14-Day Family Friendly Road Trip from Boston to Washington D.C.

Day 1: Exploring Boston

Boston, MA

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your day with a delicious almond croissant and fresh coffee at this popular local spot.
Head to Tatte Bakery located in Brookline, a short drive or T stop from downtown Boston.
USD15, 1 hour

9:30AM

Freedom Trail Tour

This 2.5-mile-long path will take you past key historical sites, introducing your family to Boston's rich history.
Begin at Boston Common, easily walkable from Tatte Bakery.
USD70 (family ticket), 3 hours

1:00PM

Lunch at Quincy Market

Enjoy diverse food options in a historic setting; try clam chowder in a bread bowl, a local specialty.
Walk from the Freedom Trail to Quincy Market.
USD40, 1.5 hours

3:00PM

Visit the Boston Children's Museum

Engage your kids with hands-on exhibits that promote learning while having fun.
A short drive or bus ride from Quincy Market.
USD45 (family ticket), 2 hours

6:00PM

Dinner at Union Oyster House

Dine in America’s oldest continuously operating restaurant, enjoying fresh seafood and New England classics.
Close drive or walk from the Children's Museum.
USD80, 2 hours
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Day 2: Rhode Island Adventures

Providence, RI

8:00AM

Breakfast at Ellie’s Bakery

Start your day with freshly baked pastries and artisanal coffee.
Drive from Boston to Providence (approx. 1 hour).
USD20, 1 hour

9:30AM

Visit the Roger Williams Park Zoo

Explore animal exhibits and enjoy the beautiful park scenery.
A short drive from Ellie’s Bakery.
USD55 (family ticket), 2.5 hours

12:00PM

Lunch at Federal Hill

Enjoy delicious Italian cuisine in one of Providence's best dining districts.
Drive to Federal Hill, about 10 minutes.
USD60, 1.5 hours

1:30PM

Explore the Museum of Natural History and Planetarium

Enjoy fascinating exhibits and a planetarium show that will amaze your kids.
Drive to the museum, approximately 10 minutes away.
USD20 (family ticket), 2 hours

4:00PM

Visit Waterfire

If visiting during the summer, catch this unique art installation where bonfires light the rivers—an unforgettable experience.
Stroll around Waterplace Park in downtown Providence.
Free, 1 hour

6:00PM

Dinner at Hemenway’s Seafood Grill

Savor fresh seafood with a stunning view of the Providence River.
Walk or quick drive from Waterfire.
USD80, 2 hours
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Day 3: New Haven Highlights

New Haven, CT

8:00AM

Breakfast at The Pantry

Enjoy a cozy breakfast with classic American fare to fuel your day ahead.
Drive from Providence to New Haven (approx. 1.5 hours).
USD30, 1 hour

9:30AM

Yale University Tour

Take a guided tour of this prestigious university while learning about its history and architecture.
Walk to Yale University from The Pantry.
Free, 2 hours

11:30AM

Visit the Yale Peabody Museum of Natural History

Explore dinosaur skeletons, mummies, and more, making science fun for the family!
Short walk from Yale campus.
USD50 (family ticket), 2 hours

2:00PM

Lunch at Frank Pepe Pizzeria

Savor some of the best pizza in the country at this iconic New Haven eatery.
Drive to Frank Pepe's, about 5 minutes away.
USD50, 1.5 hours

3:30PM

Visit the Lighthouse Point Park

Enjoy the beach, lighthouse, and stunning views of Long Island Sound.
Drive to the park, approximately 15 minutes away.
USD20 (parking), 2.5 hours

6:30PM

Dinner at Spanish tapas at Olé

Experience a variety of small plates in a lively family-friendly atmosphere.
Drive back to New Haven center.
USD75, 2 hours
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Day 4: New York City Exploration

New York City, NY

8:00AM

Breakfast at a local diner

Grab a classic NYC breakfast with pancakes and eggs to fuel your adventure.
Drive from New Haven to NYC (approx. 2 hours).
USD35, 1 hour

9:30AM

Statue of Liberty and Ellis Island Tour

Experience a ferry ride to both iconic sites, learning about history along the way.
Catch the ferry from Battery Park.
USD80 (family ticket), 4 hours

1:30PM

Lunch at Eataly NYC Downtown

Delight in various Italian specialties at this bustling marketplace and restaurant.
Walk back to Eataly from the ferry terminal.
USD60, 1.5 hours

3:00PM

Visit One World Observatory

Enjoy breathtaking views of the city from the top of this iconic skyscraper.
A short walk to the observatory from Eataly.
USD100 (family ticket), 2 hours

5:30PM

Explore Battery Park

Relax with stunning views of the harbor while the kids play in the park.
Walk to Battery Park.
Free, 1 hour

7:00PM

Dinner at Junior’s Restaurant

Indulge in famous New York cheesecake and a family-friendly diner environment.
Drive or take public transportation to Junior's in Brooklyn.
USD70, 2 hours
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Day 5: Philadelphia Historical Sites

Philadelphia, PA

8:00AM

Breakfast at Reading Terminal Market

Taste local specialties like scrapple or a classic Philly breakfast sandwich.
Drive from NYC to Philadelphia (approx. 2 hours).
USD25, 1 hour

9:30AM

Visit Independence Hall

Step where the Founding Fathers made history during the signing of the Declaration of Independence.
A short walk from the market.
Free, 1.5 hours

11:00AM

Explore the Liberty Bell

See this important symbol of American independence just steps away from Independence Hall.
Short walk to the Liberty Bell Center.
Free, 30 minutes

12:00PM

Lunch at Campo's Philly Cheesesteaks

Enjoy a famous cheesesteak, a hallmark of Philadelphia cuisine.
Walk to Campo's just a few blocks away.
USD40, 1 hour

1:30PM

Visit the Philadelphia Museum of Art

Marvel at an extensive art collection and climb the famous 'Rocky Steps'!
A short drive or public transit ride from the restaurant.
USD60 (family ticket), 2.5 hours

4:00PM

Explore Fairmount Park

Enjoy some downtime at one of the largest urban parks in the U.S., with playgrounds and natural beauty.
Drive to Fairmount Park.
Free, 2 hours

6:30PM

Dinner at The Capital Grille

Dine in style with fine dining while the kids are treated like family.
Drive back to the city center.
USD120, 2 hours
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Day 6: Delaware Discoveries

Wilmington, DE

8:00AM

Breakfast at Brewed Awakening Coffee

Grab fresh coffee and baked goods to start your day right.
Leave Philadelphia to Wilmington (approx. 30 minutes drive).
USD20, 1 hour

9:30AM

Visit the Delaware Museum of Natural History

Explore the hands-on exhibits, perfect for sparking curiosity in your kids.
Drive to the museum located about 15 minutes away.
USD40 (family ticket), 2 hours

12:00PM

Lunch at Iron Hill Brewery

Enjoy some local craft brews and family-friendly food options.
Short drive from the museum.
USD60, 1.5 hours

2:00PM

Explore Brandywine Zoo

Enjoy a local wildlife experience in this small yet delightful zoo.
Drive to the zoo approximately 10 minutes away.
USD30 (family ticket), 2 hours

4:30PM

Visit the Nemours Estate

Explore the gardens and mansion of this beautiful estate, providing both beauty and education.
Drive to the estate, around 15 minutes from the zoo.
USD40 (family ticket), 2 hours

7:00PM

Dinner at Chelsea Tavern

Enjoy a family-friendly atmosphere with classic American fare.
Short drive from the estate.
USD70, 1.5 hours
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Day 7: Baltimore Fun

Baltimore, MD

8:00AM

Breakfast at Blue Moon Cafe

Indulge in a famous 'Captain Crunch French Toast' or a hearty breakfast combo.
Drive from Wilmington to Baltimore (approx. 1 hour).
USD30, 1 hour

9:30AM

Visit the Maryland Science Center

Engage in interactive science exhibits perfect for kids and families.
Short drive from the cafe to the museum.
USD80 (family ticket), 2.5 hours

12:00PM

Lunch at Phillips Seafood

Savor delicious crab dishes at this renowned location in the Inner Harbor.
A short drive or walk from the science center.
USD90, 1.5 hours

1:30PM

Exploring the Inner Harbor

Enjoy the waterfront with attractions, shops, and stunning views.
Walk around the Inner Harbor area.
Free, 2 hours

4:00PM

Visit the National Aquarium

Admire marine life in this beautiful aquarium, a must-visit for all ages.
Walk to the National Aquarium from Inner Harbor.
USD100 (family ticket), 2 hours

6:30PM

Dinner at Akbar Palace

Explore diverse Indian cuisine that's sure to please the entire family.
Short drive from the aquarium.
USD70, 1.5 hours
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Day 8: Annapolis Charm

Annapolis, MD

8:00AM

Breakfast at Chick & Ruth's Delly

Delight in homemade pancakes or their famous crab cakes for breakfast.
Drive from Baltimore to Annapolis (approx. 30 minutes).
USD35, 1 hour

9:30AM

Visit the U.S. Naval Academy

Take a guided walking tour of the iconic naval academy and learn about its history.
Short drive from the restaurant.
Free, 1.5 hours

11:30AM

Explore Historic Annapolis

Stroll through the charming historic district featuring shops, galleries, and local art.
Easily walkable from the Naval Academy.
Free, 2 hours

1:30PM

Lunch at cantler's Riverside Inn

Enjoy fresh crabs with waterfront views; a local favorite!
Drive to Cantler’s (approx. 10 minutes).
USD70, 1.5 hours

3:00PM

Visit the Chesapeake Bay Maritime Museum

Learn about the region's maritime heritage with engaging exhibits for kids.
Drive to the museum (approx. 30 minutes).
USD45 (family ticket), 2 hours

5:30PM

Dinner at The Boatyard Bar & Grill

Enjoy a casual atmosphere with a diverse menu of seafood and American dishes.
Short drive from the museum.
USD80, 1.5 hours
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Day 9: Washington, D.C. Landmarks

Washington, D.C.

8:00AM

Breakfast at Founding Farmers

Taste farm-fresh breakfast dishes in a charming, family-friendly restaurant.
Drive from Annapolis to D.C. (approx. 1 hour).
USD60, 1 hour

9:30AM

Visit the National Mall

Explore iconic monuments like the Lincoln Memorial and Washington Monument.
Stroll around the National Mall; parking available nearby.
Free, 2 hours

12:00PM

Lunch at food trucks on the National Mall

Grab tasty lunch options from various food trucks lining the Mall, offering diverse cuisines.
Walk to the food truck area.
USD50 (for the family), 1 hour

1:30PM

Visit the Smithsonian National Museum of American History

Experience exhibits dedicated to U.S. history and democracy, great for learning while having fun.
Walk to the museum from the food trucks.
Free, 2 hours

4:00PM

Explore the National Archives

See the Declaration of Independence, Constitution, and other important American documents.
Short walk to the National Archives.
Free, 1.5 hours

6:00PM

Dinner at The Old Ebbitt Grill

Delight in classic dishes with a historic ambiance located near the White House.
Drive or walk from the Archives.
USD150, 2 hours
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Day 10: Smithsonian Museums Day

Washington, D.C.

8:00AM

Breakfast at Le Pain Quotidien

Start your day with healthy options like tartines and organic coffee.
Walk from your hotel if centrally located.
USD40, 1 hour

9:30AM

Visit the Smithsonian National Air and Space Museum

Discover space and flight exhibits perfect for kids and aspiring astronauts.
Taking a short walk from breakfast.
Free, 2.5 hours

12:00PM

Lunch at the museum cafe

Recharge with kid-friendly lunch options within the museum.
In the same building.
USD50, 1 hour

1:30PM

Explore the National Museum of Natural History

Marvel at dinosaurs, mummies, and the Hope Diamond in one of DC’s most popular museums.
Short walk to the adjacent museum.
Free, 2.5 hours

4:00PM

Visit the National Gallery of Art

Experience art masterpieces spanning many eras, engaging and inspiring for the whole family.
Walk to the National Gallery from the previous museum.
Free, 2 hours

6:30PM

Dinner at Founding Farmers

After a long day of learning, relax with hearty American fare back at Founding Farmers.
Walk back to Founding Farmers from the gallery.
USD100, 1.5 hours
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Day 11: Visit Historical Sites

Mount Vernon, VA

8:00AM

Breakfast at The Virginia House

Enjoy homemade country breakfast dishes in a cozy atmosphere.
Drive from D.C. to Mount Vernon (approx. 30 minutes).
USD40, 1 hour

9:30AM

Explore George Washington's Mount Vernon

Tour the estate and learn about George Washington's life and legacy during this interactive experience.
Short drive to Mount Vernon estate.
USD70 (family ticket), 3 hours

12:30PM

Lunch at Mount Vernon Inn Restaurant

Enjoy a colonial-style lunch with dishes sure to please the family.
Located on the estate grounds.
USD60, 1.5 hours

2:00PM

Visit the Mount Vernon Museum

Learn more about Washington’s life through informative exhibits in the museum.
Near the restaurant on the estate.
Included with estate ticket, 1 hour

3:00PM

Stroll through the gardens

Enjoy the beautiful gardens and views of the Potomac River.
Easily accessible on foot within the estate.
Free, 1 hour

5:00PM

Dinner at The Wharf

Dine waterfront with seafood and American delicacies in a casual setting.
Drive back to D.C. (around 30 minutes).
USD90, 1.5 hours
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Day 12: Richmond Explorations

Richmond, VA

8:00AM

Breakfast at The Breakfast Club

Savor oversized omelets and pancakes in this friendly diner.
Drive from D.C. to Richmond (approx. 1.5 hours).
USD30, 1 hour

9:30AM

Visit the Virginia State Capitol

Explore this striking building and learn about Virginia’s legislative process.
Drive to the Capitol building in the city center.
Free, 1 hour

10:30AM

Explore the American Civil War Museum

Learn about the Civil War's impact with exhibits that engage visitors of all ages.
Short drive to the museum.
USD40 (family ticket), 2 hours

12:30PM

Lunch at Mama J's Kitchen

Try some traditional Southern dishes in a cozy diner atmosphere.
Short drive to the restaurant.
USD50, 1.5 hours

2:00PM

Visit Maymont Park

Spend the afternoon exploring gardens, animals, and historical exhibits in this sprawling park.
Drive to Maymont Park, approx. 10 minutes away.
Free, 3 hours

5:30PM

Dinner at 2nd Street Bistro

Wrap up the day with delicious Southern cuisine in a laid-back setting.
Drive back to the city center.
USD70, 1.5 hours
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Day 13: Colonial Williamsburg

Williamsburg, VA

8:00AM

Breakfast at The Blue Talon Bistro

Indulge in homemade pastries and hearty breakfast classics to fuel your exploration.
Drive from Richmond to Williamsburg (approx. 1 hour).
USD30, 1 hour

9:30AM

Explore Colonial Williamsburg

Immerse your family in 18th-century life at this living history museum with hands-on activities.
Short drive to the historic area.
USD100 (family ticket), 3 hours

1:00PM

Lunch at Christiana Campbell's Tavern

Dine in an authentic colonial tavern with dishes inspired by the 18th century.
Easily accessible in the historic area.
USD80, 1.5 hours

2:30PM

Visit the Governor's Palace

Explore this stunning historical site that showcases colonial architecture.
Just a short walk from the Tavern.
Included with tickets for Colonial Williamsburg., 1 hour

3:30PM

Stroll through Merchant's Square

Enjoy some shopping and unique souvenirs in this charming outdoor space.
Short walk from the Governor's Palace.
Free, 1 hour

5:00PM

Dinner at The Fat Canary

Enjoy fine dining inspired by local ingredients, with options everyone will love.
Short drive back to the historic area.
USD150, 2 hours
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Day 14: Beach Day

Virginia Beach, VA

8:00AM

Breakfast at Doc Taylor's Restaurant

Fill up on a hearty breakfast of eggs benedict or pancakes before heading to the beach.
Drive from Williamsburg to Virginia Beach (approx. 1 hour).
USD30, 1 hour

9:30AM

Relax at Virginia Beach

Unwind on the sand enjoying the sun and surf in this family-friendly beach environment.
Arrive at the Virginia Beach waterfront.
Free, 4 hours

1:30PM

Lunch on the Boardwalk

Enjoy delicious seafood or ice cream while people-watching along the boardwalk.
Stroll along the Boardwalk.
USD50, 1.5 hours

3:00PM

Visit the Virginia Aquarium & Marine Science Center

Explore interactive exhibits, including a large shark tunnel and touch pools for kids.
Short drive from the beach.
USD70 (family ticket), 2 hours

5:30PM

Dinner at Waterman's Surfside Grille

Finish your trip with beachfront dining, enjoying great views and fresh seaside cuisine.
Short drive from the aquarium.
USD80, 1.5 hours
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