5-Day Ultimate Boston Exploration Itinerary

Day 1: Historic Boston

Boston, MA

8:00AM

Breakfast at The Paramount

Start your day with a classic American breakfast featuring their famous pancakes and farm-fresh eggs.
The restaurant is located in Beacon Hill, easily accessible by the 'T'.
USD 20, 1 hour

9:30AM

Freedom Trail

Walk the iconic Freedom Trail, a 2.5-mile route through 16 historical sites, including the Boston Common and Paul Revere's House.
Follow the red brick road and enjoy guided tours at key locations.
USD 0 (self-guided), 3 hours

1:00PM

Lunch at Cheers Restaurant

Enjoy a hearty lunch at the iconic Cheers, where everybody knows your name, with classic burgers and beers.
Located in Beacon Hill, a short walk from the Freedom Trail.
USD 30, 1 hour

2:30PM

Visit the Museum of Fine Arts

Immerse yourself in art from around the world and admire one of the most comprehensive art collections in the USA.
Take the 'T' to the Museum of Fine Arts Station.
USD 25, 2 hours

5:00PM

Dinner at Legal Sea Foods

Indulge in fresh seafood at this Boston institution, trying the clam chowder and lobster rolls.
Located near the museum, easily reachable on foot.
USD 50, 1.5 hours

7:00PM

Evening stroll along the Charles River Esplanade

Take a leisurely walk along the river with breathtaking views of the Boston skyline.
Head towards the river; it’s a slight walk or a short ride on the 'T'.
USD 0, 1 hour
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Day 2: Innovation and Academia

Cambridge, MA

8:30AM

Breakfast at Tatte Bakery & Cafe

Enjoy a delightful breakfast with baked goods, shakshuka, and rich coffee in this charming café.
Take the 'T' to Alewife and transfer to the bus for Tatte.
USD 15, 1 hour

10:00AM

Harvard University Tour

Join a student-led tour of one of the world’s most prestigious universities and learn about its rich history.
It's a short walk from Tatte to Harvard.
USD 0 (self-guided options available), 2 hours

12:30PM

Lunch at Mr. Bartley's Burger Cottage

Savour a tasty burger at this legendary burger joint famous for its creative patties.
Just a few blocks from Harvard Yard.
USD 20, 1 hour

2:00PM

Visit the MIT Museum

Explore the intersection of science and art at MIT's dedicated museum featuring fascinating exhibits.
Head over via the 'T' to Kendall Station.
USD 10, 2 hours

4:30PM

Explore Kendall Square

Walk around Kendall Square, boasting beautiful parks, shops, and the vibrant local tech scene.
Walk from the museum.
USD 0, 1 hour

6:00PM

Dinner at The Capital Grille

Experience an upscale steak dinner at this renowned restaurant with a sophisticated atmosphere.
Easily reachable via the 'T' back to Boston.
USD 70, 2 hours
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Day 3: Historical Salem

Salem, MA

7:30AM

Breakfast at Red’s Sandwich Shop

Dive into the day with a hearty breakfast at this well-loved café known for its delicious omelettes.
Take the commuter rail from North Station directly to Salem.
USD 15, 1 hour

9:00AM

Salem Witch Museum

Explore the history of the infamous witch trials and view informative exhibits.
A short walk from the train station.
USD 12, 1.5 hours

10:30AM

Salem Maritime National Historic Site

Visit this historic site showcasing the maritime heritage of Salem through guided tours.
Just a few blocks away on foot.
USD 0, 1.5 hours

12:00PM

Lunch at The Lobster Shanty

Savour casual seafood dining with lobster rolls and clam chowder in a rustic setting.
Located in the heart of Salem, a short walk.
USD 25, 1 hour

1:30PM

The House of the Seven Gables

Tour this historic home made famous by Nathaniel Hawthorne, full of fascinating history.
A leisurely walk along the waterfront.
USD 15, 1.5 hours

3:30PM

Peabody Essex Museum

Explore an extensive collection of art and culture from New England and beyond.
Short walk from The House of the Seven Gables.
USD 20, 2 hours

6:00PM

Dinner at Finz Seafood and Grill

End your day in Salem with fine dining focusing on local seafood with a view of the harbour.
A convenient walk from the museum.
USD 45, 1.5 hours
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Day 4: Revolutionary History

Lexington, MA

8:00AM

Breakfast at The Depot

Enjoy a delicious breakfast at this charming spot known for its waffles and coffee.
Take the commuter rail from North Station towards Fitchburg and get off at Lexington.
USD 15, 1 hour

9:30AM

Explore Lexington Battle Green

Visit the historic site of the first battle of the American Revolutionary War; see the monuments and old North Bridge.
It's nearby and well-marked for easy walking.
USD 0, 1 hour

11:00AM

Lexington Historical Society

Learn more about the local history and see artifacts from the revolutionary era.
A short walk from Battle Green.
USD 10, 1.5 hours

12:30PM

Lunch at Max & Dante’s

Savour American comfort food at this local favourite featuring fresh ingredients and craft beers.
Just a short stroll across town.
USD 20, 1 hour

2:00PM

Visit the Buckman Tavern

Discover this historic tavern, where colonial militia gathered before the battles of Lexington and Concord.
Only a quick walk from the restaurant.
USD 5, 1 hour

3:30PM

Drive or take a taxi to Minuteman National Historical Park

Explore the park dedicated to the battlefields and patriotic heritage of the area.
Requires transport; taxis or rideshares are available.
USD 20 (taxi), 2 hours

6:00PM

Dinner at The Colonial Inn

Enjoy a delightful dinner in this historic inn featuring seasonal dishes and colonial charm.
Return to Lexington for dinner at the inn.
USD 60, 1.5 hours
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Day 5: Leisurely Boston

Boston, MA

8:00AM

Breakfast at Flour Bakery + Cafe

Treat yourself to a scrumptious breakfast, specially the sticky buns and breakfast sandwiches.
Located in the Fort Point area, easily accessible via the 'T'.
USD 15, 1 hour

9:30AM

Boston Public Library

Visit the beautiful Boston Public Library, a stunning architectural gem and peaceful haven for book lovers.
Take the 'T' to Copley Square.
USD 0, 1 hour

11:00AM

Trinity Church

Admire the stunning interior and architecture of this historical church located next to the library.
Walk next door from the library.
USD 10, 30 minutes

12:00PM

Lunch at The Food Lab

Indulge in an experimental lunch featuring unique dishes inspired by culinary science.
Short walk away from Trinity Church.
USD 30, 1.5 hours

1:30PM

Visit the New England Aquarium

Explore marine life from the local area to the tropics; this is a wonderful place for all ages.
Travel via the 'T' to the waterfront.
USD 30, 2 hours

4:00PM

Harbour Cruise

Enjoy a scenic cruise around Boston Harbour, taking in the city skyline and beautiful islands.
Board at the nearby pier, tickets available on-site.
USD 40, 1.5 hours

6:00PM

Final Dinner at Mamma Maria

Close your trip with a delicious Italian dinner at this renowned North End restaurant, known for its traditional dishes.
Legally in the North End, accessible through 'T' or Uber.
USD 80, 2 hours
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