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Ultimate USA Cross-Country Trip Itinerary: New York to San Francisco in 16 Days

Viewed by 303 travelers

Day 1: Iconic NYC Landmarks

New York City, USA on October 18, 2025

8:00am

Breakfast at Ess-a-Bagel

Start the day with authentic New York bagels renowned for their chewy texture and variety of spreads.
USD10, 1h

9:30am

Statue of Liberty & Ellis Island Tour

Take a ferry from Battery Park to visit these iconic symbols of American freedom and history. Book tickets ahead as tours run from 9am to 5pm.
USD25, 3h

1:00pm

Lunch at Eataly Downtown

Enjoy Italian fare in this bustling food market with diverse options from fresh pasta to pizza.
USD30, 1h

2:30pm

Visit 9/11 Memorial & Museum

Explore the powerful memorial and museum commemorating the events of 9/11. Open daily 9am to 8pm.
USD26, 2h

5:00pm

Walk Through Wall Street and Battery Park

Stroll through the financial district and relax at Battery Park with skyline views and waterfront ambiance.
Free, 1h

7:00pm

Dinner at Keens Steakhouse

Savor classic New York steaks and historic ambiance at this legendary restaurant open until 11pm.
USD60, 1.5h
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Day 2: Central Park & Museums

New York City, USA on October 19, 2025

8:00am

Breakfast at Sarabeth's Central Park South

Enjoy a refined breakfast with delicious pastries and classic American dishes just steps from Central Park.
USD25, 1h

9:30am

Central Park Exploration

Spend the morning walking or biking through Central Park visiting Bethesda Terrace, Bow Bridge, and the Conservatory Garden.
Free, 3h

12:30pm

Lunch at The Loeb Boathouse

Dine lakeside at this charming restaurant in Central Park with American cuisine and lovely views.
USD40, 1h

2:00pm

The Metropolitan Museum of Art

Explore one of the world's largest art museums featuring diverse collections. Open until 5:30pm.
USD30, 3h

6:00pm

Dinner at Carmine's

Family-style Italian dining with generous portions, lively atmosphere, open till 11pm.
USD50, 1.5h
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Day 3: Brooklyn & Nightlife

New York City, USA on October 20, 2025

8:30am

Breakfast at Juliana’s Pizza

Famous for New York style pizza for breakfast or brunch, located near Brooklyn Bridge Park.
USD20, 1h

10:00am

Walk Brooklyn Bridge and Explore DUMBO

Walk the scenic Brooklyn Bridge, then explore DUMBO’s art galleries, shops and waterfront park with Manhattan views.
Free, 3h

1:30pm

Lunch at Time Out Market Brooklyn

Sample a variety of cuisines from local chefs inside Brooklyn’s lively food hall.
USD30, 1h

3:00pm

Visit Brooklyn Museum

Explore extensive art collections and dynamic exhibitions, open 11am-6pm on Sunday.
USD16, 2h

6:30pm

Dinner at The River Café

Upscale dining under Manhattan Bridge with stunning night views of Manhattan skyline.
USD80, 2h
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Day 4: Miami Beach Fun

Miami, USA on October 21, 2025

7:30am

Breakfast at Big Pink

Start your Miami day with a hearty breakfast at this casual eatery known for large portions and classic diner fare. Open 8am-11pm.
USD20, 1h

9:00am

Relax at South Beach

Enjoy the morning sun and iconic pastel lifeguard towers on the famous sandy beach.
Free, 3h

12:30pm

Lunch at Joe’s Stone Crab

Taste Miami’s renowned seafood, especially the stone crab claws; open 11:30am-10pm.
USD50, 1h

2:00pm

Visit Art Deco Historic District

Take a guided walking tour to admire Miami Beach’s vibrant Art Deco architecture, tours run till 4pm.
USD25, 2h

5:00pm

Explore Lincoln Road Mall

Shop and browse this pedestrian street filled with shops, cafes, and street performers.
Free, 1.5h

7:30pm

Dinner at Yardbird Southern Table & Bar

Enjoy elevated southern comfort food in a stylish setting, open until 10pm.
USD40, 1.5h
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Day 5: Everglades & Nightlife

Miami, USA on October 22, 2025

7:00am

Breakfast at The Front Porch Café

A local favorite for fresh and casual breakfast, opens at 7am.
USD15, 45m

8:00am

Airboat Tour in Everglades National Park

Take a thrilling airboat ride to see unique wildlife including alligators and exotic birds. Tours usually start early until late afternoon.
USD35, 3h

12:00pm

Lunch at Robert is Here

Enjoy fresh local produce and smoothies at this legendary fruit stand en route back to Miami.
USD15, 1h

2:30pm

Visit Vizcaya Museum and Gardens

Explore this stunning historic estate with beautiful gardens overlooking Biscayne Bay. Open until 5:30pm.
USD25, 2h

6:00pm

Sunset at South Pointe Park

Experience panoramic views of the Miami skyline and ocean during sunset.
Free, 1h

7:30pm

Dinner at Cvi.che 105

Taste outstanding Peruvian cuisine in a vibrant atmosphere, open until 10:30pm.
USD35, 1.5h
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Day 6: Historical Washington

Washington D.C., USA on October 23, 2025

7:30am

Breakfast at Founding Farmers DC

Enjoy a sustainable American breakfast menu in a rustic chic environment, opens at 7am.
USD25, 1h

9:00am

Visit National Mall & Monuments

Tour the iconic Lincoln Memorial, Washington Monument, and WWII Memorial, perfect for history lovers.
Free, 3h

12:30pm

Lunch at Old Ebbitt Grill

Historic tavern steps from the White House serving classic American dishes, open 11am-11pm.
USD40, 1h

2:00pm

Smithsonian National Air and Space Museum

Explore world-famous aircraft and space artifacts with interactive exhibits, open until 7:30pm.
Free, 3h

5:30pm

Walk Around Tidal Basin

Relax by the water’s edge and see the Jefferson Memorial especially enjoyable at dusk.
Free, 1h

7:00pm

Dinner at The Hamilton

Dine on American fare with live music in a bustling venue near the White House, open until 10pm.
USD50, 1.5h
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Day 7: Chicago Architecture

Chicago, USA on October 24, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Popular spot for hearty pancakes and breakfast all day, opens at 7am.
USD20, 1h

9:30am

Chicago Architecture River Cruise

See the city’s famous architecture from the river with a guided informative tour, cruises run 9am-4pm.
USD50, 1.5h

11:30am

Millennium Park & Cloud Gate (The Bean)

Walk around this iconic city park and take photos with the famous reflective sculpture.
Free, 1h

12:30pm

Lunch at Giordano’s

Try famous Chicago deep-dish pizza in a lively setting, open 11am-10pm.
USD25, 1h

2:00pm

Visit Art Institute of Chicago

Explore world-class art collections including American Gothic and impressionist masterpieces. Open until 5pm.
USD30, 3h

6:00pm

Dinner at The Signature Room at the 95th

Dine with stunning city views atop John Hancock Center, reservation recommended.
USD60, 1.5h
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Day 8: Museum & Lakefront

Chicago, USA on October 25, 2025

8:00am

Breakfast at Lou Mitchell’s

Iconic breakfast spot known for friendly service and fresh food, opens at 5:30am.
USD20, 1h

9:30am

Field Museum of Natural History

Discover extensive natural history exhibits, dinosaur fossils including Sue the T. rex, open from 9am to 5pm.
USD40, 3h

1:00pm

Lunch at Shake Shack

Enjoy casual American burgers and shakes in a quick, convenient setting.
USD15, 45m

2:00pm

Shedd Aquarium

Explore aquatic life from freshwater to ocean habitats, open 9am-6pm.
USD40, 3h

6:30pm

Dinner at RPM Italian

Trendy Italian dining with modern dishes and drinks, open late.
USD50, 1.5h
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Day 9: Vegas Entertainment

Las Vegas, USA on October 26, 2025

9:00am

Breakfast at The Henry, Cosmopolitan

Modern American breakfast at this upscale hotel restaurant, open from 6am.
USD25, 1h

10:30am

Explore the Las Vegas Strip

Walk the famous strip to see themed resorts, fountains, and attractions at your own pace.
Free, 3h

1:30pm

Lunch at Gordon Ramsay Hell’s Kitchen

Dine on Chef Ramsay’s signature dishes near the Strip, reservations recommended.
USD50, 1.5h

3:00pm

Visit Bellagio Conservatory & Botanical Gardens

Free entrance to seasonal themed gardens inside Bellagio, open all day.
Free, 1h

4:30pm

Relax at Hotel Pool

Enjoy a refreshing break at your hotel’s pool or spa facilities.
Varies, 2h

7:30pm

Dinner & Show at Caesars Palace

Combine dinner with a headline show such as a Cirque du Soleil performance; check schedules and book in advance.
USD150, 3h
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Day 10: Red Rock & Fremont Street

Las Vegas, USA on October 27, 2025

8:00am

Breakfast at Bouchon

French bistro style breakfast in Venetian Resort, opens at 7am.
USD30, 1h

9:30am

Red Rock Canyon Scenic Drive

Take a scenic 13-mile drive and short hikes in this beautiful desert conservation area about 30 minutes from the Strip.
USD15, 4h

2:30pm

Lunch at Yard House

Casual dining with extensive beer menu and American dishes, open until late.
USD25, 1h

4:00pm

Explore Fremont Street Experience

Immerse in vintage Vegas with a light show canopy, casinos, and street performers.
Free, 3h

7:30pm

Dinner at Le Thai

Enjoy vibrant Thai cuisine in a relaxed setting on Fremont East, open till 11pm.
USD30, 1.5h
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Day 11: LA Culture & Beaches

Los Angeles, USA on October 28, 2025

8:00am

Breakfast at Sqirl

Enjoy inventive and fresh breakfast fare in a trendy Silver Lake location, opens at 8am.
USD20, 1h

9:30am

Visit Getty Center

Explore impressive art collection, stunning architecture and gardens. Open 10am-5:30pm, closed Tuesdays.
USD20, 3h

1:00pm

Lunch at In-N-Out Burger

Lunch on a California classic fast food burger chain for a quick iconic experience.
USD10, 45m

2:00pm

Santa Monica Pier & Beach

Relax on the beach, walk the pier with rides and aquarium, perfect for afternoon fun.
Free, 3h

6:30pm

Dinner at The Lobster

Dine seaside at this upscale seafood restaurant with Pacific Ocean views in Santa Monica.
USD50, 2h
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Day 12: Hollywood & Museums

Los Angeles, USA on October 29, 2025

8:00am

Breakfast at The Griddle Cafe

Known for huge pancakes and creative breakfast options, opens at 8am.
USD20, 1h

9:30am

Hollywood Walk of Fame & TCL Chinese Theatre

Stroll the famous sidewalk stars, handprints and explore the Hollywood Boulevard area.
Free, 2h

11:30am

Visit the Los Angeles County Museum of Art (LACMA)

Explore wide-ranging art exhibits including modern and contemporary pieces. Open 11am-5pm.
USD25, 3h

3:00pm

Visit The Broad Museum

Contemporary art museum with free general admission but reserve tickets in advance. Open until 5pm.
Free, 1.5h

6:30pm

Dinner at Bestia

Trendy Italian dining destination in the Arts District, reservation required.
USD60, 2h
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Day 13: San Francisco Icons

San Francisco, USA on October 30, 2025

8:00am

Breakfast at Tartine Bakery

Famous bakery with outstanding pastries and breakfast dishes, opens at 7:30am.
USD15, 1h

9:30am

Visit Golden Gate Bridge & Park

Walk or bike across the iconic bridge and explore the surrounding parks with stunning views.
Free, 3h

12:30pm

Lunch at Fisherman’s Wharf - Boudin Bakery

Taste San Francisco’s famous clam chowder in sourdough bread at this renowned spot.
USD20, 1h

2:00pm

Explore Alcatraz Island

Take the ferry from Pier 33 for a tour of the historic former prison, tours run until early evening.
USD45, 3h

6:00pm

Dinner at Scoma’s

Seafood restaurant on the Wharf offering fresh catches and waterfront dining, open until 9:30pm.
USD50, 1.5h
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Day 14: Culture and Departure

San Francisco, USA on October 31, 2025

8:00am

Breakfast at Mama’s on Washington Square

Popular brunch spot serving hearty American breakfasts with a wait, so come early. Opens at 8am.
USD25, 1h

9:30am

Visit Exploratorium

Interactive science museum great for all ages, open 10am-5pm.
USD30, 2h

12:00pm

Lunch at Ferry Building Marketplace

Sample local artisanal food and shop for souvenirs inside this historic waterfront terminal.
USD25, 1h

1:30pm

Stroll Through Chinatown & Union Square

Explore vibrant shops and cultural spots, a perfect last walk before heading to the airport.
Free, 2h

4:00pm

Head to San Francisco International Airport

Allow ample time for travel and airport security for your departure flight.
Varies, 2h
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