As frost settles across Canada and daylight fades by mid-afternoon, the thought of turquoise surf and golden sun feels like an indulgent dream. But this winter, Sunwing Vacations is turning fantasy into possibility with its 2025 Winter Holiday Promotion — a nationwide travel contest giving readers the chance to win a vacation to iconic destinations like Mexico and Jamaica. For anyone yearning to swap snow boots for sandals, this is your golden ticket to summertime in the tropics.
How to Enter Sunwing’s Winter Holiday Promotion 2025
Participation in the Sunwing contest 2025 is remarkably straightforward. Travellers can submit their entry online through Sunwing’s official website during the Contest Entry Period, which runs from December 1, 2025, to January 15, 2026.
To qualify, entrants must meet the eligibility requirements for entering the summer holiday sweepstakes set out in the official contest rules and regulations, including being a legal resident of Canada and at least 18 years of age at the time of entry.
Each participant automatically joins the draw for one of the 20 contest prizes, each representing an all-inclusive Sunwing vacation valued at approximately CAD $2,500. Winners will enjoy a 7-night stay at a participating resort destination in Mexico or Jamaica, with return flights included — a complete sun-soaked experience curated by one of Canada’s most trusted travel brands.
According to Samantha Kelly, Director of Marketing at Sunwing Vacations, “We know how much Canadians long for warmth during the winter months. This contest is our way of turning that wish into reality — offering not just a trip, but a moment of joy and connection during the coldest time of year.”
Why Now Is the Perfect Time to Win a Winter Escape
There’s something poetic about 2025 being a year of rediscovery in travel. With international tourism fully rejuvenated, Canadian travellers are embracing the freedom to explore again — not merely chasing luxury, but seeking authentic experiences that restore emotion and perspective.
The Winter Holiday Promotion embodies that post-pandemic travel energy: spontaneous, bold, and deeply personal.
A recent Travel Alberta report noted that winter travel searches for “all-inclusive escapes” in December have surged by 36% year-over-year.
As Kelly adds, “We’re seeing an emotional rebound in travel — people are more spontaneous, more eager to celebrate life’s milestones abroad.”
The Sunwing sweepstakes for all-inclusive resort stays rides this wave perfectly, giving Canadians a tangible way to chase the light again.
Experience Mexico and Jamaica Through an All-Inclusive Sunwing Vacation
Winners of the 2025 contest will have their pick of Sunwing Vacations’ premier resorts across the Caribbean and Mexico. Imagine waking to the rhythmic pulse of reggae along Jamaica’s Seven Mile Beach, or drifting through Mexico’s Riviera Maya, where palm fronds shimmer under cenote-blue skies.
At each destination, guests enjoy curated stays designed to celebrate local textures and flavours — from Jerk-spiced seafood cooked beachside in Negril to archaeological explorations at Chichén Itzá, followed by a swim in ancient limestone pools.
Beyond the postcard perfection, Sunwing Vacations emphasizes cultural connection. Travellers are encouraged to explore local art markets, take cooking classes, or join guided reef conservation tours.
As Marisol García, Tourism Director for Quintana Roo, notes: “Visitors aren’t just tourists — they become part of the story our communities are telling.”
What Happens After WINNER SELECTION — How to Make the Most of Your Prize
Winners will be notified of the Sunwing giveaway directly via email and public announcement on Sunwing’s website, where the following steps are clearly outlined. Once verified, participants will have several months to finalize travel arrangements.
Each prize includes flexible booking options, allowing winners to travel between February and December 2025, subject to resort availability.
For those planning ahead, now’s the time to check passport expiry dates, review travel insurance, and research destination entry policies — particularly for those seeking cultural add-ons beyond the resort.
Sunwing’s travel advisors can help customize itineraries to include nature excursions, spa pampering, or culinary tours. “Treat it like a dream realized,” advises Janet Lee, a former winner of Sunwing’s previous holiday giveaway. “We added an extra day to wander local villages — it made the trip unforgettable.”
Maybe This Winter, Paradise Really Is Just One Entry Away
As Canadian evenings stretch longer and the air sharpens with cold, the Winter Holiday Promotion feels like a warm, hopeful retreat. There’s something profoundly human about the idea of escape, especially when it’s tied to sunlight, shared laughter, and discovery.
Whether you’re drawn to Mexico’s Maya ruins or Jamaica’s rhythmic soul, Sunwing’s seasonal giveaway promises not just travel, but transformation.
So this winter, when you scroll through vacation images yearning for warmth, remember — the invitation is real.
All it takes is one chance to win to step into the story for yourself. In a season of giving, Sunwing Vacations might just redefine what it means to truly win a vacation.
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