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Yes, it’s already February, and your warm tropical vacations might already be booked or over this year. But hey, 2027 is very much in the cards, and with an unusual cold snap in my hometown of Ottawa and much of southern Ontario, I figured it’s nice to take a gander at flying to sun destinations for the next trip.
Aeroplan
Aeroplan is a fantastic program when it comes to booking flights to the Caribbean (and beyond), with economy flights generally costing 12,000-20,000 points one-way per person. Much of the Caribbean falls into the awkward length where you want to fly in business class, but the flights are operated on narrow-body aircraft and/or business-class prices are very high.
As Air Canada does observe dynamic pricing, you’ll want to keep an eye on prices and book as soon as it’s reasonable. United will also have lots of options with a connection.
In the above example, I’d take the 25,000-point business class flight for sure (though there is a 24h layover in Washington D.C.).
My main recommendation would be to begin your search the year before; do not wait until the fall when everyone starts booking their winter getaways, as that is when prices increase dramatically.
The first flight is operated on an A330-300 on mainline Air Canada with lie-flat business class seats. While I wouldn’t pay 86,000 points, I’d try to be flexible with dates and book when there is reasonable premium economy pricing, then apply my eUpgrades.
WestJet via Air France KLM Flying Blue
WestJet is another option for direct flights to sunny destinations, and the best way to book them is through Air France KLM Flying Blue. Delta Skymiles is another option for booking WestJet flights, but Skymiles prices increase dramatically outside the U.S. and Canada.
For example, a flight from Toronto to Cancun costs 14,000 Flying Blue miles per passenger, while Delta SkyMiles charges 33,000 miles.
Flying Blue is also 25% off the points price for kids 11 and under, so in the above example, kids would cost just 10,500 Flying Blue miles. Last month, Amex also improved the transfer ratio to Flying Blue from 1:0.75 to 1:1, making Flying Blue redemptions more attractive than ever.
Porter via Atmos Rewards
I’ve already extolled the value of Atmos Rewards, and one of their best use cases is flying Porter Airlines. Specifically, redeeming for Porter Reserve, where the premium over the regular standard economy cost is minimal. As a reminder, Porter is now flying to Nassau, Grand Cayman, Puerto Vallarta, Cancun, and even to Costa Rica.
Take this direct flight from Ottawa to Liberia, Costa Rica – it’s nearly 6 hours of flight time and paying an extra 5,000 points for Reserve is such a sweet spot.
From the West Coast with Finnair Avios
You might have noticed most of the article is focused on flying from Eastern Canada; the reality is that it is easier to find award space from this side and many flights from West Coast will involve a connection of higher prices due to it being a longer distance.
The above tactics still apply, like booking Aeroplan far in advance when dynamic pricing is reasonable and booking WestJet via Flying Blue.
There is one particular sweet spot I wanted to highlight: booking American Airlines business class for just 25,000 Finnair Avios one-way between Canada and the Caribbean.
As the Finnair Avios award chart is regional, flying from the West Coast is a better value. A friend of mine booked Vancouver – Dallas – Cancun entirely on American Airlines business class for just 25,000 Avios per person. The same price should apply for AA’s entire Caribbean network, and I am eyeing a redemption from Toronto to Sint Maarten (SXM) via Chicago, Philadelphia, or Miami.
Acquiring Finnair Avios
Search for award space on the American Airlines or British Airways websites and then call Finnair to make this booking.
You can transfer Avios between flavours (that is, between British Airways, Finnair, Qatar, and more) online at Avios.com. Therefore, you can transfer your Amex MR or RBC Avion points to British Airways (even better when there is a 30% transfer bonus) and then move them to Finnair once you confirm award space.
Takeaway
Sun destination vacations over peak winter periods can be expensive, but for good reason – how much I’m willing to pay to escape southern Ontario does increase in proportion with the snow levels on my driveway.
But with some finagling and a little finesse, you can save a big chunk of vacation costs by booking flights on points. A highlight reel of good redemption options includes Aeroplan for Air Canada and United, Air France KLM Flying Blue for WestJet, Atmos Rewards for Porter, or Finnair Avios on American Airlines.
