Your Guide To The Perfect Girls’ Trip In New York City This Winter

My heart sang along to the beat of my heels hitting the concrete as I got off the new Uber shuttle to 34th Street Penn Station from LGA. The familiar whistling of the subway below made me smile. It felt like I was back where I belonged.

The soul, the spark, the endless sense of possibility, all of it drew me in. A hopeful romantic, I chose to ring in 2026 with a truly magical date: the one and only New York City. Even as a native who spent my formative years here, returning as a single adult felt entirely new. The girlies who know, know. And if you don’t, let this be your introduction. Welcome to the ultimate romantic guide to the city, created for anyone who needs a getaway that might just change her life, right as winter softens into spring and the world begins to bloom again.

Call me dramatic. I am from New York after all, but I fully agree with Lin-Manuel Miranda as he penned the iconic lyrics, “History is happening in Manhattan, and we just happen to be in the greatest city in the world.” The birthplace of Broadway, the Brooklyn Bridge, hip hop, and my goodness, pizza! There is more history in these 22.82 square miles than all of the United States combined, and that doesn’t even include the other four boroughs: Brooklyn, Queens, the Bronx, and Staten Island.

Take a moment to imagine that, less than 150 years ago, over 12 million immigrants (each one recorded in preserved ship manifests) passed through Ellis Island between 1892 and 1954, making New York the gateway to America for millions. My great-grandfather came from Spain. My grandfather was born in Puerto Rico and made his way here. My mom became a first-generation New Yorker, and I am the second. History didn’t just happen here. It made me. It’s part of the love story I hold with this city and all it offers, and why I hope everyone experiences it at least once in their lifetime, not as a tourist, but as someone woven into its very heart.

So consider this your sign to start planning a romantic city escape for 2026. Don’t let the cold weather deter you. Make it fashion. Pro tip: you’ll earn instant credibility with locals since it’s not tourist season.

There’s also no shortage of experiences that make the city feel rich without straining your budget, including:

Hotel Week: Jan 2–Feb 12 (25% off stays)

Broadway Week: Jan 20–Feb 12 (2-for-1 tickets)

New York Fashion Week: February 9-16 (with all the Galentine’s energy)

Evie's First Live Event: Feb 15 A Celebration of Romance & Beauty (tickets are extremely limited)

Cherry Blossoms Bloom at Brooklyn Botanical Gardens: March/April

All of that's to say: the city is generous right now, especially if you know where to look. You don’t have to do it all to feel like you’re living in it, though. Here’s how my own trip unfolded, starting the moment I landed.

Arrival Rituals: The City Starts at the Airport

I moved out of Manhattan in 2017, and to my surprise, LaGuardia has had a total facelift, especially in Terminals B and C, now home to Delta and American Airlines. This girl was blissed out, past the surprise upgrade to business (always worth asking!). The terminal is stunning: light-filled, modern tech like AI baggage systems, new shops, and jaw-dropping skyline views, turning what used to be a dreaded travel experience into a first-class New York welcome.

Enter the new Uber shuttle. Long gone are the days of $80 rides or freezing for an hour and a half on buses. I clicked the shuttle option in the app, added my hotel address, and almost passed out: $18 to glide into Manhattan in a Mercedes Sprinter? File this under small miracles. In five minutes, I was en route with other riders, soaking in the city skyline and that familiar energy that makes your heart race. My stop: NoMad, and the hotel that would be home base for the weekend, Ace Hotel New York.

Where to Stay: Ace Hotel

If you want to be close to the energy without being swallowed by the chaos of Times Square, NoMad is your answer. North of Madison Square Park and home to the iconic Flatiron Building, it’s a charming Midtown neighborhood that strikes the perfect balance between downtown and uptown. As a local, I remember how iconic Ace Hotel was for its Lobby Bar and all the parties in the retro basement club now known as Libera, a vibrant wine bar and event space inspired by the disco era and Italian clubs from the 1960s. Staying here felt like a true home base, designed for artistic nomads who appreciate a great lobby, good coffee, reliable Wi-Fi, and a soundtrack worthy of inspiration. Whether you’re traveling for work, play, or somewhere in between, Ace Hotel strikes the perfect balance. Even more than that, the staff made it feel personal. As a solo traveler, that sense of care makes all the difference.

I checked into my cozy suite, which was way bigger than anticipated, with a king bed and a whole living room area to unwind, plus stunning views of pre-war architecture. The in-room record player and vinyl collection felt like the perfect finishing touch. And then there was Milk Bar downstairs. My welcome gift was a confetti cookie, and yes, the hype is justified.

The next day, my friends arrived, officially turning the trip into a girls’ getaway. We spent the morning snapping photos in what felt like a content creator’s playground, energized and ready to take on the city just outside our door. A truly unbeatable location.

The Neighborhood That Holds You: NoMad

Day one is all about walking culture, so lace up your boots. You’ll easily clock 15,000 steps, and honestly, you could orbit Ace Hotel all day and still have a perfect New York experience. Start with a Stumptown coffee, and don’t skip a Black Seed bagel with egg and cheese on everything.

Stroll a few blocks to Madison Square Park for iconic views of the Flatiron Building. Its triangular silhouette, once nicknamed Burnham’s Folly, remains one of the most photographed landmarks in the city.

If vintage shopping calls your name, the Fashion District is a treasure hunter’s dream. Walk along 26th Street from Fifth Avenue west and explore Crossroads, Buffalo Exchange, Thrift NYC, 2nd Street, and Flamingo’s Vintage. Each shop feels like stepping into a different decade, so give yourself time to wander. You’ll thank me later.

By now, you’ll have earned a late lunch. We stumbled into Hole in the Wall, a cozy Aussie café with glowing reviews, and it did not disappoint. Another must is 230 Fifth for rooftop views of the Empire State Building. It was freezing, which meant no line, but the city glittering below still took our breath away. For an extra-special moment, ask for one of the igloos and settle in with a cocktail. Consider it your reward.

Day Two: Broadway & the Staples

Yesterday, we barely needed the subway. Today, you’ll ride like a true New Yorker. Full disclosure: I took my final MetroCard ride on the last day of 2025, when the city quietly said goodbye to an icon. If you still have one tucked away, treasure it. It’s officially a relic of New York’s golden era. Enter OMNY. I was skeptical of the tap-and-go at first, but once I tried it, it cured that familiar “where is my MetroCard?” panic for good. Head to your nearest station (ours was just steps from Ace Hotel) and ride uptown to Times Square–42nd Street.

Time to mentally prepare for Broadway rush. Each show releases a limited number of discounted tickets when the box office opens, usually between 10 a.m. and noon. The seats are often incredible. Don’t ask why. Just trust.

Make a game plan. Decide which theaters you’ll try first, because this is very much a one-shot moment. I aimed for Hamilton (sadly, it no longer offers rush, though standing-room sometimes appears) or Hell’s Kitchen, Alicia Keys’ new musical. My friends set their sights on Chess with Lea Michele and Buena Vista Social Club, both highly recommended. Then, we divided and conquered.

Once your plan is set, ignore the glittering distractions of Times Square. You are a woman on a mission. My goal: three seats at $44 each, third row. When I arrived at the Shubert Theatre, only a few people were already waiting. I stepped up to the box office and asked, “Hi, do you have any rush tickets for tonight’s show?” The usual looks of confusion or sympathy came… and then, jackpot. Three tickets at $44 each. Evening plans were officially locked in, and suddenly we had a whole day to explore.

Now is when you can finally get distracted. Take your Times Square photos, then walk uptown along Fifth Avenue toward Central Park, passing St. Patrick’s Cathedral, Louis Vuitton, and the Plaza Hotel. Once inside the park, keep an eye out for a street photographer with a newspaper stand. It’s a charming, donation-based photo-op and your permission to be delightfully unhinged for a moment.

We grabbed hot cocoa and wandered toward Columbus Circle, a place heavy with memory for me. I used to work in fine dining, and seeing one of my old stomping grounds still standing made me unexpectedly emotional. If you’re in the mood for a true splurge, Jean-Georges’ tasting menu remains a showstopper.

By then, hunger had fully set in, so we headed back to Ace Hotel for a quick snack at Lobby Bar. The cheese plate is divine and the perfect reset before curtain time.

Curtain time. Hell’s Kitchen wrecked me in the best possible way. Alicia Keys’ music already lives deep in my soul. Her Element of Freedom album carried me through one of the hardest breakups of my life, and the mother-daughter storyline only deepened the connection. This production of “No One” is now permanently etched into my heart. Kelsee Kimmel delivered one of the most extraordinary performances I have ever seen. Her vocals genuinely altered my brain chemistry. After the final curtain call, the three of us could only sit there in stunned silence.

I always cry at curtain call. Maybe it’s because I’m a lifelong performer, but there is something transcendent about what these artists give night after night. Go see theater. Keep Broadway alive.

Afterward, we needed food, and fast. I was determined to explore Hell’s Kitchen itself, just a few avenues west along Ninth Avenue. Enter Obao, an Asian fusion spot blending Thai and Vietnamese classics. Two words: Kao Soi. That’s it. Google it. Order it. Nate, our server, was the second-best part of the night.

Day Three: Museums, Comfort Food & Old New York

This Saturday was made for slowing down. No alarms. No rushing. Just letting the city meet you where you are.

We began at the Met, which always feels like a reset for the soul. Moving through rooms filled with centuries of beauty has a way of reminding you that life is far bigger than whatever is weighing on you. It softens your edges, widens your perspective, and invites you back into wonder. We paused in front of Washington Crossing the Delaware, which, surprisingly, none of us had ever seen outside of a history book. In person, it is breathtaking.

Afterward, we did what every proper New York day requires: a street hot dog and gourmet hot cocoa from the Mark Hotel stand. Another Jean-Georges classic, it’s one of those small rituals that makes old New York feel close enough to hear it whisper, I’m still here. For a moment, it feels like stepping back into the Gilded Age. From there, stroll through the Upper East Side and take in the grand historic mansions lining the streets.

From there, we crossed the park to the Upper West Side to meet friends for dinner at Jacob’s Pickles, where comfort food feels like a warm vacation in the middle of winter. Think fluffy biscuits, house-made butters, and apple pie hot toddies. It’s indulgent in the best possible way, the kind of place that invites you to linger. And we did.

Day Four: Brooklyn Dreams & Full-Circle Moments

Day four was about changing scenery. I booked part of our stay through Kindred, a home-swapping app that lets you travel like a local, yes, very The Holiday. Instead of paying per night, you use credits earned by hosting or referring others. They generously gifted me credits to try it for the first time, and I couldn’t wait to experience it and share it with you.

Our Kindred stay landed us in DUMBO, one of my favorite Brooklyn neighborhoods. Think cobblestone streets paired with a new wave of elevated, wellness-forward living. The building itself felt like a boutique spa, complete with a signature scent, gym, sauna, rooftop with sweeping Manhattan views, and a serene one-bedroom that became our home for the second half of the trip.

Nearby, we grabbed coffee at Devoción, walked toward the Manhattan Bridge for that iconic view, and wandered through Brooklyn Bridge Park and the famous carousel. I slipped into Front Street General Store for souvenirs and vintage finds and left with the cutest minimalist tote. Lunch was at Time Out Market, and if the weather allows, walk the Brooklyn Bridge. I’ve done it many times, and it never gets old.

That night, we headed back to Manhattan for dinner in Tribeca at Locanda Verde inside the Greenwich Hotel. The whipped ricotta is otherworldly. More than a restaurant, this place feels like an institution for Hollywood A-listers, co-owned by Robert De Niro, and for me, it was deeply full circle. I used to work here, too. Returning as a guest felt like a quiet reclaiming of old dreams. The city has a way of whispering, You may have left, but I never left you.

As a hospitality veteran, that moment mattered. That industry shapes you in ways both beautiful and bruising. I’ve seen the highs, the lows, the late nights, and the stories poured out over martinis. Sitting there now, welcomed as a guest instead of staff, I felt it deep in my bones. No moment is ever wasted.

We ended the night at the Django Jazz Bar inside the Roxy Hotel for a truly jaw-dropping performance. Make a reservation. It often sells out. The sound, the mood, the femininity, the romance. It is the perfect nightcap. I cannot recommend it enough, whether you consider yourself a jazz lover or not.

Sunday: Soft Landings

Sunday needed to feel like home, so we began in a familiar sanctuary. Church wasn’t about ritual as much as it was about grounding, breathing, and thanking God for a week that held more meaning than I could have planned. The entire trip felt quietly guided, and I believe you can experience that too, no matter what you believe.

From there, we went straight to brunch at Lafayette in NoHo, a true French staple and always a yes. The room buzzed softly, coffee clinking against porcelain as warm golden light bounced off every perfectly baked pastry. The shakshuka was rich and spiced, one of those meals that makes you sigh because you don’t want it to end.

After brunch, we wandered into the Village, and honestly, it could be a full day all on its own. We love the Village. Tree-lined streets, crooked brownstones, and little corners that feel like movie sets. It slows you down in the best way. Of course, we stopped at Molly’s Cupcakes, because you simply have to. Something sweet in hand, no agenda, laughing about nothing. What else could a girl need?

One of my friends decided this was the trip she would finally treat herself to a new phone, and naturally, she wanted to do it in style. So we headed to the Apple Store at Grand Central. Even with the crowds, that space still feels cinematic.

There is a special kind of joy in walking through New York without a plan. On our last night together, we trusted the city one more time. We wandered. We let it lead. And of course, it did.

The cold eventually sent us searching for warmth, which is how we stumbled into Il Fiorista, a modern Italian restaurant that doubles as a floral shop. We had no idea it existed until candlelight and soft florals caught our eye through the window. The Italian staff recommended the delicate chamomile-infused linguini cacio e pepe and a warm chocolate cake that tasted like pure comfort. You can’t Google moments like that. It was the perfect goodbye kiss.

And just like that, New York did it again. Five days of adventure with the one person who will thank you most: yourself.

This is me letting you in on something sacred, yet entirely attainable.

You can find romance in this city whether you’re single, with your girls, or with someone you love. It isn’t about doing everything. It’s about choosing moments that reflect who you are now. Leave space for spontaneity. Let the city meet you halfway. New York is not just a destination. It’s a mirror. And every time I return, it shows me how far I’ve come.