town boasts more than 800 buildings that pre-date the Civil War. “It is this concentration of architectural beauty that creates a remarkable and captivating atmosphere of historical continuity,” Mr. Harper notes.
Start with a visit to the fascinating Whaling Museum. After a stroll in the historic downtown, browsing the appealing galleries featuring local art, have lunch at the White Elephant’s Brant Point Grill, which serves some of the island’s best steak and lobster, or Oran Mór, where Mr. Harper enjoyed “a heavenly slow-roasted Atlantic salmon with soba risotto and edamame.”
Before heading back on the ferry, comb one of the magnificent beaches or penetrate the interior, a gently rolling moorland dotted with dark ponds, cranberry bogs and a scattering of traditional cottages clad in distinctive weathered-grey shingles.
Whichever day trip you choose, be sure to reserve your ferry tickets in advance.
Drive back to Boston, return your rental car at the airport and take your flight home.