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Roam Around

Ultimate 20-Day Northern USA Road Trip from Boston Itinerary

Last updated: 2024 Jun 14

Historic Boston Beginnings

Morning

Start your journey with a delightful breakfast at Mike's Pastry, known for its delicious pastries. Afterward, immerse yourself in history with a guided walking tour of the Freedom Trail, visiting iconic sites like the Boston Common and the Bunker Hill Monument.

Afternoon

For lunch, savor the fresh seafood at Legal Sea Foods. Then, continue your historical exploration with a visit to the USS Constitution, also known as "Old Ironsides," and the Bunker Hill Monument.

Evening

Conclude your day with a delicious dinner at Union Oyster House, the oldest operating restaurant in the United States. Afterward, take a leisurely stroll along the North End, Boston's Little Italy, and enjoy the vibrant atmosphere.

Bedtime

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Freedom Trail
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Boston Common
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Revolutionary Boston and Harbor Cruises

Morning

Enjoy a hearty breakfast at The Capital Grille before embarking on a guided tour of the Boston Tea Party Ships and Museum. Immerse yourself in the events that sparked the American Revolution.

Afternoon

For lunch, experience a unique buffet cruise on Boston Harbor with Spirit of Boston Lunch Cruise. Afterward, take a relaxing Harbor Sunset Yacht Cruise to enjoy the city from the water.

Evening

Dine at Top of the Hub, where you can enjoy a gourmet meal with panoramic views of the city. After dinner, take a Boston Harbor Champagne Sunset Sail for a magical end to the day.

Bedtime

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4.75
Boston Tea Party Ships and Museum
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4.51
Spirit of Boston Lunch Cruise
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Innovative Boston: MIT and Cambridge

Morning

Start your day with a visit to the Massachusetts Institute of Technology (MIT), where you can take a public tour of this prestigious institution. Afterward, explore the Kendall Square area.

Afternoon

Enjoy a leisurely lunch at Eastern Standard Kitchen & Drinks in the heart of Cambridge. Then, visit the Harvard University campus and take a student-led tour to learn about the history and culture of this renowned university.

Evening

For dinner, indulge in a culinary experience at Oleana, known for its innovative Mediterranean cuisine. Afterward, take a relaxing walk along the Cambridge Common.

Bedtime

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Massachusetts Institute of Technology (MIT)
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4.82
Kendall Square
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Fenway Park and Local Eats

Morning

Enjoy a classic Boston breakfast at Neptune Oyster, famous for its seafood. Then, take a guided tour of the iconic Fenway Park, home of the Boston Red Sox.

Afternoon

For lunch, head to Myers + Chang for a unique blend of Chinese, Taiwanese, Thai, and Vietnamese flavors. Afterward, explore the trendy Fenway area.

Evening

Dine at Island Creek Oyster Bar and savor the fresh oysters and seafood. After dinner, experience the vibrant nightlife in the Back Bay area.

Bedtime

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Fenway Park
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Fenway
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Maritime Boston and Harbor Islands

Morning

Start your day with a visit to the New England Aquarium and enjoy the fascinating marine life. Then, take a ferry to the Boston Harbor Islands and spend the morning exploring.

Afternoon

Have a picnic lunch on the island. In the afternoon, you can choose to relax on the beach or hike one of the island trails. Take the ferry back to the city in the late afternoon.

Evening

For dinner, try the award-winning seafood at Row 34. Afterward, take a leisurely walk along the Waterfront and enjoy the views of the harbor.

Bedtime

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