Since the late 1990s, I’ve traveled pretty extensively almost every year. Multiple round-the-world trips in a single year, hundreds of flights per year, new countries and cities, and month-long trips where I don’t know in advance which cities I’ll be visiting. I’ll share some tips I’ve discovered over the years. None of this is “secret”, but it’s useful information for people who travel like me (value-sensitive more than price sensitive, a mix of work/expensed and personal travel, often flexible on specific dates and routings, often flexible on locations or trip-or-not, and willing to put in a lot of planning and tie up $10-20k to get better/cheaper flights throughout the year.)
Elite status matters a lot
For me, I get more value from elite status with hotels and airlines than almost anything else. I’ve been a Starwood Preferred Guest Platinum for most of my adult life, and now it’s Marriott (Ambassador). I also have IHG Diamond/Spire/Ambassador, Hilton Diamond, and for airlines, Delta Diamond (Skyteam Elite Plus), Alaska MVPG75K (Oneworld Emerald), and Turkish Airlines Elite Plus (Star Alliance Gold), along with Caesars Rewards Diamond, National Car Rental Executive Elite, and some other random programs. These get me upgrades, and most importantly, priority handling during irregular operations or disruptions. Elite status with airlines also gets me up to 3x70 pound checked bags. With hotels, 4pm checkouts (and with Marriott, “Your24” so I can check in at 10pm and leave at 10pm the next day). Free breakfast, hotel lounge, etc. are also great, and sometimes take the place of other meals for an entire day (Asian hotel breakfast buffets are amazing).
Make your work asynchronous
I have multiple business interests/jobs/etc, and the only way that works with travel is to make most interactions asynchronous rather than bound to specific weekly times. I probably have 10 hours total of scheduled meetings per week (largely on US time zones), and I’ve definitely had to wake up at 2am for those when in Japan, but usually it’s fine. Usually I can just get my work done at any time and check it in or push. I don’t know how one could travel very much with a 9-5 in-office job. (I also actively try to avoid having direct reports in any job, as that tends to turn into scheduled meetings…)
Points/miles are nice, but not as essential
I collect lots of points on credit cards, airlines, and hotels, but don’t usually redeem them unless it’s a good deal. I google search “value of X points” before redeeming (they tend to devalue over time…). Generally, they are about $0.005-$0.03 per point/mile depending on program. There are times when redemption is an excellent outright value (fixed point cost redemptions at hotels during conferences or other events), and other times when it’s merely ok (especially booking rooms for friends or colleagues, allowing me to still earn points on my own stay). One time when points are often a particularly good value is if travel might get cancelled, as point-redemptions often have flexible cancellation policies (returned to your point balance), especially for airlines you don’t fly often and thus wouldn’t want a cash balance on. Careful, as some hotels have 90 day cancellation windows and insane penalties for close cancellations.
Flight search tools are your friend
I used to love ITA Software until Google bought them. They were basically a superpower, letting you search by routing, fare basis, etc. Google turned it into Google Flights, which is a lot more limited and less useful, but does have purchasing links integrated into the results, and is still probably the best search tool for flights. Google Flights can be fairly powerful once you learn how to use it; I tend to exclude non-alliance airlines (Frontier, Spirit, Southwest), enable alternate airport search, and “add a bag” and “add a carryon” to disable showing basic economy fares.
Wash and fold
I tend to travel with 7-10 days of laundry, and I absolutely hate paying hotel prices for laundry (or worse, dry cleaning). A $2-10 pair of socks or underwear might cost $5 to launder at a hotel; a $10-50 shirt can be $15, so it’s easy to pay $50/day for launder one set of clothes. Instead, I either find a pickup/delivery laundry service which charges by the bag or by the kilo (so, $30-50 for a week+ of laundry), or stay one night in a hotel with self-service laundry facilities. Unfortunately these tend to be lower end or extended-stay hotels, but it’s often worth it.
Book speculatively and cancel/change
Post-Covid, especially (and always for elite status holders), airlines have had pretty generous cancellation policies for flights. Often flights get much cheaper 30-90 days out, then get much more expensive 21 or 7 days from flights. Sometimes I know I’ll need to fly to one of two cities on a certain date, so I just book both flights, or sometimes it will be a potential 3-stop vs. 2-stop trip, and I just book all possible combinations, and cancel the flights I won’t take. This credit is frequently returned as airline credit vs. a refund the original purchase instrument, which is inconvenient, but for airlines I fly a lot (Delta, American) it’s not a big deal to maintain a $2-5k credit balance, as it means I’ve been flying on $100-200 tickets vs. $500-1000 tickets. This is more true for domestic than international travel.
Flyertalk has the best information
By far the best source of information about travel is FlyerTalk. I am particularly a fan of Premium Fare Deals where mispriced or just abnormally low priced business and first class tickets are listed, such as the notorious Christmas Cathay Pacific $1000 First Class Vietnam-USA roundtrips, and the AA/BA Casablanca to Miami (via London, Madrid) First Class roundtrips for $600-800 (I bought 6 last year and flew 3).
Flightfox can handle most of this for you
The biggest problem with frequent flyer games is it can become a massive time suck. I’ve actually spent an entire evening booking flights/hotels/etc. for a month long trip, and most of that is getting the last 10% of value — I can find something “good enough”. Flightfox is a corporate travel service which does the “travel hacking” I do myself, and can do it for your entire organization. I use them sometimes for personal travel (although usually I do it myself for “fun”), and it’s my top recommendation for how companies should handle employee travel — you can set some high-level policies like “generally book coach except for long flights or when a meeting happens day of arrival or when it is a small price increase or where the employee is staying in free or heavily discounted hotels”, can take into account your frequent flyer point balances and elite status earning needs, and they’ll do crazy stuff like suggest buying avios and redeeming them immediately for discounted business class airfares, getting you an effectively $800 transatlantic business class flight.
In-flight Internet
I know it seems like nickel and diming, but $5-50 to have Internet (and often pretty fast Internet) on longer flights is well worth it to me. While it’s nice to have an excuse to disconnect, I usually end up paying for Internet.
SeatGuru and other maps to get the right seats
Where you sit on the plane can make a big difference in how comfortable a flight is. Obviously, middle seats suck, but a 2-2-2 seating arrangement might mean picking window+aisle if you’re traveling with another person, vs. picking one of the middle two seats if you’re traveling alone, except on planes where the middle pair of seats are actually closer than the window/aisle pair, and thus might be preferable as a couple. Sites like SeatGuru show maps of nearly every airline’s entire fleet and have reviews of individual notable seats.
Aircraft type matters
Related to seat maps, but also more generally, aircraft vary as much as airlines. Some airlines (Qatar!) have world-class amazing business class (Q Suites) on some aircraft, and a mediocre 20 year old business class product on other aircraft, sold on the same routes for the same price. Also, some aircraft are just generally more pleasant (787, A350, A380) vs. others (narrowbodies generally, A330, 777, 767).
Fuck Basic Economy
I essentially never book Basic Economy fares except by accident, and when I do (rarely) I get pretty angry about it. These fares don’t get upgraded, lack most benefits of status, and generally suck in every way possible, for only a relatively small discount from regular economy.
Great luggage helps a lot
I pretty much exclusively use a Vertx Gamut 2.0 as my EDC backpack and carryon, a Rimowa 35L carryon suitcase, and Pelican Air 1615 and Pelican Air 1626 cases as checked luggage (and sometimes Pelican 1700-series rifle cases). The Pelican cases aren’t as rugged as “regular” Pelican cases but are much lighter (50%), are relatively difficult for airlines to destroy, and with the addition of padlocks, are perfectly acceptable to transport firearms.
Food delivery service beats room service
I almost never order room service at hotels. It’s overpriced, often low quality, and post-Covid has become limited hours and even worse price/quality value in many hotels (especially in the US). It’s nice to get the tray with silverware, glasses, etc., but really not worth $40 for a mediocre burger. Instead, I order DoorDash, UberEats, or other delivery service to the hotel. Far better value. Biggest complaint is they often don’t include utensils even when requested, so I tend to keep a couple sets (and chopsticks) in my backpack.
Certain cities/routes are much cheaper than others
There are some amazing arbitrage opportunities. As of now (and for several years), roundtrip flights originating in Europe and going to the US are far cheaper than originating in US and going to Europe. Point redemptions are usually symmetric and with most programs a one-way is half the price of a round-trip, so they’re excellent for positioning flights and other things like that. Certain cities in Europe (ARN, DUB, WAW, MAD) are especially cheap, so getting to one of them first can be well worth it. From the US, flights ex-NYC are often among the cheapest international, so I tend to fly to NYC and spend a few days there before booking a separate ticket elsewhere.
Corporate discounts can be huge
Corporate codes for hotels, car rentals, etc. can be great. Sometimes, conferences also negotiate hotel room blocks (and sometimes airfare discounts). Some corporate codes are restricted to employees of a company, some can be used by contractors and partners, and some are for professional associations which often have inexpensive memberships (notoriously the American Bar Association).
High-end credit cards are often great values
Ironically, the credit cards with the highest annual fees often include benefits which, if used, reduce the effective cost of the credit card to $0 or less. For instance, American Express Personal Platinum is $695/yr annual fee but includes $200 on FHR bookings, $240/yr for Audible, free Walmart+, Free TSA Pre, $200 in airline fee credit (can be used for lounge memberships), and $200 in Uber/UberEats credit, free Clear, $300 off Equinox, $100 at Saks Fifth Avenue, and $300/yr for Equinox, plus Priority Pass and Amex Centurion Lounge access, plus some other random discounts, plus 5 points per dollar spent on airfare booked directly with airlines. Amex Delta SkyMiles Reserve is $550/yr but includes Delta Sky Club access which otherwise costs $695/yr. Other high-end credit cards like Chase Sapphire Reserve have similar benefits. I probably have $3000/yr in annual fees of credit cards and get about $6-10k/yr of value from them.
(If you want, please use my referral code for AmEx Platinum for extra points or my Marriott Brilliant card or my AmEx Delta Skymiles ReserveTravel routers make life easier
A travel router lets you connect all of your devices to the same wifi network (and potentially wired ethernet) on the secure side, and then one connection from the travel router to the hotel’s wifi network or wired network. This lets you do connection sharing (useful if the hotel charges per device), but even more usefully, means you don’t need to use the stupid captive portal authentication for each and every device — just one. For a lot of devices, captive portals don’t even work very well (web browsing on IoT stuff you might want to use), and for others it’s just inconvenient, so this can be a big improvement. Additionally you can then have higher speed sharing among your devices, plus a single VPN connection on the travel router to cover all of your devices.
Carplay makes rental cars acceptable
I like nice cars, and have status with a few corporate chains which let me pick the best car available (I’ve had Mercedes C55 AMG, Maserati SUVs, BMW 7-series, etc.). However, my baseline requirement for a car to be decent these days is simple: Apple Carplay. With that, I’ve got an easy to use navigation system which works roughly the same everywhere, access to audiobooks and podcasts, and minimal hassle. Fortunately in 2022+ almost all cars in corporate rental fleets have this.
Nexus, Global Entry, TSA Pre, Clear, APEC BTC
Last thing I want to do before or after a long flight is wait in line — since credit cards often reimburse fees for these programs, they’re nearly free. Nexus is great for frequent travel to Canada, but is a pain to enroll and maintain. Global Entry makes sense for international travel, TSA Pre and Clear are useful for domestic travel, and the APEC BTC is a line-pass into the diplomatic line for Asian travel. All of them are worth it to me.
Lounges ftw
Airports are often crowded, and while there are sometimes good restaurants and bars, they’re often expensive, noisy, and not great places to work. Also, for long connections, it’s nice to have access to a shower or dedicated work area. I like airport lounges, even the mediocre ones, but very much appreciate the better lounges (e.g. Doha Qatar First Class, JAL First Class at Narita, AA Flagship First at Miami…). Sometimes you get access by flying in a premium cabin, other times frequent flyer status, other times through the right credit card, other times Priority Pass, or sometimes paid access.
Podcasts and audiobooks make flights great
I listen to a lot of audiobooks and podcasts, and doing so on planes (or drives) is my favorite. It’s easier than video content, using a laptop, or reading.
Pre-packed bags and duplicate items
I keep some luggage pre-packed for 3 day and 7 day trips, with duplicates of toiletries and other items.
Fly pets for adoption
Puerto Rico, where I live, has a huge surplus cat problem. There are charities which deliver cats for adoption to travelers at the airport, pay the pet fees, and then have travelers take them on their flights, delivering them to adopters at the destination airport (usually met in baggage claim). I’ve done this about 10 times and it’s a great experience. Flying with a carrier and cute kittens leads to interesting airport conversations.
Have a good passport
Obviously this isn’t as easy or voluntary as the other things, but having a passport with extensive visa-free travel is great (EU and a few other places are best; US is pretty good). Also, having at least 6 months validity is needed for some travel. I tend to replace mine every 3-5 years because it’s full of stamps or physically worn out.
Airtags defeat baggage idiocy
Airlines have some baggage tracking features in their apps now, but putting an airtag in each bag makes it easier to figure out where the bag is, when it’s about to be brought out onto the belt, and if it’s stuck in oversized or in a baggage office instead.
VPNs are useful beyond privacy
VPNs (commercial or personally operated or employer provided) can protect you from some security and privacy threats (although less needed with sites generally using HTTPS, and many VPNs are themselves privacy concerns), but they’re useful for other purposes. When I travel to a non-US, non-English speaking country, rarely if ever do I want localized versions of various websites, and a VPN terminating at my home in the US solves that. It also prevents sites from detecting change in location and invalidating my sessions or credentials.
Traveling with luggage is fine
Lots of frequent travelers try to do carry-on only, but I generally don’t. 1) I do longer trips where I want stuff 2) I often bring a firearm, which has to be checked no matter what 3) I get free luggage and use it to shop, since Puerto Rico has limited retail — I’ve filled up pelican cases with alcohol padded in clothing, coolers with food from Trader Joe’s, etc.
GaN chargers (Anker!) and great cables
Anker makes a bunch of really high quality, small, high power output chargers for USB-C and other devices. They’re better than OEM.
Mail forwarding/scanning
If you travel a lot, and for extended periods, depending on physical mail delivery at home/office is bad. When I worked in Iraq, I missed a <$1 credit card bill (I paid something early in a month but they calculated interest as if it were paid at end of period) which caused an accumulation of late fees and eventually cancellation of a card, all because I wasn’t checking mail. Since then, I switched to using a mail receiving/scanning service for my mail, making it accessible from anywhere. There aren’t any great services for this, but the best right now is Anytime Mailbox which has 1800+ locations to choose from.
Backups!
Data backups are obvious, as well as device backups. If you’re traveling and your laptop breaks, it is helpful to have the ability to do some work from a phone, and to replace the laptop with something locally purchased and restored from a backup. (Maybe you can repair it, but in general I’d just buy a new one, repair the old one, and return it to company device pool — and being without a laptop for a week+ might be a bigger cost than just buying a new laptop anyway.) For some people, just getting back to a web browser on a new laptop might be enough for a while. For Apple users, having Apple stores in many cities is great, but there’s a problem internationally finding US keyboards in local stores, etc. For some trips I take two laptops.
Storing luggage at hotels is great
I often take a short trip during a longer trip and leave checked luggage at a hotel; almost always this is free and I’ve never had a problem doing so.
Global roaming cellphone plans save money
Google Fi is pretty good for global roaming service, charging the same price everywhere. Some other carriers have similar plans, although at reduced speed or higher cost. In general I like having a global roaming SIM for data (I don’t really care about voice) and only get a local data or voice SIM if I’m going to be in a place for weeks or need to make a lot of local calls (e.g. working with people locally or at a conference or something).
Founderscard is useful in Las Vegas
Founderscard is a membership program which gets mid-tier frequent flyer benefits on various programs and some other moderate discounts. It’s worth it at the rate I’m grandfathered into, but probably more debatable at current prices. However, there’s one amazing perk: Caesars Resorts Diamond status, which gets me casino rate hotel rooms, line passes, no resort fees, free valet parking, and a $100/yr dining credit. Since I’m in Las Vegas 4+ times/yr, this is well worth it to me. (If you are going to join, please use my referral code.)
Amazon Lockers delivery
I often get items delivered to me while traveling, and since some hotels charge for package receiving (usually if they have an externally-managed business center), delivery to a nearby Amazon Locker is great. Otherwise, shipped to the hotel works.
Select-service hotels often beat 5-star hotels
I like the comfort and luxury of 4 and 5 star hotels (great bedding, luxurious bathrooms, etc.) but rarely use the facilities other than room itself. Select-service or extended stay hotels often are better set up for this, with a nice (although rarely luxurious) room, decent desk, often a kitchenette or full-sized kitchen, and laundry facilities. I wish there were a 4-5 star select service/extended stay hotel brand.
Downloadable media should be downloaded
I have YouTube Premium to download youtube videos, and use Plex, Audible, various mp3/aac players, etc. to download content before trips. It’s a great excuse for 8TB laptop disk and 1TB phone/tablet storage, and external drives.
Yelp, TripAdvisor, Google Reviews, etc. are great
I tend to use online reviews of properties, restaurants, etc. in places around the world. Probably the best restaurant reviews are from eater.com.
Steal toiletries from luxury hotels
I collect mini bottles of high-end toiletries from hotels (especially in Asia). Some chains have pretty good stuff, like Byredo, Hermes, Malin+Goetz, Diptypque, etc. I use these at other hotels during the trip which have more mediocre products, or at home. In 2018-2019 a lot of hotels had started to phase out mini bottles in favor of larger bulk bottles, but Covid halted that, at least for a while.
Devices can be helpful
I’m a fan of tablets (iPad, specifically) e-ink readers (both reMarkable and Amazon Kindle), and the Oculus Quest 2 VR headset, and depending on trip, I might take one or more. Also, an Amazon Echo Dot or similar smart speaker can be really nice — there are privacy concerns with having an Internet-connected microphone in your hotel room, but it can be great for music, audiobooks, etc., and can be unplugged or disabled when doing calls or other privacy-centric things (if I’m alone in my hotel room, there’s no other sensitive audio going on.)
Tip service staff reasonably
Tipping bell staff on arrival, housekeeping, etc. is worthwhile, especially if you’re going to be there for a while.
Deep-discount business class is the sweet spot
I tend to shoot for $2k roundtrip transatlantic and $3k transpacific in business class. That’s a reasonable fare (and no one I work with has a problem with me expensing that), especially since it’s cheaper than walk-up coach fares people often pay. If business is $4-5k, I’ll happily sit in a $1k coach seat even if it’s not my money, although I’d be more likely to try to get a better rate by changing cities or dates or using miles.
Premium economy varies a lot
Premium economy can be a regular economy seat with extra legroom (and sometimes narrower!) to something which would easily be business class of a few years ago; it pays to know the specific airline and aircraft. Sometimes Premium Economy is worth paying for as a stepping stone to business class using an upgrade instrument, especially on airlines like Delta which do Economy to Premium Economy to Delta One as two separate steps.
Great headphones are key
I love headphones, and have about 10 great pairs. Right now my primary headphones are Apple AirPods Max (for music, comfort, and sound attenuation) and AirPods Pro 2 (for audiobooks and conference calls, plus being very portable and discreet — often wearing just one in one ear). I have some higher-end cabled headphones and some in-ear monitors but due to the convenience of Apple headphones with Apple devices, usually just use the Apple stuff.
Not everything gets cleaned in a hotel room
This mostly is an issue with decorative pillows and bed coverings. Anything which isn’t obviously a sheet or pillowcase is probably not washed between guests, so I treat it as hazmat and throw it on the floor (then wash my hands).
Grocery stores > minibars
I hate overpaying for minibar items, and they tend to be pretty horrible anyway. I’ve sometimes consumed an item from a minibar (e.g. coke zero or red bull) and replaced it from nearby shops (which I guess makes me a bad person), but usually I just go to a grocery store on my way to the hotel (or after checking in, but usually before), buy drinks and snacks, and stock my own room with what I actually want. In some places like Las Vegas there is a Whole Foods near my regular hotel so I can actually get pretty good stuff, but even a gas station or convenience store is less of a rip-off than a minibar.
Hotel upgrades can be amazing
I’ve gotten some amazing upgrades from hotels over the years (due to status). Extra good upgrades during low season, for short stays, etc., and in some cities with a $20 or $50 slipped to hotel clerk at check-in. I’ve had the Presidential suite at 4 different hotels on a cheap regular rate, the second best suite at the Hotel President Wilson in Geneva (which normally goes for >$10k/night) for a week for my birthday for less than a normal room price, and routinely just get a nice junior suite or otherwise good room at check-in. Sometimes, hotels offer buy-up to a better room at check-in, but for frequent guests it’s often complimentary and pre-selected.
Expertflyer is next-level intelligence
I use Expertflyer to see exactly how many seats of different buckets exist on flights before booking them, as a way to figure out if upgrades will clear. That alone is worth $99/yr. There are a bunch of other services it offers.
TripIt and Flighty are useful for tracking complex itineraries
When you book lots of flights, consecutive trips, etc., it gets hard to keep track of everything unless it’s in one place. I use TripIt as a central repository, as it will parse forwarded confirmation emails and put them into an easy to digest format (most of the time). Their product has sucked more and more since they were bought by Concur a few years ago, but there’s nothing better I’ve found yet. The app Flighty can import data from TripIt and does better visualizations and flight change notifications, so if you travel enough, it’s worth having both.
Duty free arbitrage
Some airports have some really good deals on alcohol in duty free, although most don’t. Highly-taxed countries like Iceland, Sweden have expensive domestic market prices, so it might be worth buying at duty free to consume (or gift) locally, but it’s not a great deal compared to global prices. Japan Duty Free (at least pre-covid, and at Narita) had some really excellent items which were duty free specific and on the order of $20-40 and which sell for $200-300 in the US domestic market, so stocking up made sense.
ATMs and no-international-fee credit cards
Pretty common now, but using ATMs with no fees, and credit cards without international transaction fees, is way better than using currency exchange shops for physical currency. I do have stacks of leftover foreign currency from a bunch of different countries anyway, and it’s often convenient to arrive with $50-100 worth of local currency, but sitting on $2k of JPY for a year is kind of annoying.
Lifetime status
Some airlines and hotels have lifetime status if you travel enough, or something equivalent to lifetime status where you can pay a small amount to maintain status once you get it. I have Lifetime Titanium with Marriott, which is quite nice, and I suspect I’ll probably outlive that program, but it should be good for a while. This is mostly a benefit for someone who travels a lot for business and then retires, but it can also be useful if you want to maintain multiple parallel programs. Airline lifetime status usually comes from flying 1-4 million miles with the airline or alliance.
(San Juan, PR, ~1 hour)