When Should You Book Your Winter Vacations?

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Photo by Doug Scortegagna

Should you jump on booking your winter trip right now? I’ve begun seeing advertisements on CheapCaribbean.com that 2014 winter vacations are on sale now up to the end of February 2014. Also, TV commercials and airline ads have states they’re booking flights through February 2014.

I’d say you have time to wait to book a winter deal and for prices to drop. The prices listed now may seem like you’re getting a lot of money off the original price saved. But you can get more saved if you wait until October-ish.

Having watched sites such as CheapCaribbean and JetBlue for their winter getaways throughout the end of summer 2012 and into the Fall 2012…. prices do fall!

First Tip: If you want the best seats on your flight and best hotel room, book earlier October than later.

Second Tip: If money doesn’t matter to you, get your trip booked whenever you want. You can find flights and hotels at any time if you’re a “baller” although be mindful Thanksgiving and Christmas may book up if others think alike like yourself.

I recommend CheapCarribean for they’re the best for deals, and easiest to browse through flights. My one envy last year was to go to St. Maarten, from NY, for all-inclusive for 5 days and I kept seeing prices such as $899! I’m hoping to do that this year and take the whole week off after Christmas Day. I began checking for deals today and St. Maarten was not listed as one of the  “40% off winter deals” locations. So I will need to keep checking back because I know it will pop up one day.

Last tip – Try to check for deals everyday even if it’s five minutes out of your day. You never know when the right price might creep up!

Do you have tips or tricks for snagging a deal?