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Roam Around

14-Day Adventure in Boston and Dover Itinerary

Last updated: 2024 Jun 14

Exploring Historic Boston

Morning

Start your day with a visit to 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 the Freedom Trail, head over to Faneuil Hall Marketplace for lunch and some shopping. This historic marketplace has been a meeting hall since 1743 and now hosts an array of shops and eateries. Enjoy lunch at one of the many food stalls or nearby restaurants.

Evening

End your day with dinner at Oleana, known for its Mediterranean cuisine and cozy atmosphere. It's a perfect spot to relax after a day of exploring.

Bedtime

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Freedom Trail
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Faneuil Hall Marketplace
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Cambridge Highlights

Morning

Begin your morning with a visit to Harvard University. Take a stroll around Harvard Yard and soak in the academic atmosphere of one of the world's most prestigious universities.

Afternoon

For lunch, head over to Sarma, which offers an innovative take on Mediterranean small plates. Afterward, explore Harvard Square, a bustling area filled with shops, cafes, and street performers.

Evening

Conclude your day with dinner at The Capital Grille, renowned for its dry-aged steaks and extensive wine list.

Bedtime

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Harvard University
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Harvard Square
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Cultural Gems of Boston

Morning

Kick off your day with a visit to the Museum of Science Boston. This museum offers interactive exhibits that are fun for all ages.

Afternoon

Have lunch at one of the cafes near Copley Square before visiting Boston Public Library. The library is not only an architectural marvel but also offers free art tours.

Evening

Enjoy dinner at one of Boston's iconic seafood restaurants before heading over to see a performance at Boston Symphony Hall.

Bedtime

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Museum of Science Boston
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Boston Public Library
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Historic Landmarks Tour

Morning

Start your morning by visiting Granary Burying Ground, where many notable figures from American history are buried. It's a serene place filled with history.

Afternoon

Head over to Quincy Market for lunch and then explore nearby attractions like Boston Old State House and Old South Meeting House. These sites offer deep insights into America's revolutionary past.

Evening

Wrap up your evening with dinner at one of Boston's classic Italian eateries in the North End.

Bedtime

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Granary Burying Ground
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Boston Old State House
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Exploring MIT and Kendall Square

Morning

Begin your day with a visit to Massachusetts Institute of Technology (MIT). Explore the campus and take in the innovative atmosphere of one of the world's leading research institutions.

Afternoon

Head over to Kendall Square for lunch. This area is known for its tech startups and vibrant dining scene. Enjoy a meal at one of the many restaurants here.

Evening

Conclude your day with dinner at The Capital Grille, renowned for its dry-aged steaks and extensive wine list.

Bedtime

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Massachusetts Institute of Technology (MIT)
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Kendall Square
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Historic Sites and Waterfront Views

Morning

Boston Massacre Site is a must-visit in the morning. This historical site marks a pivotal event leading up to the American Revolution.

Afternoon

New England Aquarium is perfect for an afternoon visit. Explore marine life exhibits and even catch an IMAX movie. Have lunch at one of the nearby waterfront restaurants.

Evening

Oleana offers a cozy atmosphere and Mediterranean cuisine, making it an ideal spot for dinner.

Bedtime

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Boston Massacre Site
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New England Aquarium
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Scenic Boston and Harvard Museums

Morning

Boston Public Garden is perfect for a morning stroll. Enjoy the beautiful landscapes and perhaps take a swan boat ride.

Afternoon

Harvard Museum of Natural History offers fascinating exhibits that are sure to captivate you. Have lunch at one of the cafes around Harvard Square afterward.

Evening

Sarma provides an innovative take on Mediterranean small plates, making it a great choice for dinner.

Bedtime

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Boston Public Garden
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Harvard Museum of Natural History
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Farewell to Boston

Morning

Travel back to Boston in the morning. Once you arrive, start your day with a visit to Boston Common. This central public park is perfect for a leisurely stroll or simply relaxing on the grass.

Afternoon

Head over to Quincy Market for lunch and some last-minute shopping. This historic marketplace offers a variety of food stalls and unique shops.

Evening

End your trip with dinner at one of Boston's iconic seafood restaurants before heading back home.

Bedtime

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Boston Common
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Quincy Market
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Dover Arrival and Local Flavors

Morning

Travel from Boston to Dover in the morning, taking in the scenic views along the way.

Afternoon

Once you arrive in Dover, have lunch at Flight Coffee Co., known for its excellent coffee and light bites. Spend some time exploring downtown Dover or relaxing after your journey.

Evening

For dinner, head over to Christopher's Third Street Grille. This local favorite offers delicious American cuisine in a cozy setting.

Bedtime

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Dover's Natural Beauty and Local Eats

Morning

Start your day with a visit to one of Dover's beautiful parks or nature reserves. Enjoy a peaceful morning walk and take in the natural beauty of the area.

Afternoon

Head over to Dos Amigos Burritos for a delicious and casual lunch. Afterward, explore some of Dover's local shops and boutiques.

Evening

For dinner, dine at Stalk Restaurant, known for its farm-to-table cuisine and cozy atmosphere.

Bedtime

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Historic Dover and Craft Brews

Morning

Begin your day with a visit to the Woodman Institute Museum. This museum offers fascinating exhibits on local history, art, and natural science.

Afternoon

Have lunch at La Festa Brick & Brew Pizzeria, where you can enjoy some of the best pizza in town. Spend the afternoon exploring more of Dover's historic sites or taking a leisurely walk along the Cocheco River.

Evening

End your day with dinner at 7th Settlement Brewery, which offers excellent craft beers and hearty pub fare.

Bedtime

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Family Fun in Dover

Morning

Start your morning with a family-friendly activity such as visiting the Children's Museum of New Hampshire. The museum offers interactive exhibits that are fun for all ages.

Afternoon

For lunch, head over to The Farm Bar & Grille, which offers a relaxed atmosphere and delicious comfort food. Spend the afternoon at Henry Law Park, where kids can enjoy playgrounds and splash pads.

Evening

Enjoy dinner at Patty B's Ristorante Italiano, known for its delicious Italian cuisine and family-friendly environment.

Bedtime

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Artisanal Delights in Dover

Morning

Begin your day with a visit to Flight Coffee Co., where you can enjoy artisanal coffee and pastries. Take some time to relax or catch up on reading.

Afternoon

Have lunch at Earth's Harvest Kitchen & Juicery, which offers healthy and delicious options made from locally sourced ingredients. Spend the afternoon exploring more of downtown Dover or visiting local art galleries.

Evening

For dinner, dine at Chapel + Main, known for its creative dishes and vibrant atmosphere.

Bedtime

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Dover's Hidden Gems

Morning

Start your day with a visit to one of Dover's hidden gems, such as the Bellamy River Wildlife Management Area. Enjoy a peaceful morning walk and take in the natural beauty of the area.

Afternoon

Head over to Blue Latitudes Restaurant & Blue Room Lounge for a delicious lunch. Afterward, explore some of Dover's local shops and boutiques or visit the Dover Brick House for some live music.

Evening

For dinner, dine at Cartelli's North End Pizza & Pasta, known for its delicious Italian cuisine and cozy atmosphere.

Bedtime

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