How To Snag A Winter Travel Deal

With the holidays over, we’re always looking to escape during the long winter months, whether you’re dreaming of a hot destination or a cold one. We share our best tips for getting a great winter travel deal PLUS where you need to visit now.

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Use your points

Whether you’re going to take a flight, book a hotel or rent a car for a winter road trip, using your points is a great way to save on costs, or even treat yourself to an upgrade.

Book with a tour company

A lot of organized tour groups offer great deals during the winter months to winter destinations, or to last minute destinations. You can often save up to 40% by booking with a tour group. And an added bonus is you don’t have to stress about anything when it comes to an organized tour. Your hotels, flights, itinerary, etc. are all taken care of.

Avoid these days

The beginning and end of long weeks or spring break periods are often very expensive when it comes to flights and hotels. If you can swing it (use lieu or flex days) book either a couple of days before or after those keys dates for a better rate.

Don’t forget to double check your insurance

A lot of people assume they have enough travel insurance coverage through their work or benefits or on their credit cards. For example, a recent survey by TD Insurance recently found that 31% of people Canadians don’t purchase travel insurance because they are covered through their credit card. But you really need to look at the fine print to make sure you are in fact covered for cancelled flights, medical emergencies, lost bags, etc. Without the right insurance coverage, those costs could be staggering post trip and really go outside your budget.



With direct flights from Toronto to San Antonio (it’s under a 4 hour flight!), it’s easy to sneak away for a bit of warmer weather for a long weekend. You can take in the river walk in the city, eat some amazing Tex-Mex and Mexican food, and even better you’re about an hour away from Fredericksburg and Texas wine country — they actually have amazing rose!

British Columbia

BC has to be one of the most beautiful places in our country during the winter months. You can always get your ski time in at Whistler, but going inland to Kelowna (think winter wine destinations and staying at the Delta Grand Okanagan), or heading to Victoria are also great options to do during the cooler months because they’re not as busy (stay at the Ocean Pointe Resort right on the water). If you are hitting up Whistler, and are an avid skier, look at getting a ski pass that works at multiple destinations (Park City, Blue Mountain, etc), so you can get some extra bang for your buck (and a couple of extra trips!).

Puerto Rico

Coming off the terrible hurricane season, Puerto Rico is ready to welcome people back to the island, which means you’ll be able to find some good deals. It’s great for a mix of beach time and some city culture. Plus you’re helping out their tourism community and it’s always nice to give back when you’re travelling.

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