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Like any big city, it’s hard to see all that Boston has to offer in a day, but that doesn’t mean you can’t get a good feel for the sights and sounds of one of America’s oldest cities. Start off across the river in Cambridge with a quick walk through Harvard Square to see a crossroads of elite education, local characters, tourists and street musicians. Revel in the quiet of Harvard Yard behind Harvard University’s brick facades, browse through international headlines at the famed Out of Town News or grab a cup of joe at one of the square’s indie coffee shops. From there, head back to Boston proper for a stroll along the 2.5-mile Freedom Trail, which winds past 16 of Boston’s most historic sites. The Paul Revere House and Faneuil Hall are still top draws, but a favorite stop is the last,the Bunker Hill Monument, with its museum and outdoor lights that illuminate the monument.
If you need to whet your whistle along the way, duck into the Bell in Hand, America’s oldest continuously operating tavern, for a quick pint. Nearby Quincy Market makes a nice stop for lunch. Then spend the afternoon at the Institute of Contemporary Art, admiring the architectural magnificence of this daring design feat. (The art inside isn’t so bad either.) Make a stop at the style emporium Louis Boston, located near the ICA on Fan Pier, where you can refresh your wardrobe or pick up a one-of-a-kind find for your home. End your day in the Italian North End, where you will encounter tastier pasta than even your Nonna can make. Swing by Mike’s Pastry for an after-dinner treat before collapsing in your hotel room.
Get up early, and tie up your walking shoes. Take a boat to Charlestown and start at the Bunker Hill Monument, and follow the Freedom Trail back into downtown Boston. When The Freedom Trail ends at Boston Common, walk across the Common, and the Boston Public Garden, to Newbury Street. Or if you prefer not to walk, take either the Boston Duck Tours or Old Town Trolley, and relax while one of the entertaining and knowledgeable guides narrates the history of the city and its sights. There are also many private tour companies that with do custom tours of the city for guests.
In the morning, walk the Freedom Trail. Step back in time on the 2.5-mile red brick path that passes the city’s most famous historic sites such as Faneuil Hall, the Paul Revere House, the Bunker Hill Monument and the USS Constitution.
In the afternoon, take on Newbury Street. Lined with stores, galleries and restaurants, Newbury Street is a shopping Mecca and must-see destination. Afterward, venture to Charles Street in quaint Beacon Hill to browse the unique shops followed by a sweet treat at Isabella’s Curly Cakes. Be sure to snap a photo on the city’s most picturesque street, Acorn Street.
In the evening, experience the North End. Savor mouthwatering Italian cuisine in Boston’s oldest and most vibrant neighborhood. Finish the meal with an old world Italian dessert at Mike’s or Modern Pastry.