There is nothing more tedious than spending hours scouring the internet trying to find the best price on every element of your vacation.
So I don't.
Instead, I make a single decision that saves me a fortune: I choose to travel in "shoulder season."
This period of time is the months leading toward or away from the high season.
In most places, that's obvious. In the Caribbean, it's the winter. In most of Europe, it's the summer. It's the time when that place is best shown to its advantage, so people go see it.
It's also the most expensive time to go because the tourism industry knows what's up.
By choosing to travel six to eight weeks before or after high season, I save money on flights, accommodations, car rentals, and most everything else by making one decision and never thinking about it again.
It seems obvious, but a lot of people don't do it.
It isn't the off-season. I'm not going during monsoon season or blizzards. Really, the only difference is a few degrees — a light sweater, or removal thereof.
And the financial benefits are huge. For instance, a friend and I went to the Cyclades Islands in Greece a few years ago, choosing to go in early May instead of summer, the peak season.
When I plug a 12-day trip for the same dates into Kayak — leaving on the last day of April, the same days we traveled — the cheapest flight with one layover is $562:
In early August, the results are nearly twice the price, even though we'd be booking further in advance:
Bear in mind that that isn't a perfect comparison. It involved no acrobatics to find the cheapest possible flight, nor direct comparisons of flights leaving and arriving at the same time on the same day of the week, nor analyses of how airline prices fluctuate. It took me all of five minutes — which is kind of the point.
Here's another basic illustration: Accommodations were cheaper, too. On Santorini, we stayed at — the marvelous — Atlantis Hotel in Fira, which charges 240 euros, about $262, per night for our incredible caldera-view room in early May.
Using the same Sunday-through-Wednesday dates in August, that hotel is asking 320 euros — about $350 — per night:
Admittedly, I don't have children and am not limited by the school calendar, and my job isn't so highly seasonal that I wouldn't be able to travel in May rather than August, so I'm lucky enough that this strategy is easily doable. Plus, I generally don't mind that I have to put a windbreaker over my bikini to see the cliffs of Santorini or the town of Mykonos. It's more affordable, less crowded, and just as beautiful.
If you have your heart absolutely set on tanning on a yacht, I concede that this strategy might not be for you. Although if we're talking Mediterranean, you could try September!
I could keep giving examples — I used the same strategy when I went to the Balearic Islands off the coast of Spain in late May/early June last year with another friend — but there's really no need. By traveling in the shoulder season instead of the high season, I've consistently been able to save hundreds, if not thousands, of dollars on incredible trips by making a two-minute choice.
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