General, Travel Tips

How to Start Planning Your Winter Escape

Remember summer? I do.  These days it is all I can do to stop myself from wrapping up in a warm blanket and staring sadly through my window at the falling leaves. Sure, they’re pretty, but they’re also a clear indicator that winter is coming. And for those of us who crave sunshine and warm weather as much as we need water and air, that’s a problem.

winter escape beach
Wouldn’t you rather be here?

Luckily, there’s a solution. The cure to your fall weather blues is as easy as starting to plan your winter escape.

Start working through this checklist of must-dos to make sure you are the one laughing at snow-weary friends, from a beach in February…and not the other way around.

  1. Source your fares now –  The right time to book a flight out of town? When the deal appears. The internet will tell you to pop in at “midnight on a Wednesday with your fingers crossed,” but the truth is that deals often pop up at times that you could never have predicted. The smart ones have those winter escape deals come directly to them. Sites like NextDeparture.ca  and Hotwire.com allow you to sign up for alerts on social media or in your inbox. Google flights is a great way to check deals at a glance. And even your frequent flyer providers offer you options for plugging in the deals you want to keep an eye on. Do them all. The more options you have, the less likely you are to miss a great deal.
  2. Check the weather predictions – I once flew all the way to Spain in search of sunshine, only to be met with “unseasonable” snow flurries. Not cool, Spain.  Truth is, it was my fault for not paying better attention to seasons and weather patterns. Do the due diligence and make sure your winter escape won’t leave you searching for a sweater on the beach.
winter escape sunset
Double check the weather for the month you’re planning your getaway. Just because it’s an island doesn’t mean the weather will be in your favour.
  • Start saving  – Long before you hit purchase on your winter escape, you should be saving for it. I know those $7 Chai lattes are what are getting you through at the moment, but scale down a few bucks and you could be sipping better ones in India, for a fraction of the cost.  And don’t stop your saving mentality  once you’ve boarded the plane. Many of the things that will eat up your vacation dollars happen after you land. Meals, transportation, entertainment and fees can take the wind out of your “living la vida loca” lifestyle. Instead, take some time before you go to make sure you have a sense of the cost of living in the place you’re visiting.
  • Don’t scrimp on the things that matter – A deal is a deal…until it isn’t. There is no regret quite like the kind you have when you realize the flight, hotel or meal you purchased as a “deal,” means you aren’t going to be where you want to be, won’t be sleeping well or are likely to need medical care.  Ditto with your travel insurance. Buying it is only the first step. Make sure you’ve purchased a plan that makes sense for the type of trip you’re taking. Take a few minutes out of your winter escape dreams to think through the kinds of scenarios you want that insurance to cover. Investing the time (and money) now will give you peace of mind should the unthinkable happen.
winter escape coffee paradise
Coffee in paradise? Yes, please.
  • Countdown to Your Happy Place  –  Having a trip on the books will definitely help with winter blues, but it can feel like a lifetime between booking day and take-off. Give yourself reasons to get excited along the way. Whether it’s a paper calendar you can draw a daily red “X” on or mini-dates with your travel partners ahead of time that allow you to prep for the trip (by upping your sake game ahead of Japan or mastering Italian before Positano), working in some reminders of your upcoming getaway will help to keep those cold weather blues away.

Disclaimer:  I am a brand ambassador for Allianz Global Assistance (Canada) and receive financial compensation for these posts. As always, all information shared is my own opinion.

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