Exploring Boston, Massachusetts in 5 Days

Day 1: Downtown Boston

Boston, Massachusetts

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your day with a delicious breakfast at Tatte Bakery & Cafe, known for its freshly baked pastries and excellent coffee.
Walk from your accommodation to Tatte Bakery & Cafe in Downtown Crossing. It's a 10-minute walk.
$10, 1 hour

10:00AM

Freedom Trail Walking Tour

Embark on a historic journey with a Freedom Trail Walking Tour, exploring significant sites like Faneuil Hall and Paul Revere's House.
Join the tour group at the Boston Common Visitor Information Center. It's a 5-minute walk from Tatte Bakery & Cafe.
$25, 2 hours

1:00PM

Lunch at Union Oyster House

Indulge in a traditional New England seafood meal at the historic Union Oyster House, America's oldest continuously operating restaurant.
Walk from the Freedom Trail endpoint to Union Oyster House in around 10 minutes.
$30, 1.5 hours

3:00PM

Visit the Boston Tea Party Ships & Museum

Immerse yourself in the events leading to the American Revolution at the interactive Boston Tea Party Ships & Museum.
Take a short 5-minute walk from Union Oyster House to the museum.
$20, 1.5 hours

6:00PM

Dinner at Neptune Oyster

Savor some of the best seafood dishes in the city at Neptune Oyster, a cozy and popular seafood spot in the North End.
Take a 15-minute subway ride from the museum to the North End neighborhood.
$50, 2 hours
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Day 2: Cambridge

Boston, Massachusetts

9:00AM

Breakfast at Area Four

Start your day with a delicious breakfast at Area Four, known for its exceptional coffee and freshly baked pastries.
Take a 20-minute subway ride from Downtown Boston to Cambridge.
$15, 1 hour

11:00AM

Explore Harvard University

Take a leisurely stroll through the prestigious Harvard University campus, admiring its architecture and history.
Walk from Area Four to Harvard University, which takes around 15 minutes.
Free, 2 hours

1:30PM

Lunch at Craigie on Main

Enjoy a gourmet lunch experience at Craigie on Main, a renowned restaurant known for its innovative American cuisine.
Walk to Craigie on Main from Harvard University, which is approximately a 10-minute walk.
$40, 1.5 hours

3:30PM

Visit the MIT Museum

Discover the intersection of science, technology, and art at the MIT Museum, showcasing cutting-edge research and inventions.
Take a short 10-minute walk from Craigie on Main to the MIT Museum.
$12, 1.5 hours

6:00PM

Dinner at Alden & Harlow

Indulge in a farm-to-table dining experience at Alden & Harlow, known for its creative small plates and craft cocktails.
Take a 10-minute subway ride back to Downtown Boston for dinner.
$45, 2 hours
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Day 3: North End

Boston, Massachusetts

9:00AM

Breakfast at Mike's Pastry

Start your day with a sweet treat at Mike's Pastry, a famous bakery known for its cannoli and other delicious pastries.
Take a 15-minute subway ride from Downtown Boston to the North End.
$8, 1 hour

11:00AM

Walk the Freedom Trail in North End

Explore the North End section of the Freedom Trail, passing by historic sites and charming streets filled with Italian bakeries and cafes.
Start the Freedom Trail walk from Mike's Pastry.
Free, 2 hours

1:30PM

Lunch at Regina Pizzeria

Enjoy an authentic Italian pizza experience at Regina Pizzeria, a local favorite with a long-standing reputation for delicious pies.
After the Freedom Trail walk, walk to Regina Pizzeria for lunch.
$20, 1.5 hours

3:30PM

Visit Paul Revere House

Step back in time at the historic Paul Revere House, the former home of the American patriot famous for his midnight ride.
The house is a short 5-minute walk from Regina Pizzeria.
$5, 1 hour

6:00PM

Dinner at Giacomo's Ristorante

Experience a cozy and authentic Italian meal at Giacomo's Ristorante, known for its hearty portions and welcoming atmosphere.
Take a 10-minute subway ride back to Downtown Boston for dinner.
$35, 2 hours
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Day 4: Fenway-Kenmore

Boston, Massachusetts

9:00AM

Breakfast at Pavement Coffeehouse

Start your day with a cozy breakfast at Pavement Coffeehouse, offering a range of coffee drinks and delicious breakfast sandwiches.
Take a 15-minute subway ride from Downtown Boston to Fenway-Kenmore.
$12, 1 hour

11:00AM

Tour Fenway Park

Explore the iconic Fenway Park on a guided tour, learning about the history of America's oldest baseball stadium.
Walk from Pavement Coffeehouse to Fenway Park, which takes around 10 minutes.
$20, 2 hours

1:30PM

Lunch at Eastern Standard

Enjoy a delicious lunch at Eastern Standard, a brasserie-style restaurant offering French and American cuisine.
Walk to Eastern Standard from Fenway Park, which is a 5-minute walk.
$30, 1.5 hours

3:30PM

Visit Isabella Stewart Gardner Museum

Discover the stunning art collection and architecture of the Isabella Stewart Gardner Museum, housed in a Venetian-style palace.
Take a 10-minute walk from Eastern Standard to the museum.
$15, 2 hours

6:00PM

Dinner at Island Creek Oyster Bar

Enjoy a seafood-centric dinner at Island Creek Oyster Bar, known for its fresh oysters and innovative seafood dishes.
Take a 10-minute subway ride back to Downtown Boston for dinner.
$50, 2 hours
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Day 5: Back Bay

Boston, Massachusetts

9:00AM

Breakfast at Flour Bakery + Cafe

Start your day with a scrumptious breakfast at Flour Bakery + Cafe, known for its delectable pastries and sandwiches.
Take a 15-minute subway ride from Downtown Boston to Back Bay.
$10, 1 hour

11:00AM

Shop on Newbury Street

Indulge in some shopping therapy on Newbury Street, a famous upscale shopping destination with boutiques and designer stores.
Walk from Flour Bakery + Cafe to Newbury Street, which takes approximately 5 minutes.
Varies, 2 hours

1:30PM

Lunch at Atlantic Fish Company

Relish a seafood lunch at Atlantic Fish Company, a classic seafood restaurant offering a variety of fresh catches.
Walk to Atlantic Fish Company from Newbury Street, which is a 10-minute walk.
$35, 1.5 hours

3:30PM

Visit the Boston Public Library

Explore the architectural beauty and vast collection of books at the historic Boston Public Library, a cultural gem in the city.
Take a 5-minute walk from Atlantic Fish Company to the library.
Free, 1.5 hours

6:00PM

Dinner at Top of the Hub

Experience fine dining with panoramic views at Top of the Hub, located on the 52nd floor of the Prudential Tower.
Take a short 5-minute walk from the library to Top of the Hub for dinner.
$70, 2 hours
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