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Roam Around

5 Days Exploring Boston Massachusetts Itinerary

Last updated: 2024 Jun 14

Historical Boston Unveiled

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 locations significant to the history of the United States. For breakfast, head to Tatte Bakery & Cafe for some delicious pastries and coffee.

Afternoon

After exploring the Freedom Trail, visit Boston Common, America's oldest public park. Enjoy a relaxing stroll and perhaps a picnic lunch from The Paramount, known for its hearty American fare.

Evening

In the evening, explore Faneuil Hall Marketplace, a vibrant marketplace with shops and eateries. For dinner, dine at Union Oyster House, one of America's oldest restaurants serving classic New England seafood.

Bedtime

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4.54
Freedom Trail
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Boston Common
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Cultural Highlights of Boston

Morning

Start your morning with a visit to the Museum of Science Boston. Enjoy interactive exhibits that are fun for all ages. Grab breakfast at The Friendly Toast nearby for unique breakfast options.

Afternoon

Afterward, head to Boston Public Garden and take a swan boat ride or simply enjoy the beautiful landscapes. For lunch, dine at Parish Cafe which offers creative sandwiches named after local chefs.

Evening

In the evening, explore Back Bay, known for its Victorian brownstone homes and trendy shops. Have dinner at Atlantic Fish Company in Back Bay for fresh seafood.

Bedtime

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Museum of Science Boston
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Boston Public Garden
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Revolutionary Sites and Sounds

Morning

Begin your day with a visit to the historic Paul Revere House. Afterward, have breakfast at North Street Grille which is close by and offers hearty breakfast options.

Afternoon

Continue exploring revolutionary history by visiting Bunker Hill Monument. For lunch, try Warren Tavern in Charlestown which is rich in history itself.

Evening

Spend your evening at Boston Symphony Hall enjoying world-class music performances. Dine before or after the show at Brasserie JO near Symphony Hall.

Bedtime

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Paul Revere House
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4.38
Bunker Hill Monument
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Modern Meets Historical Boston

Morning

Start your final day with a trip to New England Aquarium. Have breakfast nearby at The North Street Grille offering classic American breakfasts.

Afternoon

Explore more of Boston's history by visiting the interactive exhibits at Boston Tea Party Ships & Museum. For lunch head over to Barking Crab offering seafood in an informal setting on Fort Point Channel.

Evening

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New England Aquarium
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Boston Tea Party Ships & Museum
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Cambridge Adventures

Morning

Begin your day with a visit to Harvard University. Explore Harvard Yard and take in the historic architecture. Enjoy breakfast at Henrietta's Table for farm-to-table dishes.

Afternoon

Head over to MIT Museum to explore fascinating exhibits on science and technology. For lunch, try Flour Bakery + Cafe near MIT for some delightful sandwiches and pastries.

Evening

End your day at Kendall Square, known for its innovative atmosphere and dining options. Have dinner at Legal Sea Foods in Kendall Square for fresh seafood dishes.

Bedtime

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