This dispatch is part of From the Window Seat, a series of immersive, long-form personal trip reflections, in-depth destination pieces, and sharp hospitality evaluations grounded in firsthand reporting and personal experience.
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This year, I’ve spent more time than ever away from home. 40 flights, 13 trips, and four new countries mean I’ve been treated to all kinds of amazing places all around the world. Meanwhile, I’ve lived in New York City for nearly a decade and remain embarrassingly bad at keeping up with what’s going on in my own neighborhood.
It’s particularly egregious considering it’s one of the world’s biggest tourist destinations, somewhere millions of people travel from around the globe to experience. And I get it. New York really does feel like the center of the world; every week, another crop of “must-try” restaurants, cafes, shops, hotels, and exhibitions opens. At some point, trying to keep up started to feel impossible, so I stopped trying. I settled into my familiar routines and let the city continue changing around me.
The irony is that I would never, ever travel this way. Tell me I’m going somewhere new and I’ll have a list of places I want to see before my ticket is even booked and a location-optimized itinerary before the plane touches down. Which got me thinking: could I trick myself into experiencing New York like somewhere I’d never been before?
I decided to turn it into an experiment. For 48 hours, I’d treat New York like a proper vacation: book a hotel, build an itinerary almost entirely around places I’d never been, and approach my own city with the same relentless curiosity I bring everywhere else.
Planning the trip
Every trip I plan starts with a hotel, so this was no different. Ultimately, I wanted to feel transported, and for that I kept coming back to The Greenwich Hotel in Tribeca. Between its Euro-style courtyard and Japanese-inspired spa, it doesn’t evoke one specific place, but it’s hugely atmospheric.
In terms of the itinerary, luckily I didn’t have to start completely from scratch, as I have a backlog of local places on my Maybe Someday I’ll Get to These list saved across Instagram, TikTok, Substack, various articles, and the like. Now I just had to A) consolidate them, B) figure out what was worth doing, and C) group them into a workable, location-optimized itinerary.
For this, I opened up ChatGPT for a massive brain dump. I fed it all of my saved places, the hotel, and a few parameters: avoid wasting half the day zig-zagging across Manhattan, include a booking at the hotel spa, and leave enough breathing room for spontaneity. I also wanted a visual reference I could save to my phone to be able to check on-the-go.
So, within the same ChatGPT conversation, I used the Adobe plug in for ChatGPT to turn the final itinerary into a visual guide. I knew what I wanted the finished product to look like, but I didn’t want to bother with figuring out the best Adobe tool to make it, so I simply asked it to make me an itinerary that’s very easy to follow. The plugin can pull from more than 70 Adobe creative and productivity tools inside ChatGPT, so I could describe the end result and let it figure out how to get me there.
I still had one problem: everything that went into making the itinerary was scattered everywhere. So I brought the finished guide, hotel and restaurant confirmations, menus, and my mess of saved recommendations into an Acrobat PDF Space. Think of it as one home base for the weekend: instead of remembering which email or document contained what, I could ask the Space directly. What time is my spa appointment again? Wait, what’s the address for dinner tonight again? The answer was right there.
Time to check in
Normally, my life happens in a two-bedroom apartment in Downtown Brooklyn. You can usually find me on my living room loveseat, legs outstretched on the ottoman, laptop where its name suggests, iced coffee sweating on a small tray on the armrest. More often than not, there’s broken-down cardboard and some boxed-up returns waiting by the front door beside me. Somehow the Brita filter always needs more water; the vacuum could always use more charge. These are the fixtures of my regular life.
At The Greenwich, there’s none of that—none of that anywhere I travel, really (save for the coffee, of course). Just a bed that magically gets made and a wardrobe with only clothes I want to wear. For the next two days, this was home.
Day one:
Coffee is a non-negotiable for me, so I went for a banana latte at Meadow Lane around the corner from the hotel before heading over to the day’s first activity: procuring a new read at The Mysterious Bookshop on Warren Street. Staying in theme, I went in blind and asked the staff to choose something for me, which I’d never done before. It was shaping up to be a gorgeous fall day outside—the reeeeally good kind where you can wear shorts and a sweater—so I decided to abandon part of my itinerary in favor of being outside. I went back into ChatGPT with a new request: make me a plan that includes sitting near the water for a few hours with my book. The new plan: spend the afternoon reading my new book by the Hudson at Pier 26. For how much I love A) being by water and B) reading outside, I can’t believe how much of my New York life I’ve wasted by not doing this exact thing more.
Now, I do need a little classic New York in this trip, and I don’t think there’s a better way to do that than through food—specifically, dinner at one of the city’s most beloved downtown institutions, The Odeon. I love an early dinner, especially this time of year when a 6 PM reservation means emerging just in time for sunset. And as a newly minted Martini Person, there are few places I'd rather order one (plus, the steak frites, which were impossibly good).
Day two:
The next morning, I cheated a little and went to one place I’d already been. Frenchette is right around the corner from the hotel, and they serve the best pancake I’ve ever had. I simply had to have it, and I say that as someone who never has a hankering to order one anywhere else.
After that treat, I doubled back to the hotel to disappear underground for a bit. The hotel’s subterranean Shibui Spa centers around a lantern-lit pool beneath the roof of a 250-year-old Japanese farmhouse, and this is the closest I came all weekend to really forgetting I was in New York. I opted for a Drunken Lotus massage, then spent an hour swimming by the glow of the lantern light. The best part was locking away my phone and indulging in the increasingly rare luxury of being completely, blissfully unreachable.
Eventually, I resurfaced and headed east to spend the rest of the afternoon doing one of my favorite vacation activities: wandering into shops that catch my eye. My favorites were Beverly’s 1975 for beautiful objects for the home, followed by Tumbao, a shop featuring Latin American designers, and Colbo Next Door, a very cool mishmash of fashion, music, and design that also happens to have a wine bar that I loved so much I scrapped my original plan to grab a glass at Casetta (which remains on my “to try” list).
Pics or it didn’t happen, right?
Of course, no Tori vacation, real or manufactured, would be complete without coming home with an unhinged number of photos. I love shooting New York on everything from my phone to my film camera (a bodega just hits different on Portra 400), but even the best framing can’t always save you from rogue construction, clutter, or any number of New York eyesores.
So I went back into the same ChatGPT conversation one last time and used the Adobe plug in to clean up some photos, asking it to remove specific obstructions without making the photos look overly edited. Again, I didn't need to figure out which tool I needed, I just had to tell it what I wanted changed.
The verdict
New York feels most like home when I’m in my Brooklyn bubble. But when I’m soaking at an underground spa in Tribeca or enjoying rare fall sunshine by the riverside with my nose buried in a mystery novel, it was easy for New York to feel more unfamiliar to me. To feel worthy of my curiosity and attention in a way I hadn’t given it in a long time.
And I think that’s what I was actually trying to manufacture with this experiment. Instead of trying to convince myself New York was some grand new place, I just needed to break enough of my routine to stop moving through the city on autopilot.
Forty flights into the year and what do you know? One of my favorite trips required exactly zero.
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Window Seat covers the intersection of luxury hospitality, aviation innovation, and the culture of modern travel, written by Tori Simokov, a writer and designer based in New York. For partnership opportunities: tori@v1projects.com. You can also connect with her on Instagram, TikTok, or ShopMy.