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Home to Revolutionary War history, storied universities and big bowls of creamy clam chowder, Boston is the largest city in New England and acts as a gateway to the region. Compact and easy to navigate on foot or via public transit, the city also boasts the Freedom Trail, a walking path that takes you past important sights from the Revolution.

Even if you aren’t interested in history, though, there’s enough to keep you busy for two or three days here. You’ll find a thriving culinary scene that combines classic regional fare and fusion cuisine.

Boston’s also the country’s foremost intellectual hub, with more than three dozen universities, including prestigious institutions that you can tour, like ivy-covered Harvard and the cutting-edge technological hub of MIT. The large student population supports a vibrant arts culture, as well as many bars and inexpensive eateries.

Revolutionary War history in Boston

Acorn Street, BostonThe Freedom Trail, a well-preserved pedestrian path, weaves in and out of historic areas, from the lively Boston Common and Public Garden to the gold-domed State House.

A red line painted along the ground leads you to important sights relating to the Revolution. Visit the grave of rebels and statesmen at the Granary Burial Ground, see where the first casualties of the war fell in the Boston Massacre and follow in Paul Revere’s footsteps at the Old North Church, commemorated by Longfellow’s poem with the opening line “Listen, my children, and you shall hear/Of the midnight ride of Paul Revere.”

The trail is largely flat and, for the most part, meanders through the small downtown area, making it easy to follow on your own. We can also arrange for a guide, wearing Colonial-era costume, to lead you along the trail while sharing historical titbits. Or, you could take the Old Town Trolley, which provides hop-on-hop-off transportation between the major sights, with commentary.

Sunset cruise in Boston

The city’s location, perched at the mouth of the Charles River where it spills into Boston Harbor, defines much of Boston’s character and history. To get a real feel for the city, we can arrange a narrated sunset cruise along the waterfront. Learn about the Civil War-era fort on the Harbor Islands and the Boston Tea Party as you watch the sun sink slowly behind the skyline and the city’s buildings light up in a twinkling display.

For most visitors, a highlight is having a chance to see the USS Constitution's sunset serenade. You’ll watch as the ship fires its cannon and lowers its flag ceremoniously. Known as Old Ironsides, this is the world's oldest commissioned naval vessel still afloat and a sunset cruise is the only way to see the ship from the water.

Lobster rolls and chowdah: what to eat in Boston

The city’s residents are deeply passionate about their local food (and dropping their ‘r’ sounds, a distinctive accent in the States). Ask any three Bostonians where to get the best lobster roll or bowl of clam chowder and a fourth will interrupt with another opinion.

Boston skylineYou can sample the local seafood at many places across the city. Visit James Hook & Co on the waterfront to get a feel for a classic New England lobster shack. You can enjoy a slightly more elegant style at Legal Seafood (a chain that has several locations across the region) or at Neptune’s in the North End.

In fact, the North End is home to some of Boston’s best food as well as Audley’s North American office, so we know a thing or two about the local cuisine. Over the centuries, the enclave has been home to many waves of immigrants, most recently Italians, and their influence lingers. Try cannoli at Mike’s or Modern, traditional pizza at Regina’s, espresso at Caffe Vittoria and classic dishes at Trattoria Il Panino.

For a look at the city’s cutting-edge cuisine, the Boston Public Market offers an eclectic array of ever-changing booths. You could potentially try banh mi sandwiches, locally caught cod, gourmet doughnuts and award-winning ice cream, all in one visit.

Boston’s colleges and universities

The city boasts three dozen different colleges and universities (the two terms are largely interchangeable in the States), making it the country’s foremost intellectual powerhouse. Many of the schools offer guided walking tours and if you’re interested, we suggest visiting elite Harvard University, which was founded before America was a country.

For a look at cutting-edge technology and some of the region’s most distinctive architecture (including a building by Frank Gehry), consider booking one of the guided tours at the Massachusetts Institute of Technology (MIT), where leading scientists do research and teach the brightest engineering minds in the world.

The multitude of schools gives the city a youthful and energetic atmosphere — and a large number of bars. It also creates a deep intellectual vein that manifests in some exceptional museums, including the Isabella Stewart Gardner Museum, the John F. Kennedy Library and the Museum of Fine Arts.

Best time to visit Boston

Though you can visit year-round, Boston can get very cold, with unpredictable weather between November and March. In the warmer months of July and August, it’s often very hot and humid. You can visit in May and June, when the Boston Public Garden is in bloom and before the American schools let out for summer. The city is also glorious in September and October, when the foliage starts to turn, the days are cool and the nights are crisp.

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Audley Travel specialist Carla

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Suggested itineraries featuring Boston

Our itineraries will give you suggestions for what is possible when you travel in Boston, and they showcase routes we know work particularly well. Treat them as inspiration, because your trip will be created uniquely by one of our specialists.

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    • 90 Minute Boston Harbor Historic Sightseeing Cruise
      Boston Tea Party Ships and Museum

      90 Minute Boston Harbor Historic Sightseeing Cruise

      90 Minute Boston Harbor Historic Sightseeing Cruise

      With this cruise you will be introduced to all the history, sights and lore that Boston Harbor has to offer.

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