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Boston's History, Food, and Culture in 5 Days

Boston's History, Food, and Culture in 5 Days Itinerary

Last updated: 2024 Jun 14

Historic Boston and Culinary Delights

Morning
Start your day with a delightful breakfast at Mike's Pastry, known for its famous cannolis. Afterward, immerse yourself in history with a visit to the Boston Tea Party Ships & Museum.
Afternoon
For lunch, savor the seafood at Legal Sea Foods. Afterward, take a guided tour of the iconic Fenway Park, home of the Boston Red Sox.
Evening
In the evening, enjoy a fine dining experience at O Ya, a renowned Japanese restaurant, followed by a leisurely walk in the historic Boston Public Garden.
Bedtime
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Boston Tea Party Ships & Museum

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Fenway Park

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Freedom Trail and North End Gastronomy

Morning
Enjoy a classic Boston breakfast at Union Oyster House, the oldest restaurant in the city. Then, embark on a guided walking tour of the Boston Guided Walking Tour of the Freedom Trail.
Afternoon
For lunch, indulge in Italian cuisine in the North End with a food tour from Boston's North End Secret Food Tour. Afterward, visit the Paul Revere House and the USS Constitution.
Evening
Dine at Neptune Oyster, known for its fresh seafood, and take a leisurely evening stroll in the historic Granary Burying Ground.
Bedtime
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Boston's North End Secret Food Tour

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Harvard and MIT Exploration

Morning
Start your day with a hearty breakfast at The Capital Grille. Then, take a student-guided walking tour of Cambridge Harvard University.
Afternoon
For lunch, experience the local favorite, Santarpio's Pizza. Afterward, visit the Massachusetts Institute of Technology (MIT) and explore the Kendall Square area.
Evening
Enjoy a sophisticated dinner at L'Espalier, a French-inspired restaurant, and take a relaxing walk along the Charles River.
Bedtime
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Salem Witch Trials and Haunted History

Morning
Have a spooky breakfast at No. 9 Park, known for its elegant cuisine. Then, take a day trip to Salem and explore the Salem Witch Museum and the Salem 1692 Witchcraft Trials Walk.
Afternoon
Enjoy a unique lunch experience at Giacomo's Ristorante, a local favorite. Afterward, continue your exploration of Salem with the Salem Secrets of Salem Hidden History Walking Tour.
Evening
Conclude your day with the Salem Boos and Brews Haunted Pub Crawl for a mix of history and local spirits.
Bedtime
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Culinary and Cultural Farewell

Morning
For your last morning in Boston, enjoy a leisurely breakfast at Mamma Maria in the North End. Then, take a final stroll along the Boston Harbor.
Afternoon
Experience a true taste of Boston with a seafood feast at Row 34. After lunch, visit the New England Aquarium.
Evening
End your Boston adventure with a sunset dinner at Top of the Hub, offering panoramic views of the city, followed by a Boston Harbor Sunset Cruise.
Bedtime
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