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What are the best ways to get cheap flights to the Caribbean?

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The question

What are the best ways to get cheap flights to the Caribbean? Do we book now or wait for deals?

The answer

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Forget potato versus potato. A real divide among travellers is when to book your trip: Those who pay in advance to snag deals, and those who gamble and wait. Who comes out on top? It depends on what you're after.

Eager beavers

We're approaching high sun-seeking season – roughly December to March. Booking at least 30 days in advance to get the lowest fare is a good rule of thumb, says Michael Duchesne, publisher of, an online travel deals site. This way you're getting the lowest fares from the scheduled airlines, and you've got a lot of choice in terms of when you want to go and where you want to stay. Allison Wallace, a spokeswoman for Flight Centre Canada (, recommends starting the beach watch three months in advance. If you see prices creeping up, it means seats are filling up and it's decision time. (An early start also means you can snag early booking bonuses, which usually appear between August and October. Mark your iCals for next year.)

But there are some winter weeks when sun fares tend to be lower, Wallace says. This includes November to early December, mid-to-late January and April (not including Easter week).

Of course, travelling off-season is always a way to get deals – sometimes hotels are half-price, Duchesne says. But with the mercury dipping, we want to give those flip-flops a chance now, so let's move on.

The waiting game

While some industry veterans caution against last-minute booking, I know many travellers who swear by the practice. Just prepare to be flexible and pay close attention. One friend booked an all-inclusive holiday for five to Cuba through two weeks before departure. The shockingly low price tag: roughly $1,600. "But we were able to be totally flexible," says Ottawa resident Cynthia Grant. "We didn't even particularly care what country we went to – just somewhere warm with a nice beach that was good for kids."

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It's not an exact science, says another pal, George Mota. "Sometimes if you wait too long the deals sell out, so it's a gut feeling kind of thing." Mota keeps daily tabs on his favourites. The reward for such legwork has been seeing the price on his planned trip to Dominican Republic drop several hundred dollars per person. "The key is to have a few options in terms of resorts in case your first option sells out or the price increases again closer to departure, which can happen."

More tips

Don't travel during school holidays. (As a bonus you won't have a bored kid behind you obsessively opening and closing the seat tray. There's no guarantee, however, that the passenger in front won't spend the whole flight reclined in your lap.)

Consider border airports. Departure points – from Washington State's Bellingham to Buffalo, N.Y., and Burlington, Vt., – have been attracting a growing number of Canadians. Flights can cost on average 30-per-cent less compared with Canadian carriers, says Duchesne. But Wallace notes that border airports are best for U.S. destinations. "Plan for lengthy border crossings. Insurance doesn't cover you if you miss a flight due to delays at the border."

Weigh whether it's better to book hotel and airfare together. While we Canadians tend to favour the all-in-one deals, if you have your eye on a more exclusive property, you may be able to find deals, and then later match a flight.

NEXT WEEK: A reader is spending time in Sydney and Melbourne this winter. She wants to see more of Australia but wonders where to start in such a big country. What do you suggest? Send your comments to

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Follow Karan Smith on Twitter: @karan_smith.

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