1. Dress smart
Landing in 40 C heat wearing jeans isn't fun, but you also don't want to be that fool shivering in the airport in shorts and a tank top while waiting for departure. Consider wearing convertible zip-off pants, or leggings under a sundress, with an extra layer on your top half. When you hit the sun, it'll take you about 30 seconds to be dressed appropriately.
2. Check your coat
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Schlepping a heavy winter coat all around a tropical island is a hassle – and also serves as an omnipresent reminder of the cold to which you shall soon return. Leave your cares behind – literally – by checking your coat before you hit security. Airports in most major Canadian cities, including Toronto, Vancouver, Calgary, Montreal and Halifax, will let you store gear for as little as $2 a day.
3. Protect yourself
For those of us who burn easily, our pasty winter skin can be extra-sensitive to a sudden dose of extreme sun. Visiting a tanning booth to "build a base layer" is not the way to go. Instead, pack sunscreen (of course) and consider investing in sun-blocking UPF clothing. At the very least, if you're planning on snorkelling, get a rash guard or other swim shirt. Your back will thank me.
4. Stay warm
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Business operators in sunny locales often seem to forget that many of their guests are there to escape the cold: As the temperature rises outside, they crank up the air conditioning indoors. During a recent trip to San Juan, for example, I walked into my frigid hotel room to discover the thermostat had been set to 15 C. Pack a sweater that goes with most of your outfits.
5. Pack the essentials
Finally, it's always the little things you forget to pack, so here's a handy checklist that might just save you having to fork out $40 at the resort gift shop: sunglasses, hat, sunscreen for face and for body, flip-flops or other sandals, bug spray and a bathing suit.