New York City Itinerary

We flew into LGA because it is so convenient to Midtown Manhattan.  LaGuardia is in Queens and you can typically get to  Times Square by Subway or bus or both and it's inexpensive.  We had originally booked a 3 day trip but we decided we need a few more days so we added two days staying in a house in Jersey City.  This made our travel from LGA pretty expensive.  We use Carmel Car Service to get all 8 us from LGA to Jersey City.  This cost $215 including the tax and toll and tip is extra on the day of.

Day 1 Itinerary:

After dropping bags (late morning):

• Take PATH train from Jersey City to 14th St station

• Walk to Sloomoo Institute (490 Broadway) - allow 2-3 hours or walk the Highline (pictured above)

• Late lunch at Xi'an Famous Foods (nearby, affordable Chinese) or Los Tacos No. 1 in Chelsea Market

This route stays on the west side of Manhattan, making it easy to get to Jersey City later. The High Line is free, walkable, and entertaining for all ages. Hudson Yards offers both free areas and paid attractions. 

Afternoon options (choose 1):

• Hudson River Park (free, great views)

• Chelsea Market browsing

• Washington Square Park & NYU area

• 4 PM: Return to Jersey City to check in

• 7 PM: Dinner at Rumba Cubana Jersey City

We are starting our day in Jersey City.

• Take the Path and get off on the 34th Street Station.  

• 11 AM - Meet our guide from Spotlight on NYC at the Main Door to Macy's on Broadway.

• Take a 3-5 hour tour of New York City with Spotlight on NYC Tours

• End the tour with an early dinner at Westway Diner, where Jerry Seinfeld and Larry David came up with the idea for the sitcom Seinfeld.

• Then we can head over to Hudson River Park and walk around before heading home.  Hells Kitchen is not far from the Highline, Chelsea Market

From most parts of Hell's Kitchen, you can easily walk to the High Line in about 10-15 minutes. Here are some ways to get there:

• From 9th Avenue and 42nd Street (a central point in Hell's Kitchen), it's roughly a 10-minute walk to the High Line entrance at 34th Street

• The closest High Line access points to Hell's Kitchen are:

  • The 34th Street entrance (at Hudson Yards)

  • The 30th Street entrance

  • The 28th Street entrance

This proximity makes it convenient to combine a visit to both areas - you could explore Hell's Kitchen's amazing restaurants and then walk down to the High Line for a scenic stroll, or vice versa.

If you are looking for the best hot chocolate or chocolate chip cookies.  The Carboholic rates things and has some fabulous spreadsheets with her ratings like this one for hot chocolate!

We are starting our day in Jersey City but heading to our hotel, The Hyatt Grand Central.  The Path can take up to on hour so we will likely take an Uber.

This is our first day staying in NYC and here are some things to do:

• 10 AM Sunday Mass at St Patrick's Cathedral 

• 7 PM Radio City Musical Hall for the Rockette's Holiday Spectacular.

• Dinner Reservations for Tony DiNapoli's for a family-style Italian dinner.

Things to see in NYC:

• NYC Jellycat Diner

• Bryant Park Winter Village

• Broadway and 7th - Sound Art

• AMC Theather take the escalator up and back down to see the cool ceiling

• MSocial Hotel - Elevator Up to the Lobby, go to the bar, take drink outside for the best view of Times Square

• Times Square Subway Station - Art Installation

Places to eat

• Cello's Pizza - PEPPERONI AND JALAPENO SLICE

• L'INDUSTRIE PIZZA

• Margon - Cuban place in Times Square - good Cuban coffee

We are starting the day in TimeSquare and this is the day we want to do all of the touristy things!

9:00 AM - Edge observation deck 

10:30 AM - American Museum of Natural History (take B/C subway from 50th St) 

1:00 PM - Return to Midtown, lunch and Bryant Park Winter Village 

3:00 PM - Walk to Rockefeller area 

4:30 PM - Ice skating  Reservations

5:15 Chalet Rental 

6:00 PM - Dinner

Restaurant recommendations:

• Joe's Pizza (Broadway & 40th) - NY slice institution

• John's of Times Square (historic coal-oven pizza)

• Los Tacos No.1 in Times Square (quick, affordable Mexican)

We are spending our day on the Upper East Side. This means we have some Gossip Girl sites to see!

• Central Park with the Wollman Rink is iconic and you can see more Gossip Girl Filming locations here.

9:00-10:30 AM: Start at The Met (opens 10 AM) - warm inside and perfect for cold morning

• Get photos on the iconic steps first

• Focus on highlights like Temple of Dendur, European Paintings

11:30 AM: Walk through Central Park's east side

• Bethesda Fountain

• Conservatory Garden (formal gardens, less crowded)

• The Mall's tree-lined path

12:00-1:30 PM: Lunch break Ideas:

• Pastrami Queen (authentic NY deli)

• Ellen’s Stardust Diner - Location: 1650 Broadway (near 51st St)

• Cafe Sabarsky (1048 5th Ave (Inside the Neue Galerie)  - might be too fancy

• Jacques Torres Chocolate (Upper East Side) - Location: 350 Columbus Ave (between 76th & 77th St)

1:30-3:30 PM: Choose between:

• The Plaza Hotel 768 5th Ave (at 59th St, just at the entrance to Central Park) 

• Neue Galerie (smaller museum, Klimt's "Woman in Gold")

• Shopping on Madison Avenue (luxury stores, Gossip Girl vibes)

3:30-5:00 PM: More Central Park + Gossip Girl sites

• Blair's building at 1136 Fifth Ave

• Walk down Fifth Avenue to see holiday decorations

5:00-7:00 PM: Free time before Serendipity

• Warm up with some shopping indoors. The Shops at Columbus Circle offer luxury stores, views of Central Park, and festive decorations.

• See holiday windows at Bloomingdale's

Note: The Empire Hotel is on the Upper West Side (63rd & Broadway), not Upper East Side. The rooftop bar is open daily but in winter, it's enclosed and heated. It's about a 15-minute walk from Central Park.