Tori Simokov's dream luxury train trip

And how her husband helped her overcome her fear of flying

I’ve always been endlessly fascinated by how other people travel. To me, travel is deeply personal and incredibly precious. In life, we only get so many chances to hop on a plane and explore somewhere special with someone special, and honestly, I have regular meltdowns about this. There are just so many corners of the world I’m dying to see, but since I’m not immortal, I know I’ll never get to experience it all.

Lately, though, I’ve shifted my mindset. Instead of obsessing over the number of places I can visit, I’m choosing to focus on the quality of each trip. We all know travel isn’t just about checking destinations off a list, it’s about so much more than that!

Which brings me to Travel Buddies, a new Mindholiday interview series that celebrates the idea that travel isn’t just about where you go. It’s about who you go with, the cultures you engage with, the people you meet along the way, and the memories you create.

I truly believe the right travel companions can turn any trip into something more meaningful and unforgettable. So, I’m diving into how some of my favorite creators curate their lives to craft incredible journeys. I’ll be exploring the joy of shared adventures, uncover personal travel rituals, planning strategies, and of course, some fun trip stories along the way.

My first Travel Buddy is Tori Simokov, the creator of Window Seat.

Tell us a bit about yourself.

I’m based in Brooklyn (and neighbors with Bella, actually!), I head up the Creative Strategy team at a media company, and I author the travel newsletter Window Seat. I write about the culture of travel, but I think where I stand out is my fascination with aviation. I like to help people work through flying anxiety (like I did) and appreciate the miracle that is seeing the world at 30,000 feet.

You started Window Seat a little over a year ago and you’ve built an incredible community along the way. I admire the vulnerability you’ve shared with readers about your fears — like overcoming your fear of flying. You’ve established an admirable level of trust through your honesty. What are your favorite parts about the community you’ve built?

Thank you! Reader trust means absolutely everything to me. When I get notes from readers, it motivates me to keep going. Like most people, I love that sharing my words can have any kind of impact. When you start out, you feel like you’re shouting into a void.

But a year later, I can say that I’ve helped people learn something, and that feels really good.

You’re notoriously good at travel hacking and using credit card points to get first class flights and five-star hotel stays. What is one piece of advice you would give to someone in their early 20s who doesn’t know where to get started?

As long as you have already established good financial habits, I would recommend opening two credit cards: one for your preferred airline and one for your preferred hotel chain. That way, you can get the perks (priority boarding or complimentary upgrades, anyone??), build up your points, establish even better credit, and take advantage of their sign-up bonuses – the best way to accumulate points.

What’s your definition of a perfect travel buddy?

Someone whose travel priorities and pace align with yours. For me, that means someone who is willing to splurge on a beautiful hotel and actually enjoys spending some leisure time there as opposed to someone who constantly wants to be on the go.

Tori lounging at Les Roches Rouges in the south of France, a certified gorgeous hotel

What qualities do you look for in someone you travel with?

It’s less about the qualities they have and how I feel when I’m around them. As long as I feel like I can be totally myself with someone, I’m comfortable traveling with them.

Has traveling with someone ever changed your relationship with them? How?

I think the best example of this is my husband. Obviously traveling with your partner is a great litmus test for any relationship, but I felt it was especially significant in ours.

We met while he was on tour in a band, and the first two years of our relationship were long distance while he was on the road. Traveling so much in the formative stages really accelerated our relationship and ultimately helped us understand our compatibility.

If you could take your favorite travel buddy on an all expenses paid vacation to any hotel in the world, which would you choose, and why?

My husband is my favorite travel companion, so I’d want to go somewhere romantic and luxurious. And for that, I’m going with an Aman property. Amankila – their property in Bali – jumps out at me. Nothing to me says luxury like Aman. No other properties seem to offer the deep seclusion, exclusivity, and sense of place that each Aman does.

Note from Bella: One of the coolest things about Aman is the their focus on providing cultural immersion adventures at every resort. At the Amankila, in addition to relaxing in a romantic setting, you can experience a traditional Balinese cultural blessing, take an adventure to the Ujung Water Palace, visit a living museum, or learn ancient Lontar writing techniques from a master.

Can you tell me more about how you traveled before you met your husband? I’m curious to know how finding your perfect travel buddy has affected your travel style.

It's funny, would you believe I barely traveled before I met my husband?

After we met, I was on a plane at least once every other month. I credit this exposure therapy (among other things) with helping me overcome my fear of flying. I know a lot about traveling now, but I truly owe so much of what I know to him; he passed on so many of the tips and trips I now evangelize in my newsletter.

If you could plan your dream trip with one person, dead or alive, who would it be, and where would you go?

I would treat my Mom to a two-week, early Summer trip to Europe, as she doesn’t get to travel very much. We’d fly from New York to Venice in Air France’s La Première (First Class) cabin. After sightseeing, we’d take the iconic Venice Simplon-Orient-Express to Paris (in a suite, of course), where we’d spend a few days. Then, I’d have her pick: we could go to Switzerland or spend some time in the South of France.

You’re going on a friend trip! What’s your role when it comes to planning, and how do you divide responsibilities to prevent any potential drama?

I’m the type-A friend, so I’m planning the itinerary and creating the Excel spreadsheet where everything lives.

You have a friend visiting you in town for the weekend. Where are you taking them to show them a great time?

For dinner, we’d have a no-fuss meal at Le French Diner then grab drinks at Tigre. I’d also love to do a fancier evening and treat them to dinner and live jazz at The Nines, which always hits.

For activities, I like to suggest Comedy Cellar, Bathhouse, or shopping for a new signature fragrance at Scent Bar.Do you have any travel rituals or traditions?

Do you have any travel rituals or traditions?

I have so many travel rituals!

On the plane:

• I always touch the outside of the plane before I board

• I always listen to the same Odesza song during the takeoff roll

At my destination:

• I take home as much ephemera as possible from the hotels I stay at

• I buy postcards in every city I visit

• I look for listening bars/hi-fi audio lounges

If you could sum up your travel style in 3 words, what would they be?

Curated, timeless, and elevated.

The flight attendant is coming around with the drink and snack cart. What are you ordering?

A ginger ale, always. And I’m not one to pass up a snack plate with mixed fruit, cheese, and crackers.

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To see Tori’s adventures, you can subscribe to Window Seat and follow her Instagram.

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Thanks for reading!

xx,

Bella

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