Random holiday generator + other hacks to ensure you get a break this winter

Winter in Canada can be a bit of a slog. For our family, it’s when we typically take our annual vacation. In this economy, taking a holiday is admittedly a bit of a luxury. But it you carefully budget for it and use a random holiday generator (I’ll explain later) winter vacations are quite possible. 

Hawaii coastline
Our family would way rather use our travel budget to get to a beach resort in winter than anything else.

After a decade of travel writing, I’ve learned a few tricks on how to turn vacation dreams into reality. Here are my best tips.

Vacation fund jar

There’s no one-size fits all formula when it comes to saving for your vacation. Some families literally have a vacation fund jar they pop bills into on a weekly basis. Some stash cash from any odd jobs they’ve picked up and designate this as their travel spending money.

random holiday generator
All year I save up small bills and Twoonies then use that cash for travel luxuries, like spa treatments at our destination. (Photo credit: Michael Longmire/Unsplash)

It’s a good strategy to pay yourself first and have money siphoned off into a separate bank account on a monthly basis. I’ve heard of families who earmark their tax return for their family vacation.

How to best use travel rewards

If you focus your efforts on loyalty reward programs, they can really add up. Our family’s main credit card offers air mileage points for every dollar spent. Consequently we put most purchases down on this credit card, so long as we’re able to pay off the balance at the end of each month. (Nobody needs to go into debt for travel.)

At the grocery store, our reward points transfer to an airline points program. Even our mortgage gives us mileage points that match the interest owing. Consequently, I rarely pay for airfare. I use those mileage points to the max.

How to find the best travel deals

You’ll score the best travel deals if you’re flexible on timing and location. Several booking sites have features where you plug in your budget or dates and it churns out options for you.

Kayak website
Plug in some variables and out come the options!

KAYAK has an Explore feature, where you plug in your departure city and it brings up deals for you. You can set a budget, dates and direct flights if you like. Or, leave it as open as possible and it’ll show you your best options.

Skyscanner has a similar feature when you plug in “everywhere” as your destination.

You’ll pay more when travelling during high season, which unfortunately, often coincides with school holidays. Travelling outside of peak times is not only easier on the wallet, but popular attractions are much more pleasant with less crowds.

Luckily, just because your children are off school doesn’t mean everybody else’s are. Spring break varies across the country, just as professional days vary by school division.

Value for money, I think all-inclusives are a good option. Especially when so many of them have deals where you can bring young children along for free.

In addition to the web newsletters and meta travel sites, it’s worth picking up the weekend edition of the local newspaper. This is when the travel section runs (and my wellness column!) and all the big players advertise their deals.

Random holiday generator

But where should you travel to, that’s the question. This is where a random holiday generator (Skyscanner, KAYAK) can be useful.

Unless you’re fixated on seeing a particular site, it pays to be flexible. Make a list of three or so must haves. For winter vacations, most folks want reliable, sunny weather, a beach, an ocean or resort-style pool.

family on a beach vacation
Our family wants to do a lot of this on our winter vacations.

Families may prioritize a kid’s club, waterslide and direct flights. Couples may opt for an adults only all-inclusive.

Now that you know what you want, does it really matter if you go to a resort in Barbados versus Cuba? If you’re on a budget and you’ve found a spot where your priorities are met, I think it’s worth going to the more affordable destination. This is where using the random holiday generator (provided by travel search engines) really helps narrow your decision.

If you’re really stumped on where to travel, you’re in luck. With the rise of travel bloggers there’s so much more information at your fingertips. 

Cruise Pinterest for inspiration. Plug your wish list into Google. Start reading travel sites like Canada.com (more than Canadian content). Since you’re reading this post, feel free to ask me for advice in the comment section.

My top picks for winter vacations:

kauai hotel
We once stayed at the Sheraton in Princeville, Kauai and it ticked ALL our boxes.

Cabo San Lucas – direct flights from Calgary, margaritas, guacamole. But you need to be careful on which resort you stay at! Not all sit upon a swimmable beach. If you’re

Hawaii – our family is hoping to head back for a fifth time. Finger’s crossed. It really is magical. And easy. But can be pricy, which is where using one of those random holiday generators really comes into play. 

Don’t forget….

travel essentials
Make sure your passport and all your other photo ID is up to date. (Photo credit: Cynthia Del Rio/ Unsplash)

You don’t want your long awaited vacay to come to an abrupt halt because you got sick. Make sure your vaccinations are up to date and book in with a travel health clinic or injection-certified pharmacist to ensure you have the protection you need.

Travel insurance is also something I always get. If you’re going out of the country, the Canadian government recommends you get some form of travel insurance, as provincial health care is limited if you’re ill or injured outside of Canada.

In addition to travel medical insurance, when I book my daughter and I for our March break trip, I’ll be getting trip cancellation insurance, too. You just never know – especially travelling with kids. For me, it’s a total comfort knowing my hard saved travel fund won’t go down the drain should something unexpected happen (as it often seems to with kids).

Finally, make sure your passport and driver’s license are up to date. My province stopped sending out renewal reminders, and I landed in Newfoundland with my driver’s license expiring the next day. Bye bye rental car. Here’s how I boarded a plane without valid photo ID.

I’d love to hear your tips. How do you save money for travel?

winter vacation tips

You may also be interested in reading:

How to holiday with family and friends without killing each other

Travel apps you need to download before your next trip

Disclaimer, I’m 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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6 thoughts on “Random holiday generator + other hacks to ensure you get a break this winter”

  1. Excellent tips. Can I ask which credit card you use that gives you all those points that are transferred into airline points ?

  2. Totally agree about the Canadian winter blues! I always booked vacation to get out of that lull for a little while to reset. I love the idea of a ‘random generator’, I never really thought of it that way.

    1. I actually didn’t either, but if all you care about is sun, beach and pool, and don’t plan to venture off the resort, it helps you quickly find affordable options.

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