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When Should I Start Thinking About… Planning My Summer Vacation?

The two shortest answers are ASAP, and whenever you’ve figured out how to avoid Fourth of July weekend entirely

You just got through a dreary February. The cold has had you wearing cozy hoodies during the day and huddling under blankets at night. You long for summer, but even more than that, you long to just get away from work, school and snow-shoveling and bask on a beach, have an adventure in some country you’ve never been to before, or get drunk at a resort’s pool bar. Dreaming about your summer vacation is all that’s getting you through the winter — but is it already too late to get the sort of vacation you really need?

It might not shock you to know that, much like wondering when to start filing taxes, the simple answer to “When is the best time to book summer vacation?” is “sooner rather than later.” But there’s not much that’s simple when you’re choosing where you’re going, when you’re going and how you’re going to get there, because there are a ton of factors that dictate what summer vacation options you have available to you — and how much you’re going to pay for it.

The Numbers Don’t Lie

The truth is, here in March, there are still plenty of summer vacation options available. You can set up a trip to Myrtle Beach over the Fourth of July, or book a multi-city tour of Europe only a couple of months in advance if you want. But you’re going to end up with a very different vacation than the one you would have had if you’d booked things sooner.

It’s basic math: The sooner you book something, the less time other people have to book it for themselves. If you dilly-dally, that might mean you end up with a “Garden View” hotel room as opposed to the “Ocean View” room you were hoping for, but at its worst, it could also mean your summer vacation spot won’t be available until the fall. If you plan on vacationing somewhere during its peak tourism season, your options decrease exponentially the longer you wait to book it — the prices of those decreasing options tend to increase at the same time. 

Both things are true about booking flights as well. The longer you wait to purchase tickets, the more likely it is that you’ll end up paying a ton to take a redeye from Boston to South Carolina that also inexplicably has to stop in Cleveland and Atlanta before it arrives. While airline ticket prices do tend to fluctuate, the overall trend is that they get more expensive from the moment they’re first announced, which is around 11 months before the scheduled flight. By waiting, you’re simply gambling with the hopes of saving a few bucks. “If there is a drop in pricing, generally it’s not significant enough to cover the cost of the stress of getting up and checking the [ticket prices] every morning,” says Jamie Anderson, owner of Portland, Oregon-based travel agency Travel & Cruise Desk

Besides, as in most gambling, the house usually wins. Anderson suggests you book your flights at least one month in advance at the very latest, as that last month is when the steepest price spike tends to occur, no matter how many cramped airline seats still need to be filled.

Peak Performance

The other problem with vacationing in the summer is that everyone wants to vacation in the summer. Beaches, obviously, are going to be the most crowded, whether they’re located in the U.S. or not. But the summer is also the peak tourist season for sightseeing vacations to major cities like New York, Paris and Rome, as well as natural wonders like the Grand Canyon. Since many families have to wait until their kids are out of school to take any sort of extended trip, the more family-friendly a location is, the more crowded it will be. For instance, of the many summer vacation options still available to you right now, going to a Disney park is not one of them. “You’ll want to book that about a year out,” says Anderson. 

While summers are peak tourist season for so many places, the Fourth of July is the highest peak in this particular mountain range. If you want to light fireworks at Myrtle Beach, you may be too late; Anderson suggests booking those vacations four-to-six months in advance at minimum. The Fourth of July will still mess with your vacation even if you’re traveling internationally. You may be lucky enough to have access to a direct flight out of the country, but chances are you don’t; if you have to make at least one domestic stop, you’re still going to be traveling with all the Fourth of July crowds… and paying their ticket prices, too.

There are other, less obvious problems to watch out for if you’re planning an international vacation. Make sure to do your research to see what those countries and cities might have going on that could impact your trip — these could just be local holidays that might interfere with your sightseeing plans, but they could be much more disruptive. For instance, you might want to scratch Edinburgh, Scotland off your list of potential August trips; that’s when the month-long Edinburgh Fringe Festival occurs, and hotels and Airbnbs are booked for miles around. 

Meanwhile, summer is hurricane season in the Caribbean, while Dubai regularly has temperatures over 110 degrees. If you have your heart set on visiting places like these, it might be best to hold off until the fall.

So What Can I Do?

Plenty! Whether you want to hit the beach or travel internationally, you can still achieve most summer vacation plans now (other than those Disney parks and cruises, which need to be booked even earlier). “We’re booking people already for [cruises in] 2020 and 2021,” says Anderson. “We even have a few bookings for later than that, that we’re already working on.” 

If you’re reading this at the start of March, you can still make it to the beach, go see Paris or hit an all-inclusive resort in Mexico. You might still even be able to find a place to stay in a super-popular vacation spot like Santorini in the Greek Isles — all you really need to do is prepare to be flexible with the options left to you. That partially means having as wide a range as possible for dates to take your vacation (and its length) as it’ll provide more opportunities to find better deals on flights and such. But it also means being accepting of which, exactly, of the options are still available. You may have been hoping for a Hilton, but you’ll need to find peace with staying at a Hampton Inn if everything else is already booked, or if that’s the only hotel left that’s still in your budget. 

There are plenty of beautiful places to visit this summer that aren’t going to be crowded. You can take advantage of mild New England temperatures to visit a Vermont bed-and-breakfast. Iceland is a popular summer destination, but the tourists tend to congregate in Reykjavik, and there’s more to the country than that. There’s going to be plenty of people visiting Japan, but it’s going to be less crowded in the summer than in the spring, when the cherry blossoms bloom. And whether it’s the Mediterranean or the Caribbean, you can still find islands that are going to be just as beautiful that aren’t nearly as well-known. For instance, if you can’t make it to Santorini, islands like Cephalonia and Naxos are practically next door. 

If you have your heart set on visiting an all-inclusive resort, it’s the family-friendly ones that are more likely to be booked solid. But if you don’t have kids, some resorts are adults only — not in the sense that there are constant orgies, but in that there are no little ’uns running around screaming. If you do have kids, there may still be hope, because Anderson has a heck of a protip: “A lot of the time, groups will be holding space [at resorts]. About 90 days beforehand, the resorts ask them to release any space that isn’t being used.” 

In other words, if you check out a resort’s availability four months before you want to book your stay, it may say it’s sold out. But if you look again three months prior, there might suddenly be space. 

Of course, tracking down a resort that may have secret rooms isn’t the easiest thing to do, which is why another solid way to find a good summer vacation is by having a professional do it for you. “Whether it’s pricing something or they’ve worked with the specific property before, [travel agents] have the contacts — not just directly with the hotel, but third-party suppliers that might have even better contacts with the property or are holding space,” says Anderson. “We have destination specialists that focus on different areas of the world and different experiences, and they’re booking them every single day.”

But even travel agents can’t get you the same price you would have paid last year that you’re going to pay if you book a trip this March (plus, some agencies charge a fee if you want them to figure out your vacation in less than two months). So if you have your heart set on doing something or going somewhere specific, the best thing you can do might be to turn your summer vacation into your fall vacation, if you can swing it. Things get a lot cheaper once summer ends, and plenty of beaches are still pretty sweet in September — arguably more so, if you don’t have thousands of people tanning beside you. 

If you don’t have off-season options, though, it might be worth it to start thinking about 2021’s summer vacation instead, especially if you want to do something big or go somewhere you know is going to be crowded. You don’t have to book anything now (again, except Disney trips and cruises) but you can start doing research this summer, and then book it when flights become available. It’s the best way to get the exact vacation you want, while also saving the most money — which tends to make vacations even better, since you can use that cash on more drinks at the pool bar.

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