Lifehacker’s Total Guide To A Perfect Holiday

We go on holiday to relax. Then we proceed to drive ourselves crazy dealing with reservations, airport hassles, jet lag and other annoyances. This year, let’s plan our holidays without all the stress.

Title image remixed from Chris Brindley .

This post is broken into four parts. If you’d like to skip to a certain section of the guide, use the links below:

Part One: Pre-Travel Preparation

The key to an easy holiday is planning as much in advance as is practical. That means putting together your itinerary for the trip, applying for time off work, getting all your reservations in order as soon as possible, and thinking about packing ahead of time. Here are a few tricks to make your preparations easier and your trip cheaper.

Find Great Deals on Flights, Hotels And More

Finding flights and other accommodations cheaply is no different than shopping for anything else: the key is to shop around and find the best price. In terms of flights, we have a detailed guide to scoring cheap flights. By far the most important principle is to plan in advance — cheap fares rarely show up at the last minute. The second-most important is to keep an eye out for sales. The same rules apply when booking accommodation — you’ll get more choice if you plan early.

Keep Your Trip Information Organised with TripIt

After you’ve booked your flight, your hotel, and your rental car, you’ll have a heap of confirmation numbers, reservation dates and other bits of info floating around your email inbox. TripIt is one of our favourite travel apps that organises all that info in one simple place for you. Just sign up, connect it to your Gmail inbox, and it will automatically scan your email for incoming confirmation messages, adding their info to your TripIt log when they come in. Alternatively, you can forward all your confirmations to [email protected], if you’d rather not give the service access to your email.

If you forget what time your flight leaves, you can check the TripIt app on your smartphone, or from the browser on your computer. It will give you all the information you’ll need about your reservation, notify you if anything changes, and even sync with your calendar so you always have your flight info on hand. You’ll never have to search through your inbox for that information again: it’s all just a few taps away on your phone.

Whether you use a TripIt-like service or not, an important tactic is to reread your entire itinerary the day before you leave. If you booked a long way in advance, you may have forgotten key details.

Pack Like a Pro

As travel day inches closer, the last thing you’ll want to do is pack all your luggage ahead of time. The further ahead you begin preparing, the less likely you are to forget something. I’ll usually pull out my suitcase a week or two ahead of time and just start throwing things on top of it as I think of them. That way, they aren’t all packed away, but at least they’re all in one place so I don’t forget them when I zip everything up.

When it comes time to actually pack everything away, the goal is to pack it into as small a suitcase as possible. We’ve shared a lot of great tips on packing, but nothing compares to straight up packing like a flight attendant. That means roll your clothes instead of folding them, and putting in the heaviest clothes first. The suitcase will compress well, without wrinkling everything too much. Put your toiletries bag on the top so you can access it quickly if needed (or if security needs to screen it). Make sure you’ve got travel-sized versions of everything, too — and that they’re all refilled before you leave.

If you have some more formal clothes, like suits, you can pack those like a dry cleaner to keep them wrinkle-free. Lastly, make sure you pack these handy unusual items, and consolidate some of your space with multitasking items. When you’re done, you should have no problem living out of your carry-on.

More Hacks For Perfect Preparation

If you want to do some deeper research into the art of travel preparation, here are a few tips and articles we didn’t mention above:

Part Two: Travel Day

Arguably the most stressful part of a holiday is the day you spend at the airport. Luckily, part one takes care of a lot of that stress: you’re already on top of all the details, and you haven’t forgotten to pack anything. Here are a few things you can do on travel day to make sure everything continues going smoothly.

Breeze Through Security

There are few things more frustrating than airport security, and while you can’t control how slowly the line moves, you can ensure that you don’t contribute to the slowness. We’ve outlined how to speed through the airport to help you get through as fast as possible, and packing lightly helps a lot. The less you have to fiddle with your stuff, the faster you’ll get through security. [clear]

Survive The Long Journey

So you’ve boarded the plane, successfully squeezed your luggage into the overhead bin, and you’ve plopped down in your seat for the long trip ahead. All that’s left to do is survive the boredom. Make sure you’ve packed some gadgets (you can read the magazine during take-off and landing). Once you’re powered up, make sure you make the most of your device’s battery life, whether it’s an iPhone, an Android phone, or a laptop.

Don’t forget to get some sleep, too. If you aren’t so great at sleeping on planes, we have tips to help you out . Photo by viralbus.

Part Three: Your Holiday

If you’ve done everything right so far, you shouldn’t have too much trouble relaxing on your vacation. Here are a few things to remember:

  • Don’t over-plan. Leave some free time in your itinerary each day. That way, you have time to rest if you’re feeling tired, or go see that sight the locals told you about at lunch. You’ll never be able to see everything, so prioritise the most important things and play the rest by ear. If you try too hard to see everything, your vacation will become just as stressful as work.
  • Turn off the tech. You’ve heard this one a million times before, so we won’t preach to you — just remember that it can cause a lot of stress, whether you’re trying to keep up with what’s happening at work or you’re just dealing with morons on the internet. Disconnecting yourself entirely can be just as stressful, though, so find a middle ground that works for you — maybe you stay away from computers, but email and browsing on smartphones are fine, or maybe you’re only allowed to use your phone and tablet for offline activities. Find what works for you and stick to it. You can always set up a vacation responder for the folks that email you while you’re gone — if it’s important, they’ll get back to you.
  • Take a few buffer days. I find my mind is a lot clearer when I don’t rush into my holiday. When I get there, I have a free day to relax and do nothing, or even sometimes catch up on any last minute work (like cleaning out my email inbox) before I turn off the tech and start vacationing. Similarly, give yourself an extra day off work when you come home, so you can re-adjust to your surroundings, whether it’s just getting used to being home or overcoming that horrible jet lag. Don’t worry about leaving yourself enough time to enjoy your holiday — shorter holidays are more memorable anyway.

Your holiday is your own, so use it to do whatever you want to do. If your itinerary is stressing you out, skip it and book a spa day instead. The whole point is to relax and recharge from your stressful work life, so don’t turn sightseeing into an exercise in getting things done. Photo by Kenny Louie.

Part Four: Returning Home

When the vacation comes to an end, it’s time to get back to work. After your end-of-vacation buffer day, you should feel a lot more amenable to getting back into the swing of things, but you’ll still want to ease into it a bit. Get up early on your first day back, eat a good breakfast, and carve out some alone time so you can get yourself re-situated before you’re inundated with tasks and email. And, most importantly, plan your day and week ahead of time so you can easily start working your way through that to-do list.

Don’t worry about getting big projects as soon as you get back — in fact, your clear post-vacation mindset is one of the best states for tackling them. Photo by Davide DeHetre.

This guide may stress you out on its own with all the information contained within, but remember that this is merely a guide. Your holiday can be anything you want it to be, even if it’s just avoiding travel altogether and finding new things to do at home. Find what works for you and don’t worry about the rest. If you’re starting to burn out from work, you’ll no doubt find ways to relax yourself when your break kicks in.

The Road Worrier column, looking at technology and organising tips for travellers, appears each week on Lifehacker.

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