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20-Day Boston Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Historic Boston

Morning

Start your day with a visit to the Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 locations significant to the history of the United States. It’s a great way to get acquainted with the city’s rich past.

Afternoon

After exploring the Freedom Trail, head over to Faneuil Hall Marketplace for lunch. This bustling market is filled with food stalls and shops. Enjoy a meal at one of the many eateries here and soak in the vibrant atmosphere.

Evening

For dinner, make a reservation at Ostra. Known for its seafood dishes, Ostra offers an elegant dining experience perfect for wrapping up your first day in Boston.

Bedtime

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Cultural and Academic Highlights

Morning

Begin your day with a visit to Massachusetts Institute of Technology (MIT). Take a stroll around the campus and perhaps visit some of its renowned buildings and museums.

Afternoon

Head over to Harvard University in Cambridge for an afternoon of academic exploration. Don’t miss out on visiting Harvard Square and grabbing lunch at one of its many cafes.

Evening

Dine at Mamma Maria in the North End. This Italian restaurant is known for its cozy atmosphere and delicious cuisine.

Bedtime

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Art and Science Extravaganza

Morning

Kick off your morning with a trip to the Museum of Science Boston. Spend a few hours exploring its interactive exhibits that are fun for all ages.

Afternoon

For lunch, head over to Neptune Oyster located nearby. Known for its fresh seafood, this spot is perfect for enjoying some local flavors.

Evening

In the evening, take a leisurely walk through Boston Public Garden, America’s first public botanical garden. Afterwards, have dinner at Oleana, which offers Mediterranean-inspired dishes.

Bedtime

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Historic Sites and Waterfront Views

Morning

Start your day by visiting the iconic Paul Revere House. Learn about Paul Revere’s midnight ride and his role in American history.

Afternoon

Walk over to Quincy Market for lunch. This historic market complex offers various food options and is great for people-watching.

Evening

End your day with dinner at No. 9 Park, located near Beacon Hill. The restaurant is known for its refined French-Italian cuisine.

Bedtime

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Academic and Natural Wonders

Morning

Start your day with a visit to Harvard Museum of Natural History. This museum offers fascinating exhibits on natural history, including dinosaurs, gemstones, and more.

Afternoon

After the museum, head over to Cambridge Common for a relaxing afternoon. This historic park is perfect for a leisurely stroll or a picnic lunch.

Evening

For dinner, make your way to Myers+Chang. This trendy spot offers an eclectic mix of Asian-inspired dishes in a lively atmosphere.

Bedtime

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Historic Monuments and Culinary Delights

Morning

Begin your day with a visit to the Bunker Hill Monument. Climb the 294 steps to the top for panoramic views of Boston and learn about this pivotal battle in American history.

Afternoon

Head over to Charlestown Navy Yard for an afternoon of exploration. Don’t miss the USS Constitution Museum. Grab lunch at one of the nearby cafes or food trucks.

Evening

Dine at Sarma in Somerville. This restaurant offers a unique dining experience with its Mediterranean-inspired small plates.

Bedtime

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Literary and Scenic Adventures

Morning

Kick off your morning with a visit to Boston Athenaeum. This historic library is one of the oldest independent libraries in the United States and offers beautiful reading rooms and rare collections.

Afternoon

After exploring the Athenaeum, take a walk through Beacon Hill. Enjoy lunch at one of the charming cafes in this picturesque neighborhood known for its narrow streets and brick row houses.

Evening

For dinner, head over to Island Creek Oyster Bar. Known for its fresh seafood, this restaurant is perfect for enjoying some local flavors.

Bedtime

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Architectural Marvels and Local Flavors

Morning

Start your day by visiting 200 Clarendon (John Hancock Tower). Take in stunning views from Boston’s tallest building and appreciate its modern architectural design.

Afternoon

Next, head over to Copley Square where you can explore historic landmarks like Trinity Church and the Boston Public Library. Grab lunch at one of the nearby eateries.

Evening

End your day with dinner at The Capital Grille, known for its classic American steakhouse fare served in an elegant setting.

Bedtime

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Revolutionary Boston

Morning

Begin your day with a visit to the Boston Tea Party Ships & Museum. This interactive museum offers a unique way to learn about the events leading up to the American Revolution.

Afternoon

After exploring the museum, head over to Boston Old State House. This historic building played a crucial role in the American Revolution. Enjoy lunch at one of the nearby cafes.

Evening

For dinner, make a reservation at Toro Boston. This Spanish tapas restaurant is known for its vibrant atmosphere and delicious small plates.

Bedtime

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Science and Serenity

Morning

Start your day with a visit to the New England Aquarium. Spend your morning exploring its diverse marine life exhibits and perhaps catch an IMAX film.

Afternoon

Head over to Boston Public Library for a peaceful afternoon. Explore its beautiful architecture and extensive collections. Grab lunch at one of the nearby eateries.

Evening

Dine at Giulia in Cambridge. Known for its handmade pasta and cozy ambiance, this Italian restaurant is perfect for an intimate dinner.

Bedtime

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Historic Walks and Modern Eats

Morning

Kick off your morning with a visit to Granary Burying Ground. This historic cemetery is the final resting place of many notable figures from American history.

Afternoon

Afterward, take a walk through Boston Common, America’s oldest public park. Enjoy lunch at one of the food trucks or nearby cafes.

Evening

For dinner, head over to Alden & Harlow in Harvard Square. This restaurant offers creative American dishes in a rustic-chic setting.

Bedtime

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Harbor Views and Fine Dining

Morning

Start your day by visiting USS Constitution in Charlestown Navy Yard. Explore this historic ship and learn about its storied past.

Afternoon

Next, head over to Copley Place for some shopping or simply enjoy lunch at one of its many dining options.

Evening

End your day with dinner at Row 34, known for its fresh seafood and industrial-chic vibe.

Bedtime

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Architectural Gems and Local Eats

Morning

Begin your day with a visit to Old South Meeting House. This historic site played a key role in the events leading up to the American Revolution. Explore its exhibits and learn about its significance.

Afternoon

Afterward, head over to Copley Place for some shopping or simply enjoy lunch at one of its many dining options.

Evening

For dinner, make a reservation at Coppa Enoteca. This Italian enoteca offers a cozy atmosphere and delicious small plates.

Bedtime

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Historic Sites and Waterfront Views

Morning

Boston Massacre Site is your first stop today. Learn about this pivotal event in American history through informative exhibits.

Afternoon

Boston North End is perfect for an afternoon stroll. Enjoy lunch at one of the many Italian eateries in this charming neighborhood.

Evening

Bistro du Midi offers French-inspired cuisine with stunning views of the Boston Public Garden. It's an ideal spot for a relaxing dinner.

Bedtime

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Academic Insights and Scenic Walks

Morning

John Harvard Statue is a must-see when visiting Harvard University. Take some time to explore the campus and its historic landmarks.

Afternoon

Kendall Square in Cambridge is great for lunch and some light shopping or people-watching. The area is known for its tech startups and vibrant atmosphere.

Evening

Mistral Boston offers refined French cuisine in an elegant setting, making it perfect for an upscale dining experience.

Bedtime

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Revolutionary Landmarks and Local Cuisine

Morning

Start your day with a visit to the Longfellow House (Washington's Headquarters). This historic site offers a glimpse into the life of the famous poet Henry Wadsworth Longfellow and its role during the American Revolution.

Afternoon

After exploring the Longfellow House, head over to MIT Museum. This museum showcases fascinating exhibits on science and technology. Enjoy lunch at one of the nearby cafes in Kendall Square.

Evening

For dinner, make a reservation at Bistro du Midi. This French-inspired restaurant offers stunning views of the Boston Public Garden and is perfect for a relaxing evening.

Bedtime

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