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14-Day Family-Friendly Adventure and Luxury Itinerary: New York, Orlando, Chicago, San Francisco, Cancun

Viewed by 52 travelers

Day 1: Explore the Big Apple

New York, USA

9:00AM

Breakfast at Serafina

Start your adventure with a delicious Italian breakfast at Serafina, known for its yummy frittatas and fresh pastries.
Take a short 15-minute walk to Times Square.
USD30, 1 hour

10:30AM

Visit Times Square

Immerse yourself in the lively atmosphere of Times Square, famous for its bright lights and interactive experiences.
Walk around Times Square, experiencing the buzz.
Free, 1.5 hours

12:00PM

Lunch at Carmine's

Enjoy a family-style Italian meal at Carmine’s, where sharing big bowls of pasta is the norm.
Take a short 10-minute walk to the restaurant.
USD120, 1 hour

2:00PM

Visit Central Park

Head to Central Park for a leisurely stroll, enjoying attractions like the Central Park Zoo and the Bethesda Terrace.
Take a 15-minute walk to Central Park.
USD20 (Zoo entry), 3 hours

5:00PM

Dinner at The View Restaurant

Dine at The View, New York's only revolving restaurant, offering stunning skyline views.
Take a taxi back to Times Square and walk to the restaurant.
USD200, 2 hours
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Day 2: Cultural Journey

New York, USA

9:00AM

Breakfast at Ess-a-Bagel

Fuel your day with fresh bagels and cream cheese from this classic New York spot.
Take a taxi for a 15-minute ride.
USD25, 1 hour

10:30AM

Visit the Metropolitan Museum of Art

Explore the extensive art collections at The Met, a paradise for art lovers.
A short 10-minute walk from the bagel shop.
USD25, 3 hours

2:00PM

Lunch at Shake Shack

Savor a burger and shake at Shake Shack, a beloved New York institution.
Walk 10 minutes to the nearest location.
USD55, 1 hour

3:30PM

Visit the 9/11 Memorial

Pay your respects at the 9/11 Memorial, a poignant tribute to the lives lost.
Take the subway, a 20-minute ride.
Free, 1.5 hours

5:00PM

Dinner at Tribeca Grill

Indulge in a stylish dinner at Tribeca Grill, known for its seasonal American cuisine.
A 15-minute cab ride from the memorial.
USD180, 2 hours
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Day 3: Iconic Landmarks

New York, USA

8:00AM

Breakfast at Balthazar

Start your day at Balthazar, an iconic French bistro with a bustling atmosphere.
A quick 10-minute cab ride.
USD40, 1 hour

9:30AM

Statue of Liberty Tour

Take a ferry to Liberty Island to see the majestic Statue of Liberty up close.
Tax to the ferry terminal, about 15 minutes.
USD55, 3 hours

1:00PM

Lunch at The Oyster Bar

Enjoy fresh seafood at The Oyster Bar, located in the historic Grand Central Terminal.
Return to Manhattan by ferry, then walk to Grand Central.
USD80, 1.5 hours

3:00PM

Explore the High Line

Stroll along the High Line, a unique elevated park with gardens, art, and urban views.
Take a cab for 15 minutes.
Free, 2 hours

5:30PM

Dinner at Buddakan

Experience modern Asian cuisine in an extraordinary setting at Buddakan.
A quick ride back to Chelsea.
USD150, 2 hours
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Day 4: Magic Awaits

Orlando, USA

8:00AM

Breakfast at Keke’s Breakfast Cafe

Start your Orlando visit with a hearty breakfast at Keke’s, known for their fluffy pancakes.
Take a flight from New York to Orlando, about 2 hours.
USD30, 1 hour

10:00AM

Visit Magic Kingdom

Experience the wonder of Magic Kingdom with thrilling rides and beloved Disney characters.
Take a taxi to Magic Kingdom, about 30 minutes.
USD150, 6 hours

5:00PM

Dinner at Be Our Guest Restaurant

Dine inside the enchanted castle at Be Our Guest, offering enchanting French cuisine.
Within Magic Kingdom.
USD200, 1.5 hours
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Day 5: Adventures Continue

Orlando, USA

8:00AM

Breakfast at The Waffle House

Enjoy a classic American breakfast with waffles and eggs.
A short drive downtown, 15 minutes.
USD40, 1 hour

9:30AM

Visit Universal Studios Florida

Dive into the thrills of Universal Studios with rides and shows that provide a full day of excitement.
Take a 20-minute taxi to the park.
USD150, 8 hours

6:00PM

Dinner at The Cowfish

Savor a creative mix of burgers and sushi in a fun atmosphere.
Head back to the hotel in a taxi, about 15 minutes.
USD120, 1.5 hours

8:00PM

Evening stroll at CityWalk

Enjoy live music and street entertainment at Universal CityWalk for a delightful evening.
Walk to CityWalk from the restaurant.
Free, 2 hours
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Day 6: Water Park Fun

Orlando, USA

9:00AM

Breakfast at IHOP

Start the day with fluffy pancakes and a variety of breakfast options at IHOP.
Walk to the nearest IHOP, about 10 minutes.
USD30, 1 hour

10:30AM

Visit Typhoon Lagoon

Cool off at Typhoon Lagoon, one of Disney's beloved water parks with thrilling slides and lazy rivers.
Take a taxi to Typhoon Lagoon, about 20 minutes.
USD80, 5 hours

4:00PM

Lunch at H2O Glow Nights

Enjoy a casual lunch at the water park, taking a break from the sun.
Available within the park.
USD50, 1 hour

6:00PM

Dinner at The Boathouse

Savor fresh seafood and steaks with beautiful waterside views at Disney Springs.
Taxi to Disney Springs, a 20-minute ride.
USD150, 2 hours
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Day 7: Windy City Wonders

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Enjoy a classic Chicago breakfast at Lou Mitchell's, renowned for its pancakes and sunny atmosphere.
Fly from Orlando to Chicago, about 3 hours.
USD35, 1 hour

10:00AM

Visit Millennium Park

See the iconic Cloud Gate sculpture, also known as the 'Bean,' in Millennium Park.
A short 10-minute taxi ride.
Free, 1.5 hours

12:00PM

Lunch at Giordano's

You can't visit Chicago without indulging in its famous deep-dish pizza at Giordano's.
A short walk from Millennium Park, about 15 minutes.
USD60, 1.5 hours

2:00PM

Art Institute of Chicago

Explore the impressive art collections at the Art Institute of Chicago, home to world-renowned pieces.
Just a short walk from the restaurant.
USD25, 2.5 hours

5:00PM

Dinner at The Signature Room

Experience elegant dining with panoramic views from the 95th floor of the John Hancock Center.
A 15-minute taxi ride.
USD200, 2 hours
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Day 8: Chicago Excursions

Chicago, USA

8:00AM

Breakfast at Yolk

Tantalize your taste buds with a creative breakfast menu at Yolk, known for its fresh ingredients.
Walk to Yolk, about 10 minutes.
USD30, 1 hour

9:30AM

Architecture River Cruise

Take in Chicago’s stunning skyline from a unique perspective on an architecture river cruise.
A quick taxi ride to the cruise start point, about 15 minutes.
USD50, 1.5 hours

11:30AM

Lunch at Portillo’s

Enjoy the Chicago-style hot dog at Portillo's, where the hustle and bustle make for a lively atmosphere.
Short walk to Portillo’s.
USD40, 1 hour

1:00PM

Visit the Field Museum

Explore the fascinating exhibits at the Field Museum, including Sue the T. rex.
A taxi ride to the museum, about 15 minutes.
USD25, 3 hours

4:00PM

Dinner at RPM Italian

Indulge in upscale Italian cuisine at RPM Italian, known for its chic atmosphere.
A short taxi ride, about 10 minutes.
USD120, 2 hours
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Day 9: Chicago Adventures

Chicago, USA

8:00AM

Breakfast at Breakfast House

Fuel your day with a hearty breakfast at Breakfast House, known for their famous stuffed French toast.
Walk to the restaurant, about 10 minutes.
USD35, 1 hour

9:30AM

Lincoln Park Zoo

Explore the free Lincoln Park Zoo, home to everyday animals and exciting exhibits.
Take a cab for 15 minutes.
Free, 2.5 hours

12:00PM

Lunch at The Honeycomb

Dine at The Honeycomb for delicious brunch options with a twist on American classics.
A taxi ride to the restaurant, about 15 minutes.
USD40, 1 hour

1:30PM

Visit Shedd Aquarium

Discover aquatic life at the Shedd Aquarium, home to thousands of species.
A short walk from the restaurant, about 10 minutes.
USD40, 3 hours

4:30PM

Dinner at The Olde Towne Pub

End the day with a casual dinner at The Olde Towne Pub, known for its beers and comfort food.
Take a 10-minute taxi ride.
USD60, 1.5 hours
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Day 10: West Coast Wonders

San Francisco, USA

8:00AM

Breakfast at Mama’s on Washington Square

Start your San Francisco journey with a delicious breakfast in a charming setting.
Fly from Chicago to San Francisco, about 4 hours.
USD40, 1 hour

9:30AM

Visit Fisherman's Wharf

Explore the vibrant atmosphere of Fisherman’s Wharf, famous for seafood and street performers.
Take a short taxi ride to Fisherman’s Wharf, about 20 minutes.
Free, 2 hours

12:00PM

Lunch at Boudin Bakery

Taste the iconic clam chowder served in a sourdough bread bowl at Boudin Bakery.
It's located at Fisherman’s Wharf.
USD25, 1 hour

1:30PM

Visit the Exploratorium

Engage with interactive science and art exhibits at the Exploratorium, perfect for families.
Take a taxi for 15 minutes.
USD30, 3 hours

5:00PM

Dinner at Cliff House

Savor your meal at the historic Cliff House while enjoying spectacular ocean views.
A taxi ride to Cliff House, about 30 minutes.
USD150, 2 hours
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Day 11: Golden Gate Experience

San Francisco, USA

8:00AM

Breakfast at Plow

Enjoy a farm-to-table breakfast at Plow, famous for its seasonal ingredients and cozy vibe.
A 20-minute taxi ride.
USD35, 1 hour

9:30AM

Walk the Golden Gate Bridge

Experience breathtaking views as you walk across the iconic Golden Gate Bridge.
Take a taxi for 20 minutes to the bridge entrance.
Free, 2 hours

12:00PM

Lunch at The Fish Market

Savor fresh seafood at The Fish Market, with views of the Bay.
Taxi back to Fisherman’s Wharf, about 20 minutes.
USD50, 1.5 hours

2:00PM

Visit the Asian Art Museum

Explore the extensive collections at the Asian Art Museum, a highlight for art aficionados.
A 15-minute cab ride.
USD15, 2 hours

4:30PM

Dinner at Foreign Cinema

Dine and enjoy a classic film in an outdoor space at Foreign Cinema, famous for its film screenings.
A short taxi ride, about 15 minutes.
USD100, 2 hours
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Day 12: California Culture

San Francisco, USA

8:00AM

Breakfast at Dottie's True Blue Cafe

Start the day with a homey breakfast at Dottie's, known for its delicious pancakes and friendly atmosphere.
A 10-minute taxi ride.
USD30, 1 hour

9:30AM

Visit Alcatraz Island

Take a ferry to Alcatraz Island and explore the famous historic prison.
Ferry leaves from Pier 33 nearby.
USD45, 3 hours

1:00PM

Lunch at Pier Market Seafood Restaurant

Delight in freshly caught seafood at Pier Market while enjoying views of the bay.
Short walk to Pier Market.
USD60, 1.5 hours

3:00PM

Visit the Painted Ladies

Admire the iconic Painted Ladies, a historic row of Victorian houses with a popular park nearby.
Take a taxi for 10 minutes.
Free, 1.5 hours

5:00PM

Dinner at Empress by Boon

End the day with a delightful dinner at Empress, offering modern Asian cuisine.
A short taxi ride, about 15 minutes.
USD120, 2 hours
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Day 13: Beach Bliss

Cancun, Mexico

8:00AM

Breakfast at La Habichuela

Enjoy a delicious breakfast featuring authentic Mexican flavors at La Habichuela.
Fly from San Francisco to Cancun, about 5 hours.
USD40, 1 hour

9:30AM

Relax at Playa Delfines

Unwind at Playa Delfines, known for its stunning turquoise waters and golden sandy beaches.
Take a taxi, about 20 minutes.
Free, 3 hours

12:30PM

Lunch at Casa Tequila

Savor delicious tacos and refreshing drinks at Casa Tequila, a local favorite.
Taxi to the restaurant, about 15 minutes.
USD40, 1 hour

2:00PM

Snorkeling Tour

Discover the underwater beauty of Cancun with a guided snorkeling tour.
Book a tour that includes transportation from your hotel.
USD75, 3 hours

5:00PM

Dinner at La Parrilla

Enjoy a vibrant dinner at La Parrilla, known for its lively atmosphere and delicious Mexican cuisine.
Taxi back to the restaurant, about 20 minutes.
USD70, 2 hours
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Day 14: Final Relaxation

Cancun, Mexico

8:00AM

Breakfast at Café Antoinette

Indulge in a delightful breakfast at Café Antoinette, offering a mix of French and Mexican dishes.
A short walk to the café.
USD30, 1 hour

9:30AM

Spa Day

Treat yourself to a luxurious spa day, enjoying massages and pampering treatments at your resort.
Book spa services at your hotel.
USD150, 3 hours

12:30PM

Lunch at Manglar Beach Restaurant

Dine at Manglar Beach Restaurant with stunning lagoon views and fresh seafood.
Walk to the restaurant within the resort area.
USD60, 1.5 hours

2:00PM

Beach Time

Spend your last afternoon lounging at the beach, soaking up the sun and taking in the views.
Located in front of your resort.
Free, 4 hours

6:00PM

Farewell Dinner at Puerto Madero

End your trip with a farewell dinner at Puerto Madero, known for its exquisite seafood and stunning views.
A short taxi ride, about 15 minutes.
USD160, 2 hours
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