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Ultimate New England Road Trip from Boston to New York Itinerary

Last updated: 2024 Jun 14

Historic Boston Exploration

Morning

Start your day with a delightful breakfast at Mike's Pastry, known for its famous cannolis. Afterward, visit the Boston Tea Party Ships & Museum to immerse yourself in the history of the American Revolution.

Afternoon

For lunch, head to Union Oyster House, the oldest operating restaurant in the United States. Afterward, take a leisurely walk through the Boston North End, also known as Little Italy, and enjoy the charming streets and delicious aromas.

Evening

In the evening, have a memorable dinner at No. 9 Park, offering a sophisticated and modern take on Italian and French cuisine.

Bedtime

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4.22
Boston Tea Party Ships & Museum
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4.51
Boston North End
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Iconic Boston Landmarks

Morning

Enjoy a classic Boston breakfast at Myers + Chang, known for its creative Asian-inspired dishes. Then, take a Swan Boat ride in the Boston Public Garden.

Afternoon

For lunch, savor the fresh seafood at Legal Sea Foods. Afterward, explore the Freedom Trail and visit key sites like the Faneuil Hall Marketplace and the Old North Church.

Evening

Dine at The Capital Grille for a fine dining experience with a view of the city. After dinner, take a stroll along the historic North End and enjoy the vibrant atmosphere.

Bedtime

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4.52
Boston Public Garden
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4.59
Faneuil Hall Marketplace
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Cultural Immersion in Boston

Morning

Start your day with a visit to the Museum of Fine Arts and explore its world-class collection. For a quick bite, grab a pastry at Flour Bakery + Cafe.

Afternoon

Have a leisurely lunch at Toro, a popular Spanish restaurant. Afterward, visit the Isabella Stewart Gardner Museum and admire its unique architecture and art collection.

Evening

Enjoy a memorable dinner at Oleana, known for its delicious Mediterranean-inspired dishes and vibrant atmosphere.

Bedtime

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4.65
Isabella Stewart Gardner Museum
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Harvard and MIT Experience

Morning

Indulge in a hearty breakfast at The Friendly Toast in Kendall Square. Then, explore the campuses of Harvard University and Massachusetts Institute of Technology (MIT).

Afternoon

For lunch, try the innovative cuisine at Craigie on Main. Afterward, visit the Harvard Museum of Natural History and the MIT Museum.

Evening

Dine at Eastern Standard Kitchen & Drinks, a classic French brasserie, located near Fenway Park.

Bedtime

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Harvard University
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4.33
Massachusetts Institute of Technology (MIT)
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Maritime History and Local Flavors

Morning

Start your day with a visit to the USS Constitution and the Bunker Hill Monument. For a traditional New England breakfast, head to Paramount Beacon Hill.

Afternoon

Enjoy a seafood feast at Neptune Oyster. Afterward, take a harbor cruise to learn more about Boston's maritime heritage.

Evening

For dinner, experience the local favorite, Santarpio's Pizza, known for its delicious thin-crust pizzas.

Bedtime

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4.74
USS Constitution
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4.36
Bunker Hill Monument
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Literary and Historic Boston

Morning

Begin your day with a visit to the Boston Public Library, a haven for book lovers. For a light breakfast, stop by Tatte Bakery & Cafe.

Afternoon

Have a leisurely lunch at Stephanie's On Newbury, a popular spot for American cuisine. Afterward, walk the historic streets of Beacon Hill and visit the Massachusetts State House.

Evening

Dine at L'Espalier, a renowned French restaurant, to indulge in a memorable fine dining experience.

Bedtime

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Boston Public Library
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Massachusetts State House
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Farewell to Boston

Morning

Enjoy a final breakfast at Flour Bakery + Cafe. Spend the morning shopping on Newbury Street and exploring the Prudential Center.

Afternoon

For lunch, savor the flavors of the sea at Island Creek Oyster Bar. Take a final walk along the Charles River Esplanade before heading to your next destination.

Evening

Depart Boston for your journey to Salem, Massachusetts, to explore its witch trials history and maritime heritage. Stay overnight in Salem.

Bedtime

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