Expert Advice

A 3-Day New York Itinerary From A Hilton Grand Vacations Member Who Loves The City

Make the most of your long weekend, from NYC classics to hidden gems

Kassi P.
Hilton Grand Vacations Owners in front of the Brooklyn Bridge, DUMBO, New York, New York.

It’s no secret that New York City is one of my favorite places in the world. And typically, our trips to the city are over a long weekend. We’ve mastered the Big Apple “weekend trip.” See the landmark sights and discover a few hidden gems with this three-day New York itinerary.

An aerial view of New York City during the day 

Day One


A trip to New York City isn’t complete without a New York-style bagel. Pick a Bagel is one of our favorite bagel shops in the city, and it’s located just minutes from Hilton Grand Vacations’ properties in the city, on the corner of 53rd and 8th in Midtown.


Spend your afternoon exploring one of New York City’s most popular areas, Little Italy. There’s so much to see, do and eat.

After all, how can you go wrong with authentic Italian food? And don’t forget to swing by an Italian bakery to pick up some pastries for your Studio or Suite.


Travel to the Upper West Side and spend a night immersed in the arts at the Lincoln Center. You’ll be amazed by the talent on the stage, whether you’re seeing a ballet performance by the New York City Ballet or sitting back and soaking up the sounds of the New York Philharmonic.

A man and woman drink coffee together outside in New York City 

Day Two


Start your day with a visit to one of my favorite coffee shops, Cafe Grumpy. Sip delicious coffee in their cute outdoor area or take it to-go to enjoy as you visit Chelsea Market, which is within walking distance.


Stroll above the city on the High Line for an afternoon adventure. Get a unique perspective of New York along this attraction, a repurposed freight rail, where you can see incredible art and connect with nature. 

Insider tip: Take the High Line to Hudson Yards and walk about one mile to Gotham West Market for a delicious lunch.


Calling all musical and play lovers — don’t miss your chance to see a Broadway show, whether it’s a new show or a classic, you can’t go wrong. After the show, swing by Tanner Smith’s for a delicious craft cocktail.    

Brooklyn Bridge in New York at sunrise 

Day Three


Visit one of New York’s most iconic sights — the Brooklyn Bridge.

Walk from Manhattan to Brooklyn for awe-inducing views, and don’t forget your camera to capture the most picture-perfect view of the Manhattan skyline from DUMBO. 

Insider tip: Schedule a Flytographer session, the best souvenir for any trip.


After your morning stroll in Brooklyn, visit The Battery near New York’s Financial District. It’s the perfect mini-escape from the hustle and bustle of the city — and even includes Statue of Liberty views. 

A man and a woman enter a yellow taxi before a night on the town in New York City 


Freshen up and head down to TriBeCa for a lovely dinner at One White Street. Then visit my favorite wine store in the city, Verve Wine, to purchase a nice bottle of wine to enjoy in your hotel room. It’s a perfect way to close out your trip.

Where To Stay

Choose from five Hilton Grand Vacations’ properties in New York City. West 57th Street, a Hilton Club holds a special place in my heart. It’s where my husband and I decided to become Hilton Grand Vacations Members and where we stayed when we got engaged

Read “Hilton Grand Vacations In New York City Helped A Long-Overdue Dream Come True” for another Member’s once-in-a-lifetime Big Apple getaway.


Hilton Grand Vacations Owner, Kassi P.

Kassi P.

Kassi is a three-time Explorer and Owner since 2018, when she and her husband, then in their late 20's, decided vacation ownership was the next step in building a life filled with travel. As Orlando locals, they enjoy staycations and exploring The City Beautiful, but have never actually stayed at their home resort, Hilton Grand Vacations at Tuscany Village.  

When she's not using her ClubPoints in Florida, this urban traveler has a love of international travel and a sweet spot for her second home — New York City, which is where she got engaged while staying at West 57th Street by Hilton Club. When asked about her long run in the Explorer program, Kassi says, "It's my goal to inspire someone to create new memories, get out and travel and make the most out of vacation ownership."

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