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

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
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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
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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
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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
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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
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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
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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
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