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
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
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.