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Historical Boston in 3 Days: Freedom Trail to Fenway Park Itinerary

Last updated: 2024 Jun 14

Revolutionary Beginnings in Boston

Morning

Start your historical journey with a breakfast at the iconic Mike's Pastry in the North End. Afterward, immerse yourself in the rich history of the city with a visit to the Boston Tea Party Ships & Museum.

Afternoon

For lunch, savor the seafood at Legal Sea Foods near the waterfront. Then, join a guided walking tour of the Freedom Trail, where you will see landmarks like the Massachusetts State House, Granary Burying Ground, and the Old North Church.

Evening

Conclude your day with a dinner at Union Oyster House, the oldest continuously operating restaurant in the U.S. Afterward, take a Boston Harbor Sunset Cruise to enjoy the city lights from the water.

Bedtime

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4.22
Boston Tea Party Ships & Museum
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4.85
Freedom Trail
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A Day of Learning and Exploration

Morning

Enjoy a hearty breakfast at The Capital Grille before delving into the academic side of Boston. Visit Harvard University in Cambridge, including the Harvard Museum of Natural History and take a student-led tour of the campus (Cambridge Explore Harvard University on a Student-Led Tour).

Afternoon

For lunch, experience the local favorite, Santarpio's Pizza, known for its delicious pies. Afterward, head back to Boston and explore the Museum of Science or take a Boston Duck Tour for a unique perspective of the city.

Evening

Dine at the elegant L'Espalier for a fine dining experience. Conclude your day with a Boston Harbor Champagne Sunset Sail for a touch of luxury.

Bedtime

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3.80
Harvard Museum of Natural History
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4.57
Cambridge Explore Harvard University on a Student-Led Tour
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From Patriots to Red Sox: Boston's Sporting History

Morning

Start your day with a breakfast at Neptune Oyster in the North End. Then, take a guided tour of the historic Fenway Park (Boston Fenway Park Guided Ballpark Tour).

Afternoon

Enjoy a lunch at Row 34 in Fort Point. Afterward, visit the John F. Kennedy Presidential Library and Museum to learn about the legacy of the 35th President of the United States.

Evening

Conclude your trip with a dinner at Top of the Hub, where you can enjoy panoramic views of the city. If time allows, catch a Red Sox game at Fenway Park or simply take a leisurely walk around the historic neighborhood.

Bedtime

Find amazing hotels in Boston, Massachusetts.