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Expert Advice

Owner Insider Tips: 3-Day New York Itinerary

From NYC classics to non-touristy things to do, this itinerary hits the mark for an ultimate long weekend getaway

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. So, 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.

Sunrise over the Manhattan skyline, New York, New York.    

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 is so much to see and do, especially when it comes to great places to eat.

(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 Lincoln Center. Whether it’s seeing a ballet performance by the New York City Ballet or sitting back and soaking up the sounds of the New York Philharmonic – you’ll be amazed by the talent on the stage.

Day Two

Overhead shot of a latte with a coffe art flower in the foam.    


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


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

Insider tip: Take the High Line to Hudson Yards (W 30th Street) and walk about 1 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. From new shows to the classics, you can’t go wrong. And after the show, swing by Tanner Smith’s for a delicious evening craft cocktail. 

Point of view shot of Brooklyn Bridge with the sunrising over the city skyline, New York, New York.    

Day Three


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

Walk from Manhattan to Brooklyn for the most 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, plan a visit to The Battery – located near New York’s Financial District. Nestled along the water, it’s the perfect mini-escape from the hustle and bustle of the city — Statue of Liberty views included. 


Freshen up and head down to TriBeCa for a lovely dinner at One White Street. If you’d rather savor the evening after dinner, 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.

Stay: West 57th Street by Hilton Club holds a special place in my heart. It’s where we decided to become Hilton Grand Vacations Owners and where we stayed when we got engaged. 

Read “Your Guide to Hilton Grand Vacations’ New York City Timeshares” to discover the best place to rest your head on your next 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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