14-Day Ultimate USA Road Trip Itinerary

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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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