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Roam Around

5 Days Exploring Boston Itinerary

Last updated: 2024 Jun 14

Historic Boston Highlights

Morning

Start your day with a visit to the iconic Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 significant historic sites. Begin your exploration at the Boston Common, the oldest city park in the United States.

Afternoon

After a morning of walking, head to Faneuil Hall Marketplace for lunch and some shopping. This historic marketplace offers a variety of food stalls and shops. Post-lunch, visit the Boston Massacre Site and learn about this pivotal event in American history.

Evening

In the evening, enjoy dinner at a nearby restaurant such as Union Oyster House, one of America's oldest restaurants. After dinner, take a leisurely stroll through Beacon Hill, known for its charming streets and historic homes.

Bedtime

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Academic and Cultural Exploration

Morning

Begin your day with breakfast at Tatte Bakery & Cafe in Cambridge before heading to Harvard University. Take a guided tour of this prestigious institution and explore its beautiful campus.

Afternoon

For lunch, stop by Mr. Bartley's Burger Cottage near Harvard Square. Afterward, visit the Harvard Museum of Natural History to see fascinating exhibits on natural history.

Evening

In the evening, dine at Harvest Restaurant in Harvard Square. After dinner, take a walk around Kendall Square, known for its vibrant atmosphere and innovative spirit.

Bedtime

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Revolutionary War Sites

Morning

Start your day with breakfast at The Friendly Toast in Back Bay before heading to Charlestown to visit the Bunker Hill Monument. Climb to the top for panoramic views of Boston.

Afternoon

For lunch, try Warren Tavern in Charlestown. Post-lunch, explore the nearby USS Constitution and learn about its storied history as one of America's oldest naval ships still afloat.

Evening

Return to Boston for dinner at Neptune Oyster in the North End. Afterward, take an evening walk along the waterfront and enjoy views of Boston Harbor.

Bedtime

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USS Constitution
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Artistic and Scientific Discoveries

Morning

Have breakfast at Flour Bakery & Cafe before visiting the renowned Museum of Science Boston. Spend your morning exploring interactive exhibits that captivate visitors of all ages.

Afternoon

For lunch, head over to Cambridge where you can eat at The Hourly Oyster House near Harvard Square. Then visit the fascinating MIT Museum showcasing scientific innovations from MIT.

Evening

Dine at Legal Sea Foods in Kendall Square before attending an evening performance at Boston Symphony Hall, known for its exceptional acoustics and world-class performances.

Bedtime

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Relaxation and Reflection

Morning

Enjoy breakfast at Thinking Cup Cafe near Boston Common before taking a peaceful stroll through Boston Public Garden. Admire its beautiful landscapes and iconic swan boats.

Afternoon

For lunch, try The Paramount on Charles Street. Then head over to Cambridge Common for some relaxation or explore nearby historical sites like Longfellow House (Washington's Headquarters) if time permits.

Evening