Hi friends! It’s been a little over a year since I’ve published a Reader Q&A so I figured now would be a good time to regroup here and pull back the curtain on Window Seat a bit.
If last year was defined by change, this year has been all about rapid expansion. The past eight months have flown by in a whirlwind of last-minute departures and long-haul turnarounds. While the pace has been intense, it’s also given me a well of new industry insights, travel lessons, hotel discoveries, route strategies, and perspective to share. Consider today’s Q&A my way of saying thank you for helping me make this my job, and passing that knowledge back to you.
Read on to learn:
The one hotel that’s earned a perfect 5-star rating from me this year
How swapping corporate life for a life in the air redefined my spontaneity
My unfiltered thoughts on AI in the travel industry
My non-touristy 24-hour itinerary for a perfect day in New York City
Practical tips on upgrading to lie-flat seats without spending a fortune
What’s the best hotel you’ve stayed at this year? And you can only pick ONE. —KC
I’ve been so fortunate to stay at some truly exceptional properties this year, including two that have been revealed on the World’s 50 Best Hotels list for 2026 (only half of which is currently released). For my own ranking, I’m taking aspects like the service, the comfort, the food, the amenities, and the hospitality into consideration. And there’s only one that’s gotten easy fives across the board for me.
Has becoming a travel writer made you more or less spontaneous when you travel? —Reid
Definitely more spontaneous! Many of the trips I’ve taken have come with a week or two of notice, and one even had just 24 hours. I’ve also done 5 long-haul trips this year so far (7+ hour one-way flights), all of which, except one, had just 48-72 hr turnarounds.
I used to be someone who needed to research relentlessly for months on end before a trip, ensuring I had a really tightly curated itinerary. I didn’t want to miss out on anything. But the kind of travel I do now does not allow for that. So I just do as much research as I can, and then hope for the best.
There’s also the added benefit of accumulating miles and points at a much more accelerated rate, so I can call up a girlfriend in Miami and say, “hey wanna meet me in West Palm for the weekend?” and make it happen, which is really cool.
Would you ever go back to a full-time corporate job for the right opp/$$, or do you feel like that chapter of your life is over? —Eleanor
I don’t think any amount of money could lure me back to a desk job after the year I’ve spent being a free agent. Working in corporate is definitely a chapter I consider over. I made the mistake of putting on golden handcuffs once before and learned the harsh lesson that money isn’t everything, even though living in a city like New York can lead you astray in that way. I value my autonomy, freedom, and the ability to build something that’s mine so much more, and I’m so proud of myself for getting to that point.
Favorite souvenir from this year? —Devon
I have a couple huge bulletin boards behind my desk in my office that are home to all of the ephemera I’ve collected from my travels since I started Window Seat. Hotel key cards, name tags, media credentials, handwritten notes from hoteliers welcoming me to their properties, airline trading cards, the like. It’s a living, breathing wall of gratitude that serves as a daily reminder for me to dream bigger.
Biggest “holy shit, this is my job now” moment? —Isa
I had to actually think about this for a bit—there’s been quite a few this year! But I think THE moment happened this spring on a Riva yacht speeding through the Gulf of Naples. Champagne in hand, sun shining, music blaring, not a care in the world. I was there on a press trip being hosted by a family who owns a 200-year-old hotel that’s since become one of my all-time favorites. It was a career milestone for sure—checking a new country off the list, being invited to stay at a hotel of such grand scale and legendary stature—but it was also just pure bliss incarnate. It was an “I made it” moment for sure.
I would LOVE to hear more about the business side of Window Seat. Do you think of yourself as a writer first now? A creator? I feel like you’ve built something that doesn’t really fit neatly into any of those boxes and I’m curious how you describe what you do when someone asks. —Anonymous
I definitely consider myself a writer first. Although I also create content, it’s not my bread and butter or something that comes easily to me at all. Plus, if I decided to stop creating content tomorrow, I think Window Seat could still survive as a respected publication. The converse is not true. So to answer the last part of your question, I introduce myself as a travel writer or journalist depending on the environment, or simply as the creator of Window Seat, a newsletter about luxury travel, aviation, and the culture of modern hospitality.
I’m a creative director working corporate so we’re inundated with “AI” everything. As a travel writer and brand builder, how is it, if it is, affecting you or the travel you write about? —Ashley
I toggle between two modes, travel storytelling here and brand strategy in my consultancy, so I really view AI without the panic or blind hype.
In my day-to-day, I use it as an operational engine: negotiating brand deal terms, troubleshooting issues in programs like QuickBooks (bane of my existence lol), fixing a recipe I think I screwed up, optimizing a route for errands I need to do in the city. It’s been an incredible tool that I use, essentially, as an administrative assistant. But when it comes to travel writing and brand building, we know AI can’t capture the sensorial nature of a place or offer real human discernment.
The industry split that’s happening right now is really interesting to me. On one side, you have fearmongering about getting “left behind,” and on the other, an absolute denunciation (which, I’ve found, most often comes from certain travel advisors whose pushback seems motivated by protecting their own business interests).
Have you seen that image comparing AI doing laundry and dishes to art and writing? I think the sweet spot is pragmatism: using AI for all the menial tasks and inbox management that eats up so much of our time so we have more of it to dedicate to creativity and all the human pursuits AI won’t ever be able to really replicate.
Do you have any tips for upgrading an existing ticket? Is it even possible? Backstory: I booked a nonstop to Venice on United for a wedding aka inflexible date, upgrade for lay flat for one way was $6300 and now $8500!! I have some Amex and United points and I am also willing to pay $$ but not THAT much $$$$$!! —Ally
You know, it’s funny: the first time I ever flew in business, it was because I made friends with a flight attendant who, out of the goodness of her own heart, decided to upgrade me from my economy seat to a Delta One lie-flat (the good kind, on the A330neo. I am forever indebted). But this was several years ago, and I know better than to expect this incredible stroke of luck to ever strike twice.
Another way I’ve upgraded an existing ticket was on an Air France flight. I had a Premium Economy booking, and completed my first leg of the flight. A day before my return flight, I got a push notification from the airline app offering a $300 upgrade to business. Many airlines will release last-minute paid upgrade offers to fill these seats closer to departure, so set a reminder to check the app a day or two before departure just in case.
But let’s talk United specifically: United lets you to request an upgrade to Polaris using MileagePlus miles plus a cash copay (usually ~20-35k miles + ~$500 for Europe routes). Even if you get waitlisted, you won’t pay anything upfront unless the upgrade clears (and if it fails, your cash/miles are refunded). And you mentioned you have some Amex points lying around. Unfortunately those don’t transfer directly to United, so your best move is booking through Star Alliance partners. However! If you already hold a cash United ticket, keep in mind that you can use your Amex points to cover the cash portion of a MileagePlus copay via your statement credits.
Check out this guide I wrote for more tips!
How do you choose your next vacation/travel destination?—Ally
I’m someone who typically lets a hotel anchor a trip. For example, in the past I really wanted to stay at Les Roches Rouges, so to the South of France I went. There are exceptions, of course: like Japan, which is just a place I needed to go. But the impetus for the part-time job that is planning a trip is an exceptional hotel more often than not.
24 hours in NYC this weekend - what do I do? (Not touristy!) —Emily
I’ve been dying to do a Red Hook day. Here’s my ideal route: Starting with a coffee at Black Flamingo, moving on to shopping at boutiques like Jamieri and Open Invite, grabbing a danish pastry at Frø, then pre-dinner drinks at Pony’s before a meal at Cafe Kestrel. And then picking up a key lime pie from Steve’s to take home for later, of course.
What’s your first United new route stop?! —Jamie
We’ve been blessedddd with so many new routes out of Newark! I had never heard of Ljubljana, Slovenia before the United media event announcing the new routes, and now I’m very keen to go. It looks like such a picturesque place, apparently has an amazing culinary scene, and there’s even great hiking in the Julian Alps. So basically my perfect place.
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.
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