Family-Friendly Relaxation Itinerary: Pittsburgh & New York

Day 1: Arrival and Rest

Pittsburgh, PA

17:00

Arrive at Sister's Home

After a long journey, settle in at your sister's cozy home for a relaxing evening.
Just a short drive from the airport or train station to sister's residence.
0, 1 hour
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Day 2: Exploring Pittsburgh

Pittsburgh, PA

8:00 AM

Breakfast at Pamela's Diner

Enjoy famous pancakes and a hearty breakfast to kick off your first day in the city.
Drive or walk to Pamela's Diner in Squirrel Hill.
USD 30, 1 hour

9:30 AM

Visit Phipps Conservatory

Stroll through stunning botanical gardens and glasshouses filled with beautiful plants.
Short drive to Phipps Conservatory in Schenley Park.
USD 20, 2 hours

12:00 PM

Lunch at Meat & Potatoes

Enjoy contemporary American cuisine in a vibrant atmosphere, perfect for families.
Close drive to Meat & Potatoes in the Cultural District.
USD 80, 1.5 hours

1:30 PM

Explore the Carnegie Museum of Natural History

Delve into fascinating dinosaur exhibits and interactive displays suitable for all ages.
Drive to the museum located in the Oakland neighborhood.
USD 20, 2.5 hours

4:00 PM

Ride the Duquesne Incline

Take the historic incline for breathtaking views of the Pittsburgh skyline.
Drive or ride with public transport to the incline.
USD 15, 1 hour

7:30 PM

Dinner at The Smiling Moose

Dine on delicious burgers and sandwiches at this family-friendly establishment.
Short drive to The Smiling Moose.
USD 60, 1.5 hours
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Day 3: Pittsburgh Adventures

Pittsburgh, PA

8:00 AM

Breakfast at The Breakfast Bar

Start your day with omelets and other delicious breakfast options.
Drive to The Breakfast Bar in South Side.
USD 40, 1 hour

9:30 AM

Visit to the Children's Museum

Let the kids enjoy unique and interactive exhibits perfect for imaginative play.
Short drive to the Children's Museum of Pittsburgh.
USD 15, 2 hours

11:30 AM

Walk in Allegheny Commons Park

Enjoy a peaceful stroll or playtime in a scenic park setting.
Drive to Allegheny Commons Park.
0, 1 hour

12:30 PM

Lunch at the Park House

Grab a casual lunch at this laid-back eatery overlooking the park.
Located within the park area.
USD 60, 1.5 hours

2:00 PM

Visit Point State Park

Explore this historic park at the confluence of three rivers and relax by the fountain.
Drive down to Point State Park.
0, 2 hours

4:00 PM

Interactive Fun at Dave & Buster's

Enjoy arcade games and family-friendly activities at this entertainment center.
Drive to Dave & Buster's.
USD 100, 2 hours

7:30 PM

Dinner at Olive Garden

Savor a family feast with Italian favorites in a cozy setting.
Short drive to the Olive Garden restaurant.
USD 70, 1.5 hours
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Day 4: Cultural Day in Pittsburgh

Pittsburgh, PA

8:00 AM

Breakfast at McDonald's

Enjoy quick and tasty breakfast options to fuel your day.
Drive to a nearby McDonald's.
USD 30, 1 hour

9:00 AM

Visit the Andy Warhol Museum

Discover the life and art of this iconic Pittsburgh native in a fun way.
Drive to the museum in the North Side.
USD 25, 2 hours

11:00 AM

Ride the Pittsburgh T

Take the light rail for a short trip for some local sightseeing.
Public transport to the closest T station.
USD 10, 1 hour

12:00 PM

Lunch at Fork & Spoon

Enjoy farm-to-table freshness in a modern atmosphere.
Walk or drive to Fork & Spoon downtown.
USD 80, 1.5 hours

1:30 PM

Tour of Heinz Field

Get a glimpse of this iconic football stadium and learn about local sports history.
Short drive to Heinz Field.
USD 10, 1.5 hours

3:00 PM

Relax at North Park

Spend some leisure time enjoying outdoor activities or nature.
Drive to North Park.
0, 2 hours

7:30 PM

Dinner at Blue Dust

Indulge in delicious local dishes with stunning views of the city.
Short drive to Blue Dust.
USD 80, 1.5 hours
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Day 5: Leisure and Shopping

Pittsburgh, PA

8:00 AM

Breakfast at The Commoner

Savor a hearty breakfast in a chic pub atmosphere.
Drive to The Commoner in the Cultural District.
USD 40, 1 hour

9:30 AM

Shopping at Market Square

Explore various shops and pick up local goods and souvenirs.
Short walk to Market Square.
0, 2 hours

12:00 PM

Lunch at Nicky's Thai Kitchen

Enjoy some mouthwatering Thai favorites in a family-friendly setting.
Short walk to Nicky's Thai Kitchen.
USD 70, 1.5 hours

1:30 PM

Visit the Heinz History Center

Learn all about Pittsburgh’s rich history through interactive exhibits.
Drive or ride to the Heinz History Center.
USD 20, 2 hours

4:00 PM

Playtime at Frick Park

Enjoy the outdoors with family-friendly trails and playgrounds.
Drive to Frick Park.
0, 2 hours

7:30 PM

Dinner at Max's Allegheny Tavern

Dine on traditional pub fare with a comfortable vibe.
Drive to Max's Allegheny Tavern.
USD 70, 1.5 hours
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Day 6: Rest Day in Pittsburgh

Pittsburgh, PA

8:00 AM

Casual Breakfast at Sister's Home

Enjoy a relaxed morning with breakfast made by your sister.
In-house breakfast.
0, 1 hour

9:00 AM

Free Day for Relaxation

Spend the day rejuvenating with family; catch up on books or movies.
At sister's home.
0, All Day

7:30 PM

Dinner at Sister's Home

Enjoy a comforting family meal at home.
In-house dinner.
0, 2 hours
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Day 7: Travel to New York

New York, NY

8:00 AM

Breakfast at Sister's Home

Enjoy a hearty breakfast before starting your road trip.
In-house breakfast.
0, 1 hour

9:00 AM

Drive to New York City

Embark on your road trip to New York; enjoy the scenic drive.
Via car; 6 hours drive plus breaks.
0, 7 hours including breaks

4:00 PM

Arrive in New York City

Check into your accommodation and unwind after the journey.
Short drive to your selected accommodation.
0, 1 hour

7:30 PM

Dinner at Carmine's

Dig into family-style Italian dishes perfect for large groups in Times Square.
Located in Times Square.
USD 150, 2 hours
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Day 8: Exploring NYC

New York, NY

8:00 AM

Breakfast at the Hotel

Enjoy a buffet breakfast at your hotel to gear up for the day.
At your hotel.
Included in stay., 1 hour

9:30 AM

Walk in Central Park

Take a leisurely stroll or rent bikes to explore the iconic park.
Short walk to Central Park entrance.
0, 2.5 hours

12:00 PM

Lunch at The Loeb Boathouse

Enjoy a delightful meal with views of the lake and the park.
Located within Central Park.
USD 100, 1.5 hours

1:30 PM

Visit the American Museum of Natural History

Explore amazing interactive exhibits, perfect for kids and adults alike.
Short drive or walk to the museum.
USD 30, 3 hours

4:30 PM

Explore Times Square

Enjoy the dazzling lights and vibrant atmosphere of Times Square.
Short drive or subway to Times Square.
0, 1.5 hours

7:30 PM

Dinner at Ellen's Stardust Diner

Dine while enjoying shows from aspiring Broadway performers.
Located in Times Square.
USD 90, 1.5 hours
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Day 9: Culture and Fun in NYC

New York, NY

8:00 AM

Breakfast at the Hotel

Fuel your day with a delicious breakfast at your hotel.
At your hotel.
Included in stay., 1 hour

9:30 AM

Visit the Statue of Liberty and Ellis Island

Take a ferry to explore two of America's iconic landmarks.
Ferry from Battery Park to the islands.
USD 50, 4 hours

1:00 PM

Lunch at Fraunces Tavern

Enjoy historic ambiance and classic American fare at this landmark.
Short ferry ride to Lower Manhattan.
USD 80, 1.5 hours

2:30 PM

Explore Lower Manhattan and 9/11 Memorial

Reflect at the solemn memorial dedicated to the events of 9/11.
Short walk from Fraunces Tavern.
0, 2 hours

4:30 PM

Shopping at Century 21

Find great deals on designer brands and souvenirs.
Short drive or subway ride to Century 21.
0, 1.5 hours

7:30 PM

Dinner at The View Restaurant

Indulge in a revolving dining experience with fabulous city views.
Located in Times Square.
USD 150, 2 hours
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Day 10: New Year's Eve in NYC

New York, NY

8:00 AM

Breakfast at the Hotel

Enjoy a leisurely breakfast to prepare for the big day ahead.
At your hotel.
Included in stay., 1 hour

9:30 AM

Visit the Empire State Building

Get stunning views from the observation deck of this iconic skyscraper.
Short drive or subway ride to the Empire State Building.
USD 40, 2 hours

11:30 AM

Lunch at Shake Shack

Grab some gourmet burgers and shakes in a fun atmosphere.
Short walk from the Empire State Building.
USD 50, 1 hour

1:00 PM

Explore the High Line

Walk along the elevated park featuring beautiful gardens and city views.
Short drive or subway ride to The High Line.
0, 2.5 hours

3:30 PM

Relax and Prepare for New Year's Eve

Return to the hotel to rest before evening festivities commence.
Return to hotel.
0, 3 hours

7:30 PM

Dinner at The Capital Grille

Savor a luxurious dining experience with family before the celebration.
Short drive to The Capital Grille.
USD 200, 2 hours

9:00 PM

Celebrate New Year's in Times Square

Join the excitement of the countdown surrounded by thousands.
Walk to Times Square for the ball drop.
0, 4 hours
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Day 11: Return to Pittsburgh

Pittsburgh, PA

8:00 AM

Breakfast at the Hotel

Enjoy the last breakfast in NYC before your journey back home.
At your hotel.
Included in stay., 1 hour

9:00 AM

Drive Back to Pittsburgh

Set out for your drive back to Pittsburgh reminiscing about your experiences.
Via car; around 6 hours drive with breaks.
0, 7 hours

4:00 PM

Arrive back in Pittsburgh

After a long trip, unwind at your sister's place.
Short drive to sister's home.
0, 1 hour

7:30 PM

Dinner at Sister's Home

Enjoy quality family time over a home-cooked meal.
In-house dinner.
0, 2 hours
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Day 12: Recovery Day

Pittsburgh, PA

8:00 AM

Casual Breakfast at Sister's Home

Relaxed breakfast to start the day on a calm note.
In-house breakfast.
0, 1 hour

9:00 AM

Free Day to Recover

Take the day to unwind and recharge from the holiday excitement.
At sister's home.
0, All Day

7:30 PM

Dinner at Sister's Home

Conclude the day with another enjoyable meal together.
In-house dinner.
0, 2 hours
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Day 13: Departure Day

Pittsburgh, PA

8:00 AM

Breakfast at Sister's Home

Final breakfast at your sister's before the flight.
In-house breakfast.
0, 1 hour

10:00 AM

Pack and Prepare for Flight

Get everything ready for your departure later in the day.
At sister's home.
0, 2 hours

12:00 PM

Lunch at a Local Eatery

Grab one last meal at a nearby local favorite.
Drive to a local eatery.
USD 50, 1 hour

1:00 PM

Leave for Airport

Head to the airport with ample time for your flight check-in.
Drive to the airport.
0, 1 hour

2:30 AM

Flight Departure

Catch your flight home filled with beautiful memories.
At the airport.
0, 1 hour
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