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Roam Around

3-Day Boston Historical and Cultural Adventure Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Boston

Morning

Start your day with a visit to Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 significant historical sites. This trail is perfect for history enthusiasts as it provides a comprehensive overview of the city's rich past. For breakfast, head to Union Oyster House, one of the oldest restaurants in America, offering a delightful mix of traditional New England fare.

Afternoon

After the Freedom Trail, make your way to Boston Old State House, one of the oldest public buildings in the U.S., and learn about its role in American history. Then enjoy lunch at Neptune Oyster, known for its fresh seafood and cozy atmosphere.

Evening

Conclude your day with a visit to Faneuil Hall Marketplace, a bustling market and meeting hall since 1743. Here you can shop, dine, and soak in the vibrant atmosphere. For dinner, dine at Yvonne's, an elegant supper club offering modern American cuisine.

Bedtime

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4.54
Freedom Trail
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4.48
Boston Old State House
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Cambridge and Revolutionary History

Morning

Begin your second day with a trip across the Charles River to Cambridge. Start at Harvard University for a guided tour of this prestigious institution. Enjoy breakfast at Legal Sea Foods nearby.

Afternoon

Next, visit Longfellow House (Washington's Headquarters), which served as George Washington's headquarters during the Siege of Boston. Have lunch at Mamma Maria, known for its authentic Italian dishes.

Evening

Return to Boston and explore Beacon Hill, one of Boston's most picturesque neighborhoods with its narrow streets and historic homes. End your evening with dinner at Oleana, celebrated for its Mediterranean-inspired cuisine.

Bedtime

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4.25
Harvard University
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4.33
Longfellow House (Washington's Headquarters)
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Cultural Immersion in Back Bay

Morning

Start your final day with a visit to Boston Public Garden, America's first public botanical garden. Enjoy breakfast at Myers+Chang, offering an eclectic menu inspired by Asian cuisine.

Afternoon

Head over to Museum of Science Boston for an engaging afternoon exploring interactive exhibits on science and technology. For lunch, stop by Coppa Enoteca for delicious Italian small plates.

Evening

Spend your evening at Boston Symphony Hall, home to one of the finest orchestras in the world. Conclude your trip with dinner at No. 9 Park, renowned for its sophisticated French and Italian-inspired dishes.

Bedtime

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