Nomad Handbook – Tips for Travel Hackers – Part 3 – Strategy

In the previous segments, we talked about how to plan for your trip and tips to keep you sane while on the road. This section deals more with travel strategy, setting your own expectations and maximizing your quality of life if you’re a seasoned points and miles hacker.

Slow Down and Get Out of the Hotel

In the age of limited vacation time, you’ll be tempted to fit in as much as possible. You can do 4 cities in 8 days right? Sadly, you do this enough and you start to realize that museums, tall buildings, churches/temples and castles/palaces all start to blur together, look the same and make a significant dent in your wallet. Why take the same pictures that everyone else is taking? Navigating the massive crowds will start getting old and you’ll begin to forget if that painting was in the Lourve, Prado or Pergamon or if that’s a view of Dubai, Taipei or Chicago from 1,000 feet up.

Gyeongbok-gung (one of the four very well preserved palaces in downtown Seoul) is certainly worth the $3 admission fee, but I couldn’t help compare it to others I’ve seen in Beijing, Suzhou, Kyoto, Tokyo, Osaka and Bangkok. All beautiful, but they start to blur together.

It’s much more gratifying to understand the lifestyle and neighborhoods in each city. Spending a week or more unlocks so much more than most tourists will ever see. From underground bars and nightclubs, to fantastic parklands and beaches to hole in the wall cafes, eateries and restaurants that might get discovered in a year and awarded a Michelin star in three.

The waiter is photobombing us, but we’re a few drinks in and a pretty friendly bunch!

Case in point: I came to Seoul (where I’m writing this now) without much of an agenda other than to better understand Korean culture, sit in coffee shops and work and perhaps watch a baseball game and tour the DMZ. I stayed in Hongdae in an apartment to get a better sense of how people live. Since it was raining after dinner at a market near Jongno-5ga, I ducked into a small local bar/restaurant to grab a beer and get some work done. I ended up befriending four guys out for drinks after work and we stayed until closing around midnight.

And this is me as an anime character, not bad right!?

I don’t speak Korean and they didn’t speak English, but we made it work via phones and gestures and there was a lot of toasting, sake chugging, fish jerky and discussion of Korean traditions, pop culture (PSY is just an idol, Lady Gaga is an artist) and how Koreans view the Japanese (um… not great) and Chinese (“OK”). I even got rendered into an anime character! They then walked me to a police station so I could get home (I showed the cops that I had mobile data on my phone and that I was perfectly capable of grabbing a cab back – we both found the hospitality amusing).

There is a blurry line between visiting and living. If you have the ability to take time off between jobs, or even take a sabbatical, consider going to one or two places instead of 20. Sprint vacations can be exhilarating, but they become much more expensive and exhausting.

My plan after about a year on the road is to go someplace central in a region and make it a “home base” of sorts. From there, cost of living starts to get considerably cheaper on a daily basis, from monthly apartment rentals, to grocery store shopping to knowing the best places in a neighborhood for good cost/quality food and drink. Especially with points/miles and travel know how, you can always take a weekend getaway to Uruguay or Brunei, which may be hard to justify a separate trip for. Avios and discount carriers come in handy, as you’ll just need a 3-day backpack for the trip. Locals that are now your friends will also be more knowledgeable about what’s a good and bad place to go/stay and having those recommendations are priceless when you go to an “off the beaten path” destination.

Stay in a hotel/burn points the first or last night

While I’m a huge advocate of staying with locals and am more likely to burn my points on international business or first class, I do have a healthy stash of hotel points/nights. These come in handy in two ways.

1) Hotels are great for jet lag recovery or when you need to be near the airport for an early flight. Many are the trip reports where it’s clear the reviewer rarely left the hotel, either due to jet lag, fear of the culture they’re in or only having interest in the top “landmarks” in a city.
This can get infuriating if you travel enough, and it pains me to burn a ton of points on a week-long stay at a hotel, especially if I’m by myself. Westins, by design (and confirmed by SPG reps), are meant to deliver the same experience in Columbus, OH as they do in Colombia or Colombo. You’ll get that white tea aloe scent everywhere, but they are great for having a good quality bed, wake up calls and a functional gym. They are also great if you are starting to feel under the weather from all the things you’ve been eating and burned out from all the people you’ve been socializing with. The best use of hotels, particularly luxury hotels, is recovery, productivity and personal health. I started this article from a beautiful lounge in the middle of Seoul, coming off a brutal 8 hour time change, a very large breakfast a thorough 2 hour workout and a soak in an excellent jjimjilbang. Treat it like a spa day.

Having a driving range in the hotel was pretty cool and a nice way to relax and recover from jetlag.

I’m all for free breakfast, but I’m not going to wax poetic about this hotel’s buffet vs. that. Really? A salt bar? Really? Now I know what luxury is!

2) Luxury hotels are also great if you can share the perks. I took a group of friends to Thailand last year and we availed ourselves of suites and villas at St.Regis’s, Conrad’s and Le Meridien’s. For free. Breakfast and Wi-Fi included. I took another group to Peru and having a large space for the group, awesome pool and free cocktails every night just makes the experience that much more fun and unforgettable. Booking a recovery hotel after a festival like EDC is that much better when you have a suite, full breakfast every day and the events manager takes you out in WeHo. You also feel like a G. I really like to help friends that have limited vacation time and funds make the most of it, since much of it is wasted on a guy that’s spent well over a year of his life in hotels. They really start to look the same after a while.

Excellently designed suite, but would prefer to have done the wine tour with friends.

Hosting friends in a penthouse suite for a week at Le Meridien Bangkok is probably a better use of points. Oh wait! They look the same!

A side note: Keep in mind how much things like dinner, breakfast, gym access and laundry might be worth to you. Staying at a hotel, airbnb or hostel can sometimes obviate the need and cost of those common activities.

Keep your expectations in check

Yes, you’re finally redeeming for your first international First Class flight! But it’s on a US carrier, which means a unionized flight attendant that’s a year from retirement, food that is managed, if not chosen by someone who’s idea of a good meal out it TGI Fridays and a First Class lounge with “sushi” that may or may not be sweating and broken chairs.

Even the big leagues sometimes get things wrong. ANA has forgotten to stock amenity kits. Thai forgets to load pajamas. Heaven forbid if the LH logo isn’t facing you on your champagne glass during the caviar service or the SQ IFE goes on the fritz.

Sometimes the Inflight Entertainment doesn’t work. Even on Singapore.

The truth is that words like luxury, deluxe, upgrade(d) and premium are used EXTREMELY loosely, particularly in the travel industry. A true mark of someone with taste and class is to recognize that when things go wrong, it’s not the end of the world. It’s not like you’re paying full price for this stuff anyway. How much shorter would flyertalk be if people’s expectations were kept in check?

Even in the case of the upgrade roulette you experience at some hotel chains and airlines, it’s worth putting things into perspective. You are probably booking the hotel for a good, quiet place to sleep. That’s the value. If you’re entertaining a group or it’s a special occasion, reach out before your trip (perhaps not every trip), but don’t whine if the reservation that you booked hours before isn’t getting you into the honeymoon suite.

Even at the hotel I’m stayed at this week (where I have top tier status), I didn’t get an upgrade. I asked whether suites were available at check-in and knew they were being sold on the website, but I probably got the most tactful (and honest) response I’ve ever received. “There is one suite left, but we’ve pre-blocked it for another platinum guest that booked a revenue night” — Totally fair if you’re running a business and I’m not going to sulk about it. I’m still certain I got my 10,000 points worth, particularly since I think it’s the best Starwood hotel out of the 100 or so properties I’ve stayed at in the chain.

The point is to set the bar low and be pleasantly surprised than always have your hopes dashed.

Learn how to complain with questions

If you are actively involved in this hobby, you’ve probably picked up status at N different airlines or hotel chains. And it’s probably at some point been completely ignored, perhaps because of rude or untrained agents, an IT glitch, high demand or just bad luck. Or the status doesn’t actually get you anything beyond your class of service. They can’t upgrade you to the cockpit and I certainly hope they prioritize people paying full price for that suite or premium cabin seat.

Have a problem? Take it up with Judy. She also doesn’t care :)

In those situations, it’s extremely important to keep cool, talk only in factual observations and make sure you understand the problem the way they do.

“So it seems like the problem is that I’ve made a reservation on your website for tonight, but you’ve sold every room/seat and every other guest has already checked in/boarded the plane, is that right?”

Then probe a bit, adding a collaborative tone: “Ok, so what should WE do to fix this?”

And adding industry knowledge if you have it “Are there any pre-blocked or day rooms that haven’t checked in or a hospitality suite? It IS past midnight” Or “There’s a flight on XX, your partner, that leaves just an hour later, which would still allow me to make my connection, can you call the alliance liaison/round-the-world desk? Here’s their number.”

Then sprinkle in a bit of disappointment along with a solution that makes your whole.

“Wow, this has been pretty inconvenient, any chance you can reimburse me (one night’s stay worth) of points for the trouble, given how long it’s taken to sort out?” “Gee, as a Platinum customer, I fly with you guys a lot and aren’t usually put in these situations. Any chance you can book me into (premium cabin fare class – be reasonable) or debit my account a few thousand miles for the inconvenience?”

In the worst situations, particularly if the staff is surly, it might be worth considering taking your lumps and writing in after the fact. Airlines and hotels aren’t the best at customer service, but a concise, well-reasoned, unemotional letter (remember to speak only in facts) is likely to get you a better response than screaming at a gate or front desk agent.

Though I recommend pragmatic kindness and proactive charm over histrionics, it is worth mentioning that some companies train their staff to offer compensation based on the perceived magnitude of that slight from the guest’s perspective. “My closet light wasn’t working and I AM OUTRAGED” might net you 20,000 points. Go figure.

But you probably don’t want to be THAT type of person, right?

More to come, but post in the comments if you have more tips or just want to make fun of my anime likeness!