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Roam Around

18-Day Journey through Boston, Amherst, and New York Itinerary

Last updated: 2024 Jun 14

Exploring Boston's Historic Heart

Morning

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

Afternoon

Head over to Faneuil Hall Marketplace for lunch and some shopping. This historic market and meeting hall has been a marketplace and a meeting hall since 1743. Enjoy a delicious seafood lunch at Neptune Oyster, known for its fresh oysters and lobster rolls.

Evening

In the evening, visit Boston Common, America's oldest public park. Take a leisurely stroll or relax by the Frog Pond. For dinner, dine at Ostra, which offers Mediterranean cuisine with an emphasis on seafood.

Bedtime

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4.54
Freedom Trail
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4.59
Faneuil Hall Marketplace
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Cambridge Adventures and Waterfront Wonders

Morning

Begin your day with a trip to Harvard University in Cambridge. Explore Harvard Yard and take in the historic atmosphere of one of the world's most prestigious universities.

Afternoon

After exploring Harvard University, head to Kendall Square for lunch at Mamma Maria. This restaurant offers delicious Italian cuisine in an elegant setting. Spend some time walking around Kendall Square and enjoy its vibrant atmosphere.

Evening

In the evening, visit the New England Aquarium. It's home to thousands of marine animals from around the world. Afterward, have dinner at Myers+Chang, known for its innovative Asian-inspired dishes.

Bedtime

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4.25
Harvard University
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4.82
Kendall Square
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Artistic Insights and Scenic Views

Morning

Start your day with a visit to the Museum of Science Boston. It's an excellent place for both adults and children with interactive exhibits covering various scientific fields.

Afternoon

For lunch head over to Beacon Hill area and dine at No. 9 Park, which offers refined French-Italian cuisine in an elegant townhouse setting. Afterward explore Beacon Hill, one of Boston's most picturesque neighborhoods with narrow streets lined with Federal-style rowhouses.

Evening

In the evening take a walk along Charles River Esplanade where you can enjoy beautiful views of both Cambridge and Boston skylines. End your day with dinner at The Capital Grille, renowned for its dry-aged steaks.

Bedtime

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3.99
Museum of Science Boston
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4.49
Beacon Hill
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Cultural Immersion in Back Bay

Morning

Begin your day exploring Back Bay, known for its rows of Victorian brownstone homes – considered one of the best-preserved examples of 19th-century urban design in America.

Afternoon

For lunch head over to South End neighborhood where you can dine at Toro Boston, famous for its Spanish tapas dishes prepared using local ingredients. Afterward visit nearby Copley Square which is surrounded by architectural landmarks such as Trinity Church & John Hancock Tower.

Evening

Conclude your day by visiting Symphony Hall where you can catch an evening performance by Boston Symphony Orchestra if available or simply admire this beautiful concert hall built back in 1900s . Have dinner at nearby restaurant called Oleana offering Mediterranean inspired dishes made from locally sourced ingredients.

Bedtime

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4.60
Back Bay
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Revolutionary Landmarks and Local Flavors

Morning

Start your day with a visit to Boston Massacre Site. This historic site marks the location where British soldiers killed five civilian men in 1770, an event that fueled anti-British sentiments leading up to the American Revolution.

Afternoon

Head over to Quincy Market for lunch. This historic market complex offers a variety of food stalls and shops. Enjoy some local flavors and explore the bustling marketplace. Afterward, visit Paul Revere House, the colonial home of American patriot Paul Revere during the time of the American Revolution.

Evening

In the evening, take a stroll through Boston North End, Boston's oldest residential community known for its Italian heritage. Have dinner at Mamma Maria, which offers authentic Italian cuisine in a cozy setting.

Bedtime

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4.64
Boston Massacre Site
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4.13
Quincy Market
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Academic Excellence and Historical Depth

Morning

Begin your day with a visit to Massachusetts Institute of Technology (MIT). Explore the campus and admire its unique architecture and cutting-edge research facilities.

Afternoon

For lunch, head over to Cambridge Common area where you can dine at Sarma, known for its Mediterranean-inspired small plates. Afterward, explore Cambridge Common, a historic park where George Washington is said to have taken command of the Continental Army.

Evening

In the evening, visit Harvard Square. This vibrant area is filled with shops, cafes, and street performers. Have dinner at Oleana, which offers Mediterranean dishes made from locally sourced ingredients.

Bedtime

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4.33
Massachusetts Institute of Technology (MIT)
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4.89
Cambridge Common
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Seaside Serenity and Cultural Riches

Morning

Start your day with a visit to Charlestown Navy Yard. Explore this historic shipyard that played a crucial role in America's naval history.

Afternoon

For lunch head over to nearby Charlestown neighborhood where you can dine at local favorite restaurant called Island Creek Oyster Bar offering fresh seafood dishes prepared using locally sourced ingredients . Afterward visit nearby Bunker Hill Monument commemorating one of first major battles fought during American Revolutionary War .

Evening

In evening take short ferry ride across harbor back into downtown area where you can catch performance by Boston Symphony Orchestra if available or simply admire beautiful concert hall built back in early 1900s . Have dinner afterwards Myers+Chang known innovative Asian inspired dishes made from locally sourced ingredients .

Bedtime

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Charlestown Navy Yard
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Architectural Marvels and Academic Insights

Morning

Start your day with a visit to Boston Public Library. This historic library is not only a place for book lovers but also an architectural marvel with its stunning interiors and beautiful courtyard.

Afternoon

For lunch, head over to the nearby Back Bay area and dine at No. 9 Park, which offers refined French-Italian cuisine in an elegant townhouse setting. Afterward, explore Copley Square, surrounded by architectural landmarks such as Trinity Church and the John Hancock Tower.

Evening

In the evening, visit Massachusetts State House. This iconic building with its golden dome is a symbol of the state's government. Conclude your day with dinner at The Capital Grille, renowned for its dry-aged steaks.

Bedtime

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4.11
Boston Public Library
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4.38
Copley Square
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Historic Trails and Culinary Delights

Morning

Freedom Trail - Start your day walking along this historic trail that covers significant sites related to the American Revolution.

Afternoon

Neptune Oyster - Enjoy a seafood lunch at this highly-rated restaurant known for its fresh oysters and lobster rolls. Afterward, visit Boston Old State House, one of the oldest public buildings in the United States.

Evening

Granary Burying Ground - Visit this historic cemetery where many notable figures from American history are buried. For dinner, dine at Ostra, which offers Mediterranean cuisine with an emphasis on seafood.

Bedtime

Find amazing hotels in Boston, Massachusetts, USA.

4.54
Freedom Trail
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4.48
Boston Old State House
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Seaside Serenity and Cultural Riches

Morning

Charlestown Navy Yard - Start your day exploring this historic shipyard that played a crucial role in America's naval history.

Afternoon

Island Creek Oyster Bar - For lunch head over to this local favorite restaurant offering fresh seafood dishes prepared using locally sourced ingredients. Afterward visit nearby Bunker Hill Monument, commemorating one of first major battles fought during American Revolutionary War.

Evening

USS Constitution - In evening take short ferry ride across harbor back into downtown area where you can catch performance by Boston Symphony Orchestra if available or simply admire beautiful concert hall built back in early 1900s . Have dinner afterwards at Myers+Chang, known for innovative Asian-inspired dishes made from locally sourced ingredients.

Bedtime

Find amazing hotels in Boston, Massachusetts, USA.

3.88
Charlestown Navy Yard
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4.38
Bunker Hill Monument
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Historical Depth and Academic Excellence

Morning

Massachusetts Institute of Technology (MIT) - Begin your day with a visit to MIT. Explore the campus and admire its unique architecture and cutting-edge research facilities.

Afternoon

Sarma - For lunch, head over to Cambridge Common area where you can dine at Sarma, known for its Mediterranean-inspired small plates. Afterward, explore Cambridge Common, a historic park where George Washington is said to have taken command of the Continental Army.

Evening

Harvard Square - In the evening, visit Harvard Square. This vibrant area is filled with shops, cafes, and street performers. Have dinner at Oleana, which offers Mediterranean dishes made from locally sourced ingredients.

Bedtime

Find amazing hotels in Boston, Massachusetts, USA.

4.33
Massachusetts Institute of Technology (MIT)
Book Now

4.89
Cambridge Common
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Seaside Serenity and Cultural Riches

Morning

Charlestown Navy Yard - Start your day with a visit to Charlestown Navy Yard. Explore this historic shipyard that played a crucial role in America's naval history.

Afternoon

Evening

Bedtime

Find amazing hotels in Boston, Massachusetts, USA.

3.88
Charlestown Navy Yard
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4.38
Bunker Hill Monument
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Final Boston Exploration and Farewell

Morning

Boston Public Garden - Start your day with a peaceful stroll through the Boston Public Garden. This beautiful park is known for its swan boats and vibrant flower beds.

Afternoon

Neptune Oyster - For lunch, head over to Neptune Oyster for some of the best seafood in Boston. Afterward, visit Boston Tea Party Ships & Museum, where you can relive the historic event that sparked the American Revolution.

Evening

Fenway Park - In the evening, take a tour of Fenway Park, one of America's most beloved baseball stadiums. Conclude your day with dinner at Toro Boston, known for its Spanish tapas dishes prepared using local ingredients.

Bedtime

Find amazing hotels in Boston, Massachusetts, USA.

4.52
Boston Public Garden
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4.22
Boston Tea Party Ships & Museum
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Cultural Immersion in Back Bay

Morning

Begin your day exploring Back Bay known rows Victorian brownstone homes considered one best preserved examples 19th century urban design America .

Afternoon

For lunch head over South End neighborhood dine Toro Boston famous Spanish tapas dishes prepared using local ingredients . Afterward visit nearby Copley Square surrounded architectural landmarks such Trinity Church John Hancock Tower .

Evening

Conclude your day visiting Symphony Hall catch evening performance Boston Symphony Orchestra if available simply admire beautiful concert hall built back early 1900s . Have dinner nearby restaurant called Oleana offering Mediterranean inspired dishes made from locally sourced ingredients

Bedtime

Find amazing hotels in Boston , Massachusetts , USA .

Artistic Insights and Scenic Views

Morning

Start your day visit Museum Science Boston excellent place both adults children interactive exhibits covering various scientific fields .

Afternoon

For lunch head over Beacon Hill area dine No .9 Park offers refined French Italian cuisine elegant townhouse setting . Afterward explore Beacon Hill one Boston 's most picturesque neighborhoods narrow streets lined Federal style rowhouses .

Evening

In evening take walk along Charles River Esplanade enjoy beautiful views both Cambridge Boston skylines . End your day dinner The Capital Grille renowned dry aged steaks .

Bedtime

Find amazing hotels in Boston , Massachusetts , USA .

Artistic Insights and Scenic Views

Morning

Museum of Science Boston - Start your day with a visit to the Museum of Science Boston excellent place both adults children interactive exhibits covering various scientific fields .

Afternoon

No .9 Park - For lunch head over Beacon Hill area dine No .9 Park offers refined French Italian cuisine elegant townhouse setting . Afterward explore Beacon Hill, one Boston 's most picturesque neighborhoods narrow streets lined Federal style rowhouses .

Evening

Charles River Esplanade - In evening take walk along Charles River Esplanade enjoy beautiful views both Cambridge Boston skylines . End your day dinner The Capital Grille renowned dry aged steaks .

Bedtime

Find amazing hotels in Boston , Massachusetts , USA .

3.99
Museum of Science Boston
Book Now

4.49
Beacon Hill
Book Now

Cultural Immersion in Back Bay

Morning

Back Bay Begin your day exploring Back Bay known rows Victorian brownstone homes considered one best preserved examples 19th century urban design America .

Afternoon

Toro Boston For lunch head over South End neighborhood dine Toro Boston famous Spanish tapas dishes prepared using local ingredients . Afterward visit nearby Copley Square surrounded architectural landmarks such Trinity Church John Hancock Tower .

Evening

{Symphony Hall} Conclude your day visiting Symphony Hall catch evening performance Boston Symphony Orchestra if available simply admire beautiful concert hall built back early 1900s . Have dinner nearby restaurant called Oleana offering Mediterranean inspired dishes made from locally sourced ingredients

Bedtime

Find amazing hotels in Boston , Massachusetts , USA .

4.60
Back Bay
Book Now

Amherst Adventures and Scenic Beauty

Morning

Emily Dickinson Museum - Begin your day with a visit to the Emily Dickinson Museum. Explore the home and gardens of one of America's greatest poets.

Afternoon

The Black Sheep Deli - For lunch, head over to The Black Sheep Deli for some delicious sandwiches and baked goods. Afterward, take a leisurely walk around Amherst College's picturesque campus.

Evening

Mount Holyoke Range State Park - In the evening, enjoy a hike or simply take in the scenic views at Mount Holyoke Range State Park. End your day with dinner at 30Boltwood, known for its farm-to-table cuisine.

Bedtime

Find amazing hotels in Amherst, Massachusetts, USA.