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Here at ShermansTravel, we’re always encouraging readers to take advantage of limited-time sales and last-minute deals — after all, alongside planning way in advance or looking to shoulder season, it’s one of the best ways to nab great discounts for travel. But the reality is that the best offers often require you to act fast, whether it’s a flash sale for travel five months down the road or for a cruise that departs in the next week. And more often than not, the pressure to book quickly can become overwhelming, and we find ourselves simply passing up the deal in the end.


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But it can be possible to strike the iron while it’s hot — so long as you’ve already done a bit of simple planning. Having recently booked fantastically low fares to Istanbul during a three-day sale ourselves ($535 round-trip in the beginning of November), we wanted to share our checklist for what to think about beforehand. We hope that by working through these questions, you’ll be prepared to hit the book button and save big when the next deal rolls around.


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1. Where do you want to go? 
These days, you’ll find deals pretty much every day and even every hour. It’s a lot for your brain to absorb, and often we end up scrolling through lists and ads without really reading. Which is why we’re fans of sitting down to write out a travel bucket list, either on paper or digitally, in order of priority. Not only does writing out a list flag the places you really want to go, ranking them will help you jump on deals for destinations high up on the list. Knowing you’ve already weighed them against the myriad other awesome places you could go saves you from making those comparisons all over again.

2. How much time do you need? 
This is pretty obvious to state, but again, thinking about this beforehand makes it easier to make a decision quickly. You need to know the minimum amount of time you should spend at each destination to make the trip worthwhile. We knew, for example, that we wanted at least five days to enjoy all of Istanbul’s historic sites, modern delights, and endless food. And we really wanted up to a week, really, so that we’d have a bit of time to get lost and wander. But had we been looking at a more familiar and closer destination or less active experience — say a luxe resort in the Caribbean — perhaps an extended four-day weekend would be enough.

3. How much time do you have?
As with all instances of travel planning, you also need to know the constraints in your schedule. If you’re working and have limited time off, keep tabs of the vacation days you’ve taken and have left. We keep a an Excel spreadsheet with columns for: destination; dates off; number of days taken for trip; total number of days taken this year, and total number of days left.

4. When can you travel?
Beyond a short booking period, limited-time and last-minute deals often also have a very specific window for travel. Make a habit of keeping track of dates that you absolutely can’t travel on — a weekend of a relative’s wedding, for instance — if you don’t already. We’re big fans of syncing our Google calendars across our desktop and mobile devices, so we can access our schedule from wherever we are.

5. Is the deal a really great deal?
It probably won’t surprise you that not all deals are as great as they might seem at first glance. That’s precisely why ShermansTravel has a dedicated Deals team — our Deals Experts spend their days sussing out every promotion that we might want to share with our savvy readers. When they’re assessing the value of a promotion, they typically look at a mix of the following: 1) how much the experience would cost from the same provider without the promotion; 2) how much the experience would cost through different providers, and 3) if it’s low season, how much would the experience cost in high season.

While you’ll likely have to do a bit more research when you’re interested in a specific deal, it’s not that hard, for instance, to figure out generally how much a ticket to Paris from your nearby airports cost. Once you know that, you’ll be able to evaluate a deal much more quickly. In our case, we already knew that flights to Istanbul can go well over $1,000 during popular months and still reach $750+ in slower months. So the minute we saw the $535 fare, we immediately started checking our calendars.

6. How much can you spend?
If you have a dedicated travel fund, good for you. If you don’t, you should at least know how much of your rainy day/leisure/other fund you’re willing to spend on travel. Even if the deal in question checks out and your schedule cooperates, in the end, nothing can happen without the exchange of dollars!

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