Your Essential Packing Checklist for a Warm Winter Getaway


Now that the snow has been hanging around for a little while, we can’t help but start to daydream of sun, sand, and drinks by the water. If you’re lucky enough to be planning a sunny winter getaway (talk to our friends at Flight Centre to book yours!), you’re probably wondering what to pack. “There are limited items available in stores for sunny destination packing,” says stylist Allana Schmidt of, who styled these looks. With that in mind, we did the leg work for you, hunting through the parkas and heavy boots to find sweet picks around the Centre that pack light, look great, and will take your style all the way to your hot destination! 

Here’s our complete packing checklist, full of our beach travel must-haves to keep you organized and stylish for your winter vacation:

  • A few cute and comfy dresses that can pull double-duty as swimsuit cover-ups by day, and chic evening wear by night. “Pick pieces that can transition from day to night and vice-versa,” says Schmidt. A relaxed maxi dress (like this blue striped option) “can be worn as-is in the daytime, and only needs a make-up and hair change plus a shawl for the evening.” We also found this incredible 8-way convertible black dress that packs tiny and will give you an endless supply of looks, from casual to sexy.

  • Two swimsuits you feel absolutely great in. Luckily, swimsuits take up very little real estate in your luggage – be sure to pack two, because one will always be wet from all that pool/beachside lounging! Don’t forget to start your swimsuit search early, since it’s such an important (and sometimes stressful) purchase. Our friends at Swimco, Aqua La Vie en Rose, Diva Lingerie, and other retailers carry swimwear to have you covered (and uncovered!) all winter long.

  • Two pairs of slip-on shoes. Go for comfy sandals for long walks around town and the resort, but be sure to pack a flirty pair of heels for dinner and dancing. Keep them neutral enough to go with each of your packed outfits.

  • A fun and floppy sun hat to keep you protected. Your skin is going from -30 to +30, after all… A hat will help you avoid sunburn, plus it’s a great chance to show off your style.

  • A convertible purse to carry your must-haves. We love this one from BCBGMAXAZRIA that has two halves that snap together for a multi-compartment cross-body bag, or can be pulled apart to use one half as an evening clutch. Brilliant!

  • A couple of great beach reads. This is your vacation – and you deserve to spend it getting lost in a book! If you love to read, take two and pass the time during airport waits, as well as at the resort.

  • Cute costume jewelry to accessorize your vacation style. Leave the good stuff at home where it’s safe and pack cute, inexpensive accessories to help mix up your look. Long necklaces, fun bangles, and dangling earrings are casual enough for day, or can be layered together for night.

  • Beach-friendly, travel-sized beauty products to combat the change in climate. “Don't forget those items that aren't clothing!” says Schmidt. “Make-up, sunscreen, and hair products are just as important for making sure you look good while away.” A good sunscreen is a must, as well as frizz-fighting hair products and pretty make-up to complement your look (shimmery lip glosses are especially fun in warm climates and look great in the sunshine).

  • Some tasty treats to tide you over during the flight or while you’re waiting to check in. There’s nothing worse than being tired, jet-lagged, AND famished –avoid that problem altogether with a few packed snacks.

  • A pair of cute wireless headphones. Block out all the stressful noises on the plane, then relax with your favourite tunes on the beach.

  • A roomy, yet easy-to-transport, piece of luggage to hold it all together. Make sure it has amazing internal compartments to keep you organized, and a pull handle for easy airport maneuvering. Look for unique colours (like rich raspberry or navy blue polka dots) to keep it easy to spot on the crowded luggage carousel.

Are you planning a warm weather getaway this winter? We want to hear about it! Share your favourite packing tip with our Spark readers. Bon voyage!

Look #1 (black wrap dress)
Black convertible dress: Swimco, $40
Black pumps (Steve Madden): Hudson’s Bay, $100
Diamond solitaire necklace: Silverstone, $29.99
Gold/multi-stone bracelet: Le Chateau, $25
Clear jewel drop earrings: Le Chateau, $9.95
Pearl wrap ring: Le Chateau, $18
Red luggage: Bentley, $129.99
White & grey floppy hat: Aqua La Vie en Rose, $19.95
Canada luggage tag: Bentley, $9.99

Look #2 (blue stripes)
Blue striped tank dress: Swimco, $68
Diamond solitaire necklace: Silverstone, $29.99
Gold/multi-stone bracelet: Le Chateau, $25
Clear jewel drop earrings: Le Chateau, $9.95
Black purse: BCBGMAXAZRIA, $229
Pink passport cover: Chapters, $16
Burton luggage: Spare Parts, $260

Look #3 (luggage)
Turquoise swim top: Aqua La Vie en Rose, $39.95
Turquoise swim bottoms: Aqua La Vie en Rose, $34.95
Multi-coloured swim top: Aqua La Vie en Rose, $39.95
Multi-coloured swim bottoms: Aqua La Vie en Rose, $34.95
Black pumps (Steve Madden): Hudson’s Bay, $100
Packable duffel (Herschel): Spare Parts, $30
Snakeskin headphones (Skullcandy Crusher): West49, $120
Pink & black passport covers: Chapters, $16 each
Leather passport cover (Herschel): Spare Parts, $52
What I Know for Sure (hardcover): Chapters, $28.99
The Happiness Project (paperback): Chapters, $17.99
Milk chocolate: Chapters, $5
Maple crunch: Chapters, $11
Shiseido Ultra Sun Protection Lotion SPF50: Sephora, $49
Clinique City Block Sheer SPF40: Sephora, $26
MAC Lipglass: MAC, $12 each
MAC Eye Pigment: MAC, $12
Marc Jacobs Beauty Enamored Hi-Shine Nail Lacquer: Sephora, $22

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