Seatmates: Diana-May
On the tradeoffs behind a life of constant travel, what she’s learned since moving to New York, and the hotel she can’t wait to check into
This interview is part of Seatmates, a Window Seat series decoding the travel habits, global itineraries, and design-forward recommendations of today’s most compelling tastemakers.
In a steady stream of lifestyle content constantly coming at us from all angles, Diana-May stands out for one very simple reason: her immaculate taste.
Taste is a funny thing. It’s difficult to pin down—even harder to define—but you know it when you see it. And Diana-May has it. Her style feels aspirational without being intimidating, pairing high and low pieces in a way that makes getting dressed look effortless. Even her simplest outfits feel elevated because she understands the small details that pull everything together. And that same point of view carries over into the way she travels. Whether she’s checking into a countryside estate in England or a boutique hotel in Italy, you can trust that wherever she’s staying is immediately worth adding to your list.
Read on to learn how a recent health diagnosis changed the way she approaches traveling, the reality of balancing work and wanderlust as a full-time creator, and whether London or New York comes out on top after living in both.
Tell us a little about yourself.
I am a full-time creator living in NYC and loving every moment of it. My content revolves around my passion for travel, fashion, and all things lifestyle. I have a taste for special moments, places, and outfits that I enjoy sharing across social platforms and with the people close to me.
Looking at your year so far, you’ve already been everywhere from Switzerland to Sardinia. What sacrifices, tradeoffs, or priorities have allowed travel to become such a big part of your life?
The most notable tradeoff is the task of always being on. It is, of course, not required, but for the goals I want to accomplish, it is a necessary tradeoff. That being said, I make sure to keep a balance of screentime dedicated to work and time off from any screen. The second tradeoff would then be the time spent capturing and curating content during said trips. In order to work with these different hotels and brands, it’s helpful to show them the type of content I can create for them and the analytics behind. This takes away from the trip a bit by not being fully present all the time, but it all comes back around when I can also afford to take these trips as I please.
Having lived in both London and New York, what does each city do better than the other?
I always say pub culture is better in London and is essentially a third space for many people. However, New York nightlife and access to anything late-night (stores, food, soccer pitch, anything!) can’t be beat. I also have to shout out the tube and bus system in London. Definitely superior.
Your followers have come to trust your taste in everything from fashion to travel. What’s something you’ve learned about your own taste from spending so much time exploring the world?
I’ve certainly learned that it’s expensive! That being said, I’ve learned to care deeply about detail, service, and function when it comes to where I travel (hotels) and what I wear.
You’ve spoken openly about your recent MS diagnosis. Has it changed anything about the way you approach travel, whether practically or emotionally?
I actually think about this often! My diagnosis reminded me that I have truly been living a life that is worthwhile. I didn’t feel the need to all of a sudden start checking things off of my list because I am already doing what I’d like to be doing. Emotionally, I may be a bit more sentimental and really relish in the trips I take, but I’m so lucky to feel even-keeled about it all.
What’s been your most memorable stay?
I have to say Villa San Giuliano. The property itself is so stunning including everything it offers like the pool, garden, and tennis court, but it’s rich with history, which I think makes it even more memorable.
Is there a destination or property at the top of your wishlist?
The next time I am in Paris, I’d love to stay at the Saint James.
What are your must-haves when it comes to luggage and items you travel with?
I’ve used my Beis luggage for years, but my must-haves in the suitcase would be the Clarins Cryo Face Mask, Bose QuietComfort headphones, and Josie Maran Body Butter because hotels rarely carry a good body lotion.
What is your go-to airport outfit?
I will always go for a loose pant like the GAP Easy Wide Leg or J.Crew Luna Cotton Poplin paired with a white tee (usually Leset) or tank (Aritzia) and a sweater (Reformation cardigan or The Row Ophelia). If not that, it’ll be a maxi dress (usually Doen or COS), and of course a sweater.
Do you have any rules or rituals when it comes to air travel?
Not really! I just make sure to stay highly organized prior to my trip to make it feel as seamless as possible.
Last question: aisle or window seat?
Window always!!
For more from Diana, follow her on Instagram, TikTok, and Substack. Interested in being featured in Seatmates or know someone who should be? Drop me a line here.
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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.
Loved this deep dive into the tradeoffs of constant travel. Those rituals we pack are what actually make a place feel like a home base.
Absolutely love this, can't thank you enough!!!