14-Day Itinerary: Exploring Pittsburgh and New York City

Day 1: Arrival in Pittsburgh

Pittsburgh, USA

9:00AM

Breakfast at Pamela's Diner

Start your day at Pamela's Diner, renowned for their delicious pancakes and fresh fruit toppings.
Located centrally, easy access from your accommodations.
USD15, 1 hour

10:30AM

Visit Phipps Conservatory

Explore the stunning botanical gardens and greenhouse exhibits filled with exotic plants.
A quick 15-minute drive or an Uber from the diner.
USD20, 2 hours

12:30PM

Lunch at Meat & Potatoes

Enjoy hearty, locally sourced dishes at this vibrant gastropub.
A 10-minute drive or a short walk from Phipps.
USD25, 1.5 hours

2:00PM

Tour the Andy Warhol Museum

Dive into the life and works of Pittsburgh's most famous native son, with engaging exhibits.
A 10-minute drive from the restaurant.
USD20, 2 hours

4:30PM

Stroll Around Point State Park

Relax by the water and enjoy views of the city skyline at the confluence of three rivers.
Just a 5-minute drive from the museum.
Free, 1 hour

6:00PM

Dinner at El Burro Purto

Savor creative tacos and a vibrant atmosphere at this beloved local spot.
Located a short 10-minute drive away.
USD30, 1.5 hours
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Day 2: Discovering Pittsburgh

Pittsburgh, USA

8:00AM

Breakfast at The Breakfast Joint

A popular spot known for its excellent omelets and fresh coffee.
Approximately 15 minutes from your hotel.
USD12, 1 hour

9:30AM

Ride the Duquesne Incline

Experience panoramic views of the city as you ride the historic incline.
10-minute drive to the incline station.
USD5, 1.5 hours

11:00AM

Visit the National Aviary

Meet over 500 exotic birds and enjoy interactive exhibits.
20-minute drive from the incline.
USD15, 1.5 hours

12:30PM

Lunch at Franktuary

This unique hot dog spot specializes in gourmet dogs and toppings.
10-minute drive from the aviary.
USD12, 1 hour

2:00PM

Explore the Carnegie Museum of Natural History

Witness incredible dinosaur fossils and engage exhibits.
5-minute drive from lunch.
USD19, 2.5 hours

5:00PM

Dinner at Blue Dust

Enjoy their farm-to-table dishes with views of the trestle bridge.
15-minute drive from the museum.
USD30, 2 hours
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Day 3: Final Day in Pittsburgh

Pittsburgh, USA

8:00AM

Breakfast at The Cafe at the Frick

Enjoy a healthy breakfast in a beautiful garden setting.
15-minute drive from downtown.
USD12, 1 hour

9:30AM

Visit the Frick Art & Historical Center

Discover art, history, and a lovely estate with scenic grounds.
Located near the cafe.
Free, 2 hours

11:30AM

Explore the Strip District

Wander through this vibrant neighborhood full of shops and markets.
15-minute drive or short Uber ride.
Free, 2 hours

1:30PM

Lunch at Gaucho Parrilla

Indulge in Argentinian-style grilled sandwich and delectable sides.
Located in the Strip District.
USD20, 1.5 hours

3:00PM

Visit Mount Washington

Catch breathtaking views of the Steel City from one of its highest points.
15-minute drive from lunch.
Free, 2 hours

5:30PM

Dinner at Sienna Mercato

Relish in modern Italian dishes and shareable plates.
20-minute drive back to the city.
USD25, 1.5 hours
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Day 4: Travel to New York City

New York City, USA

10:00AM

Breakfast at your hotel or local café

Grab a light breakfast before checking out.
Conveniently arranged in your accommodation.
USD10, 1 hour

11:00AM

Depart for New York City

Travel to NYC via car or flight; the trip typically takes around 6 hours by car or 1.5 hours by plane.
Stay on I-76 E and then I-95 N if driving.
USD150 (flight or gas), 6 hours

5:00PM

Check-in at your hotel in NYC

Settle into your accommodation in Manhattan or surrounding areas.
Depending on flight times, this could be adjusted.
USD200, 1 hour

6:30PM

Dinner at Joe's Pizza

Savor a classic New York slice at this iconic pizzeria.
Located in Greenwich Village.
USD5, 1 hour
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Day 5: Exploring New York City

New York City, USA

8:00AM

Breakfast at Ess-a-Bagel

Grab a famous New York bagel with delectable cream cheese.
Short walk or subway ride from your hotel.
USD10, 1 hour

9:30AM

Visit Central Park

Take a leisurely stroll through this iconic park and enjoy the beauty of nature in the city.
Subway to 59th St. Central Park South.
Free, 2 hours

12:00PM

Lunch at The Loeb Boathouse

Dine lakeside with fresh seasonal fare in Central Park.
Located within Central Park.
USD35, 1.5 hours

1:30PM

Explore the MET Museum

Discover an extensive collection of artwork from around the globe.
A 10-minute walk from the restaurant.
USD25, 3 hours

4:30PM

Visit Times Square

Experience the buzz and neon lights of this entertainment hub.
Take the subway to Times Square.
Free, 1 hour

6:00PM

Dinner at Carmine's Italian Restaurant

Enjoy family-style Italian dining in a lively atmosphere.
Short walk from Times Square.
USD40, 2 hours
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Day 6: Cultural Day in NYC

New York City, USA

8:00AM

Breakfast at Café Grumpy

Savor expertly brewed coffee and freshly baked pastries.
Located in Brooklyn, a short subway ride away.
USD8, 1 hour

9:30AM

Visit Brooklyn Museum

Explore rich art collections, including ancient artifacts.
10-minute walk from café.
USD16, 2 hours

12:00PM

Lunch at Smorgasburg

Taste a variety of local street food in this popular outdoor market.
15-minute walk from the museum.
USD20, 1.5 hours

1:30PM

Walk Across Brooklyn Bridge

Enjoy stunning views of the Manhattan skyline as you walk across the iconic bridge.
Begin at the pedestrian entrance in Brooklyn.
Free, 1 hour

3:00PM

Visit One World Observatory

Experience breathtaking views from one of the tallest buildings in the city.
Short walk from the Brooklyn entrance of the bridge.
USD38, 2 hours

5:30PM

Dinner at The River Café

Enjoy fine dining with a stunning view of the Manhattan skyline and Brooklyn Bridge.
10-minute walk from the observatory.
USD60, 2 hours
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Day 7: Adventures in NYC

New York City, USA

8:00AM

Breakfast at Balthazar

Indulge in pastries and classic French breakfast items in this iconic bistro.
Conveniently located in SoHo.
USD25, 1 hour

9:30AM

Shopping in SoHo

Browse trendy boutiques and famous stores in this fashionable district.
Short walk from breakfast.
Free, 3 hours

1:00PM

Lunch at The Dutch

Enjoy delicious American comfort food in a relaxed atmosphere.
Located nearby in SoHo.
USD25, 1.5 hours

2:30PM

Visit the Museum of Modern Art (MoMA)

Explore the contemporary art exhibits in this renowned museum.
Short subway ride to 53rd St.
USD25, 2.5 hours

5:00PM

Dinner at STK

Experience upscale steak dining with a vibrant atmosphere.
A short walk from MoMA.
USD60, 2 hours
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Day 8: More NYC Exploration

New York City, USA

8:00AM

Breakfast at Jack’s Wife Freda

Enjoy Mediterranean-inspired dishes in a cozy setting.
Located in Greenwich Village.
USD18, 1 hour

9:30AM

Explore the High Line

Walk along this elevated park featuring art installations, gardens, and city views.
Take the subway to 14th St.
Free, 1.5 hours

11:00AM

Visit Chelsea Market

Indulge in shopping and sampling local treats in this iconic market.
Exit the High Line at 10th Ave.
Free, 1.5 hours

1:00PM

Lunch at Los Tacos No. 1

Savor delicious authentic tacos in a vibrant setting.
Located within Chelsea Market.
USD15, 1 hour

2:30PM

Visit the Guggenheim Museum

Marvel at the unique architecture and impactful modern art.
Short subway ride to 88th St.
USD25, 2 hours

5:00PM

Dinner at Bar Pitti

Enjoy authentic Italian dishes in a lively setting.
15-minute subway ride back downtown.
USD40, 1.5 hours
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Day 9: Culinary Adventures in NYC

New York City, USA

8:00AM

Breakfast at Sarabeth's

Start your day with a delectable array of breakfast options.
Located near Central Park.
USD25, 1 hour

9:30AM

Visit the NYC Food Tour

Join a guided food tour through one of NYC's famous neighborhoods.
Meeting point varies; check ahead.
USD75, 3 hours

1:00PM

Lunch at Katz's Delicatessen

Experience a classic New York pastrami sandwich at this iconic deli.
A short walk from the food tour.
USD20, 1 hour

3:00PM

Visit the Tenement Museum

Explore the immigrant history of the city in this historical site.
A 15-minute walk from Katz's.
USD30, 1.5 hours

5:00PM

Dinner at The Spotted Pig

Enjoy a Michelin-starred gastropub experience with seasonal dishes.
15 minutes by subway.
USD45, 2 hours
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Day 10: Sightseeing in NYC

New York City, USA

8:00AM

Breakfast at Clinton St. Baking Company

Savor pancakes and classic brunch dishes at this popular spot.
Located in the Lower East Side.
USD20, 1 hour

9:30AM

Visit Statue of Liberty and Ellis Island

Take a ferry to visit these historical landmarks.
Ferry terminal located in Battery Park.
USD25, 3.5 hours

1:00PM

Lunch at Fraunces Tavern

Dine in this historic tavern with a rich past.
Short walk from the ferry terminal.
USD25, 1.5 hours

2:30PM

Tour Wall Street and the Financial District

Walk through this iconic area and learn about its history.
Walking distance from the restaurant.
Free, 1 hour

4:00PM

Visit the 9/11 Memorial & Museum

Pay your respects and learn more about this historic event.
Located near Wall Street.
USD28, 2 hours

6:30PM

Dinner at Dinnertable

Enjoy an innovative dining experience with chef's specialties.
A short walk from the memorial.
USD60, 2 hours
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Day 11: Art and Leisure in NYC

New York City, USA

8:00AM

Breakfast at Panna II

Delight in a unique dining atmosphere with Indian-inspired breakfast.
Located in the East Village.
USD15, 1 hour

9:30AM

Visit the Whitney Museum of American Art

Check out contemporary American art exhibitions.
Located in the Meatpacking District.
USD25, 2 hours

12:00PM

Lunch at Chelsea Restaurant

Enjoy classic American comfort food.
Short walk from the museum.
USD20, 1.5 hours

1:30PM

Explore the West Village

Wander through charming streets and unique stores.
15-minute walk from the restaurant.
Free, 2 hours

3:30PM

Visit the Edge Observation Deck

Enjoy panoramic views from one of the city’s newest observation points.
Short subway ride to Hudson Yards.
USD38, 1.5 hours

5:30PM

Dinner at Los Tacos No. 1

Delight in authentic tacos in a vibrant setting.
Quick subway ride back downtown.
USD15, 1.5 hours
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Day 12: Last Full Day in NYC

New York City, USA

8:00AM

Breakfast at The Smith

Indulge in a delicious brunch at this trendy spot.
Located in the East Village.
USD20, 1 hour

9:30AM

Visit the American Museum of Natural History

Explore fossils, stars, and cultures in one of the most famous museums.
Take the subway to 81st St.
USD23, 2.5 hours

12:00PM

Lunch at Shake Shack

Enjoy burgers and shakes at this popular fast-casual chain.
Located nearby.
USD15, 1 hour

1:30PM

Visit the Top of the Rock

Take in the views of Manhattan from this iconic observation deck.
Short subway ride to Rockefeller Center.
USD38, 2 hours

3:30PM

Shopping along Fifth Avenue

Explore trendy stores and flagship locations on this famous street.
Located just a few blocks from Top of the Rock.
Free, 2 hours

6:00PM

Farewell Dinner at Keens Steakhouse

Enjoy a classic New York dining experience with prime steaks.
A 10-minute walk from Fifth Avenue.
USD70, 2 hours
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Day 13: Travel Day: New York to Home

New York City, USA

8:00AM

Breakfast at your hotel

Enjoy a relaxed breakfast before departure.
Located within your hotel.
USD15, 1 hour

9:00AM

Last-minute Shopping

Grab some souvenirs in the area around your hotel.
Walking distance from your accommodation.
Variable, 2 hours

11:00AM

Check-out and depart for airport

Head to the airport for your return flight.
Using either taxi or subway based on your proximity to JFK or LaGuardia.
USD50 (approx.), 1.5 hours
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Day 14: Return Home

New York City, USA

N/A

Fly Back Home

Travel back home with wonderful memories of Pittsburgh and New York City.
Fly from JFK or LaGuardia Airport.
Variable, N/A
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