Motherhood changes everything, and travel is no different. The way I think about trip planning—when we’ll go, where we go, what we’ll do—starts with the right hotel and then we build from there. Before having a kid, if I hung out in the hotel more than a few hours I felt like I was doing something wrong. My goal was to go, go, go 100% of the time and then I could rest after my vacation (ha, ha, ha) which I think came from a combination of growing up going to Disney as our vacation (not relaxing) and feeling major FOMO about everywhere in the world and I just HAD to see and do it all.
Now, of course, most of our travel time is spent in one place, and at a hotel. I’m also choosing destinations that allow for long, unspooled hours of relaxation in a way I never thought I would. I would not describe myself as a “beach person” even as a kid and here I am, planning another beach vacation for this spring because my little beach baby could spend all day there.
Basically, I feel like I’m learning how to travel plan all over again. That’s why I asked Tori Simokov, from Window Seat, about her travel tips for this week’s newsletter. I know I’m here to talk all about traveling with toddlers, but I think it’s important to zoom out and think through the big picture about what travel means for you, and Tori does that better than anyone I’ve seen recently.
Tori Simokov on Travel with Toddlers
If you haven’t read Window Seat yet, it’s all the stuff I used to love about growing up reading Conde Nast Traveler—interesting travelogues from well-traveled people, detailed travel guides for destinations I’m excited about, and cool deep-dives into the history of travel, like this piece on aviation design I’m still thinking about weeks later.
Tori hanging out in Tokyo, Japan.
Travel is about pushing the boundaries of what you know and think you can do. With a toddler, just getting out the door can feel that way. But I love how Tori describes these bigger “V1” moments in our lives—where you just have to take the leap anyway.
As an airplane is speeding down the runway for takeoff, it reaches a critical point called the “decision speed”—also known as “V1”—at which point pilots must determine if it is safe to continue. If something goes wrong, they have enough runway left to abort the takeoff safely. But beyond the decision speed—should anything go awry—it’s safer for the pilots to deal with any issues in the air as they climb out. At this point, they have fully committed to takeoff and the pilots trust the airplane to keep climbing into the sky.
“Feel the fear, do it anyway,” is one of the mantras that got me through a very difficult postpartum experience, where buckling the carseat would make me feel jittery panic. I didn’t want to be that kind of mom. I knew I had to just get OUT of the house. Every step forward—to the grocery store, for an overnight away, to our first plane ride—I meant committing to takeoff. And now that I’ve got a little bestie travel toddler, I’m so glad I did.
Here is how Tori approaches her trip planning:
Tell me about your travel style. What does a typical trip look like for you?
“My travel style is pretty Type A: I’m extremely detailed with research prior to a trip so I can map out the things I absolutely must do or see. But I also like to leave white space in my itineraries because I do think that when you wander, that’s when you come across the best hidden gems. (Editor’s note: Yes! I’m also a Type A planner, but I always leave “random exploration” time in there.)
My typical trips are luxury-leaning. I like to splurge on design-forward hotels and try to fly business when I can; I use points, miles, and credit cards to offset the cost.”
One of the things Window Seat is known for is your “Seatmates” interviews. Part of why I do interviews for Travel with Toddlers is because I love the format. Tell me about your favorites.
“I love that! Everyone I interview for the series is fascinating in their own ways. I’ve interviewed what feels like the full spectrum of travelers, from people who work in the travel industry—i.e. travel advisors like Helen and Jordan—to my dear friend Erika who famously hates traveling.
In each issue, the first batch of questions is tailored to the individual and how travel has influenced their world. For example, when I interviewed Margot, she had just launched a travel journal product, so I asked her about how it came to be and what she hoped it would bring to others.
There is something so special about handwritten, tangible, weathered mementos. I’ve held onto travel journals since I was 10 years old, and it has been such a gift to return to them now. [Prompts help you] tune into and record every part of your journey, not just the things you’d typically snap a quick picture of. These include interesting people you met, meals you shared, clothes you wore, conversations you had, lessons you learned…Once the trip is booked, the next step is to actually revel in it!
The rest of the questions I ask are standard across each article so you always get to hear what their air travel rituals are, what must-have items they always travel with, and their go-to airport outfits. I think that’s really fun, too.”
How do you pick your next destination? What factors do you consider?
“The short answer is: Hotels. I’m a bit of a hotel snob, and when I find a hotel I want to visit, that’s usually what gets me most excited to visit a destination.”
Les Rouches Rouges, wow! Kids are allowed age 6+, so sadly, not in my immediate future. But a mom can dream!
I wrote a whole post about this. In it she wrote:
For example: have you ever heard of Saint-Raphaël, the little resort town in the South of France? If someone mentioned it as their next vacation destination, would you have the same knowing reaction as if they’d mentioned Saint-Tropez instead? I’m betting you wouldn’t. But if you knew about the hidden gem of a hotel nestled within its rocky coastline called Les Roches Rouges, you would definitely get it.
When my husband and I started planning our first European vacation together, step one was figuring out where exactly to go. With Les Roches Rouges in mind, I convinced him it should be the French Riviera. It was the first time I’d planned a trip with a hotel as a destination, which has since become a guiding principle in how I plan my travel.
What are your tips for finding a great hotel?
“I loooove spending time in hotels. Great hotels for me have these qualifiers in common: they’re design-forward meaning each space is considered, and they usually have great branding. They offer a sense of intimacy (aka not too big), and they usually either have a nice spa or a great restaurant—preferably both.
It is 20 degrees outside where I am right now and wow would I love to be by this pool in Grand Cayman instead!
I don’t have a preferred brand per se, but I do have a Hyatt credit card so that I can redeem points for Park Hyatt stays across the world. I’ve stayed at a few now and would like to experience as many as I can. My other favorite hotels I’ve stayed at include Palm Heights (Grand Cayman) and Hotel Costes (Paris).”
Where are you headed this year?
For 2025, I’ll be heading to Portugal in the fall to see my friend get married, with a stop in Amsterdam beforehand. If I can swing it with work, I’d also love to get out to the Balearic Islands, revisit Paris or Tokyo, or do a wintery mountain trip in the Dolomites or Swiss Alps.
You’ve talked before about your fear of flying. I also hate flying, but as a mom I can’t really zone out—should I just give up on an eight-hour flight with my toddler??
“I can actually relate to this, as I used to have an all-consuming fear of flying. There are a lot of tips and tricks I’ve honed over the past decade that have converted me from someone who used to white-knuckle it through an hour-long flight to someone who gets just as excited about the plane ride as the trip itself.
One of them is exposure therapy. You just have to do the hard thing again and again, and, like a muscle straining to lift a heavy weight, it’ll get easier over time. Another is information. Learning how airplanes actually stay in the sky gave me a lot of comfort; noises that used to startle me no longer do. And lastly, rituals are very important to me. I always touch the outside of the plane as I board (I view it as a formal relinquishing of control), I always play the same song during the takeoff roll, and I have a playlist I created that keeps me calm in-flight.”
The gear Tori doesn’t leave home without…
Nothing like a good travel uniform! Mine is leggings, a sweatshirt, and a puffy vest because you can’t make me stop dressing like it’s 2012.
- Away Everywhere Tote: I’ve been evangelizing this tote for a couple years now with no plans to stop anytime soon. I looked far and wide for the best travel tote and this is it.
- Rimowa Carry-On Plus: I had a banner year last year, so I got *the* suitcase status symbol as a gift to myself for my hard work and success. Gotta get that cost-per-use!
- Cadence Capsules +Ries Bottles: Firmly on my “out” list for traveling are drugstore travel bottles. Decant any and all toiletries into these chic containers and thank me later.
The best destination to travel is…
“My number one favorite place I’ve been to is Tokyo. I was really nervous leading up to the trip about the language barrier and trying to get around, especially taking the train to Kyoto. I’d also heard horror stories about locals being unkind to tourists. But my experience was amazing; I was welcomed everywhere I went and getting around couldn’t have been easier. Tokyo is so fun; everything feels vibrant and alive. Plus, the food is unbeatable.” 🍣
If you’re staying in one destination, plan your trips hotel-first
Thank you, Tori! I think I’ve resisted the idea of going hotel-first in the past and I love thinking about planning trips that way. The right hotel can make a big difference in how relaxed I feel on a trip. Last year, we did Turks and Caicos which I highly recommend, and we split our time between two properties. Both were billed as family-friendly, but different flavors. (One was a free-for-all, like dropping into a gigantic children’s museum; the other had impeccable service but less family-oriented policies, like dinner service starting at 7 PM.)
I’m looking at a bunch of different trips this year, mostly around upcoming weddings (yay!) and beyond the where do we have points? question, I’m hoping to choose wisely with our hotels as a home base to explore.
Thanks for being here.
It’s so, so easy for me to worry about doing something because it will be “too hard.” Lately I’ve been trending on the vacation side of travel, where I just need to relax. Chatting with Tori was a good reminder of why I think travel is so important as a mom—not just because I like it, but because getting outside your comfort zone is the whole point!
It’s snowy here in Boston which I thought would mean lots of toddler negotiation to get outside and then whining for the 10 minutes we spend out there. (That’s been the norm this whole winter, so…) Instead, our toddler led the charge, running around the yard making snow angels and silly tracks in circles for an hour. We laughed so hard! I LOVE when I get surprised like this. It’s one of my favorite parts of seeing my toddler grow.
Here’s to more of the good kind of surprises in your life,
Kayla
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This post was originally published on Travel with Toddlers. Subscribe for more real-talk travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
