Day 1: The OH-SO Iconic Manhattan  

No trip to NYC is complete without a trip to one of Manhattan’s most iconic holiday attractions: the Rockefeller Center

Begin at the Rockefeller Center Rink: Hit the ice! Get your skates and helmet on (because you know, safety first) and glide to your heart’s content. Save yourself some extra dollars by getting tickets for the time slots between 9 a.m. and 4:30 p.m.

Now it’s time to grab a cup of hot cocoa and marvel at this year’s tree lighting ceremony on November 30th, marking the landmark’s 90th anniversary (known as the unofficial start to the holiday season).

No matter the season, you can come for the shops (from picking the perfect holiday scent at Apotheke to the Swarovski flagship), or come for the eats (from the newly opened 21 Green Point to a classic like Mendy’s Kosher Deli). A holiday bonus: the tree stays up till after the new year!!

Followed by a FREE Museum trip: 

The American Folk Art Museum houses the nation’s premier collection of American folk art from the 18th century through the present, right here in NYC. Be sure to stop at the museum’s holiday shop, featuring all sorts of specialty items that you can exclusively find here! 

Holiday lighting at the Rockfellar Center

Lastly, dinner and a show:

Make a stop at a TKTS Ticket Booth for same-day performances at up to 50% off full price to Broadway shows. There are two TKTS Booths, one in Times Square on Father Duffy Island (47th St. & Seventh Ave.) and a satellite booth at the Lincoln Center in the David Rubenstein Atrium (61 W. 62nd St.). Great, now that you have your tickets, let’s eat! 

You can hardly call yourself a New Yorker without having a favourite dish at the famous East Village Ukrainian eatery Veselka Restaurant. In business since 1954, it offers neighbours and visitors 24-hour comfort food in a diner-type atmosphere. Specialising in handmade dumplings and homemade soups at a suitable price for humble allowances. Now that you’re stuffed, head over to the show that you scored for a discount and call it a day! 

Day 2: Little Italy & Queens 

Begin in Little Italy: Start your morning off right with a cup of Italian Joe and pastry at Artuso Pastry. More than 60 years strong, Artuso Pastry stands as a testament to the power of old-world Italian baking in the Bronx’s Little Italy. 

As you’re strolling around Little Italy, make sure you stop at the store, Christmas In New York. Head to this store for fully decorated Christmas trees. There’s also a Christmas museum on the lower level, if you want to find out where exactly Christmas trees come from. (They date back to the 1500s, so yeah, there’s lots to cover.)

Christmas in New York (store)

Next: All aboard the New York Botanical Garden Holiday Train Show—a tradition for more than 30 years!​ See model trains zip through an enchanting display of more than 190 replicas of New York landmarks, each delightfully re-created from natural materials such as birch bark, lotus pods, and cinnamon sticks.​ Score a discount on Groupon and act quick as tickets are known to sell out fast!

NYBG Holiday Train Show

Now let’s go to Queens: 

Take a free walk-around the winter wonderland at the world-famous Corona Park – home to the Queens Museum’s Panorama, an architectural model of all five boroughs.

End the day with a holiday feast at the Rolf German restaurant: From the moment you step inside, you’ll be enveloped in the festive atmosphere (thousands of lights upon thousands of ornaments and icicles all strung and lined throughout the restaurant). Rolf’s offers a truly unique holiday dining experience all year long.

Day 3: Brooklyn and Staten Island 

Start the day shopping and dropping at the hip and happening Brooklyn Flea Market (open year-round):

You will not believe your eyes when you enter this indoor market. It’s in a gorgeous building with limestone and marble interior and stunning mosaics. The Brooklyn Winter Flea + Holiday Market (open early November to Christmas eve) features around 75 vendors selling vintage, antique, handmade, and food, in a modern setting. The market is open every week in winter, rain or shine, and is dog-friendly. 

Time to eat:

Who doesn’t like tacos? Head over to the affordable yet chic King David Tacos for a savoury filler-up! The PEC, Mom’s Migas and Queen Bean (all three vegetarian) are the most popular. Get there early as they go quickly!!

Next, take a 5-minute walk over to Grand Army Plaza: 

Witness the world’s largest Hanukkah menorahs during the Jewish festival of lights. There’s a kick off concert on Sunday, November 28, and each subsequent night of Hanukkah is celebrated with music, latkes, and gifts.

Hanukkah Menorahs Grand Army Plaza

Now it’s time for an evening Staten Island escape:

FREE and easily accessible by a 25-minute scenic ride on the Staten Island Ferry ​(runs 24 hours a day/ 7 days a week, even on holidays and weekends, make sure you check the schedule for the next ride). 

Once you’re off the ferry, head over to the annual Winter Lantern Festival at the SIUH Community Park (back for a fourth year and for the first time in SIUH). Starting from Oct 21 until Jan 8, take a Journey To The East with friends and family to explore the wonders of over 1000 Chinese lanterns; all handmade by artisans with decades of dedication to their craft. Be prepared to indulge yourself in an Insta-worthy photo spree! Grab your tickets while they last.

It’s pizza time: 

Pizza is kind of a big deal in New York City, and Staten Island is no exception. For dinner, try a pie at this St. George pizza joint called Pier 76, an offshoot of the illustrious Joe & Pat’s. The long menu includes casual-food favourites like buffalo wings and pasta primavera—but the crispy, customizable thin-crust pizza is the must-order.

Pier 76 Pizza Restaurant

Let’s kiss-off the day with a show shall we:

Around the corner from Pier 76, find post-pizza entertainment at the historic St. George Theater. It first raised its curtain in 1929 and maintains a calendar of comedy shows, concerts, movie screenings or and family-friendly theatre performances.

NYC Winter Outing – An honourable mention as I conclude this 3-Day New York City Holiday Weekend Itinerary is the fan-favourite NYC Winter Outing. Returning for its fourth year from combining deals across all five boroughs on dining out, Broadway shows, attractions, museums and performing arts, with the addition of NYC Hotel Week deals for the second time this year.

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