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

Viewed by 424 travelers

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
Find Hotels in Annapolis

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
Find Hotels in Washington DC

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
Find Hotels in Alexandria

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
Find Hotels in Richmond

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
Find Hotels in Williamsburg

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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