Two Trips, One City: Falling in Love with New York, Again and Again
New York City is one of those rare places that lives a hundred lives—and every time you visit, it shows you a new one. I've been twice now: once with Jake and my brother James in December for a magical, Christmassy first-timer experience, and again for a quick weekend getaway with just Jake in March. And even though both trips were short, NYC left its mark—twice.
It’s hard to explain exactly why I love this city so much. Maybe it’s the energy, maybe it’s the blend of cultures, or maybe it’s how turning a single corner can feel like stepping into a different world entirely. What I know for sure? I’m already planning my third visit—this time in September, when the weather is warmer, the parks are alive, and I can see a whole new side of the city.
Trip 1: New York at Christmas (Jake + James)
Our first visit had that wide-eyed, “we’re really here” energy. We soaked up the city’s iconic holiday magic—twinkling lights, storefront displays, and the buzz of Times Square. We went full tourist, proudly: Top of the Rock, Radio City Music Hall, the Brooklyn Bridge, Rockefeller Center. But some of my favorite moments were the quieter ones—walking through West New York for skyline views and exploring Brooklyn with my brother James. I swear he’ll live there someday, and I’d bet on it.
Trip 2: March Magic (Just Jake & Me)
Our second trip was a quick weekend escape, but New York doesn’t need much time to impress. We kicked off the weekend in Central Park under blue skies and live music, then devoured the most amazing curry lamb noodles and dumplings in Chinatown. I got to show Jake around Brooklyn—he’d missed it the first time—so we explored Brooklyn Heights, walked along the water at the Brooklyn Bridge Park, grabbed pizza in DUMBO, and crossed the bridge at sunset. The sky turned peachy-pink as the skyline lit up behind us. It was everything.
The next day, we wandered from East Midtown down to Greenwich Village, passing the Flatiron Building, popping into a dreamy independent bookstore, and trying to stay warm with way too much coffee (and a detour for Irish coffees in a pub where everyone had accents—it truly felt like a mini trip to Ireland). We ate our way through Chelsea Market, walked the High Line, and ended the night with tiramisu from a wine bar near our hotel.
We may have caught a cold from the wind… but it was worth every single step.
A City of Five Worlds
New York City isn’t just one city—it’s five: Manhattan, Brooklyn, Queens, The Bronx, and Staten Island. Each borough has its own heartbeat, but what makes the city truly incredible is how each one holds multitudes. In many ways, NYC is the ultimate culturally immersive destination—like traveling the world just by changing neighborhoods.
So far, we’ve explored Manhattan and Brooklyn (with a little West New York thrown in for skyline views). And we’ve only just scratched the surface.
There’s so much I still want to see:
Queens for its unparalleled global food scene and incredible diversity
The Bronx for Afro-Caribbean flavor, hip-hop history, and Yankee pride
Staten Island for coastal views and that iconic ferry ride
Long Island for a quick city escape and a different pace
You can go to New York a dozen times and still discover something new. That’s exactly what I plan to do.
My Favorite NYC Spot: Washington Square Park
If I had to pick one place that captures the soul of the city, it’s Washington Square Park. Street musicians, skaters, local artists, professionals walking home, kids chasing bubbles—it’s a mix of humanity that somehow feels perfectly harmonious. Maybe I love it even more because it’s featured in When Harry Met Sally (one of my forever favorite movies). But even without that? It’s pure magic.
Looking Ahead: NYC in September
Our first visit was in December—dreamy and festive. The second was March—crisp, cultural, and full of layered coats and warm drinks. But now I’m planning a 3–4 day return trip for September to see the city in a new season. I want to walk the West Village without freezing, picnic in Central Park, and enjoy rooftop views without windburn.
The best thing about New York? It always gives you a new story—and I can’t wait to write the next one.
Want My NYC Favorites?
For Views: The view from West New York/Hoboken NJ + Brooklyn Bridge at sunset
For Food: Chelsea Market, DUMBO pizza, Chinatown noodles
For Culture: Washington Square Park, independent bookstores, the High Line- but seriously the whole place is just amazing!
For Vibes: The West Village, Brooklyn Heights, SoHo
I’ll be updating the blog after my September trip with even more recommendations—especially for couples & families. Stay tuned 💫
