Planning Ahead vs Last Minute

Since I’ve sort of become known amongst my friends and co-workers as “the one who’s always travelling”, it’s become quite common for people to ask me for tips on getting good travel deals. One of the most frequent questions I’m asked is when is the best time to book. Is it better to book well ahead or hold back and wait for a good deal? My short answer to that question is “yes”. Both methods can get you great deals, but it depends on your travel goals and your personality.

Here’s one thing I do know for sure. If you want to be absolutely sure you’re getting the worst possible deal, wait until about 3-4 months out before deciding where you want to go. Then immediately set your plans in stone and don’t look at any other locations. Don’t look at any other travel dates, either. Check out the prices, but then hold back because they seem so high. When they start creeping even higher, panic and book. Check Tripadvisor as soon as you’ve made your non-refundable booking. Also, don’t start looking at guidebooks until after the trip is booked. If you really want to get completely fleeced you can go to the next level by booking your accommodations before checking flight prices or vice versa.

Does any of this sound familiar? I’m constantly encountering people who complain how much travel costs, but always book in the most expensive way possible. In my experience, there are two times to get really good deals on travel; far in advance and last minute.

Full disclosure here: I am a “plan in advance” traveler. There are two main reasons for this. One is that I need to submit my vacation requests for work a year in advance, usually in October for the next calendar year. This means that my days off for Christmas 2014 had to be chosen back in October 2013. My husband is a teacher, so his dates are set in stone as well. So snapping up last minute deals isn’t really an option for us right now. The other reason is that I am a massive control freak. I love planning my trips and booking them last minute would rob me of all those lovely months of planning I get to do when I book well in advance.

That’s not to say that last minute travel doesn’t have it’s perks. For many years I worked as a nurse “on call”. I often didn’t know where I was going to work for the day until the phone rang in the morning and some weeks had less work than others, but I could book time off whenever I wanted. Once I bought a ticket to Amsterdam on a Saturday and left on Wednesday and paid less than $500 return. Another time I snapped up a seven day Caribbean cruise for $247 plus the $500 it cost to fly to Miami. If you have that kind of flexibility there can be great last minute deals out there.

My basic guideline for timing is this: if you know your dates and know where you want to go, book as soon as possible. If you are flexible, you may be able to wait until the last minute. One thing you should always book as soon as you can is anything that doesn’t require a deposit. For example, most hotels will let you book a room at a certain rate, then cancel within 24-72 hours of your arrival date with no penalty. So if you see a good rate, book it! If prices go down you can always cancel and re-book. Of course you do need to keep track of what you’ve booked and what you’ve cancelled, but it’s easy enough to keep a separate file for those emails in case something gets missed.

Car rentals can also be re-booked quite easily if a better deal comes along. Unlike flights and hotels, I’ve found that car rental prices can be best a few weeks out. I usually check prices every few weeks after I’ve booked to see if something better has come along.

Cruises are another great opportunity to nab good prices with no risk. Always check the fine print. A lot of cruises require a deposit to reserve a cabin, but allow you to cancel with a full refund of your deposit up to 60 days before the cruise. If you want to be really sneaky, plan a two week trip and book a cruise as soon as possible for the 2nd week of your trip. Wait until a week before the date you have to pay for in full, then browse for last minute deals on the first week of your trip. These cruises will have just had their paid in full date pass and any empty cabins (for example, someone couldn’t come up with the money for the cruise and cancelled at the last minute) will be offered at a bargain. If you can find a last minute deal for week one of your trip, cancel the cruise for week two, get back your deposit and book for week one. If there are no deals for week one, keep the cruise for week two. Of course you will also have made a booking for each week for a hotel well in advance and you can cancel the hotel for the week you will be cruising and keep the hotel for the week you are not. Simple, right?

If you want to really go overboard in planning ahead to get the best deals, you can even start two years out. Now you may be saying, I don’t even know what job I’ll have/ where I’ll be living/ how many kids I’ll have in two years time! How could I possibly plan my travel that far in advance? Well, you don’t have to know exactly where you’re going, but it never hurts to have an idea. For example, I knew we wanted to take the kids to Europe for the summer of 2014 about two years in advance. So last year I kept an eye on the prices of flights to Europe throughout the year. I noticed that unlike a few years ago, there were very few sales in spring or last minute reductions. The best deals for summer seemed to be right after Christmas. With this in mind, I watched the flight prices to Europe for summer 2014 and sure enough, there was a sale at the end of January and I was able to get a fairly decent price. Now this doesn’t mean there won’t be a big sale with lots of deals in May that will make me regret buying back in January, but at least I know that didn’t happen last year so I’m making my decision with as much information as possible.

So that’s my long answer to the question of when to book a trip to get the best deals. Just remember, knowledge is power and the more research you do the easier it will be to find that great deal, whether you’re booking the day the prices are released or the day before you leave.

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