What to See and Do in Boston and Cape Cod

From centuries-old churches to Revolutionary War landmarks, Boston is a city that prides itself on its history. Add in contemporary institutions like the world-class Museum of Fine Arts-Boston, and you’ve got a well-rounded cultural destination. Meanwhile, less than two hours’ drive southeast of the city, Cape Cod offers a traditional New England seaside experience, where you can dig into an oversized lobster roll or bird-watch from a salt marsh boardwalk.

To make the most of a Massachusetts vacation in just one getaway, check out this guide to experience the historical and cultural charms of the Commonwealth’s capital city and catch some of Cape Cod’s relaxing coastal vibes.

How to Get There

• From Boston Logan International Airport, drive 4 miles west to downtown Boston and about 60 miles southeast to Cape Cod.
• From F. Green Airport outside Providence, Rhode Island, drive about 60 miles northeast to Boston and 70 miles east to Cape Cod.

Boston

Walk on History’s Trail

The self-guided, 2.5-mile Freedom Trail makes it easy to visit the city’s major historical attractions. Park your car in the garage beneath the Boston Common and start exploring the city’s expansive central park by following the red line painted on the ground. Before you exit the park, take the kids for a carousel ride in the center of the Common at Frog Pond. Or when the pond is frozen in the winter, enjoy an hour or two of ice skating with the whole family. After you’ve burned off some energy in the park, stroll along the trail past downtown sights like the 1809 Park Street Church and the historic marketplace Faneuil Hall,. Stop here for a bowl of traditional clam chowder from vendors like Boston Chowda Co.

Next, walk 10 minutes northeast to the North End, the city’s Italian enclave known for winding cobblestone streets and tightly packed houses. Here you’ll find the Paul Revere House and the Old North Church, where Revere is said to have received the “one if by land, and two if by sea” signal before his famous midnight ride. While you’re in the North End, top off your lunch with a cannoli from Mike’s Pastry, a beloved Boston favorite dating back to 1946.  

Finally, follow the Freedom Trail across the Charles River to Charlestown, where you and your kids can climb to the top of the Bunker Hill Monument and walk aboard the docked USS Constitution. The world’s oldest commissioned warship still afloat, the USS Constitution also serves as a museum featuring hands-on exhibits including Forest to Frigate, where you can test your shipyard skills while learning about how the U.S. Navy was born. While you’re there, encourage your little ones to ask the sailors onboard questions as you explore the ship’s deck and below.

Admire Artistic Endeavors

For culture lovers, the city’s top-notch art museums house classic and contemporary collections in striking spaces. The largest, the Museum of Fine Arts-Boston, contains works ranging from Egyptian and Nubian sculptures to an impressive Monet gallery to Jackson Pollock paintings. Just a five-minute walk away is the Isabella Stewart Gardner Museum, which showcases paintings, sculptures and decorative arts in a Venetian-style palace with a serene courtyard.

For a taste of the cutting-edge art scene, drive just east of downtown to the Institute of Contemporary Art-Boston, in the up-and-coming Seaport District. The sleek waterfront museum features innovative visual and multimedia exhibits, back dropped by beautiful views of Boston Harbor. On the first Friday of the month, the museum hosts an evening event full of art, activities, specialty cocktails and dancing. If you’re traveling with little ones, ask for sketching materials at the front desk for them to use during your visit. Or stop by the Holly and David Bruce Visitor Center to pick up a free ICA Gallery Games pack full of engaging, art-related activities for kids.

Where to Stay

For a central home base, stay at Hilton Boston Downtown/Faneuil Hall, which is just a block from the waterfront and close to Faneuil Hall and many of the Freedom Trail attractions. Take advantage of the hotel’s family-fun package, which comes with free breakfast and Wi-Fi for the whole gang.

Upper Cape Cod

Explore the Coastal Outdoors

Drive less than 60 miles southeast of Boston to the Upper Cape for a city escape full of waterfront play and relaxation. Comprised of the towns of Bourne, Falmouth, Mashpee, Sandwich and Woods Hole, this part of Cape Cod generally takes less than 90 minutes to reach by car when traffic is not a factor. However, slow traffic can be common en route to Cape Cod, especially on summer weekends and holidays, so try to leave early or on a weekday if possible.

For an easy and scenic bike ride past charming, historic homes, the paved Cape Cod Canal Bikeway runs about 8 miles along the canal from Buzzards Bay to Cape Cod Bay. You can rent adult and kids bikes by the hour or day at Sailworld Cape Cod in Buzzards Bay, located in Bourne.

From Buzzards Bay, hop on the scenic Old King’s Highway, also known as Massachusetts Route 6A, and drive toward the east end of the canal to Boardwalk Beach in Sandwich. Tip: Exit at Town Neck Road from Route 6A and park for $10 a day in the lot next to Horizons on the Bay restaurant. Admire the white cliffs past Sagamore as you stroll along the boardwalk that leads you over a salt marsh and onto a sandy beach.

Alternatively, take Massachusetts Route 28 south to Falmouth’s crescent-shaped Old Silver Beach, another one of the area’s most popular sandy stretches because of its traditionally warmer waters and views of Buzzards Bay.

For a firsthand look at area wildlife, drive less than 10 miles south of Old Silver Beach to the compact Woods Hole Science Aquarium, featuring seals and touch tanks where the kids can meet marine life such as lobsters, hermit crabs and starfish.

Savor Seafoodland Sweets

A seafood feast is obligatory during any Cape Cod trip. The tucked-away Raw Bar in Mashpee serves massive lobster rolls (sharing is recommended) to pair with cocktails and steamers. In Bourne, the waterfront Lobster Trap is a traditional seafood shack where you can enjoy lobster rolls and fried clams on the patio overlooking the Back River. Or head to the nautical-themed Quarterdeck Restaurant in Falmouth for seafood potpie, fish-and-chips and local scallops.

Polish off the day with fudge or ice cream from Ben & Bill’s Chocolate Emporium in Falmouth. The family-owned business is famous for its butter-flavored lobster ice cream, made with chunks of lobster from a local pound, a common term used to describe the holding area where lobsters are kept prior to their sale. Alternatively, Mashpee’s Polar Cave Ice Cream Parlour dishes out large portions served in house-made, cinnamon-infused waffle cones.

Where to Stay

Spoil yourself in Cape Cod by lodging at the more than 300-year-old Dan’l Webster Inn & Spa in Sandwich. This boutique hotel will charm you with its fireplaces, four-poster beds and large whirlpool tubs. Make sure you also grab a meal — like the duck duo on the chef’s special dinner menu — from the inn’s restaurant, which is recognized as a Distinguished Restaurant of North America, placing it in the top 1 percent of restaurants in the country.