You'll have a hard time finding anyone more connected to the cost of a winter getaway than Chris Myden.
The Calgary-based travel writer has 500,000 subscribers for his newsletters, which send alerts on discount flights and packages from 22 different Canadian cities.  
"I've been looking at prices every day for the last six years," says Myden, who makes a living from his living room, where he's set up a home office with a dual computer monitor setup.
So what's the best deal out there right now? Legions of Canadians will be craving sun and sand very soon, as the temperature dips lower and lower.

'Insane' prices for Central America

"Costa Rica has some insane prices," he says. "Most of Central America is on sale right now, probably because of Zika."
Myden
Travel writer Chris Myden poses while on holiday near Mount Maunganui, New Zealand. (Chris Myden)
The Zika virus is still around, even though it's no longer dominating headlines. So if you're not pregnant and you don't mind running the risk of fever, rash and joint pain, then you can get a sweet deal on a hot holiday in Guatemala, Panama, or Nicaragua.
But is it always necessary to make a sacrifice of some sort, to get a great price? Most travel tips from professional bargain hunters involve unappealing options. For example:
  • Drive to a less-travelled airport to catch a flight. Ottawa residents might be interested in a flight Myden is promoting: round-trip flight to Orlando, Fla., for $154, taxes included — but you have to drive an hour from Ottawa to Ogdensburg, N.Y.
  • Pick an unpopular travel day, such as Christmas Day or New Year's Eve. It may not sound like great timing, but a drop in demand typically means airlines will attempt to entice travellers with discounts.
  • Be completely flexible regarding your destination and accommodation in order to take advantage of a truly last-minute bargain at a resort.
  • Consider a stopover. If you don't mind hanging out at an airport for several hours while en route to your final destination, there are better prices to be found. Myden recently featured a trip from Toronto to Panama for $254 round trip including taxes, but you would have to cool your heels for five hours at the Mexico City airport.
  • Sign up for deal sites such as Groupon or Travelzoo, or get deal alerts from sites such as Kayak or Expedia.
  • Look beyond the luxury of an all-inclusive and do some of your own cooking at a tropical VRBO or Airbnb rental.

Know your travel style

Travel and lifestyle writer Joanne Sasvari of Vancouver has a word of caution for bargain hunters. "You need to know what kind of traveller you are," she says. "It's all well and good to book a cheap one-star hotel to save money, but if you're the kind of person who will be unhappy staying there, you may save money but you won't enjoy your holiday."
Joanne
Joanne Sasvari writes about travel and lifestyle from her base in Vancouver. (Joanne Sasvari)
Sasvari learned the lesson first-hand when she booked an apartment in Budapest through an Irish company, aiming to save money on meals. But the company went bankrupt prior to the trip.
"We arrived, nobody was there, it was a big huge mix-up just trying to get in," she says. And she takes some of the blame herself. "If we'd done a bit better research we might have found out what was going on."
In Sasvari's experience, every great deal means making a sacrifice.
"There's a cost of some sort, and you need to know what you can put up with and what you can't. Honestly, at a certain point it can become so unpleasant you might as well just stay home."

Book 8 weeks ahead

Myden says that every now and then he's surprised to see a well-priced, non-stop flight on a great airline at an ideal time of year. It doesn't happen often, though. And you have to be strategic with your timing.
"Booking about eight weeks ahead of your departure day is a sweet spot," he said during a telephone interview with CBC News. "There's no magic number of days, but one thing for sure, the first price is the worst price. The earliest you can book any flight is a year ahead, and that's always full price. Two to three months before departure is when prices start to drop — the airlines are getting nervous that the flights won't fill up. But then about a month before departure, that's when prices come back up again."

Good deals in January

He also recommends heading south in January, after the holiday rush and prior to February's reading week and the March break. His favourite tip, naturally enough, is that people sign up for his bargain alerts.
Bottom line: if you don't want to spend big money to get to a hot spot during the long winter ahead, you'll need to invest the time required to search and evaluate deals. The reward will come when you toast your frugality with a pina colada on the beach.
@chayil$