New York City is one of those places we keep returning to — not because we’ve “done it all,” but because it feels different every time we go. Over the years, our trips to NYC have shifted with both the seasons and our own lives: visits as kids with our parents and siblings, later as a couple, then as pet parents traveling with two cats, and eventually as parents with a baby in tow.
This post is a look back at all our NYC trips so far — not as a checklist or a guide, but as a timeline. Some visits were slow and museum-focused, some were wintery Broadway weekends, and one in particular stands out as our favorite: a summer trip centered in Midtown that felt exciting, and complete.
Why We Keep Going Back to New York City
NYC is an easy return trip for us — a straightforward drive from Boston — but convenience isn’t the only reason. There’s something comforting about how familiar and unfamiliar the city feels at the same time.
We love that:
- You can build an entire trip around Broadway, museums, or food
- Each neighborhood feels like its own little world
- The city works surprisingly well for different travel styles — short trips, slow trips, and even trips with pets or kids
Summer Travels — Leaning Into Being a Tourist
Summers in NYC feel open-ended, with endless possibilities for shaping a trip. But one summer trip remains our favorite — not because it was our first time in New York, but because it was our first NYC visit as a couple, and the first one where our entire little family came along: the two of us and our two cats.
We stayed at The Algonquin Hotel, and that choice shaped the entire experience. Between its literary history, cozy interiors, and genuine cat-friendly atmosphere, it felt like a calm pocket within the constant motion of Midtown. Our cats settled in immediately, which made the trip feel less rushed and more grounded.
We leaned fully into a classic, touristy NYC itinerary with a focus on Midtown, and it was exactly right for that moment in our lives.
Highlights from this trip included:
- Exploring Midtown icons like Rockefeller Center, St. Patrick’s Cathedral, and Times Square
- Visiting the Statue of Liberty
- Taking a helicopter tour over Manhattan
- The Friends Experience, the Harry Potter Store, and Harry Potter on Broadway
- Ending a full day with nighttime views from the Empire State Building
- Quiet breaks back at the Algonquin for tea and drinks, which became some of our favorite moments
We wrapped up the trip by driving back to Boston via the Brooklyn Bridge, which felt like the perfect closing scene.
This trip eventually became the blueprint for what I now consider a great first-time NYC itinerary.
Fall and Winter in NYC — Broadway, Lights, and Holiday Energy
Some of our subsequent travels were winter trips, and it felt completely different from the summer energy of the city.
These trips revolved around:
- Broadway shows
- The Rockefeller Christmas Tree
- The Met
- The American Museum of Natural History
It was colder, busier, and more compact — a trip built around evenings rather than long walking days. We still ventured out on foot for sightseeing and grabbing some bites to eat. Winter NYC feels beautiful in its own way, and our first winter visit solidified how much we enjoy the city during Broadway season.
How Our Trips Slowed Down Over Time
By this point, our relationship with NYC had shifted. After experiencing the city at its most energetic and most festive, our trips to New York became less about timing and more about purpose. We sometimes stayed in Edgewater and approached the travels more slowly. Some trips became museum-focused weekends, while others were centered around catching up with friends and family. These experiences felt less and less like a checklist and more like a familiar city we returned to for specific reasons.
Not every visit was about enjoyment or exploration — some were about presence, reflection, and meaning. One of our later visits was brief and intentional, focused primarily on visiting the 9/11 Memorial. It wasn’t about sightseeing or food — just about being present and paying respect. Not every trip needs to be full, and this one served its purpose quietly.
Our Repeat Favorites
Some places have become constants across trips:
- Joe’s Pizza
- The Kati Roll Company
- Broadway shows
- Central Park
- The Algonquin lobby — even on trips we didn’t stay there
These repeats are part of what makes NYC feel familiar rather than overwhelming.
What Visiting NYC Over the Years Has Taught Us
Seeing the city across different trips and seasons taught us a few things:
- Summer is ideal for skyline views, harbor experiences, and longer sightseeing days in New York City.
- Winter trips to NYC are perfect for Broadway shows, museums, holiday lights, and cozy meals.
- Repeat visits to New York City don’t need packed itineraries; choosing one focus makes each trip more enjoyable.
- New York City adapts surprisingly well to different life stages, from traveling with pets to visiting with a young child.
Traveling With Cats, Then Later With a Baby
Those lessons became practical necessities once we started traveling with dependents — first with two cats, and later with a baby. Traveling with pets required us to prioritize pet-friendly hotels, downtime between activities, and a central location to minimize transit. Later trips with a toddler reinforced those same decisions, proving that New York City can work surprisingly well for slower, comfort-focused travel when planned intentionally.
Looking Ahead
We know we’ll be back. Maybe for Brooklyn next time, or a food-focused trip, or another quiet museum weekend when our son is a little older. New York has a way of fitting itself into different chapters of life — and taken together, these trips tell a story we’re glad we documented.
If you’re planning your own visit, there are countless detailed NYC guides available elsewhere. This post isn’t meant to compete with them. It’s simply our timeline — the memories behind the itineraries, and the way the city kept meeting us where we were.
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