We go on vacations to relax. Then we proceed to drive ourselves crazy dealing with endless reservations, airport hassles, jet lag, and other annoyances. This year, let’s plan out that vacation without all the stress.
This post is broken into four parts. If you’d like to skip to a certain section of the guide (maybe, for example, you’ve already finished your pre-travel prep), you can do so with the links below:
- Part One: Pre-Travel Preparation
- Part Two: Travel Day
- Part Three: Your Vacation
- Part Four: Returning Home
The key to an easy vacation is planning as much in advance as is practical (though there is something to be said for awesome, last-minute vacations). That means putting together your itinerary for the trip, applying for time off from work, and getting all your reservations in order as soon as possible (and packing, of course). Here are a few tricks for making your preparation easy and cheap.
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. Figure out the best time to buy—usually on a Tuesday afternoon eight weeks away from your vacation—and then use a travel-oriented search engine to help you find a good deal. Kayak was far and away your favorite when we polled you on the subject, due to its ability to search multiple sites at once and provide you with seriously low prices. It also has a lot of advanced search features, like a “Hacker Fare” checker that will let you know if two one-way tickets is cheaper than a round trip ticket, and things like that.
We’re also pretty big fans of Hipmunk (pictured right), too, which offers some other cool features. For example, it lays all the available flights out on a day calendar so you can more easily see when you’d depart and arrive, with little graphics for layovers, in-flight Wi-Fi, and more. All in all, both sites excel at their own specific things, and it’s hard to recommend one over the other. Kayak may have an edge when it comes to powerful search, but Hipmunk is handy for comparing flights to one another in more visual way. I recommend giving them both a try, just so you have your bases covered. When you’re done, you might want to check out an automatic price tracking service to notify you of any price drops, so you can grab yourself a refund.
Lastly, if you’re planning your vacation far in advance, you can use a service like Farecast to find out when those tickets will be cheapest, then wait to buy them then.
Of course, if you really want to dig your heels into the deal-finding part of the process, be sure to check out our much more detailed ultimate travel hacking guide.
Keep Your Trip Information Organized with TripIt
So now that you’ve booked your flight, your hotel, and your rental car, you have a ton of confirmation numbers, reservation dates, and other bits of info floating around your email inbox. TripIt is one of our favorite travel apps that aims to organize 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@example.com, if you’d rather not give them access to your email.
Now, when you forget what time your flight leaves, you can check the TripIt app on your smartphone, or from the browser on your computer. It’ll give you all the info you’ll need about your reservation, notify you if anything changes, and even sync with your calendar so you always have your flight info right there. You’ll never have to search through your inbox for that information again: it’s all just a few taps away on your phone.
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 put 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 these multitaskers. 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 a bit of deeper research into the art of travel preparation, here are a few tips and articles we didn’t mention above:
- How to (Almost) Guarantee You’ll Never Have to Check Your Luggage Again
- Prepare Your Smartphone and Laptop Travel Toolkit
- Be Prepared for Your Next Trip by Filling Out This Geek-Friendly Travel Checklist
- Five Best Cheap Travel Booking Sites
- The Best and Worst Airlines for Redeeming Rewards Miles
- Get Better Hotel Deals with This Hotwire and Priceline Negotiating Strategy
- The Best and Worst Hotels for Wi-Fi, 2012 Edition
- Use Frequent Flier Miles for Upgrades Instead of Flights to Get Your Money’s Worth
- How to Protect Your Home While Traveling
- Tidy Up at Work and Home to Make Your Return Less Stressful
Arguably the most stressful part of vacation 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 any delays that may happen, you’ve got the perfect seat on your flight, 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 created a handy checklist to help you get through as fast as possible, and it’s all about dressing and packing right for your day of travel. That means slip-on shoes, warm clothes that don’t zip up, empty pockets, and a TSA-approved laptop bag. The less you have to fiddle with your stuff, the faster you’ll get through security. You might also quickly scope out the lines on both sides of the airport—sometimes one is noticeably shorter than the other just because it’s a bit farther away from the more popular terminals.
Survive the Long Journey
So you’ve boarded the plane, successfully gotten your luggage to fit in 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, especially during that pesky electronic-free takeoff. Electronic devices aren’t actually a huge deal during takeoff and landing, and while we think it isn’t that bad to have a few electronic-free moments, there are ways to use your device without getting caught. Just make sure you make the most of its battery life, whether it’s an iPhone, an Android phone, or a laptop. And speaking of laptops, if your flight makes you pay for Wi-Fi, take advantage of these tricks to get a better price. And, lastly, 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 there as well (like not eating the in-flight meal). Photo by viralbus.
More Hacks for Surviving Travel Day
We’ve covered a lot of good travel day hacks over the years. Here are a few we didn’t mention above, but still warrant a look:
- How Can I Best Handle the TSA’s Creepy Tactics When Traveling?
- How to Lie, Cheat, and Steal Your Way to a Perfect Flight
- Get 15 Minutes of Airport Wi-Fi by Asking and by Sitting Near Airport Lounges
If you’ve done everything right so far, you shouldn’t have too much trouble relaxing on your vacation. We’ve shared a few ways to find things to do in a new city, from smartphone travel guides to strategies for finding interesting places, but chances are you’ve already planned out a good portion of this vacation ahead of time. That said, here are a few things to remember as you enjoy your trip:
- 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 prioritize 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 vacation. 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 vacation—shorter vacations are more memorable anyway.
Your vacation 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.
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 vacation 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 vacation time kicks in.
Title image remixed from Chris Brindley .