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Boston Itineraries
If you have 5 days in Boston, you'll be able to do the complete tour of the city at a leisurely pace, plus venture out to the surrounding towns. Use our itinerary as a guide for how to manage your time to see all the sights without feeling rushed.
Day 1
Walk the Freedom Trail, pausing to shop at Downtown Crossing and Faneuil Hall. After visiting the USS Constitution in Charlestown, catch the water shuttle to downtown. Walk into the North End for dinner.
Day 2
Visit the Museum of Science, and then take a stroll along the Charles and the Esplanade. Spend the afternoon in Cambridge. Hop the T into Kenmore Square for dinner and spend the evening club-hopping on Lansdowne Street. Or, on a more sedate Wednesday, Thursday, or Friday night, spend the evening at the Museum of Fine Arts.
Day 3
Wander through Beacon Hill and explore the Black Heritage Trail. Shop for antiques and trendy accessories on Charles Street. Explore the Boston Common and the Public Garden. Dine in the evening in or near the Theater District, and follow that with a show.
Day 4
Leave the city for Plymouth, to the south, where you can visit Plimoth Plantation and the Mayflower II. If you return to the city in time for dinner, sample one of the South End's gourmet eateries.
Day 5
Walk through Back Bay to marvel at its mansions, with stops at the Boston Public Library and the Gibson House. Stroll along Newbury Street for fine shopping and dinner. When the sun goes down, see the Boston Symphony or the Boston Pops at Symphony Hall, or watch the Red Sox play at Fenway Park.
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