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14-Day Ultimate USA Road Trip Itinerary

Viewed by 258 travelers

Day 1: Explore NYC

New York City, NY

8:00AM

Breakfast at Ess-a-Bagel

Start your day with a classic New York bagel topped with cream cheese at this iconic spot.
Located in Midtown Manhattan, easily accessible via subway.
USD10, 1 hour

9:30AM

Visit Central Park

Stroll through Central Park, enjoying the beautiful landscapes and landmarks.
Head north from Ess-a-Bagel for a 15-minute walk.
Free, 2 hours

12:00PM

Lunch at Shake Shack

Grab a delicious burger and fries at this famous fast-casual eatery.
Walk 20 minutes south to Madison Square Park.
USD15, 1 hour

1:30PM

Visit The MET

Explore world-renowned art collections at the Metropolitan Museum of Art.
Take a 15-minute subway ride to the Upper East Side.
USD25, 3 hours

5:00PM

Dinner at Katz's Delicatessen

Enjoy a classic pastrami sandwich at this legendary deli.
Travel by subway for 20 minutes to the Lower East Side.
USD20, 1.5 hours

7:00PM

Broadway Show

End your day with an iconic Broadway show - book tickets in advance.
Take a 15-minute subway ride to the Theater District.
USD100, 2 hours
Find Hotels in New York City

Day 2: D.C. Day Trip

Washington, D.C.

7:00AM

Breakfast at Founding Farmers

Fuel up with a hearty breakfast at this farm-to-table restaurant.
Drive approximately 4 hours from NYC to D.C.
USD20, 1 hour

9:00AM

Visit the National Mall

Discover the iconic monuments and memorials of the National Mall.
Stroll to the Lincoln Memorial and beyond.
Free, 2 hours

11:30AM

Lunch at Old Ebbitt Grill

Savor delicious seafood at this historic D.C. eatery.
Walk 15 minutes from the National Mall.
USD30, 1 hour

1:00PM

Tour the Smithsonian

Explore one of the many Smithsonian museums located on the National Mall.
Walk over to the National Museum of American History.
Free, 3 hours

4:30PM

Dinner at The Capital Grille

Enjoy a fine dining experience with steak and seafood in the heart of D.C.
Drive 15 minutes to the restaurant.
USD70, 1.5 hours

7:00PM

Drive back to NYC

Conclude your day trip with a scenic drive back to New York City.
Return to NYC via I-95.
USD75 (gas), 4 hours
Find Hotels in Washington

Day 3: Philly's Best

Philadelphia, PA

8:00AM

Breakfast at Green Eggs Cafe

Indulge in gourmet brunch favorites at this popular spot.
Drive 1.5 hours from NYC to Philly.
USD20, 1 hour

9:30AM

Visit the Liberty Bell

See the iconic symbol of American independence.
Walk 15 minutes from the cafe.
Free, 1 hour

11:00AM

Explore Independence Hall

Take a guided tour of this historic site where the Constitution was debated.
Located next to the Liberty Bell, just a short walk away.
USD15, 1 hour

12:30PM

Lunch at Reading Terminal Market

Sample various local foods at this bustling market.
Walk 10 minutes to the market.
USD20, 1.5 hours

2:00PM

Visit the Philadelphia Museum of Art

Check out the famous Rocky Steps and impressive art exhibits.
Drive 10 minutes from the market.
USD20, 2 hours

4:30PM

Dinner at Otto's

Delight in modern Italian cuisine and a casual atmosphere.
Drive back to the city center for 15 minutes.
USD40, 1.5 hours

6:00PM

Return to NYC

Head back to New York for the night.
Drive 1.5 hours on I-95.
USD20 (gas), 1.5 hours
Find Hotels in Philadelphia

Day 4: Pittsburgh Charm

Pittsburgh, PA

8:00AM

Breakfast at Pamela's Diner

Enjoy famous pancakes at this local diner.
Drive 5.5 hours from NYC to Pittsburgh.
USD15, 1 hour

9:30AM

Visit Point State Park

Relax in this scenic park with stunning views of the city.
Short drive to the park entrance.
Free, 1.5 hours

11:00AM

Explore the Andy Warhol Museum

Discover the life and art of the famous pop artist.
Drive 10 minutes to the North Shore.
USD20, 2 hours

1:00PM

Lunch at Primanti Bros.

Savor the iconic sandwich stuffed with fries and coleslaw.
Drive 10 minutes to the Strip District.
USD15, 1 hour

2:30PM

Ride the Duquesne Incline

Take this funicular for panoramic views of Pittsburgh.
Drive 5 minutes to the base of the incline.
USD5, 1 hour

4:00PM

Dinner at Bella Notte

Enjoy delicious Italian dishes with a wonderful view of the city.
Drive back to the city center for 15 minutes.
USD50, 1.5 hours
Find Hotels in Pittsburgh

Day 5: Cleveland Adventure

Cleveland, OH

8:00AM

Breakfast at West Side Market

Sample local pastries and fresh coffee at this vibrant market.
Drive 2 hours from Pittsburgh to Cleveland.
USD10, 1 hour

9:30AM

Visit the Rock & Roll Hall of Fame

Explore the rich history of rock music at this iconic museum.
Drive 15 minutes east along the waterfront.
USD25, 2 hours

12:00PM

Lunch at Barrio

Indulge in delicious tacos at this lively restaurant.
Drive 10 minutes to the restaurant.
USD15, 1 hour

1:30PM

Explore Cleveland Botanical Garden

Wander through beautiful gardens and glasshouses.
Drive 15 minutes from the restaurant.
USD15, 2 hours

4:00PM

Dinner at The Capital Grille

Savor a memorable dinner at this upscale steakhouse.
Drive 20 minutes back to downtown.
USD70, 2 hours
Find Hotels in Cleveland

Day 6: Chicago Style

Chicago, IL

8:00AM

Breakfast at Lou Mitchell's

Enjoy a traditional Chicago breakfast at this favorite diner.
Drive 5 hours from Cleveland to Chicago.
USD15, 1 hour

9:30AM

Visit Millennium Park

Take a photo with the famous Cloud Gate sculpture.
Short drive to the park.
Free, 1.5 hours

11:30AM

Explore the Art Institute of Chicago

Visit one of the oldest and largest art museums in the country.
Walk 15 minutes to the museum.
USD25, 2 hours

2:00PM

Lunch at Giordano's

Experience Chicago's famous deep-dish pizza.
Drive 10 minutes to the iconic pizza place.
USD25, 1.5 hours

3:30PM

Take a Lake Michigan Boat Tour

Enjoy stunning views of the city skyline from the water.
Book and meet at the boat dock nearby.
USD40, 1.5 hours

6:00PM

Dinner at RPM Italian

Indulge in Italian cuisine with a modern twist.
Drive 15 minutes to the restaurant.
USD50, 2 hours
Find Hotels in Chicago

Day 7: Milwaukee Experience

Milwaukee, WI

8:00AM

Breakfast at Charles E. Fromage

Delight in gourmet breakfast options in a cozy setting.
Drive 1.5 hours from Chicago to Milwaukee.
USD15, 1 hour

9:30AM

Visit the Milwaukee Art Museum

Explore the stunning architecture and impressive art collections.
Drive 10 minutes to the museum.
USD20, 2 hours

12:00PM

Lunch at Milwaukee Public Market

Taste local cheeses and fresh meats at this bustling market.
Drive 5 minutes to the market.
USD15, 1 hour

1:30PM

Explore Harley-Davidson Museum

Discover the history of this iconic American brand.
Drive 10 minutes from market to museum.
USD22, 2 hours

4:00PM

Dinner at Lake Park Bistro

Enjoy French-inspired cuisine with a view of Lake Michigan.
Drive 15 minutes to the restaurant.
USD45, 1.5 hours
Find Hotels in Milwaukee

Day 8: Minneapolis Delights

Minneapolis, MN

8:00AM

Breakfast at The Jasper House Cafe

Savor artisanal breakfast dishes in a warm atmosphere.
Drive 1.5 hours from Milwaukee to Minneapolis.
USD15, 1 hour

9:30AM

Visit Mall of America

Explore the massive shopping complex with entertainment options.
Drive 15 minutes to the mall.
Free (shopping at own cost), 3 hours

1:00PM

Lunch at Cheesecake Factory

Indulge in a variety of dishes with their famous cheesecake for dessert.
Located within the mall.
USD25, 1.5 hours

2:30PM

Explore Minnehaha Park

Relax at the beautiful park featuring a waterfall and trails.
Drive 15 minutes to the park.
Free, 2 hours

5:00PM

Dinner at Manny's Steakhouse

Enjoy an exceptional steak dinner in an upscale atmosphere.
Drive 20 minutes from the park.
USD70, 2 hours
Find Hotels in Minneapolis

Day 9: Kansas City BBQ

Kansas City, MO

8:00AM

Breakfast at The Classic Cup

Enjoy a cozy breakfast with delicious coffee.
Drive 7 hours from Minneapolis to Kansas City.
USD15, 1 hour

9:30AM

Visit the Nelson-Atkins Museum of Art

Explore impressive art collections, including Asian art.
Drive 15 minutes from the cafe.
Free, 2 hours

12:00PM

Lunch at Joe's Kansas City Bar-B-Que

Treat yourself to mouth-watering BBQ at this local favorite.
Drive 15 minutes from the museum.
USD20, 1 hour

1:30PM

Explore Country Club Plaza

Stroll through this beautiful shopping district with Spanish architecture.
Drive 10 minutes to Country Club Plaza.
Free, 2 hours

4:00PM

Dinner at Jack Stack Barbecue

Indulge in more delicious BBQ, known for its unique sides.
Drive 10 minutes to the restaurant.
USD30, 1.5 hours
Find Hotels in Kansas City

Day 10: St. Louis Adventures

St. Louis, MO

8:00AM

Breakfast at Rooster

Enjoy creative breakfast dishes and local favorites.
Drive 4 hours from Kansas City to St. Louis.
USD15, 1 hour

9:30AM

Visit Gateway Arch

Experience breathtaking views from the top of this iconic monument.
Drive 10 minutes to the Arch.
USD15, 1.5 hours

11:30AM

Explore Citygarden

Stroll through this urban park featuring beautiful sculptures.
Walk 10 minutes from the Arch.
Free, 1 hour

1:00PM

Lunch at Pappy's Smokehouse

Relish in award-winning Memphis-style BBQ at this popular eatery.
Drive 10 minutes to the restaurant.
USD25, 1.5 hours

2:30PM

Visit the St. Louis Zoo

Explore one of the top-rated zoos in the country, with free admission.
Drive 15 minutes to Forest Park.
Free, 2 hours

5:00PM

Dinner at Sidney Street Cafe

Enjoy innovative American dishes in a cozy atmosphere.
Drive 20 minutes to the restaurant.
USD50, 2 hours
Find Hotels in St. Louis

Day 11: Memphis Music

Memphis, TN

8:00AM

Breakfast at Brother Juniper's

Savor a unique Southern breakfast at this local gem.
Drive 4 hours from St. Louis to Memphis.
USD15, 1 hour

9:30AM

Visit Graceland

Tour the famous home of Elvis Presley and learn about his legacy.
Drive 20 minutes to Graceland.
USD40, 2 hours

12:00PM

Lunch at Gus's World Famous Fried Chicken

Enjoy award-winning fried chicken that’s a Memphis staple.
Drive 15 minutes from Graceland.
USD20, 1 hour

1:30PM

Explore Beale Street

Experience the live music and vibrant atmosphere of this historic street.
Drive 10 minutes to Beale Street.
Free (drinks and music at own cost), 2.5 hours

4:00PM

Dinner at The Rendezvous

Indulge in delicious Memphis-style ribs in a legendary restaurant.
Walk to the nearby restaurant.
USD30, 1.5 hours
Find Hotels in Memphis

Day 12: Nashville Vibes

Nashville, TN

8:00AM

Breakfast at Biscuit Love

Fulfill your cravings with a southern-style breakfast featuring fluffy biscuits.
Drive 3 hours from Memphis to Nashville.
USD15, 1 hour

9:30AM

Visit the Country Music Hall of Fame

Discover the rich history of country music in this extensive museum.
Drive 10 minutes to the museum.
USD25, 2 hours

12:00PM

Lunch at Hattie B's Hot Chicken

Taste Nashville's famous hot chicken at this beloved restaurant.
Drive 10 minutes to the restaurant.
USD20, 1 hour

1:30PM

Explore the Parthenon

Visit this full-scale replica of the original Parthenon in Athens.
Drive 15 minutes to Centennial Park.
USD10, 1.5 hours

3:00PM

Visit the Grand Ole Opry

Take a tour of this iconic music venue and learn about its history.
Drive 20 minutes to the Opry House.
USD30, 1.5 hours

5:00PM

Dinner at The Capitol Grille

Relish a special dinner with Southern-inspired dishes in a refined setting.
Drive 15 minutes back downtown.
USD45, 2 hours
Find Hotels in Nashville

Day 13: Atlanta Excursion

Atlanta, GA

8:00AM

Breakfast at The Breakfast Bar

Enjoy a hearty Southern breakfast before hitting the road.
Drive 4 hours from Nashville to Atlanta.
USD15, 1 hour

9:30AM

Visit the Georgia Aquarium

Explore one of the largest aquariums in the world.
Drive 20 minutes to downtown.
USD40, 2 hours

12:00PM

Lunch at Busy Bee Cafe

Indulge in some down-home Southern cooking at this legendary restaurant.
Drive 10 minutes to the cafe.
USD15, 1 hour

1:30PM

Explore the Martin Luther King Jr. National Historical Park

Learn about the civil rights leader's legacy at this moving historic site.
Drive 15 minutes to the park.
Free, 2 hours

4:00PM

Dinner at The Varsity

Experience the famous hot dogs and burgers at the oldest drive-in restaurant.
Drive 15 minutes to The Varsity.
USD10, 1 hour
Find Hotels in Atlanta

Day 14: Orlando Finale

Orlando, FL

8:00AM

Breakfast at Keke's Breakfast Cafe

Start your day with a delightful breakfast at this popular chain.
Drive 5 hours from Atlanta to Orlando.
USD15, 1 hour

9:30AM

Visit Walt Disney World

Spend the day creating magical memories in the happiest place on earth.
Drive 20 minutes to the park.
USD120 (ticket price), 8 hours

6:30PM

Dinner at Be Our Guest Restaurant

End your trip with a special dining experience in the Magic Kingdom.
Dine within Walt Disney World.
USD60, 2 hours
Find Hotels in Orlando
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