14-Day Family Friendly Road Trip Itinerary: Boston to Washington DC

Day 1: Boston Exploration

Boston, MA

8:00AM

Breakfast at The Friendly Toast

Start your day with unique breakfast dishes at The Friendly Toast, a family-friendly diner known for its quirky decor and delicious flavors.
Located in Back Bay.
USD30, 1 hour

9:30AM

Boston Freedom Trail

Explore the 2.5-mile trail filled with historical sites such as Boston Common and Paul Revere's House.
Follow the red brick path starting from Boston Common.
Free, 3 hours

12:30PM

Lunch at Faneuil Hall Marketplace

Discover a variety of food options in a vibrant atmosphere, perfect for any palate.
Short walk from the end of the Freedom Trail.
USD60, 1.5 hours

2:00PM

Visit the Boston Children's Museum

Engage in hands-on exhibits that focus on education and play, perfect for children to learn in a fun environment.
Subway (Red Line) from Haymarket to Broadway.
USD38, 2.5 hours

5:00PM

Dinner at Legal Sea Foods

Enjoy fresh seafood in a family-friendly atmosphere known for its clam chowder.
Short drive back to the waterfront area.
USD100, 1.5 hours

7:00PM

Walk around Boston Harbor

Stroll along the scenic harbor for beautiful views of the city at sunset.
Directly accessible from Legal Sea Foods.
Free, 1 hour
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Day 2: Hartford Highlights

Hartford, CT

8:00AM

Breakfast at Max Downtown

Savor a delicious breakfast at this upscale spot known for its fresh ingredients.
Short drive from your hotel.
USD50, 1 hour

9:30AM

Mark Twain House & Museum

Visit the historic home of the famous author and explore the museum dedicated to his life adventure.
Short drive to Farmington Ave.
USD40, 2 hours

12:00PM

Lunch at Salute

Enjoy Italian-American cuisine with a cozy and welcoming atmosphere.
10-minute drive back to the city center.
USD70, 1.5 hours

1:30PM

Connecticut Science Center

Join hands-on exhibits and explore the wonders of science in this family-friendly center.
Short drive from lunch spot.
USD40, 2.5 hours

4:00PM

Bushnell Park

A lovely park to relax, with a carousel that the kids will enjoy.
Short drive or a nice walk from the Science Center.
Free, 1 hour

5:30PM

Dinner at The Capital Grille

Dine on delicious steaks and seafood while enjoying a view of the park.
Short drive from the park.
USD120, 2 hours
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Day 3: New Haven Education

New Haven, CT

8:00AM

Breakfast at Claire's Corner Copia

Enjoy a hearty vegetarian breakfast at this local favorite known for its sustainability.
Short drive from hotel.
USD40, 1 hour

9:30AM

Yale University Art Gallery

Explore an impressive collection of art spanning centuries, all for free!
Short drive to Yale Campus.
Free, 2 hours

11:30AM

Lunch at Frank Pepe Pizzeria

Try the famous New Haven-style pizza at this iconic establishment.
Short drive from the gallery.
USD50, 1.5 hours

1:00PM

Explore the Peabody Museum of Natural History

Engage with exhibits on dinosaurs and the natural world at this fascinating museum.
5-minute walk from lunch.
USD20, 2 hours

3:30PM

New Haven Green

Relax and let the kids play in this central park area with occasional performances.
10-minute walk from the museum.
Free, 1 hour

5:00PM

Dinner at Union League Cafe

A refined dining experience featuring French cuisine in an elegant setting.
10-minute walk from the Green.
USD100, 1.5 hours
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Day 4: New York Wonders

New York City, NY

8:00AM

Breakfast at Sarabeth's Central Park South

Indulge in a delightful breakfast at this lovely eatery just steps away from Central Park.
Short drive from New Haven to NYC.
USD70, 1.5 hours

10:00AM

Visit the American Museum of Natural History

Spend your morning exploring dinosaurs, the planetarium, and a vast array of exhibits.
Take the subway (A/C Line) or drive.
USD100, 3 hours

1:00PM

Lunch at Shake Shack

Grab iconic burgers and shakes at this beloved fast-casual restaurant.
Walk back toward the Upper West Side.
USD50, 1 hour

2:30PM

Central Park Exploration

Enjoy a leisurely stroll through Central Park, allowing kids to play at the playgrounds.
Short walk from Shake Shack.
Free, 2 hours

4:30PM

Top of the Rock Observation Deck

Marvel at the breathtaking views of the city skyline and Central Park from above.
Short cab ride to Rockefeller Center.
USD80, 1.5 hours

6:00PM

Dinner at Carmine's Italian Restaurant

Family-style dining with hearty Italian classics ensures everyone leaves happy.
Short walk from Top of the Rock.
USD120, 1.5 hours
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Day 5: Philly History

Philadelphia, PA

8:00AM

Breakfast at breakfast at Sabrina's Cafe

Start your day with oversized portions and creative dishes at this popular brunch spot.
Short drive from NYC.
USD60, 1.5 hours

10:00AM

Liberty Bell Center

Visit this iconic symbol of American independence and learn its history.
A short drive to the Liberty Bell Center.
Free, 1 hour

11:30AM

Lunch at Reading Terminal Market

Explore a plethora of food vendors offering a variety of local and international food options.
Walk to Reading Terminal Market.
USD50, 1.5 hours

1:00PM

Philadelphia Museum of Art

Discover a stunning collection of art along with the famous Rocky Steps.
Short cab ride to the museum.
USD50, 2 hours

3:30PM

Franklin Square

Enjoy a relaxing afternoon at this park featuring a carousel and mini-golf.
Short cab ride from the museum.
USD20, 2 hours

5:30PM

Dinner at The Olde Bar

Dine in a beautifully restored historic setting known for its great seafood and drinks.
Short drive back to the city center.
USD90, 1.5 hours
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Day 6: Baltimore Excursion

Baltimore, MD

8:00AM

Breakfast at Blue Moon Cafe

Enjoy a hearty breakfast in this charming cafe known for its stuffed French toast.
Short drive from Philadelphia.
USD40, 1 hour

9:30AM

National Aquarium

Visit the stunning National Aquarium and see marine animals from around the globe.
Short drive to the waterfront.
USD80, 2.5 hours

12:00PM

Lunch at Phillips Seafood

Indulge in fresh Maryland crab cakes and other local seafood dishes.
Located on the harbor.
USD100, 1.5 hours

1:30PM

Inner Harbor Exploration

Stroll around the picturesque harbor area filled with shops and attractions.
Easy walk from lunch spot.
Free, 2 hours

3:30PM

American Visionary Art Museum

Discover unique and unconventional art at this museum dedicated to self-taught artists.
Short drive or easy walk from Inner Harbor.
USD20, 1.5 hours

5:00PM

Dinner at The Rusty Scupper

Enjoy fine dining with beautiful views of the harbor at this upscale seafood restaurant.
Easy drive back from the museum.
USD150, 2 hours
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Day 7: Annapolis Adventures

Annapolis, MD

8:00AM

Breakfast at Chick & Ruth's Delly

Start your day with a hearty breakfast including their famous pancakes.
Short drive from Baltimore.
USD40, 1 hour

9:30AM

U.S. Naval Academy Tour

Explore the historic grounds and learn about the academy's rich history.
Short drive from breakfast spot.
Free, 1.5 hours

11:30AM

Lunch at McGarvey's Saloon & Oyster Bar

Savor delicious seafood in an informal setting known for fresh oysters.
Walk to the waterfront.
USD70, 1.5 hours

1:00PM

Maryland State House

Visit the historic state house, a vital part of Maryland's history.
Short walk from McGarvey's.
Free, 1 hour

2:15PM

Stroll along ego Beach

Relax on the beach and allow kids to enjoy water activities.
Short drive to ego Beach.
Free, 1.5 hours

4:00PM

Shopping at Eastport Gateway

Browse local shops for unique gifts and souvenirs.
Short drive from ego Beach.
Free, 1.5 hours

5:30PM

Dinner at The Boathouse

Enjoy casual dining with views of the marina.
Short drive from shopping.
USD70, 1.5 hours
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Day 8: Washington DC Arrival

Washington DC

8:00AM

Breakfast at Founding Farmers

Dig into hearty American breakfast classics at this popular restaurant.
Short drive from Annapolis.
USD70, 1.5 hours

10:00AM

Visit the National Mall

Explore monuments and memorials such as Lincoln and Washington with tremendous historical significance.
Short drive to the National Mall.
Free, 3 hours

1:00PM

Lunch at Old Ebbitt Grill

Try the famous oysters and other classic American dishes in a splendid atmosphere.
Short drive from the National Mall.
USD80, 1.5 hours

2:30PM

Smithsonian National Air and Space Museum

Engage with aviation and space exhibitions that will fascinate children and adults alike.
Short walk from lunch.
Free, 3 hours

5:30PM

Dinner at The Hamilton

Enjoy a diverse menu with something for everyone in this family-friendly restaurant.
Short walk from the museum.
USD100, 2 hours
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Day 9: Washington DC Adventures

Washington DC

8:00AM

Breakfast at Le Pain Quotidien

Start your day with wholesome pastries and fresh coffee in a charming cafe.
Short walk from your hotel.
USD40, 1 hour

9:30AM

Capitol Building Tour

Take a guided tour of the iconic Capitol Building to learn about the legislative process.
Short taxi ride to the Capitol.
Free, 1.5 hours

11:15AM

National Museum of Natural History

Explore captivating exhibits featuring the wonders of natural history.
Short taxi ride back toward the National Mall.
Free, 2.5 hours

1:45PM

Lunch at The Whistle Stop

Enjoy a cozy lunch featuring seasonal and local ingredients.
Short walk from the museum.
USD60, 1.5 hours

3:15PM

Visit The White House

Stop for a photo-op outside the iconic residence of the President.
Short walk from lunch.
Free, 30 minutes

4:00PM

Tour of the National Gallery of Art

Admire masterpieces from around the world housed in this stunning museum.
Short walk from The White House.
Free, 1.5 hours

5:30PM

Dinner at Carmine’s Italian Restaurant

Finish your day with family-sized portions of delicious Italian cuisine.
Short walk from the gallery.
USD120, 1.5 hours
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Day 10: Exploring Alexandria

Alexandria, VA

8:00AM

Breakfast at The Goodhart

Start your day with a fresh breakfast sandwich and coffee at this quaint local spot.
Short drive to Alexandria.
USD40, 1 hour

9:30AM

Explore Old Town Alexandria

Wander the historic streets and enjoy shops, restaurants, and galleries.
Walking distance in Old Town.
Free, 2 hours

11:30AM

Lunch at Fish Market

Savor fresh seafood with a beautiful waterfront view.
Short walk from historic area.
USD70, 1.5 hours

1:00PM

Stabler-Leadbetter Apothecary Museum

Visit the oldest continuously operating pharmacy in the USA for a glimpse into history.
Short walk from lunch.
USD10, 1 hour

2:15PM

Take a Water Taxi to National Harbor

Enjoy a scenic boat ride to National Harbor and explore the area.
Walking distance to the dock.
USD20, 2 hours

4:30PM

National Harbor Exploration

Visit The Capital Wheel for stunning views and explore shops along the waterfront.
Walking distance from the water taxi drop-off.
USD15, 2 hours

6:30PM

Dinner at The Walrus Oyster and Ale House

Finish your day with delicious seafood and a kids-friendly menu in a fun atmosphere.
Short walk from the harbor.
USD80, 1.5 hours
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Day 11: Richmond Discoveries

Richmond, VA

8:00AM

Breakfast at Perly's

Delight in delicious Jewish delicacies and fantastic breakfast options.
Short drive from Alexandria.
USD50, 1.5 hours

9:30AM

Virginia State Capitol

Discover the history of Virginia and the Capitol's architectural beauty.
Short drive from breakfast.
Free, 1 hour

10:30AM

The American Civil War Museum

Learn about the Civil War through engaging exhibits and artifacts.
Short drive from the Capitol.
USD15, 2 hours

1:00PM

Lunch at Mama J's Kitchen

Enjoy delicious Southern comfort food that the entire family will love.
Short drive from the museum.
USD60, 1.5 hours

2:30PM

Explore Maymont Park

Wander through beautiful gardens and visit the Nature Center for kids to explore.
Short drive from lunch.
Free, 2 hours

5:00PM

Dinner at The Frontier Kitchen

Wrap up the day with casual dining featuring fresh, local ingredients.
Short drive from the park.
USD70, 1.5 hours
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Day 12: Williamsburg History

Williamsburg, VA

8:00AM

Breakfast at The Whaling Company

Enjoy breakfast with a view at this waterfront restaurant.
Short drive from Richmond.
USD40, 1 hour

9:30AM

Historic Jamestowne

Explore the birthplace of American democracy and discover artifacts from the first settlement.
Short drive to the site.
USD30, 2 hours

11:30AM

Lunch at the Caps Pizza

Have a casual lunch at a family-friendly pizza place.
Short drive or a 10-minute walk.
USD50, 1.5 hours

1:00PM

Colonial Williamsburg

Experience living history as you stroll through reconstructed buildings and interact with costumed interpreters.
Short drive from lunch.
USD40, 3 hours

4:30PM

Dinner at The Kings Arms Tavern

Dine in a historic setting with delicious colonial-inspired dishes that appeal to all ages.
Short drive from Colonial Williamsburg.
USD90, 2 hours
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Day 13: Beach and Relax

Virginia Beach, VA

8:00AM

Breakfast at The Bee & The Biscuit

Enjoy a farm-to-table breakfast at this charming eatery offering fresh ingredients.
Short drive from Williamsburg.
USD50, 1 hour

9:30AM

Visit Virginia Beach Boardwalk

Take a stroll along the boardwalk, perfect for relaxing and enjoying ocean views.
Short drive to the beach.
Free, 1.5 hours

11:00AM

Beach Time

Spend your late morning enjoying the sand and sun at Virginia Beach.
Collection is directly on the beach.
Free, 3.5 hours

3:00PM

Lunch at Waterman’s Surfside Grille

Savor casual beach fare with lovely ocean views.
Short walk from the beach.
USD70, 1.5 hours

4:30PM

Explore the Virginia Aquarium

Engage with marine life exhibits and special activities for kids.
Short drive from the beachfront.
USD30, 2.5 hours

7:00PM

Dinner at Capt. George’s Seafood Restaurant

Indulge in an all-you-can-eat seafood buffet that will satisfy everyone’s cravings.
Short drive from the aquarium.
USD90, 2 hours
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Day 14: Return to DC

Return to Washington DC

8:00AM

Breakfast at Doc Taylor's

Enjoy a laid-back breakfast with hearty portions in this family-friendly diner.
Short drive from Virginia Beach.
USD60, 1 hour

9:30AM

Drive back to Washington DC

Embark on your journey back, reflecting on your memorable road trip.
Take I-64 W and I-95 N.
Free, 3 hours

12:30PM

Lunch at Founding Farmers Radnor, PA

Make a leisurely stop on your way back for a fantastic farm-to-table lunch.
Quick stop along the way.
USD80, 1.5 hours

2:00PM

Drive to Washington DC

Continue your journey to the final destination.
Easy route back to DC.
Free, 1.5 hours

3:30PM

Arrival in Washington DC

Enjoy your arrival and reflect on the memories created during this amazing road trip.
Navigation through DC.
Free, N/A
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