Travel Q&A: Points, Packing, Planning & More

Answering 10 questions about how I travel, write, and keep it all organized

One of my favorite things about writing Window Seat is the back-and-forth. The replies, the DMs, the “wait, how do you actually ___?” that pop up after I publish. So for the first time, I decided to flip the script and let you guys take the lead.

I asked for your questions—big or small, practical or personal—and you delivered. In this first-ever reader Q&A, I’m answering 10 of them, spanning everything from how I find high-value points redemptions, to how I make time to write this newsletter, to which destinations didn’t quite live up to the hype.

Yes, it’s about travel, but it’s also about giving you a clearer picture of the person behind this letter. If you find this helpful (or just fun to read), let me know. I’d love to make it a recurring thing.

Read on to learn:

• A calculator to instantly know if your points are worth it

• The tools I swear by for stress-free trip planning

• The one travel item I always pack that no one talks about

• The shoes that got me through 20,000-step days in Tokyo

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How to assess the value of your points and find routes to optimize for that! —Kez

To understand the value of your points, you can divide the cash price by the points required (and factor in taxes/fees) to get your cents-per-point value. Here’s a calculator you can bookmark to make this super easy.

A 70,000-point flight that would’ve cost $1,400 cash? That’s 2.0¢ per point, a solid redemption. But take my real-world example from my trip to Japan: I transferred 170,000 AmEx points to ANA’s Mileage Club and redeemed them for two business class flights at an outstanding value of 10.6¢ per point! The cash value? A staggering $18,038!

Singapore Business Class, booked on points

To find airline routes to maximize your points, you first have to understand where your points transfer. For example, I transferred AmEx points to ANA, but they could also transfer to AirFrance/KLM, Delta, Emirates, and more. Other kinds of points, like Chase, have different transfer partners. From there, you can look at the award charts of specific airlines (if, like me, you are dead set on flying in a specific cabin at times), or you can use a tool like point.me to help you find the best routes for your points. The more flexible you can be with your plans, the better luck you’ll have playing this game.

How do you plan your days when traveling? I have many recs for spots I've never been and it feels daunting at times to plan/organize/not have FOMO if I miss a few lol —Lindsey

I feel the same way! Essentially, I use one of two tools depending on the kind of trip I’m taking: Notion (for laid-back, beachy trips), and Wanderlog (for city-based, fast-paced trips). I aggregate all the things I want to see/do/eat and organize them using ChatGPT, then use one of the above tools to plan the itineraries.

My Notion itineraries are essentially just lists because on slower-paced trips (like my most recent to Menorca), I prefer not to have every day planned out in advance. Wanderlog, on the other hand, is very intense with its level of detail.

During my trip to Japan, I used it to group together activities/sights that were near each other to maximize what I was able to see and do. In the above screenshot, you can see a couple spots I added to the itinerary (along with my own notes); in between each, Wanderlog automatically adds the transport time between each and picks the transport method (walking, driving) that makes the most sense. It also adds all of the details related to your itinerary items, as shown on the right-hand side of the screenshot, where I’ve expanded the info for Tsukiji Outer Market. It’s this kind of stuff that makes this tool immensely helpful.

What’s the most random thing you have in your travel-day kit? Your favorite? —Stephanie

Random: Thermacare patches! I love bringing a few for my back or stomach because there are just too many opportunities when traveling for aches and pains to arise—cramped airplane seats and 20k+ step days in the wrong shoes can wreak havoc on your back, and you might unexpectedly get your period or eat something funky that calls for some stomach soothing. They take up so little space in any kind of luggage that it’s like, why not at least have them just in case? Even at home, I think they’re a luxury.

As for my favorite, tell me if you guys are sick of hearing me say it yet, but: my Away Everywhere Tote. It’s the perfect travel tote, and I can say that after how many years I spent looking for one. Three years later, I’m still obsessed (and she still looks brand new).

Away Everywhere Tote <3 <3 <3 (and my travel outfit)

Favorite travel outfit? Favorite walking shoes for many miles in Europe? —Stacey

My favorite travel outfit will always be a variation of this formula: comfy pants that read chic + slim fit tee or tank + sweater + low-profile sneaker. For t-shirts, I—no joke—own five of these because they’re so good (and affordable). I don’t like being without one if I have some in the wash or I stain one. I always bring a sweater because, duh, planes are cold. Recently, this wool zip-up has been my go-to, but I also like this pullover. I have yet to find pants I like better for travel than the aptly-named Everywhere Pant, and I have worn these sneakers on every single flight for a year now.

I did my most walking in Tokyo, and my Nike Vomeros were the most comfortable shoe. My travel outfit sneaker has to double as a great walking shoe, so whatever I wear also has to have some cushion. If you don’t want to wear a sneaker, you can’t go wrong with these Rothy’s slingbacks.

Why did you decide to start Window Seat? —Jenn

If you’re new here, you might not know that I used to have a debilitating fear of flying. I’ve written about how I overcame that fear, and why I decided to even try in the first place, but what was special about those exposure flights is that on each one, I’d distract myself with writing. Even though I was just typing disjointed thoughts into my Notes app, I’d journal my feelings on the way there and chronicle the trip’s adventures on the way back. It wasn’t until recently that I realized these notes were really the genesis of Window Seat.

You can probably guess where I would always sit on the plane. :)

How do you set time to write your Substack and how do you decide what to write about?! —Sylvie

The age-old question! I publish twice a week, which is…a lot. My Friday Window Shopping letters have a set format with content that’s more of-the-moment, so I typically write those a day or two before publishing. My Wednesday letters, however, are usually a bit more involved and are either a guide, an essay, or occasionally a Seatmates feature. Those require more planning, but the longest lead time I usually have is a week.

As for what I write about—there are sooo many things I’m interested in: hospitality, aviation, points hacking, travel products, industry news, and more. That’s why I’ve created different content series to cover those themes, and I use the in-between space to explore everything else. This is where my content calendar comes in. I use Notion to plan everything out, and as of writing, I have my content mapped out through December 10th. Once you’ve nailed down a consistent publishing cadence and a few go-to content formats, it really becomes plug-and-play. If anything, I find I don’t have enough time to publish everything I want to write about, which is ultimately why I upped my cadence to twice a week.

What are your go-to travel sources to keep up with it all? Love your writing! —Erin

Outside of the obvious names to read, I like to follow accounts like

SmartFlyer

, Hotels Above Par, and Fora on social media for hotel & destination inspo. Plus, stylish people like

Lucy Williams

,

Olive Cooke

, and

Emma Hoareau

who are always jetsetting to lust-worthy locales.

For news, one of my favorite newsletters is GOOD THINKING.

Chris Danton

is always reporting on really interesting happenings across culture, travel included. Her letter is one I consistently open in my inbox.

Lucerne Views (via Pinterest)

What’s on your destination list for 2026? What’s the most challenging thing been about going on your own? Most surprising? —Nicole

If I could have it my way, in 2026 I’d be going to Copenhagen, Sicily, Lucerne, and Seoul. You know, one for each quarter. That’s the dream!

I’ve been “on my own” (aka a solopreneur) for about two months now, and it has been a whirlwind! The most challenging thing has been structuring my days, for sure. There are just too many things to do: writing this newsletter, client work, creating content, planning travel, and updating my website. It’s hard to find time for it all.

The most surprising thing has been the significant interest my business and Window Seat have received purely through inbound inquiries alone. I love opening my inbox each morning and seeing all of the potential opportunities. It makes me feel extra validated in my decision to go solo.

Places you’ve traveled that you didn’t love/understand the hype and why? —Lindsay

I have two, and I hope they won’t cause a riot.

Firstly: Tulum. It’s fine! I did have a good time when I went. But it’s such a scene, even if you’re not looking for one, and I prefer my beach getaways a bit more low-key. Plus, not being able to access the ocean because of all the seaweed on the beach was a major bummer.

Secondly: Nashville. I think the world is divided into two camps: those who love Nashville and those who don’t. It’s not that I have anything against it: I just don’t understand it. For all the things Nashville is so well-known for, I don’t connect to any of them, so it didn’t feel like there was much there for me.

Top 10 hotels / destinations you’ve been to, and what’s still on your bucket list (and why) —Marta

Answering this in its entirety might be better for a dedicated article, but I can tell you my favorite destinations have been Tokyo, Paris, and Menorca, and my favorite hotel brand is Park Hyatt (you can read my full hotel hall of fame here).

As for my bucket list, it’s as long as the world is wide. I’m increasingly drawn to places that feel like variations on a theme, like Menorca-adjacent destinations with a slower pace and stunning scenery. High on the list: Formentera, Costa Brava, Corsica, Sicily, Lucerne, and Puglia.

As for my city list, Copenhagen and Seoul currently sit at the top. Copenhagen for the design culture, and Seoul as a kind of sequel to Tokyo (similar energy but with its own edge).

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Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.