The One-sentence Guide to Getting Great Vacation Deals

All-inclusive for 3, at $108 per night

Magazines and websites constantly run stories about finding great travel deals and vacation bargains. Usually they highlight some nifty new website, the latest apps, or some Twitter stream that you have to catch at 3:30 pm each Thursday. Really though, it’s not complicated. Here’s the one-sentence answer on how to save the most:

Pick the right place, at the right time, and pay less than what most others are paying.

Pick the right place

Destinations are not priced equally. Internationally, a trip to Japan can literally cost you five times more on the ground than what a trip to Indonesia will cost you. Denmark will be exponentially higher than a vacation in Bulgaria. Two weeks in Chile or Brazil will cost you three times as much as two weeks in Nicaragua or central Ecuador.

Quito lunch

If you start with an expensive destination, all other cost-cutting attempts become much harder and less effective.

Even within countries though, major capitals and popular tourist resort areas occupy the top end of the scale. Compare New York City to Austin, Cabo San Lucas to Guanajuato, or Prague to any town in the Moravia region of the Czech Republic. Sure, we’d all like to spend a week in Paris, but if you’re looking to lower expenses, head to the villages instead.

At the right time

Nearly every destination has a high season and a low season. The optimal time is in between—the proverbial “shoulder season.” This is when the weather is still good and everything is still open, but the tourist hordes and peak prices have gone home.

In some places this is easy to figure out, like Europe in the spring or late autumn, the Caribbean or Mexico after the spring break crowds and snowbirds have left. In others it’s not as obvious, but a quick glance at a guidebook or destination website will usually clue you in.

The tough one for parents is always our summer, when school is out. But even then, it’s not high season in the southern hemisphere, in African safari country, and much of Southeast Asia. It’s not high season for cities in the U.S. You can find rock-bottom deals in places where it’s sweltering outside: think Las Vegas, Scottsdale, and Florida outside Orlando. Avoid the obvious and you’ll be rewarded.

Pay less than what most others are paying

If you open up a common online travel agency site, book your hotel, and add on a few local tours, you’re probably paying top dollar. You can almost always do better.

Hotel chains spend millions of marketing dollars to make you believe their 20 percent off deal or $100 spa credit thrown in is some terrific bargain. If you go shopping around on the likes of Expedia and Travelocity, it’ll look that way too. Contracts with those online agencies ensure that nobody is showing a price much lower than anyone else’s.

There’s a whole other booking system though that’s hidden–it’s even called “opaque booking.” You know this system by the brand names participating in it: Hotwire with its hidden hotel names, Priceline with its bidding on properties you can’t identify. Then there are the membership flash sale sites where you have to get the e-mails from the likes of Jetsetter, Vacationist, SniqueAway, and TripAlertz. Plus there are a few semi-hidden ones operating in between the light and dark, like LuxuryLink and SkyAuction.

You can iron out most of the uncertainty on Hotwire and Priceline by using message boards that will clue you in, but if the idea makes you uncomfortable or you don’t want to commit your money up front, there are other strategies to take. The best one is to avoid the international chains entirely and book an independent hotel. You can find these in guidebooks, on websites dedicated to the destination, or on value-focused sites like EuroCheapo for Europe and for Southeast Asia.

My sub-$50 hotel in San Cristobal de Las Casas

Sure, if you’ve got hotel loyalty points banked up you want to spend, by all means go with the corporate hotel or resort using that hard-won currency. But in many cases you’ll pay far less and get more personal service by staying at an independent hotel that is less visible but really wants your business. If you’re staying for more than a night or two, you’ll also have a better chance here of negotiating for a better rate or an upgraded room. Just ask a long-term traveling backpacker—they’re doing this every week.

This “pay less than most others” strategy applies to dining and attractions as well. Avoid tourist restaurants, sniff out the specials, and ask real locals (not a concierge) where they like to go. Find the local coupon books and consider using something like the Entertainment Book or signing up for Groupon or Living social in the place where you’re headed.

There’s one expense I haven’t mentioned in all this and it’s a sizable one: airfare. In today’s mostly transparent climate for flights, finding a real airfare deal is not easy no matter where you’re going. Use miles to pay for long-haul flights when you can and watch for specials. Many sites will let you search all flights from your own airport to spot the bargains or will send you a weekly rundown on sales. Some (like Flight Network out of Canada) will refund the difference if the price drops. If you’re not dead-set on a certain place, you’ll find many more opportunities to save. In other words, return to #1 because that’s a different angle on “Pick the right place.”

For more timeless advice on getting more for your travel budget, pick up the book Make Your Travel Dollars Worth a Fortune, available in paperback and for the Kindle. 

  1. Anna

    I personally always start my search for the best holiday from airfares. Within Europe accommodation expenses are more or less the same, but not the flights. So I pick up three-five destination, two-three weekend dates, run a search for all carriers, choose three top airlines then continue on their home sites, course you always have the best fare departing at 5 am, so I check prices for convenient departures. It usually takes a couple of evenings, but usually I have a good price as a result.

  2. James B.

    Yeah, I always laugh when friends ask where I got all my money when I talk about my vacations. They plan for a year and go wherever the hot place in Europe or the Caribbean is right now, always staying at the top place. So they come back broke, even if they only go for a few days. I go for weeks and make less than they do.

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