I’m coming up on 50 flights flown this year. Fifty! I remember when I thought 20 was a lot. So adorable.
You’d think that spending this much time sitting on airplanes and lounging in hotel robes would mean I’ve got the whole travel thing down to an exact science. And to some extent, maybe I do. But the thing about traveling near constantly is that I’m still learning things that make me wonder what the hell I’ve been doing all these years.
There have been more lessons than I can count. I’ve figured out ways to save money and learned where spending it is well worth it. I’ve made plenty of mistakes along the way. And I’ve also developed some pretty strong opinions about what it means to travel well.
So, in honor of my upcoming 50th flight, below are 50 things I think are worth knowing. Take what resonates, ignore what doesn’t and please, for the love of god, don’t forget to look out the airplane window!!!
Things I wish I’d known sooner
Check the seat map until the last possible minute. I am borderline neurotic about refreshing mine, even after checking in. Better seats can open up at the last second as upgrades clear or passengers miss connections or switch flights. And this obsession has served me well: it’s how I scored a coveted bulkhead seat in Singapore Airlines business class a day before leaving.
Don’t sleep on JFK Terminal 4’s little-known security line. This is for my New York friends: I know we all typically beeline straight for the lines on the departures level, but did you know there are other lines downstairs? They’re not always open, but if they are, wait times are usually much shorter.
Consider hotel day-use rooms. Long layovers can be hell on earth, but some hotels have discounted daytime rooms that can provide much-needed respite. Who wouldn’t want an actual bed and shower (and possibly pool access) on a 10+ hour layover?
Cross the ocean first, then handle regional flights. Flying directly into a smaller European or Asian city can be ridiculously expensive. Instead, see what it costs to fly into a major hub like London or Paris, then book a cheap regional flight for the final leg. It’s a little more work, but the savings can be worth it. Crucial caveat! Travel light and leave a 4+ hour buffer between tickets.
Create blackout curtains using a hanger. You know what I hate? When I’m trying to nap but a tiny gap in the hotel curtains means the sun is blasting directly into my eyes. Solve the problem with a skirt/pants hanger from the hotel closet. Just use the metal clips to clamp the two curtain panels together in the middle. Easy!
Spend money to save time and energy. You might think booking a hotel outside the city center to save some money is worth it, but have you factored in the additional cost of transit back and forth? Same goes for pre-booked ground transfers, when you’re coming off of a grueling long-haul or red-eye, and your energy is at its lowest.
Turn one vacation into two. A lot of people don’t know this, but some airlines (Etihad, Turkish, Copa, and more) offer free stopovers, aka will let you spend a few days in one of their hub cities on your way to your final destination. My pick: spend up to 7 days in Reykjavík on your way between North America/Europe, courtesy of Icelandair, at no additional cost!
Travel with a no-foreign-transaction-fee credit card. Those little fees add up real quick, and frankly, I’d rather spend that money on literally anything else. Depending on your card, you might also get some nice purchase protections.
Never get jetlagged again. If you’ve been here for a while you know of my great love for the app Timeshifter, which I’ve used for years now. It creates a personalized schedule to help your body adjust to a new time zone before you arrive. Your first use is free!
Look up your hotel on Google Street View before booking. Hotel photos are always beautiful, so they rarely show a full picture. Street View will show you the real like: is any noisy construction happening nearby? Is the hotel actually in a weird district that’s not very walkable? Do certain floors look directly into an office building next door? And the like.
At the airport and in the air
Where you sit matters more than you think. Sitting near the wings can mean a smoother ride (thank you, center of gravity), while choosing the right side of the plane can offer spectacular views. Then there are aircraft-specific quirks: sometimes a window seat might not have a window (immediately jail) or limited recline. I like using AeroLOPA to see details like these that an airline might not always disclose.
Book the earliest flight when possible. Early morning flights are usually more on-time because they’re less susceptible to delays that tend to pile up throughout the day. Plus, you’ll have more chances to get rebooked and still arrive the same day if you get canceled or significantly delayed.
Brace yourself for busted IFE or Wi-Fi outages. Never assume you’ll have a fully functioning seatback screen or Wi-Fi for your whole flight. Always come prepared with some movies and shows downloaded as backup, and make sure any documents you might need to work on are available offline. Nothing’s worse than opening your laptop midflight and realizing you can’t access what you need!
I am begging you: look. out. the. window. Especially during takeoff. We’ve somehow normalized flying through the clouds, and people can’t even be bothered to look outside. It’s crazy and wonderful and frankly I’m sick of everyone acting like it isn’t!!!
Research your aircraft. Rookie mistake: assuming every plane in an airline’s fleet offers the same experience. Sometimes you might get a gorgeous new cabin with massive screens, orrrrrr a seat that looks like it hasn’t been updated since the early aughts. On the exact same route! I always check the aircraft and cabin configuration before booking because why on earth wouldn’t I want the better plane given the choice?
Premium economy should be in your consideration set. Take United’s new A321XLR. I liken its Premium Plus seats to domestic first. They’re wide with privacy wings, ample armrest space, and a deeper recline. I’ve experienced it myself, so I can tell you the difference is actually something you can feel (and IMO: worth paying for).
Know your passenger rights. Don’t count on airlines to hand over what you’re owed in a crisis—they’re counting on you not knowing any better! EU rules can mean hundreds in compensation for delays and cancellations, while US regulations guarantee a full refund if they cancel your flight. Do a bit of research before a big trip so you have a handle on your rights before you step up to the desk.
Understand when an upgrade is actually worth it. True story: I once upgraded from premium economy to business class on an Air France flight from Paris to New York for just $300. A lie-flat bed for an eight-hour journey? Yeah, that’s a big no-brainer. Before you decide, consider the duration and what you’re actually getting for the extra cost.
Lounges are not created equal. We’ve become so fixated on just getting into the lounge that we’ve stopped asking whether it’s actually worth visiting. Some are: they have proper restaurants and showers and coffee bars, but others are packed to the gills with only mediocre buffet food and not enough outlets. I’d rather spend an hour at a good airport restaurant (looking at you LGA Terminal C) than two in a bad lounge.
Prioritize Starlink-equipped flights. If you haven’t experienced Starlink in the air yet, wowww you’re in for such a treat. It’s fast enough to stream video seamlessly, upload and download impressively fast—it makes regular plane Wi-Fi feel like dial-up. While carriers are aggressively retrofitting their planes, fleet rollouts are still very much underway. Check your airline's app or site before you fly to see if you lucked out.
Making the most of your destination
Compare cash + award prices using Google Flights. One of my favorite tech developments in the travel space this year has been the Seats.aero browser extension, which lets you see award options alongside cash fares in Google Flights. It’s so user-friendly and I genuinely cannot believe how much easier it’s made my life. (We love efficiency around here.)
Set on booking with points? Use Seats.aero. It’s the easiest way to search award availability across multiple loyalty programs, and after paying $10/month for all the advanced features for years, I can attest to its value. My most recent win: round-trip New York to Columbus flights for just 6.5K Flying Blue miles through Air France (compared to 30K+ SkyMiles for the exact same flight!).
For public transit in cities, the Citymapper app is your best friend. It’s such a godsend in cities with public transport. I love that it’ll tell you which train to take, map out the best entrance to use, and even tell you the best spot to stand on the platform. It’s really useful in places like NYC, London, and Paris.
Head to a grocery store as a first stop. Wandering through a local grocery store is a fascinating slice of local life and a great first activity in a new place. Pick up something you’ve never seen before that looks good, then find a scenic spot for a little picnic. Plus, I think anything edible makes for the best souvenirs and gifts for friends and family.
Figure out the apps locals actually use. In Japan, Yelp is useless. Locals use Tabelog for food while in South Korea, Google Maps has limited walking directions, so you’ll want Naver Map instead. A little research before your trip can save you a ton of frustration.
Optimize for spontaneity. I love wandering aimlessly. What I do not love, however, is realizing somewhere I want to go to was just two blocks away from someplace I’ve already been this week. Tools like Wanderlog can help you geographically optimize your important itinerary items without scheduling down to the minute. I’m a big fan of using it in overwhelming places like Tokyo or Paris where it feels like my “must” lists are endless.
Unique vantage points = best sightseeing. In Amsterdam, seeing the city from its canals is simply a must. Elsewhere, it might be by bike or even a scenic tram.
Book a food tour early in your trip. It’s one of my favorite things to do in a new city, especially on the first few days. You can try local specialties (fun!), learn about the culture through its food (informative!), and get acquainted with different areas you might want to revisit later (useful!). Plus, a good tour can be surprisingly good value when you consider how much you get to eat.
Compare eSIMs with your carrier’s international plan. I’ve used eSIMs like Holafly in Spain and Ubigi in Japan before, but the T-Mobile plan I got earlier this year includes international roaming (so clutch). Before paying for a separate eSIM, check what your existing plan covers—you might not need one!
Befriend your hotel concierge. Be honest: when was the last time you spoke to one? If you can’t recall, time to fix that. A good one can help you with everything from securing restaurant reservations that are otherwise impossible to get to giving you helpful local recs to pre-booking transport (sometimes even complimentary!).
What I’ve learned about packing
Pack for your arrival order. If you’re arriving to your hotel early and won’t get in for most of the day, keep whatever you’ll need near the top of your bag. Maybe it’s a swimsuit and flip-flops so you can go straight to the spa or pool. Or an outfit to change into for exploring. The same goes for pajamas and toiletries after a late arrival.
Ditch the mini bottles for long trips. Here’s something I’ve changed my mind on this year. For products I go through quickly (shampoo/conditioner, body lotion), those little bottles you can decant into barely last me a few days. If I’m checking a bag for a longer trip, I’d rather just bring the full-size product and call it a day.
Leave home with a backup bag. I almost always return with more than I left with (sue me: I’m just a girl), and a foldable tote or bag is the best remedy for this. It takes up little space and gives you extra capacity for shopping and souvenirs.
Keep a grab-and-go toiletry kit. The best thing I’ve done for myself is having a dedicated set of toiletries always packed and ready to go. When I get home, I simply replenish what I’ve used. One less thing to think about before the next trip!
Watch out for split-ticket baggage traps. If you’re booking separate tickets, don’t assume the luggage included on your first flight will be included on the next. You might fly across the Atlantic with two checked bags included, only to discover your budget airline connection charges extra for both. Always check the baggage rules before booking, especially if combining airlines.
Ask the hotel before you pack bulky items. From clothing steamers and yoga mats to premium hair tools, most front desks carry a lineup of bulky essentials you can borrow for free.
Send your bags ahead of you. Luggage-forwarding services can transport your suitcase for you, so you don’t have to worry about dragging it through train stations or between hotels. Some destinations even offer services that ship luggage directly from the airport to your hotel. (Japan is a great place to do this.) Genius, no!?
Find your travel uniform. I’ve reached the point where I wear some variation of the same outfit on almost every trip. I know what’s comfortable and what I feel good in. And the individual pieces are versatile enough to work with the rest of what I pack. It’s a little boring, maybe. But packing takes me a fraction of the time it used to.
Rolling is not the way. As a former overpacker who’s still determined to use every square inch, I can tell you from experience that laying garments flat and layering them can actually make better use of space.
Keep in-flight essentials within reach. I use my TUMI split travel kit to keep all the little things I might need in the air (like lip balm, hand sanitizer, headphones, meds, and the like) all in one place. It’s small enough to slip into the seatback pocket, allowing me to stow my larger tote overhead (only if there’s space; I’m not a monster) instead of constantly rummaging through it/sacrificing precious legroom.
My travel hot takes
Carry-on-only travel is not a personality trait. And I say this as someone who travels almost exclusively with a carry-on these days! It’s practical for my frequent two/three-day trips, but being able to bring as many outfit options and full-size toiletries as you please is a luxury that far outweighs having to wait an extra 20 minutes at the baggage claim.
Eat the McDonald’s abroad. Nobody wants to admit that sometimes you just want a meal that feels familiar and maybe reminds you of home. (Nothing hits like the first cheeseburger after a week in Europe.) But my bigger argument here is that the McDonald’s regional menus are actually really good. Peri-peri shrimp in Japan? Fire.
Ignore the “best-of” hotel lists. A hotel can win every possible award and still be totally ill-suited to how you actually like to spend your vacation. Prioritize the factors that actually matter to you over arbitrary scores.
Revisit places you’ve already been. I used to think this was a travel sin—why go somewhere again when you could go somewhere new? But I think there’s a huge case for traveling “deep” versus “wide,” aka becoming intimately familiar with a place instead of trying to check off as many as possible. And also giving places you maybe didn’t jive with immediately a second chance.
Traveling isn’t the end-all, be-all. As much as I love traveling, I don’t believe vacation should be the only time you feel like you’re living. Travel should add to your life, not be an escape from it.
Try not to prioritize documentation all the time. I’ve found that the times I’ve simply allowed myself to exist in a moment, rather than trying to perfectly capture it, are my favorite travel memories. And it should go without saying but: don’t plan things just because of how good you might think they’ll look in photos.
Go ahead, recline your seat. That’s your right! Just be considerate of the person behind you, especially during meal service.
Stay disconnected from the airplane Wi-Fi. Planes used to be the only place we could be untethered to the burden of constant contact and nonstop notifications. It still can be. Give that gift to yourself.
Stop trying to find the hidden gems. Traveling doesn’t need to become some weird gatekeeping contest. A restaurant doesn’t become less delicious because it’s popular in the same way a locale doesn’t become less special because you’ve seen it all over Instagram. Some things are famous for good reason.
You don’t need to romanticize uncomfortable travel. This is a broader life lesson I am currently contending with that bears repeating in the context of travel: there is no prize for suffering.
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Window Seat covers the business, culture, and experience of traveling well, 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.
Love this list, especially with my upcoming travels to NYC! 😉
Great list! I found myself agreeing with nearly all - especially visiting the grocery store for edible souvenirs and to fight against the urge to find “hidden gems” and “the 10 best X in Y city” lists on TikTok. Tumi link broken btw, but I found the correct item.