How to set yourself up to meet all your travel goals

This could be you.
This could be you.
Image: Reuters/Oswaldo Rivas
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After the frenetic pace of the holiday season, getting back to the routine of January can feel like a blessing. But that feeling won’t last forever, and by early spring many of us are yearning for vacation again.

If you want to avoid the panicked-travel-booking trap in February (“anything that’s cheap in six weeks”), or you’re determined to make this the year that you finally visit that place you’ve always wanted to see, a little pre-planning right now can go a long way.

Indeed, the outset of any year is a perfect time to get your travel house in order, even if you’re still months away from booking a trip. Best of all, it sets you up for desk-bound travel daydreaming so that when you come across a bargain business-class fare to Singapore, or a dirt-cheap round-trip to Aruba, you’re prepared to actually grab the opportunity.

Here’s how to do it:

Prioritize your paid time off

For some people—freelancers and remote workers among them—this is less of a problem. But if you’re one of the many people with limited days off work per year, start by writing down what you will absolutely have to take time off for, such as weddings, holidays, family reunions and the like. After that, add in a few spare days for unexpected things that crop up throughout the year. Then, see what’s left.

If you have a significant chunk of time left over, you might set that aside for a bucket-list trip to a far-off destination. Or you may choose to break it up into several smaller trips over the course of the year. Or you may choose to tack on days (and perhaps add to the itineraries of) the trips you are obliged to take throughout the year, including business trips.

If you’re a freelancer or a remote worker who can set up shop away from your home base, look at your calendar and think about when is the best block of time to be on the road—keeping in mind the weather you want to avoid, and working around any immovable commitments at home.

The point is to know what you have to work with, so you can start planning when in the year you’ll travel. Mark your calendar, tell your boss or work associates, and start putting your travel-booking skills to work.

Set flight price alerts

There’s no hard-and-fast rule about how far in advance of a trip you should book flights to score a good deal (it varies by location, but in general and with the exception of freak last-minute deals, once you get less than two months to six weeks out, prices start going up). But, if you’ve followed the step above, then you have a general idea of when you might go but aren’t wedded to certain dates. Now you have the two most powerful tools on your side: lead time and flexibility.

If you have a dream destination in mind, set price alerts on sites such as Kayak, Airfarewatchdog, Google Flights, and Skyscanner, so you can get a sense of the price fluctuation over a few weeks. In addition to this, you can also set yourself a weekly calendar reminder to plug your rough dates into a flight search engine. Give it a month or so; if you notice a big drop from week to week, you can feel pretty confident it’s a good time to book.

It can also be helpful to subscribe to the email newsletters of airlines you regularly fly on, or ones that fly a lot of routes out of your city, as well as flight deal websites (though prepare for plenty of spam too, so you might want to set up an email folder that accumulates it all). That way, you can be alerted to sales and price drops, which often sell out fast.

The point is: If you know far ahead of time—and haven’t yet committed to departing on Thursday when Tuesday is actually far cheaper—you’ll have a better chance of finding a cheap flight.

Start gathering points and miles

Even if you’re not an obsessive credit card magician or airline miles/points freak, you can still use your everyday spending to help you travel more. As Emily McNutt of the The Points Guy told Quartzy last year, for laypeople or beginners, it’s useful to set a yearly goal when it comes to the points and miles game.

Apply for a card that suits the spending you already do, meet the minimum spend to earn a sign-up bonus, and then use that same card for everyday purchases throughout the year. In six or nine month’s time, you could find yourself with enough points for a free flight somewhere. The point is to make a (financially responsible) game plan and chip away at it with every grocery bill, round of drinks, and bus fare. It adds up.

Hotels have deals too

Join the email mailing lists of all the boutique hotels or chains that fit your aesthetic, as well as curated booking sites like HotelTonight and Mr and Mrs Smith. That way, when there are sales (often in slow months like January) you can be there to take first pick. And know that there is no shame—at least not to fellow hotel geeks—in planning an entire trip around the property you want to stay in, rather than the destination.