​Don’t Trip Out: Tips for Planning a Late-Summer Vacation

Hands On

If you’re like anyone anywhere ever, you spend a fair amount of time each year fantasizing about your summer vacation. It’s natural. You work hard all year long, wear uncomfortable suits or shoes, bust your back each day, deal with an insane boss—no matter what the circumstances, you deserve a break. And while taking a vacation any time of year is grand, no vacation is more revered than the magical wonder of the summer vacation. Especially late summer. You’ve got good weather, a lighter workload, no school—and tons of end-of-season travel sales. Read on for some top tips to get you out the door and into an Instagram-worthy late-summer vacation.

It may be hard to believe, but Summer vacation wasn’t always a thing. So how did this mid-year magic begin? History time!

Like so many other fun things, vacation has its origins with the Romans. They had their fingers in a lot of stuff. Anyway, the Romans were the first to enjoy traveling for pleasure. Also, Italy is a great destination. Just saying. Summer vacation specifically, though, is a more recent invention. And it came from this perfect storm of vacation-encouraging events in the mid-19th century:

  1. The white-collar middle class was on the rise
  2. Doctors began warning people of brain fatigue and encouraged them to refresh and rejuvenate in the great outdoors
  3. The railroads were expanding

There was one piece holding things back, however—kids. Shakes fist. Schools at the time ran on one of two calendars: in rural areas, schools were open in the winter and summer, but closed in the Spring and Fall (this is when parents needed their help on the farm); and in the cities, schools were open year-round. Luckily, school reformers took the same position as those doctors saying that brain fatigue was also no good for kids. And perhaps most importantly there were teachers who also wanted a break. The summer vacation was born.

Methods of travel and favorite destinations may have changed over the years, but the fact is that summer vacation is still ritual and that isn’t likely to change. This year approximately 2.5 million people are expected to travel every day from June through Labor Day in the U.S. And that’s just by air. With all those other people flying and training and driving as you’re trying to make your way to your own personal paradise, you could run into some difficulties. Whether you’ve already made your plans or you’re still at square one, these tips can help make your trip tip-top instead of a big flop.

Crazy stat time: 55% of Americans don’t use their full vacation time and leave hundreds of millions of days untaken. What the heck??!! You’ve earned your days. You should take them. Fact is that taking time off will not only make you feel great because you’re on vacation—woot!—but it will also make you more productive at work in the long run.

Be flexible. Having flexible dates is key for saving some dough-re-mi. Leaving a day earlier or returning two days later can keep a fair amount of cash in your pocket. Not flying on weekends is also a money-saver. If your friends often refer to you as “money bags” and you don’t need to worry about these things, good for you. Also, maybe you’d like to bring us along on your next trip?

Wait for it. Saving travel for the end of the season can be hugely rewarding. When summer strikes, everyone and their little cousin are itching to get away. But patience can pay off in your wallet. There are often more flights, rooms and packages available during the dog days of summer—after many have already made their escape. Looking for inspiration? Check out sites like Travelzoo for smart deals on just about everything vaction-y. Flights to Europe for under $500. Only $799 for a week-long Caribbean vacation. Just $899 for a 16-night cruise to Spain. That’s just a sampling of the vacation values you can score.

Try new stuff. Heading to a new or unusual destination is an excellent way to explore the world and to also possibly cut expenses. Don’t ignore international possibilities—these days a ticket across the pond can cost less than one across the country. Poke around. The world is your oyster.

Let the experts do all the work. Cut down on irritation out and make your search work better for you by using an aggregator. Going through tons of airline sites and discount sites can make your brain pop, but signing up for an alert from Skyscanner or other similar sites, which pull from all those sources, can save your brain from said devastation.

Sign up for TSA PreCheck or Global Entry. Just do it. You’ll never regret it.

Lounge around. Don’t get left out of the airport lounge just because you don’t have the right membership. The LoungeBuddy app can help you find pay-for-the-day lounges to book and enjoy their cozy seating and free snacky bits. Elite status, shmelite status.

Tap into more travel apps. Speaking of apps, you should just app it up. There are a ton of travel apps that can help make your journey easier. AirHelp can help with getting compensated for delays and cancellations, aww yeah. Roomer finds discount hotel rooms. AutoSlash is good for getting good car rental rates. SeatGuru helps you find the perfect seat on a plane—is it close to a bathroom, are there power outlets, and so on.

Grab a hotspot. Unless the point of your trip is a digital detox, you’re going to need at least a little connectivity. Shared WiFi can be slow (and full of creeps looking to steal your life) and data costs can get way out of hand before you’ve even left the airport. Skyroam is a mobile hotspot that you can buy or rent that costs about $10 per day to use no matter how much data you use in that 24-hour period. And you can use five devices on it. So download or search or whatever to your heart’s desire without blowing your budget on data costs. It doesn’t work in every country, but works in a lot—just be sure to check before you go.

Da-da-da DA-da-DAAAA…CHARGE! Running out of juice at the wrong time can be hazardous to your happiness. Get a portable charger and keep it charged and with you.

Keep it light. And by that, we mean luggage. If it’s possible, stick to carry-on. If you and the crew have excess baggage, check one bag with everyone’s extras in it. Buy things like toiletries and sunscreen and such at your destination if you can. And don’t forget the TSA’s travel checklist—they won’t. And rolling your clothes to pack them will take less space and reduce wrinkling.

Don’t forget the obvious. Check that your name matches on tickets and IDs, make sure your passport is current (and has at least six months of validity if traveling internationally). Also scan your ID, itinerary and passport and email them to yourself in case you lose anything. And also try not to lose anything.

Stay alert(ed). Even though most airports are well-oiled machines, ahem, you might experience some delays. Sign up for alerts from your airline so you can be notified of any changes. If you’re driving, check your traffic. Google Maps can get you a time-travel estimate and show traffic problems. And most importantly, make sure you have a decent amount of tasty snackage and then get some more so no one has to experience hunger rage.

Get more bang for your buck. Mo’ money should not mean mo’ problems. Currency converters in airports tend to have higher conversion fees, but an ATM in your destination will likely have a more affordable rate.

Breathe. When you’re finally on the ground, the temptation will be to go, go, go. And while that will certainly up the number of sites you get to see, it will also up the chances of you getting seriously grumpy. You need to take breaks. Nap, just sit, have a beer, have two beers, do something to get a little rest in and recharge. You’ll enjoy the trip more and you and your traveling companions will all enjoy each other more.

Book it. If you have museums or abbeys or towers you want to visit, see about booking ahead—hop online and try to get tickets. Or book a guided tour. The last thing you want to do is wait in a long line in the heat for hours while everyone is getting irritated and questioning your judgement. Also make sure you know what days an attraction is opened/closed. Depending on how popular the spot is, you might want to go early or late to avoid crowds (check opening times).

Avoid bottle shock. Perhaps you’re going someplace with an excellent distillery, brewery or winery. Perhaps you want to purchase some of the delicious nectar from said booze emporium. Make sure said nectar travels safely. Bring some travel bottle protectors (like WineSkin bags) to make sure your booze don’t ooze.

Get lost. It’s easy to get caught up in logistics, planning, scheduling and making everything fit. But one of the best parts of traveling is getting lost. Well, relatively speaking. Taking at least one day to just wander and discover something your schedule may not have allowed will make the destination more special and your trip more memorable. Just keep your GPS turned on (but don’t look at it unless you absolutely have to).

Know a guy. Or know a guy who knows a guy. Having someone on the ground who can make recommendations on which spots to hit (and which to miss) will make your trip that much better. Ask friends if they have a friend in your destination city, talk to a concierge or try a restaurant with a communal table and talk to some locals. Locals are the best!

Relax and enjoy. Summer vacation should be all about a good time. So don’t worry if you don’t hit every spot on your itinerary or if it rains or if you get arrested. Just kidding—don’t get arrested. Just take it all in and enjoy the company you’re in and if you don’t get to do it all, you’ll just do it next time. But seriously don’t get arrested.