8 Days in Boston & Cape Cod

Best of the City and the Sea

This Boston and Cape Cod itinerary delivers the best of both worlds: rich, complex history of a big city and laid-back coastal living with breathtaking beaches and wetlands.

In Boston you can stroll across the central area in about an hour, and whether you saunter through gracious Beacon Hill or the stately boulevards of Back Bay, the dimensions of the city often seem more European than American. Charles Street’s bookstores, cafés and antique shops recall Paris, while fashionable Newberry Street bears a resemblance to London's posh Mayfair district.

Cape Cod is a 65-mile-long peninsula that extends east from the mainland and curls north, cat-tail like, to form Cape Cod Bay. The islands of Martha's Vineyard and Nantucket are situated off the Cape's southern coast, making them ideal day trips.

Read the full account of our editor’s trip to Boston.

Itinerary Highlights

Our itineraries are for your inspiration. Please contact a travel advisor to customize this itinerary to fit your needs.

  • Explore, shop and dine in Back Bay, North End and Beacon Hill 
  • Visit Harvard University and one of its fine museums
  • Walk the beautiful stretch of beaches and wetlands of Cape Cod
  • Make a day trip of your choice: Martha‘s Vineyard or Nantucket

Trip Overview

Day 1 : Back Bay
Shop, dine and drink in the Back Bay neighborhood
Day 2 : North End
Explore Freedom Trail, Faneuil Hall and Boston Common
Day 3 : Harvard Square
Visit Harvard University and its fine museums
Day 4 : Cape Cod
Stop at the famous Plymouth Rock
Day 5 : Relax at Wequassett
Enjoy a day of pure relaxation back at the resort
Day 6 : Cape Cod National Seashore
Walk a gorgeous stretch of beaches and wetlands
Day 7 : Day Trip
Choose your escape: Martha's Vineyard and Nantucket
Day 8 : Return to Boston
Drive back to Boston for your flight home
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Day 1 : Back Bay

After you settle into your Boston hotel, start your explorations in the Back Bay 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 Copley Square. 

Back Bay neighborhood in Boston
Back Bay neighborhood in Boston

Day 2 : North End

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, with period furnishings and a gorgeous collection of Paul Revere silver.

Continue on to historic Faneuil Hall, once a hotbed of revolutionary activity. The nearby Faneuil Hall Marketplace has 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.

Boston's Public Garden
Faneuil Hall

Day 3 : Harvard Square

Start this morning with highlights of the Museum of Fine Arts, which is home to a dramatic “Art of the Americas” wing, designed by Sir Norman Foster. 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. Spend some time in Harvard Square, and 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.

Beacon Hill neighbhorhood of Boston
Harvard University

Day 4 : Cape Cod

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.

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Wequassett Resort and Golf Club

Located near the historic village of Chatham, this resort contains 120 cottage-style rooms and suites.

Plymouth Rock
Plymouth Rock

Day 5 : Relax at Wequassett

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.

Golf course -
Golf course - - Photo courtesy of Wequassett Resort and Golf Club

Day 6 : Cape Cod National Seashore

Explore 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.

Cape Cod National Seashore
Cape Cod National Seashore

Day 7 : Day Trip

Option 1: Martha's Vineyard

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. Be sure to stop by the tranquil Japanese gardens of Mytoi.

After working up an appetite, have a sophisticated lunch at Alchemy 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.

Sunset over cliffs at Martha's Vineyard
Martha's Vineyard Harbor at sunset

Option 2: Nantucket

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 an hour and is available April 24 through Oct. 15). The wonderfully preserved Nantucket Town has 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 gray shingles.

Whichever day trip you choose, be sure to reserve your ferry tickets in advance.

Nantucket Island
Nantucket Island

Day 8 : Return to Boston

Drive back to Boston, return your rental car at the airport and take your flight home.

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