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Roam Around

4 Days Exploring Boston's Vibrant City Life Itinerary

Last updated: 2024 Jun 14

Historical Landmarks and Gardens

Morning

Start your day with a visit to the Boston Common, the oldest city park in the United States. Enjoy a leisurely stroll through its beautiful landscapes and historic monuments. For breakfast, head to Tatte Bakery & Cafe for some delicious pastries and coffee.

Afternoon

In the afternoon, explore the Freedom Trail, a 2.5-mile-long path that passes by 16 significant historical sites. Make sure to stop by the Granary Burying Ground along the way. For lunch, dine at Neptune Oyster, known for its fresh seafood and famous lobster rolls.

Evening

End your day with a visit to the Boston Public Garden, America's first public botanical garden. Afterward, enjoy dinner at No. 9 Park, offering exquisite French and Italian cuisine.

Bedtime

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Boston Common
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Freedom Trail
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Exploring Back Bay and Fenway Park

Morning

Start your morning with a walk around Back Bay, known for its Victorian brownstone homes and upscale shopping on Newbury Street. Enjoy breakfast at The Friendly Toast for hearty American fare.

Afternoon

In the afternoon, take a tour of historic Fenway Park, home of the Boston Red Sox. Afterward, have lunch at Bleacher Bar located inside Fenway Park itself for an unforgettable dining experience.

Evening

Conclude your day with some shopping at Copley Place, an upscale shopping mall in Back Bay. For dinner, enjoy Spanish tapas at Toro Boston.

Bedtime

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Back Bay
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4.19
Fenway Park
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Charlestown Navy Yard and North End Delights

Morning

Begin your day by visiting the historic naval yard at Charlestown where you can see the famous warship at the USS Constitution. Have breakfast nearby at The Paramount Beacon Hill known for its classic American breakfasts.

Afternoon

Spend your afternoon exploring Boston's North End neighborhood starting with a visit to the iconic Paul Revere House. Enjoy lunch at one of Boston's best Italian restaurants: Mamma Maria.

Evening

Wrap up your trip with a stroll through Quincy Market followed by dinner at seafood haven Row 34.

Bedtime

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USS Constitution
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Paul Revere House
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Cultural Immersion in Cambridge

Morning

Begin your day with a trip to Cambridge to visit the prestigious Harvard University. Don't miss seeing the iconic John Harvard Statue. Grab breakfast at Flour Bakery & Cafe nearby for some mouth-watering treats.

Afternoon

Spend your afternoon exploring Harvard Square, a bustling area filled with shops, cafes, and street performers. Have lunch at Giulia, an Italian restaurant known for its handmade pasta.

Evening

In the evening, visit the fascinating MIT Museum which showcases innovations in science and technology. For dinner, head back to Boston and dine at Myers+Chang, offering Asian-inspired dishes.

Bedtime

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