Get a Good Deal on Your Tropical Winter Vacation


Editor’s note: This article was originally published on December 3, 2013 and was updated on January 14, 2016.

Canadians love taking winter vacations, and we love getting deals. But with all the travel deal websites out there, how do you sort out the good deals from the bad deals? It can be daunting for even the most seasoned Internet researcher. Here are a few tips you can use to get the best price on your winter vacation.

Winter is Peak Season for Warm Destinations

The main obstacle in your path to a travel deal is that winter is the peak travel time for most tropical destinations. But that doesn’t mean deals can’t be found; it just means you have to dig a bit deeper for them, especially if you plan on traveling over the Christmas and New Year holidays.

Be Methodical and Compare

Research deals on,, and other travel deal sites. Once you’ve found a couple of good prospects, bring in the prices to a local travel agent to see if they can beat them. There’s a misconception that travel agents will always be more expensive, when that’s simply not the case. Many of them are experienced with price matching and may be able to offer perks that you can’t get on the deal websites.

Make sure to research the property on TripAdvisor before booking to make sure that your experience will be a good one before you get there. Pay special attention to negative reviews, as some properties have been known to “pad” their online reviews with glowing accounts. Negative reviews should generally feature a management response to the review, and you can make up your own mind as to if the incident was isolated or is a chronic feature of the property. Plus, the negative reviews can be very entertaining.

You’ll also want to call the property directly to make sure that your deal really is an actual discount, and to see if they offer deals of their own.

Be Flexible About Your Destination

If you have your heart set on a particular resort or a particular location, it will be harder to get a deal. Sure, you can search the travel deal websites for the best cost, but you may be able to save hundreds or even thousands of dollars if you are willing to settle for another spot. If you can settle for a non-tropical destination for your vacation, such as Europe or America, you’ll find even better deals.

Start Following Travel Hacking Blogs

Blogs may feel a little 2009 in the world of social media, but there’s a huge online world out there of people who style themselves as “travel hackers”. They’ll post deals as they come up, and offer tips for maximizing your Aeroplan and other bonus points. A couple of good starting points:

These blogs won’t just tell you about deals, but they’ll give you tips on how to avoid being scammed and how to properly make a complaint about your vacation. Keep in mind that some tips may not work for Canadians, which makes the Canadian Travel Hacking blog the most attractive.

Develop a Profile on TripAdvisor and Yelp

When negotiating directly with a property, it’s helpful to have an online presence on TripAdvisor and Yelp. If you don’t have time for both, go with TripAdvisor. You can start by reviewing restaurants in your city and properties that you’ve been to, and after a certain number of reviews you can earn badges which you can name drop when negotiating your deal, especially if you are speaking directly with the company. Hotels and resorts live and die by these reviews, so they may go the extra mile to make sure you are satisfied. This is something that may work better with a privately owned property than a property owned by a giant conglomerate, but it never hurts to have it in your pocket.

Get Travel Insurance

Wherever you plan to go, the one area you don’t want to skimp on is travel insurance. Cut-rate online plans can lack essential coverage that you may need, or may not allow for preexisting conditions that can invalidate your coverage if something happens while you’re away.

Come in and talk to us about getting solid, reliable health insurance for your vacation.

The cost is negligible compared to that of your trip, and can cover things like trip cancellation, lost luggage, and much more besides medical.

Many travel deals are delivered on a “final sale” basis and may not allow for cancellation that this insurance can provide.

Founded Working Web Copy in 1996, specialize in financial services writing. With First Foundation since 2010. In my spare time, you will find me in a kayak or watching episodes…

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