Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Weeklong Revolutionary America Driving Tour: From Boston to Philadelphia’s Historic Gems

Viewed by 169 travelers

Day 1: Arrival and Boston Intro

Boston, Massachusetts on May 1, 2025

8:00am

Breakfast at Tatte Bakery & Cafe

Start your day with a delicious breakfast of pastries and coffee at this popular local bakery known for fresh ingredients.
USD15, 1h0m

9:30am

Freedom Trail Part 1: Boston Common to State House

Walk the first segment of the trail, visiting Boston Common, the Massachusetts State House, and Park Street Church.
Free, 2h0m

12:00pm

Lunch at The Paramount

Enjoy classic American brunch favorites at this cozy, family-friendly eatery in Boston’s South End.
USD20, 1h0m

1:30pm

Freedom Trail Part 2: Granary Burying Ground and King's Chapel

Explore sites where notable patriots are buried and the historic King's Chapel, both critical to revolutionary history.
Free, 1h30m

3:30pm

Visit Old North Church

See the historic church famous for “One if by land, two if by sea” signal that started the Revolution.
USD5, 1h0m

5:00pm

Dinner at Union Oyster House

Dine at America’s oldest restaurant serving historic charm and fresh seafood in the heart of Boston.
USD30, 1h30m
Find Hotels in Boston

Day 2: Boston Historic Sites

Boston, Massachusetts on May 2, 2025

8:00am

Breakfast at Flour Bakery & Cafe

Get energized with a freshly baked pastry and coffee at this beloved local spot.
USD15, 1h0m

9:30am

Bunker Hill Monument and Museum

Climb the monument commemorating the first major battle and explore the museum’s exhibits on Revolutionary battles.
USD10, 2h0m

12:00pm

Lunch at Quincy Market

Enjoy a variety of local and international foods in this historic marketplace.
USD20, 1h0m

1:30pm

USS Constitution Museum

Visit “Old Ironsides,” the oldest commissioned warship afloat, with fun and educational exhibits.
Free, 2h0m

4:00pm

Walk through Charlestown Navy Yard

Stroll around the scenic historic shipyard adjacent to the USS Constitution Museum.
Free, 1h0m

6:00pm

Dinner at The Barking Crab

Family-friendly seafood dining with a casual atmosphere along the Boston waterfront.
USD30, 1h30m
Find Hotels in Boston

Day 3: Travel to New York City

Travel Boston to New York City on May 3, 2025

7:30am

Breakfast at Mike & Patty’s

Start with a quick, tasty breakfast featuring sandwiches to-go perfect for travel day.
USD15, 0h45m

8:30am

Drive from Boston to New York City

Enjoy the scenic 4-hour drive south to New York City; stop for rest breaks as needed.
Car rental and fuel approx USD150, 4h0m

1:00pm

Lunch at Eataly NYC Downtown

Experience Italian-inspired food hall near the World Trade Center, great for families.
USD25, 1h0m

2:30pm

Tour Fraunces Tavern Museum

Explore the museum and historic building where Washington said goodbye to his officers.
USD8, 1h30m

4:15pm

Walk Battery Park and Visit Castle Clinton

Relax in the park overlooking the harbor and visit the historic fortification.
Free, 1h0m

6:00pm

Dinner at Adrienne’s Pizzabar

Enjoy delicious Sicilian-style square pizza in an inviting atmosphere.
USD20, 1h30m
Find Hotels in Travel Boston to New York City

Day 4: New York Revolutionary Experience

New York City, New York on May 4, 2025

8:00am

Breakfast at Westville Chelsea

Eat fresh and healthy breakfast dishes with friendly service in Chelsea.
USD15, 1h0m

9:30am

Visit The New-York Historical Society Museum & Library

Discover exhibits on the American Revolution and New York’s history with engaging displays.
USD22, 2h0m

12:00pm

Lunch at Shake Shack Madison Square Park

Enjoy classic American burgers and shakes in a family-friendly outdoor setting.
USD20, 1h0m

1:30pm

Walk the Hudson River Greenway

Take a scenic stroll along Manhattan’s west side waterfront for fresh air and views.
Free, 1h30m

3:30pm

Visit St. Paul’s Chapel

Explore the chapel where George Washington worshipped during the Revolution, a serene spot in the city.
Free, 0h45m

5:00pm

Early Dinner at Fraunces Tavern Restaurant

Savor hearty meals in one of New York’s oldest colonial taverns.
USD35, 1h30m
Find Hotels in New York City

Day 5: Travel to Philadelphia

Travel New York City to Philadelphia on May 5, 2025

7:30am

Breakfast at Bluestone Lane

Light, Australian-style breakfast and coffee to energize travel day.
USD15, 1h0m

8:30am

Drive New York City to Philadelphia

Enjoy a roughly 2-hour scenic drive to Philadelphia to begin your exploration of America’s historical heart.
Car rental and fuel approx USD80, 2h0m

11:00am

Check-in and Lunch near Historic District

Grab lunch at High Street Philly, known for fresh, quality sandwiches and family-friendly options.
USD20, 1h0m

12:30pm

Visit Independence National Historical Park

Explore Independence Hall, the Liberty Bell, and other historic sites foundational to the Revolution.
Free, 3h0m

5:30pm

Dinner at City Tavern

Experience colonial-era-inspired cuisine in an atmospheric tavern perfect for families.
USD30, 1h30m
Find Hotels in Travel New York City to Philadelphia

Day 6: Philadelphia Museums and Neighborhoods

Philadelphia, Pennsylvania on May 6, 2025

8:00am

Breakfast at Sabrina’s Cafe

Hearty, creative breakfast to fuel a full day of exploring Philadelphia's historical and cultural sites.
USD15, 1h0m

9:30am

Museum of the American Revolution

Engage with immersive exhibits and interactive displays perfect for both adults and children, exploring the Revolution’s history deeply.
USD20, 3h0m

12:30pm

Lunch at Reading Terminal Market

Enjoy a bustling market with diverse food stalls offering local favorites and international cuisine.
USD20, 1h0m

2:00pm

Visit Betsy Ross House

Explore the home and legacy of Betsy Ross, credited with sewing the first American flag.
USD10, 1h0m

3:30pm

Explore Elfreth’s Alley

Walk this charming historic street, the oldest continuously inhabited residential street in America.
Free, 1h0m

5:00pm

Relax at Washington Square Park

Enjoy a quiet afternoon break in this peaceful park surrounded by historic buildings.
Free, 1h0m

6:30pm

Dinner at The Bourse Food Hall

Sample a variety of local and international dishes in a lively food hall setting.
USD25, 1h30m
Find Hotels in Philadelphia

Day 7: Final Philadelphia Explorations & Departure

Philadelphia, Pennsylvania on May 7, 2025

8:00am

Breakfast at Green Eggs Cafe

Enjoy innovative and hearty breakfast dishes, ideal for a final day in Philadelphia.
USD15, 1h0m

9:30am

Visit Franklin Court and Benjamin Franklin Museum

Delve into the life of Benjamin Franklin through engaging exhibits and historic sites.
USD10, 2h0m

11:30am

Stroll Historic Society of Pennsylvania

Browse exhibits and archives that tell the story of Pennsylvania’s and America’s heritage.
Free, 1h0m

12:30pm

Lunch at Distrito

Enjoy vibrant Mexican dishes in a lively setting, great for a last memorable meal in the city.
USD25, 1h0m

2:00pm

Return Car and Prepare for Departure

Head to Philadelphia International Airport, return rental car, and check in for your flight home.
Car rental return fee approx USD30, 1h30m
Find Hotels in Philadelphia
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed