THERE IS NO BAD SEASON IN NEW YORK CITY, but there is something extraordinarily special about the city during the holidays. For those who have never ventured to The Big Apple during late November and December, or those who haven’t been in a while, here’s my review on 48 hours in the city with all things merry and bright in mind.

Sisters, sisters, there were never such devoted sisters. I took this trip with my incredible sister Sara (who is an accomplished writer and holds a Ph.D. in education), in the hopes of finding some Christmas magic. And while we didn’t take The Big Apple by storm with the intention of sharing our experience, it was simply too good not to! We also paid for everything ourselves, so you know the reviews are honest.

How We Got There

I love the JetBlue route from MCO Terminal C to LaGuardia, though JFK isn’t a bad option either. Terminal C feels a bit like a vacation in and of itself; it’s so clean, open and new. Everything is shiny and polished, and the gates are chock full of local brands and establishments Orlandoans already frequent. This time we stopped at Cask & Larder Southern Public House but in the past, we’ve frequented The Sunshine Diner (more on them below). With its experienced culinary team, Cask & Larder creates modern interpretations of classic Southern dishes and interesting new takes on some of the South’s most well-loved favorites. You can only enjoy this favorite in Terminals A, B and C.

And what about that diner? Sunshine Diner is a fun, bright signature concept developed by none other than award-winning celebrity chef Art Smith. A sixth-generation Floridian, Chef Smith loves the idea of bringing people together through food. That’s what has paved the way to his success today. Fresh, seasonal fruits and vegetables, buttermilk pancakes and Johnny cakes, eggs benedict, omelets, steak and eggs and avocado toast make this breakfast-all-day diner a delight for travelers.

We also popped into the Plaza Premium Lounge Orlando during our travels located inside Terminal C across the Palm Court. It’s designed to cater to Orlando’s unique mix of families, business and leisure travelers, with offerings that change daily, but expect fresh food, beverages, pebble ice, beer and wine at no cost. Travelers can access the lounge by purchasing a day pass, holding a qualifying lounge membership (such as Priority Pass or DragonPass), using select credit cards (like American Express Platinum or Capital One) or flying in an eligible class.

Now let’s get this show on the proverbial road, shall we?

our home away from home, Virgin Hotels on Broadway, in the heart of Manhattan. Photo by Omag Staff.

Where We Stayed

The holiday season is pricey, and hotels are no exception. You’ll pay top dollar for weekend stays from Thanksgiving until New Year’s, but can you really put a price on a truly great experience? Most hotels are decorated for the season, some ornately like Lotte New York Palace or The Ritz-Carlton New York, Central Park. Posh places like The Plaza will let you live out your wildest Kevin McAllister fever dreams, complete with an ice cream sundae cart via room service and a limo with a hot, fresh cheese pizza. They also offer the most coveted tea reservation in the city: The Plaza Holiday Afternoon Tea. For those not staying at the hotel, reservations open up 60 days prior. Mark those calendars. Many hotels, like the St. Regis New York, also offer holiday suites with special décor, cookies and milk, hot cocoa and even fresh Christmas tree deliveries in-room.

We stayed at Virgin Hotels New York City (on Broadway). A less expensive option, they still offer Christmas trees (for an additional fee) for guests staying in their largest rooms. Our room was small (not by New York standards, but in that general “rooms are so much bigger in Florida” standard) but clean and had a great view of the Empire State Building. Virgin Hotels New York City is situated in the heart of Manhattan on Broadway in the hip NoMad neighborhood, an area privy to some of New York’s most iconic architecture. The hotel rises 38 stories with floor-to-ceiling windows and a rooftop pool offering breathtaking views of Lower Manhattan and the Empire State Building.

The Mariah Carey Pop-Up Bar

Coincidentally, the Virgin Hotels New York City was one of just a few locations worldwide hosting Mariah Carey’s Black Irish Holiday Bar. In the wise words of Mariah Carey—IT’S TIME! We had reservations planned right after check-in and settled nicely into a little corner spot where we could view all of the holiday madness before us. Each guest received a signature Black Irish cocktail, inspired by the spirit of Mariah Carey. We also opted for a few of the food items on their brunch menu, including the frittata and a breakfast bread made with chestnuts.

Guests could also recreate memorable, Mari h Xmas moments, along with other holiday-themed backdrops, write a Letter to Mariah: Cast your holiday wish list to the Queen of Christmas, and sing along to 30 years of Mariah’s hit Christmas tunes, including “All I Want for Christmas Is You” and other jubilant jingles. But that’s not the only pop-up bar we tried.

A visit to Macy’s is a must for every NYC traveler, particularly during the holidays. Courtesy Oscar Wilde NYC.

Oscar Wilde NYC

Filled to the brim with Irish liquor and chestnuts, we stumbled down the bright-red, carpeted steps of the Mariah Carey pop-up and headed outside to brave the cold and perhaps discover some of that over-the-top Christmas magic you can only find in the city. Oscar Wilde NYC is one of those places, and, located just a few blocks from the hotel, it’s almost too easy to get there. But there’s a catch; you’ll need reservations to snag a coveted spot inside. We highly recommend making one.

This one-of-a-kind bar and restaurant celebrates the legendary Irish playwright by embracing the elegance and eccentricity of the Victorian era. Just like Wilde himself, it’s a place where convention is turned upside down while style, wit and indulgence remain at the forefront. Guests are welcomed into an atmosphere rich with antiques, ornate details and whimsical touches that honor Wilde’s flair for the dramatic. The philosophy here is simple: Life should be lived to its fullest, with a splash of sophistication and a dash of debauchery.

During the holidays, however, the spirit of Old St. Nick infuses those same spaces, when Oscar Wilde’s interior is transformed into an over-the-top holiday spectacle. With animatronic polar bears adding theatrical charm and holiday lighting enhancing its elegant interiors, the bar’s unique mix of history, whimsy and warmth makes Christmas at Oscar Wilde memorably magical. It is bustling and loud, with guests packed in tightly like little holiday sardines, but that’s part of the fun. We sat at a little table right in the middle of an incredibly ornate room. Bells and tinsel hung from the ceiling; lights adorned every wall; it was really something to behold.

Whether or not you’re belting out songs like a hardcore Swiftie, there’s something for everyone to love at Champagne Problems. ©champagneproblemsnyc.com

Champagne Problems

The next morning, we hailed a cab and headed toward the Lower East Side for a little bubbly and brunch, courtesy of Taylor Swift. Fans of Taylor Swift and non-Swifties alike will love a visit to Champagne Problems, though it helps to have an aficionado with you to point out all of the nods and tie-ins. This Taylor-themed bar and lounge serves up a lot of sass, glamour, good food and great times, hidden behind a secret wall inside a potato chip store! The faux chip store boasts real products, an attendant and even a register. But all you need to do is press a bag of chips to trigger the entrance to the Taylor Swift-themed speakeasy.

Step inside, and you’ll find two incredible levels of Swift easter eggs. The first floor houses the mirror-backed bar and a sea of half table/half booths. TVs played Taylor’s music videos in black and white. A larger-than-life champagne glass filled with “bubbles” was available for photo ops. But there was a catch; you had to climb up a tiny ladder into the glass first! Alas, I wasn’t brave enough to climb in, but we watched many patrons struggle to get in and out of it for the perfect shot. We even played photographer for several groups of well-intentioned influencers.

Now, on to the food and drinks! We tried the Bao Bun Maple Chicken and Bacon sliders, with lao gan ma aioli and maple syrup, and the Granola and Yogurt Parfait with oats, almonds, chocolate chips, honey, yogurt and fresh fruit. We also opted for two of their brunch mocktails, the P.A.N.D.A., which came in an adorable panda mug, and another presented in an equally cute unicorn mug. Upstairs you’ll find even more nods to Taylor Swift and her albums, including a private “Red” themed room.

Get the most bang for your buck at the Union Square Holiday Market, with more than 175 visitors and an enchanting view of the skyline. ©Jacob Williamson

Holiday Markets

Fully stuffed with plenty of time until we set out for Broadway that evening, we decided to tackle the busiest holiday market first: Union Square Holiday Market. This isn’t your grandma’s holiday market, unless your grandma grew up in the city. Union Square is one of the city’s largest and longest-running holiday markets, featuring more than 175 vendors selling unique gifts, clothing, home décor and artisanal food. Plus, the subway exit for Union Square drops you right into the center of the market, so it’s super easy to commute to! There is no wrong place to start; just make sure you’re going with the flow of traffic.

Here you’ll find some of the friendliest vendors across all the NYC markets. Many are eager to share their process and show off their wares. We did so much shopping in this market, and while we cannot guarantee these vendors will be back in 2026, we sure hope they are, and that you have a chance to visit them too. Our first stop was mogutable, based in Williamsburg, Brooklyn, and their adorable chopstick holders. Made in the Mino Province of Japan, they are sure to bring joy to your dinner table. We bought several sets as stocking stuffers for our sushi-loving friends and family.

Holiday ornaments are big business at these markets, and craftspring is no exception. These ethically made ornaments are designed in Brooklyn and handmade with love and joy by female artisans around the world. DAN’s Parents’ House is another winner, a husband-and-wife-run vintage toy and collectibles store specializing in items from the 1970s, ‘80s and ‘90s in the Bronx. This booth has so much to look at; it’s very nostalgic. The market is filled with incredible things to eat and drink too, like waffles, truffle fries and cheese wheel pasta.

You can’t leave NYC without going to a Broadway show—we saw “Romeo +Juliet,” but any show is great!

A Broadway Play (Any Will Do)

After a full day of shopping, brunching and refueling on coffee, we set out to see Rachel Ziegler and Kit Connor in “Romeo + Juliet” (performances ended in February 2025). This play was a modern reimagining of William Shakespeare’s timeless tragedy, blending the classic narrative with fresh staging, vibrant music and contemporary design.

The production’s stunning choreography and energetic score inject a modern pulse into the ancient tale, capturing the passion, tension and inevitable heartbreak between the two lovers from feuding families. The circular stage and auditorium made it so no one had a bad seat; many of the actors ran right by us, climbed above us or sang next to us. The play utilized cutting-edge technology, with projections and lighting enhancing the emotional depth of the scenes, making the story feel both timeless and immediate. Though “Romeo + Juliet’s” time on Broadway has ended, there are plenty of great shows to catch this holiday season.

We squeezed so much more into our weekend in New York City, from trips through Central Park, to a stop at Macy’s to see the windows, coffee shops and more holiday markets, but we’re out of space and coffee! The holiday season in the city is magical, no matter how you choose to experience it.