4-Day Boston Itinerary: Exploring History and Culture

Day 1: Historical Highlights

Boston, MA

8:00AM

Breakfast at Flour Bakery

Start your day at Flour Bakery with their famous sticky buns and a locally roasted coffee.
Located in Fort Point, Flour Bakery is a short 10-minute walk from your accommodation.
USD15, 1 hour

9:30AM

Freedom Trail Walk

Embark on the 2.5-mile Freedom Trail, visiting iconic sites like Boston Common, Paul Revere's House, and the Old North Church.
The beginning of the Freedom Trail is just steps from Flour Bakery.
Free, 3 hours

12:30PM

Lunch at Quincy Market

Savor a plethora of options at the historic Quincy Market, from clam chowder to fresh lobster rolls.
Quincy Market is situated right on the Freedom Trail, so simply walk over after your tour.
USD25, 1.5 hours

2:00PM

New England Aquarium

Visit the New England Aquarium and marvel at the sea turtles and penguins, plus the impressive IMAX theater.
A quick 15-minute walk or a short subway ride on the Blue Line from Quincy Market.
USD32, 2 hours

4:30PM

Stroll along the Boston Harborwalk

Enjoy a leisurely walk along the waterfront on the beautiful Harborwalk, perfect for taking photos and soaking in the scenic views.
The Harborwalk is adjacent to the aquarium.
Free, 1 hour

6:00PM

Dinner at Union Oyster House

Conclude your day at America’s oldest continuously operating restaurant, known for its clam chowder and fresh seafood.
Just a 15-minute stroll from the Harborwalk.
USD40, 1.5 hours
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Day 2: Culture & Education

Boston, MA

8:00AM

Breakfast at Tatte Bakery

Visit Tatte Bakery for exquisite pastries and house-roasted coffee to energize your day.
Located in Back Bay, a 15-minute ride on the Green Line from your hotel.
USD15, 1 hour

9:30AM

Museum of Fine Arts

Immerse yourself in art at the Museum of Fine Arts, where you can explore an extensive collection ranging from Ancient to Modern art.
A 5-minute walk from Tatte Bakery.
USD25, 2 hours

12:00PM

Lunch at The Capital Grille

Indulge in a delicious lunch featuring a variety of steaks and seafood at The Capital Grille.
A short 15-minute walk from the museum.
USD45, 1.5 hours

2:00PM

Visit Harvard University

Take a trip to nearby Cambridge and walk the historic grounds of Harvard University, the oldest institution of higher education in the U.S.
Take the Red Line subway to Harvard Square, approximately 20 minutes.
Free, 2 hours

4:30PM

Harvard Art Museums

Explore the Harvard Art Museums, which feature collections from the Asia, European and American art movements.
A 10-minute walk from Harvard University.
USD15, 1.5 hours

6:30PM

Dinner at Alden & Harlow

Enjoy dinner at Alden & Harlow, known for its inventive seasonal dishes and vibrant atmosphere.
Located in Harvard Square, a short walk from the art museums.
USD40, 2 hours
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Day 3: Exploring the Neighborhoods

Boston, MA

8:00AM

Breakfast at Cafeteria

Start your day with brunch at Cafeteria, a popular spot known for its creative take on classic breakfast dishes.
Located in Back Bay, about a 10-minute walk from your stay.
USD20, 1.5 hours

10:00AM

Visit Beacon Hill

Explore the historic neighborhood of Beacon Hill, filled with charming cobblestone streets and historic brownstones.
A 15-minute walk from Cafeteria.
Free, 1.5 hours

11:30AM

Louisburg Square

Admire one of Boston’s most photographed areas at Louisburg Square, an iconic public park surrounded by exquisite townhouses.
A short walk through Beacon Hill.
Free, 30 minutes

12:00PM

Lunch at Cheers

Grab lunch at the original Cheers restaurant, known for its friendly atmosphere and classic American fare.
About a 15-minute walk from Louisburg Square.
USD25, 1 hour

1:15PM

Explore the North End

Wander through the North End, known for its rich Italian heritage and delicious pastry shops.
A 20-minute walk from Cheers.
Free, 2 hours

3:30PM

Stop by Mike's Pastry

Treat yourself to an authentic cannoli from Mike's Pastry, a legendary bakery in the North End.
Mike's Pastry is well-known and located near many of the North End’s attractions.
USD8, 30 minutes

5:00PM

Dinner at Bricco

End your day enjoying homemade pastas and traditional Italian meals at Bricco, a North End favorite.
A short walk from Mike's Pastry.
USD38, 1.5 hours
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Day 4: Day of Relaxation

Boston, MA

8:00AM

Breakfast at The Paramount

Start your morning at The Paramount, a popular diner-style restaurant in Beacon Hill famous for its breakfast hash.
A 15-minute walk from your hotel.
USD18, 1 hour

9:30AM

Boston Public Garden

Stroll through the beautiful Boston Public Garden, famous for its swan boats and meticulously maintained landscape.
Easily accessible just a 10-minute walk from The Paramount.
Free, 1 hour

10:30AM

Visit Boston Common

Enjoy a peaceful walk in Boston Common, the oldest public park in the U.S., adjacent to the Public Garden.
Simply continue your walk from the Public Garden.
Free, 1 hour

11:30AM

Lunch at The Continental

Enjoy a casual lunch at The Continental featuring upscale comfort food and a rooftop patio.
A 15-minute walk from Boston Common.
USD30, 1.5 hours

1:00PM

Visit Isabell Stewart Gardner Museum

Discover the remarkable Isabella Stewart Gardner Museum, known for its stunning architecture and art collection.
A short subway ride on the Green Line to the Museum of Fine Arts station, then a 10-min walk.
USD20, 2.5 hours

3:30PM

Afternoon Tea at The Courtyard

Unwind with an afternoon tea experience at The Courtyard, offering a selection of teas and delightful pastries.
Walking from the museum, it’s approximately a 15-minute stroll.
USD35, 1.5 hours

5:00PM

Dinner at Legal Sea Foods

Indulge in a delicious seafood dinner at Legal Sea Foods, renowned for its fresh catch and New England specialties.
A short 15-minute walk from The Courtyard.
USD50, 2 hours
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