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5 Days Exploring Boston

5 Days Exploring Boston Itinerary

Last updated: 2024 Jun 14

Historic Boston Beginnings

Morning
Start your day with a visit to the 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, enjoy a hearty meal at The Friendly Toast, known for its eclectic menu and vibrant atmosphere.
Afternoon
After exploring the Freedom Trail, head over to Boston Common, America's oldest public park. Take a leisurely stroll and enjoy the beautiful scenery. For lunch, stop by Union Oyster House, one of the oldest restaurants in America serving delicious seafood.
Evening
In the evening, visit Faneuil Hall Marketplace for some shopping and entertainment. End your day with dinner at Neptune Oyster, famous for its fresh oysters and seafood dishes.
Bedtime
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Cultural Highlights of Boston

Morning
Start your day with a visit to the impressive Museum of Science Boston. Have breakfast at Flour Bakery + Cafe nearby for some delightful morning treats.
Afternoon
Afterward, make your way to the historic Boston Public Library in Copley Square. Enjoy lunch at The Courtyard Restaurant inside the library for a unique dining experience.
Evening
In the evening, explore the charming neighborhood of Beacon Hill. Dine at The Paramount on Charles Street which offers American comfort food in a cozy setting.
Bedtime
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Seaside and Sports

Morning
Begin your day with a trip to the popular tourist attraction New England Aquarium. Have breakfast at The Thinking Cup which is known for its great coffee and pastries.
Afternoon
After visiting the aquarium, take a walk along Boston's waterfront area before heading over to see an afternoon game or tour at historic Fenway Park. Grab lunch at Bleacher Bar located inside Fenway Park itself.
Evening
Conclude your day with an exploration of Boston's North End neighborhood known as 'Little Italy'. Enjoy dinner at Giacomo's Ristorante which is famous for its Italian cuisine.
Bedtime
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Revolutionary History Uncovered

Morning
Kick off your final day by visiting historical sites such as the Paul Revere House followed by exploring more landmarks along The Freedom Trail including Old North Church. Have breakfast nearby at North Street Grille offering classic American breakfasts.
Afternoon
Continue delving into history by visiting landmarks like Copp's Hill Burying Ground followed by exploring Charlestown Navy Yard where you can see USS Constitution 'Old Ironsides'. Stop by Warren Tavern in Charlestown for lunch; it's one of America's oldest pubs dating back to 1780s!
Evening
End your trip on high note by enjoying dinner cruise aboard Spirit Cruises from Seaport District offering stunning views while dining! Alternatively dine around Seaport District choosing among various eateries like Legal Harborside or Row 34!
Bedtime
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Cambridge Adventures

Morning
Begin your day with a visit to Harvard University. Explore Harvard Yard and see the iconic John Harvard Statue. For breakfast, try Tatte Bakery & Cafe for some delicious pastries and coffee.
Afternoon
Next, head over to MIT Museum to explore fascinating exhibits on science and technology. For lunch, dine at Alive & Kicking Lobsters, known for its lobster sandwiches.
Evening
Spend your evening at Kendall Square, an area bustling with innovation and activity. Enjoy dinner at Legal Sea Foods, renowned for its clam chowder and seafood dishes.
Bedtime
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