Exploring Boston in 5 Days

Day 1: Historic Boston

Boston, USA

8:00AM

Breakfast at Quincy Market

Start your day with a delicious breakfast at Quincy Market, known for its diverse food options and historic setting.
Quincy Market is located in Downtown Boston, easily accessible via the 'T'.
15 USD, 1 hour

10:00AM

Freedom Trail Walk

Embark on a self-guided tour along the Freedom Trail, exploring Boston's rich history and iconic landmarks.
Begin your walk from Faneuil Hall and follow the red-brick trail markers.
Free, 3 hours

1:00PM

Lunch at Union Oyster House

Indulge in a traditional New England seafood lunch at the historic Union Oyster House, the oldest restaurant in the U.S.
The restaurant is a short walk from the Freedom Trail.
30 USD, 1.5 hours

3:00PM

Explore the North End

Stroll through Boston's charming North End neighborhood, known for its Italian culture, pastry shops, and historic sites.
Walk from Union Oyster House to the North End, approximately 15 minutes on foot.
Free, 2 hours

6:00PM

Dinner at Giacomo's

Enjoy a cozy Italian dinner at the popular Giacomo's restaurant, known for its delicious pasta dishes.
Giocomo's is a short walk from the North End.
40 USD, 1.5 hours
View Hotel Availability

Day 2: Fenway-Kenmore Exploration

Boston, USA

9:00AM

Breakfast at Tatte Bakery & Cafe

Start your day with a scrumptious breakfast at Tatte Bakery & Cafe, known for its pastries and coffee.
Tatte Bakery & Cafe is located in Fenway-Kenmore, easily accessible by the 'T'.
20 USD, 1 hour

10:30AM

Visit Fenway Park

Take a guided tour of Fenway Park, home of the Boston Red Sox and a historic baseball landmark.
From Tatte Bakery & Cafe, take a short walk to Fenway Park.
25 USD, 2 hours

1:00PM

Lunch at Time Out Market

Savor a diverse lunch at Time Out Market, a culinary hub featuring various food vendors and cuisines.
Time Out Market is a short walk from Fenway Park.
25 USD, 1.5 hours

3:00PM

Explore Kenmore Square

Discover the vibrant Kenmore Square, known for its shops, cafes, and proximity to Boston University.
Walk from Time Out Market to Kenmore Square, approximately 10 minutes on foot.
Free, 1 hour

6:00PM

Dinner at Eastern Standard

Enjoy a sophisticated dinner at Eastern Standard, a classic American brasserie in Kenmore Square.
Eastern Standard is located in Kenmore Square.
50 USD, 2 hours
View Hotel Availability

Day 3: Back Bay Beauty

Boston, USA

9:00AM

Breakfast at Flour Bakery + Cafe

Start your day with a delightful breakfast at Flour Bakery + Cafe, famous for its pastries and sandwiches.
Flour Bakery + Cafe is located in Back Bay, easily accessible by the 'T'.
15 USD, 1 hour

10:30AM

Shop on Newbury Street

Indulge in some retail therapy on Newbury Street, a fashionable destination lined with boutiques and cafes.
Walk from Flour Bakery + Cafe to Newbury Street, approximately 5 minutes on foot.
Variable, 2 hours

1:00PM

Lunch at Stephanie's On Newbury

Enjoy a delicious lunch at Stephanie's On Newbury, a popular eatery offering American comfort food.
Stephanie's On Newbury is located on Newbury Street.
35 USD, 1.5 hours

3:00PM

Explore Copley Square

Visit the historic Copley Square, home to Trinity Church, the Boston Public Library, and striking architectural landmarks.
Walk from Newbury Street to Copley Square, approximately 10 minutes on foot.
Free, 1 hour

6:00PM

Dinner at Atlantic Fish Company

Dine at the Atlantic Fish Company for a seafood feast in a cozy atmosphere in Back Bay.
Atlantic Fish Company is a short walk from Copley Square.
45 USD, 2 hours
View Hotel Availability

Day 4: Harvard and MIT Exploration

Cambridge, USA

9:00AM

Breakfast at Tatte Bakery & Cafe (Harvard Square)

Start your day with a delicious breakfast at Tatte Bakery & Cafe in Harvard Square, known for its cozy atmosphere and pastries.
Take the 'T' to Harvard Square in Cambridge.
20 USD, 1 hour

10:30AM

Explore Harvard University

Take a self-guided tour of Harvard University, strolling through its historic campus and iconic landmarks.
Walk from Tatte Bakery & Cafe to Harvard Yard.
Free, 2 hours

1:00PM

Lunch at The Sinclair

Enjoy a casual lunch at The Sinclair, a hip eatery near Harvard Square offering a variety of dishes.
The Sinclair is located near Harvard University.
30 USD, 1.5 hours

3:00PM

Visit MIT

Explore the Massachusetts Institute of Technology (MIT), known for its cutting-edge research and innovative campus.
Take a short ride from Harvard Square to MIT using public transportation.
Free, 2 hours

6:00PM

Dinner at Alden & Harlow

Indulge in a farm-to-table dining experience at Alden & Harlow, a renowned restaurant in Harvard Square.
Alden & Harlow is located in the heart of Harvard Square.
50 USD, 2 hours
View Hotel Availability

Day 5: Cambridge Discovery

Cambridge, USA

9:00AM

Breakfast at Tatte Bakery & Cafe (Kendall Square)

Start your day with a delightful breakfast at Tatte Bakery & Cafe in Kendall Square, known for its artisanal pastries and coffee.
Take the 'T' to Kendall Square in Cambridge.
20 USD, 1 hour

10:30AM

Visit Harvard Art Museums

Explore the rich collections at the Harvard Art Museums, showcasing art from diverse cultures and time periods.
Walk from Tatte Bakery & Cafe to the Harvard Art Museums.
15 USD, 2 hours

1:00PM

Lunch at Cafe Sushi

Enjoy a fresh and flavorful sushi lunch at Cafe Sushi, a popular spot in the heart of Cambridge.
Cafe Sushi is located near the Harvard Art Museums.
35 USD, 1.5 hours

3:00PM

Walk along Charles River

Take a leisurely stroll along the picturesque Charles River, enjoying the scenic views and outdoor ambiance.
Walk from Cafe Sushi to the Charles River, approximately 15 minutes on foot.
Free, 1 hour

6:00PM

Dinner at Craigie on Main

Indulge in a fine dining experience at Craigie on Main, known for its innovative and seasonal menu in Cambridge.
Craigie on Main is a short walk from the Charles River.
70 USD, 2 hours
View Hotel Availability