Day 1: Morning
Begin your trip at the visitor information center on Boston Common near Tremont Street and follow the Freedom Trail.On this first section, you'll see the State House , Granary Burying Ground , King's Chapel , Old South Meeting House and Old State House . These are fun places to go when in Boston if you want to get a taste of the city's rich history.
Day 1: Afternoon
Stop at Faneuil Hall , a Georgian-style building donated to the city by a wealthy merchant in 1742. So many fiery gatherings denouncing British rule were held here that it is often called “the Cradle of Liberty.” At the top of the hall's bell tower stands its iconic gilded copper weather vane, which is in the shape of a grasshopper. During the Revolutionary War, suspected spies were asked to identify the object atop Faneuil Hall; those who couldn't name this easily recognizable landmark (easily recognizable for a Bostonian, at least) were reputedly convicted of espionage.
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Today, Faneuil Hall is part of a bustling marketplace that includes designer shops and pushcarts displaying handmade crafts and souvenirs. If you're not in the mood to shop, enjoy the jugglers, puppeteers and street performers. Take your pick of places to eat including the casual tavern The Black Rose. You also can take your pick from the casual food stalls of the Quincy Market Food Colonnade. Or, walk to nearby restaurants like Union Oyster House , open since 1826. Ask for the private Kennedy Booth, where then-Senator John F. Kennedy sat on many a Sunday afternoon, poring over newspapers and savoring mouthfuls of lobster stew.
After you've grabbed lunch and a few souvenirs, continue along the Freedom Trail, passing the Paul Revere House , Old North Church and Copp's Hill Burying Ground in the North End.
Day 1: Evening
You'll find no shortage of local restaurants serving Italian food in the North End. One of the oldest restaurants in the neighborhood is the casual and charming Cantina Italiana , a favorite since 1931. Upscale Mamma Maria features five romantic and private dining rooms. The Daily Catch only has 10 tables, but it's worth the wait for some of the freshest Sicilian-style seafood in town.
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After dinner, join the parade of people, muscle cars and motorcycles on Hanover Street, the North End's main thoroughfare. Then, laugh 'til your sides hurt at Improv Asylum , where a troupe of talented actors leaves audiences in stitches with an energetic mix of sketch and ad-lib comedy.
Day 2: Morning
Stroll through the botanical beauty of the Public Garden and ride a swan boat around the lagoon (the swan boats typically operate from late June through Labor Day). Stop to take your picture outside Cheers Beacon Hill , on the north end of the lagoon, where exterior shots for the long-running TV sitcom were filmed.
Day 2: Afternoon
Your travel plans should include exploring the cool wonders of the New England Aquarium on the waterfront at Central Wharf. Highlights include a colony of African and rockhopper penguins, a rare collection of Australian seadragons and an outdoor home for harbor seals. For a behind-the-scenes look, sign up for one of the animal encounter programs, which let you meet aquarium stars like Myrtle the green sea turtle and shadow members of the staff during feeding and training sessions. It shouldn't be surprising that this tops the list of fun things to do when visiting the aquarium.
Day 2: Evening
If you're visiting Boston for a summer (June to September) vacation, take a sunset sail aboard the 125-foot Liberty Clipper. This beautiful vessel from The Liberty Fleet of Tall Ships departs from Long Wharf for a cruise around the islands of Boston Harbor; weekend trips range from a Sunday brunch cruise to a re-creation of the Boston Tea Party.If you prefer to stay on land, Long Wharf boasts one of the city's most popular seafood restaurants with beautiful views of the waterfront: Legal Sea Foods.
Day 3: Morning
Take the subway (the “T”) across the river and explore the hallowed ground of Old Cambridge , which includes the 1761 Christ Church, the 1759 Longfellow House and Harvard University , the oldest institution of higher learning in the country, founded in 1636. Among the university museums' many hidden treasures are the glass flowers at the Harvard Museum of Natural History .Casual eateries such as Spicies Thai Street Food & Noodles and Oggi Gourmet surround Harvard Square, where you can rub elbows with the locals and watch a speed-chess game.
Day 3: Afternoon
Spend the afternoon with Monet, Picasso and Whistler at the Museum of Fine Arts, Boston . If you still have time (and energy), the Venetian-style palazzo of the Isabella Stewart Gardner Museum is two blocks away. For an art alternative, take the kids to the Museum of Science , one of the city's fun travel sites which is surprisingly fun for adults, too.