Expert Advice

Make The Most Of New York City With This 4-Day Itinerary

Broadway, Brooklyn Bridge, Billy Joel and delicious bites

Deanna and Mike O
Two Hilton Grand Vacations Members on the Brooklyn Bridge on vacation in New York

Visiting New York City can be overwhelming — especially when you try to do as much as possible in just four days. Here’s how we spent a long weekend in the Big Apple.

Exterior shot looking up at the skyscrapers surrounding West 57th Street, a Hilton Club in New York 

Day 1

From the airport, we used our Lyft credit (thanks to our Elite Premier status) to get to West 57th Street, a Hilton Club. Since we were flying on a Friday morning, we booked the resort for the night before. That way our Suite would be ready when we arrived and wouldn’t need to wait until check-in Friday afternoon. It’s always nice to freshen up after traveling, especially in your Suite.

If you’re willing to take the subway, you’ll save time and money getting to your locations versus a taxi or rideshare. After checking in, we hopped on the train and headed to City Hall station, near the famous Brooklyn Bridge.

To maximize your time in New York, the most important thing to consider is logistics. You can cover a lot of ground when you know the proximity of the places you’d like to visit.

After walking over the bridge, we entered the neighborhood known as DUMBO — which stands for “down under the Manhattan Bridge overpass” — to take iconic pictures of the Empire State Building peeking through the bridge.

Next, we explored a few neighborhoods for some quick bites. We stopped at Nom Wah Tea Parlor in Chinatown for delicious dumplings and a cold beverage. After a short walk, we enjoyed pizza from La Nonna in Little Italy. Then, we headed to Washington Square and Pomme Frites — an amazing gem serving up French fries with different toppings. We also visited Wilfie & Nell and The Stonewall Inn in the West Village for happy hour. It’s easy to see so much of NYC with so many different communities within short walking distances of one another.

Two Hilton Grand Vacations Members in front of the Manhattan Bridge on vacation to New York 

We headed to Little Island via the Meatpacking District. Across the street is the start of one of our favorite attractions, the High Line — an abandoned rail line turned into an elevated park, giving a different perspective of the city. There are coffee shops and restaurants along the way.

After 20 miles total of walking, we decided to take the subway back. We stopped at Morton Williams food market to pick up a sandwich to eat at the resort.

Day 2

Saturday morning, we started at the Russian Tea Room, which is on the same block as West 57th Street. Then, we made our way to the Metropolitan Museum of Art (also called the Met) via Central Park. On the way, we strolled past the Ramble, Bethesda Terrace, Sheep Meadow and the Cherry Hill Fountain, which is featured in the show “Friends.”

The Met features beautiful artwork and fascinating exhibits — a great way to spend an afternoon. Unfortunately, the rain interrupted our walk back, so we took a taxi back to West 57th Street.

Day 3

The main purpose of the trip was to see Billy Joel at Madison Square Gardens — one of our bucket list items. Before the concert, we decided to hit Broadway. We ventured to the TKTS booth in Lincoln Center for discounted tickets. We got to see “The Book of Mormon” at the Eugene O'Neill Theatre for a good rate. After the show, we had a short window before the Billy Joel concert. We were not disappointed. After the concert, we enjoyed a quick dinner at Jack Doyle’s for fish and chips.

Two Hilton Grand Vacations Members in front of the battleship Intrepid in New York 

Day 4

Monday was our last full day, and we still had so much to see. We started in Central Park to walk through the Rambles on our way to Belvedere Castle and the Mall before making our way to the Upper West Side.

From here, we took the Hudson River Walk, where we saw the battleship USS Intrepid and the many piers that dot the river. We made a quick stop in Hell’s Kitchen before heading to Times Square to catch “Chicago.”

Depending on the season, some restaurants close early on Mondays. We had to book it out of “Chicago” to have a wonderful dinner at Redeye Grill.

Make a plan, pack your walking shoes and pace yourselves. There’s so much to see in New York. We love it so much that we’ve already planned to return for the holidays.

Check out more things to do in New York City, and how Hilton Grand Vacations can help you stay close to NYC’s top attractions.

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Hilton Grand Vacations Owners Mike and Deanna pose at the beach

Deanna and Mike O

Mike and Deanna are Centum+ Owners who’ve owned with Hilton Grand Vacations since 2019. Their favorite vacation destinations include Barbados, Orlando, Arizona and Hilton Head Island, South Carolina. They enjoy golfing, seeing historical sites and attending HGV Ultimate Access events like the Hilton Grand Vacations Tournament of Champions. So far, they’ve visited 26 properties — with plans to visit more thanks to HGV Max.

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