How to Spend Seven Days in and Around Boston, Massachusetts

Boston is a fascinating place to visit
Boston is a fascinating place to visit | © Sean Pavone / Alamy Stock Photo
Photo of Mark Nayler
18 November 2020

Boston’s central role in the founding of the United States makes it a fascinating place to visit, and seven days will only let you scratch the surface. But in that time, you can get a true taste of what makes Beantown special. To see the highlights of the Massachusetts capital and tour the surrounding area, try this week-long itinerary.

Day 1: Tour Boston’s iconic neighborhoods

Start your Bostonian odyssey with an espresso and cannoli in Little Italy. Otherwise known as North End, this small but lively area is packed with Italian eateries and cafés (Regina Pizzeria’s brick-oven pies are heavenly.)

From there, enjoy a 20-minute stroll to the affluent Beacon Hill neighborhood, where the streets are lined with handsome 19th-century brownstones. Check out Acorn Street, often named the country’s prettiest street.

While here you can also visit Boston Common, America’s oldest public park. This is where the Freedom Trail begins, a 2.5mi (4km) route that takes in 16 key landmarks in the Revolutionary War.

Spend the evening in South Boston’s trendy Seaport area. This once unloved harbor now offers dozens of places to eat and drink, including Mexican sports bar Scorpion and the Envoy Hotel’s sleek rooftop hangout.

Acorn Street is often named the country’s prettiest street | © dmac / Alamy Stock Photo

Day 2: Splash the cash in Boston’s markets

Start your second day at Boston Public Market, an indoor marketplace with a host of artisanal vendors and fresh food. After a bite to eat, pop over the road to Faneuil Hall, an entertainment and shopping complex founded in 1742.

From there, it’s a half-hour walk to the smart shopping avenue of Newbury Street, home to Rick Walker’s – a madcap clothes store selling rock’n’roll cowboy outfits. Other noteworthy stops include Brattle, one of the country’s oldest used-books stores, and Bodega, a streetwear outlet hidden inside a scruffy convenience shop.

Dedicate the afternoon to roaming Boston’s historic burial grounds, starting with the oldest, King’s Chapel, which was founded in 1630. Striking reminders of mortality can also be seen in the Copp’s Hill (1659) and Granary (1660) burial grounds.

Wind up day two in South End, Boston’s premier restaurant district. Celebrated eateries in this attractive neighborhood include upmarket gastropub the Gallows and fish specialist B&G Oysters.

Boston Public Market is an indoor marketplace with a host of artisanal vendors and fresh food | © dbimages / Alamy Stock Photo

Day 3: Tour two of the world’s great universities

Cross the Charles River into the quaint town of Cambridge: it’s about an hour’s walk from Downtown or a ten-minute metro ride from Park Street station. Here, explore the grounds and facilities of two of the world’s top universities, Harvard and the Massachusetts Institute of Technology (MIT.)

At Harvard, current students lead campus tours, taking in key sites such as Harvard Square, a bronze statue of founder John Harvard (rub his left shoe for good luck) and Memorial Hall. The square is a great place to have a rest and soak up the vibe.

From Harvard, it’s a 25-minute walk to MIT, where you can either join a student-led tour or visit the MIT Museum, which showcases the pioneering science, engineering and technology work carried out by its academics.

The Massachusetts Institute of Technology is one of the world’s top universities | © Philip Scalia / Alamy Stock Photo

Day 4: Go island hopping in Boston Harbor

Of the 34 islands and peninsulas that comprise the Boston Harbor Islands, the 105ac (42ha) Spectacle Island is the best for hiking. Its five miles of trails lead to Boston Harbor’s highest point, North Drumlin, from where you can enjoy views of the city.

A little further out from Spectacle is George’s Island, where the main draw is Fort Warren. Built between 1833 and 1861, this sprawling structure helped to protect Boston throughout the American Civil War and both World Wars. It was decommissioned in 1947 and is said to be haunted by the Lady in Black, the ghost of a woman who tried to rescue her husband from its dungeons in the 1860s.

Other harbor islands that are worth a visit (or at least inspection from a passing cruiser) include Little Brewster, home to the country’s oldest lighthouse, and Lovells, a great spot for swimming, sunbathing and camping.

You’ll get gorgeous city views from the Boston Harbor Islands | © DejaVu Designs / Alamy Stock Photo

Day 5: Hike the Blue Hills Reservation

Located 10mi (16km) south of the city, the Blue Hills Reservation offers 125mi (201km) of hiking trails suitable for all ages and levels of experience.

For a short stroll, try the short Dark Hollow Loop, which skirts the base of Tucker Hill, or the undemanding Wolcott and Border Path.

If you’re after a more challenging walk, the 3mi (5km) Skyline Loop takes you to the top of the Blue Hill, the reservation’s highest peak. From its summit, enjoy views of Boston and the surrounding area. Maps of the park’s color-coded trails are available at Reservation Headquarters.

Day 6: Escape the hubbub at Cape Cod and Nantucket

Resembling a giant flexed bicep jutting out into the Atlantic, Cape Cod is 70mi (113km) south of Boston – about an hour’s drive. Although virtually all its eastern coastline is protected, there are several wild and beautiful beaches to explore. Coast Guard, Nauset Light (overlooked by its famous lighthouse) and Marconi are among the most popular.

If you’ve had enough of the beach, the island of Nantucket – formerly the world’s whaling capital – is a 30-minute ferry ride away. Here you can visit the island’s three charming lighthouses, tour the Whaling Museum or eat locally caught fish at French-inspired restaurant Le Languedoc Inn and Bistro.

Nantucket was formerly the world’s whaling capital | © Julian Castle / Alamy Stock Photo

Day 7: Soak up the last bit of city life

Finish where it all began, touring Boston’s neighborhoods. Start at Chinatown, the country’s third-largest. Browse the colorful street markets, or head to China Pearl for delicious dim sum.

Next, stroll north for 25 minutes to reach Back Bay, a community of smart brownstones and glittering skyscrapers. Here lies the Charles River Esplanade, a charming waterfront walk used by the locals for a variety of sporting and fitness endeavors.

End your week dining on the fish and seafood for which New England is famous. Head to Neptune Oyster in North End, where you can tuck into one of the best lobster rolls in Boston.

Boston’s Chinatown is the USA’s third-largest | © agefotostock / Alamy Stock Photo

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