Where Are Canadians Vacationing This Winter? Our Top Picks — Near & Far

The Ultimate Winter Escape Guide for Canadians:
Let's be honest—January and February in Ontario can feel long. Really long.
You've got two choices: chase the sun or lean into winter. But let's skip the same tired all-inclusive recommendations everyone's been to three times already. Here's where to go when you actually want to experience a place, not just survive beside a pool.
The Sunny Escapes (When You Need Vitamin D)
Tulum, Mexico - Rent Your Own Place
Flight time from Toronto: 4.5 hours (fly into Cancún, 90-min drive)
Forget the mega-resorts. Rent an Airbnb or villa in Tulum and you'll get a completely different Mexico experience. We're talking jungle casitas with private pools, walking distance to cenotes, and that boho-beach town vibe that Instagram made famous (but is still genuinely cool).
What makes it worth it: You're living like a local, not trapped in a resort compound. Hit beach clubs like Papaya Playa Project, eat at local spots in town (try Antojitos La Chiapaneca for real tacos), explore Mayan ruins without tour groups, and swim in cenotes most tourists never find.
Budget sweet spot: $150-$300/night for a solid Airbnb, plus your own food/entertainment budget. Total trip: $1,500-$2,500 per person for a week.
Pro tip: Stay in Aldea Zamá (5 minutes to the beach, close to town) or La Veleta (more local, better prices).
Puerto Vallarta - Old Town Airbnb
Flight time from Toronto: 5 hours
The Romantic Zone (Zona Romántica) in Old Town Puerto Vallarta is where you want to be. Rent a condo with a rooftop terrace, walk to everything, and experience the cobblestone-street charm that resort guests never see.
What makes it worth it: You're in the heart of authentic PV—local restaurants, the Malecón boardwalk, beach clubs, street tacos at 2am. You control your schedule and budget. Want a fancy dinner? Go for it. Want street food? That too.
Budget sweet spot: $120-$250/night for an Airbnb in Zona Romántica. Total trip: $1,400-$2,400 per person for a week.
Pro tip: Book places near Playa Los Muertos for walkability. The Wednesday evening art walk is worth timing your trip for.
Unico 20°87° Riviera Maya (All-Inclusive Done Right)
Flight time from Toronto: 4 hours
If you're doing all-inclusive, do it properly. Unico is adults-only, boutique-sized (only 448 rooms compared to massive resorts), and includes stuff that actually matters—premium liquor, pop-up dining experiences, and excursions to cenotes and Mayan ruins included in your rate.
What makes it worth it: No buffet lines. No kids screaming at the pool. Three chef-driven restaurants, mezcal tastings, and a concierge who'll book you authentic local experiences beyond the resort walls.
Budget sweet spot: $3,500-$5,500 per person for a week (watch for January promos). Worth it for milestone trips.
Cartagena, Colombia
Flight time from Toronto: 6 hours (direct on Avianca or via connecting flight)
Here's one most Canadians haven't been to yet. Cartagena combines colonial architecture, Caribbean beaches, and incredible food at prices that'll make Mexico feel expensive. The Old City is UNESCO-listed for good reason—wandering those streets feels like stepping into another century.
What makes it worth it: Unique. Affordable. Warm year-round (28-30°C). Stay in a boutique hotel in the walled city, take day trips to Rosario Islands for beach time, eat your way through the local food scene (arepas, ceviche, fresh fruit you've never heard of), and still come in under budget.
Budget sweet spot: $1,800-$2,800 per person for a week including boutique hotel and activities.
Pro tip: Stay in Getsemaní neighborhood—hipper, more local, better value than the tourist center.
Barbados
Flight time from Toronto: 5 hours (direct on Air Canada)
Another one flying under Canadian radar. Barbados has British colonial charm mixed with Caribbean beaches, better infrastructure than most islands, and a food scene that rivals anywhere in the region. It's not overcrowded with tourists, and locals genuinely enjoy visitors.
What makes it worth it: Beautiful beaches without the resort chaos. Rent a villa on the west coast (calm waters) or south coast (surf and local vibe). Explore rum distilleries (Mount Gay is the world's oldest), eat flying fish, and actually relax without feeling like you're on a tourist conveyor belt.
Budget sweet spot: $2,200-$3,500 per person for a week with villa rental and activities.
Pro tip: Rent a car. The island is small and easy to navigate, and you'll want to explore beyond your home base.
The Classics (Still Worth It)
Varadero, Cuba - Still the closest warm beach at 3.5 hours, still incredible value ($1,000-$1,500/person for a week all-inclusive). If you haven't been, go.
Turks & Caicos - If you want that pristine, world-class Caribbean experience and don't mind spending more ($2,500-$4,000/person for a week). Grace Bay Beach is as good as advertised.
The Stay-Close Escapes (When You Want Winter, Just Better)
Not everyone wants to fly. Some of us actually like winter—we just need it served up right, with hot chocolate and a fireplace instead of shoveling the driveway.
Blue Mountain Resort, Collingwood
Drive time from Barrie: 45 minutes
You know this one, but have you done it properly? Book a mid-week stay, hit the slopes without the weekend crowds, and spend your evenings at the Scandinave Spa alternating between hot pools and cold plunges under the stars.
What makes it worth it: Close enough for a spontaneous getaway, far enough to feel like you left. The Village at Blue has enough restaurants and shops to keep non-skiers happy.
Budget sweet spot: $300-$500/night for a decent condo (split with another couple and it's very reasonable)
Muskoka in Winter
Drive time from Barrie: 1-1.5 hours
Everyone thinks Muskoka is just for summer. They're wrong. Winter up here is magical—frozen lakes, snowshoeing trails, and resort properties you can actually afford in the off-season.
Stay at Taboo Resort or JW Marriott The Rosseau and enjoy ice fishing, fat biking, and the kind of quiet you forgot existed. Huntsville's downtown has solid local restaurants (try 3 Guys and a Stove).
What makes it worth it: No crowds, lower prices, and that cabin-in-the-woods feeling without roughing it.
Budget sweet spot: $250-$400/night for resort properties
Stratford
Drive time from Barrie: 1.5 hours
Not just for theatre season. This town knows how to do winter—boutique hotels in heritage buildings, farm-to-table restaurants that'll ruin you for chain dining, and enough small-town charm to reset your nervous system.
Hit Bijou for French-inspired dinner, Revival House for craft cocktails, and walk off your meal browsing the antique shops on Ontario Street.
What makes it worth it: You can unplug completely without feeling like you're missing out. The food scene punches way above its weight.
Budget sweet spot: $200-$350/night for boutique accommodations
Ottawa Winterlude (February)
Drive time from Barrie: 3.5 hours
Time it right for Winterlude (usually first three weekends of February) and you get a full winter festival—ice sculptures, the Rideau Canal Skateway, sugar shack treats, and enough outdoor activities to make you remember why Canada in winter is actually awesome.
What makes it worth it: It's a proper winter celebration instead of just enduring the season. Plus ByWard Market has year-round food halls and pubs worth the trip alone.
Budget sweet spot: $150-$250/night for downtown hotels
Prince Edward County
Drive time from Barrie: 2.5 hours
The County in winter is underrated. Wineries stay open, local restaurants shift to cozy winter menus, and you can explore without the summer crowds clogging Highway 33.
Book a heritage B&B, do a winery tour (Huff Estates and Closson Chase stay open), and hit Drake Devonshire for upscale comfort food with Lake Ontario views.
What makes it worth it: Feels like a proper getaway despite being close. The wine is legitimately good, and the local food scene rivals anything in Toronto.
Budget sweet spot: $180-$300/night for B&Bs or inns
The Real Advice
If you need sun and want flexibility: Rent an Airbnb in Tulum or Puerto Vallarta. Live like you actually live there, not like you're on vacation lockdown.
If you want all-inclusive but elevated: Skip the 2,000-room mega-resorts. Book somewhere like Unico where quality beats quantity.
If you want to tell people about somewhere they haven't been: Cartagena or Barbados. Both are warm, affordable, and genuinely interesting.
If you need a reset but don't want airports: Stay within 2 hours of home. A genuine change of scenery doesn't require a passport—it requires getting out of your routine.
If you're on the fence: Consider this: winter's already long. A 3-4 day break in January or February makes the second half of winter infinitely more bearable.
Whatever you choose, just go. We're not built to hibernate for six months straight.
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