Smart Cancun
Room OnlyCancun
Mexico
From Toronto (YYZ)Sunwing Vacations · Direct flightDeparts Wed, Sep 23
- 7 nights
- Smart Room
- Flights incl.
From
$915
per person · taxes incl.
or $76/mowith FlexPay
Winter Vacation Deals
Book by August 31 and save an extra $100 with code SUN100.
Top winter vacation deals
Explore hand-picked winter packages to warm-weather favourites across Mexico, the Caribbean and beyond.
Winter packages by departure city
Live packages by departure city — flights, hotel and transfers in one price.
Flying from
3.8 (876)
Reserva Real By Harper
Room OnlyPunta Cana
Dominican Republic
From Toronto (YYZ)Air Canada Vacations · Direct flightDeparts Thu, Oct 29
- 7 nights
- Run Of The House
- Flights incl.
From
$1,012
per person · taxes incl.
or $84/mowith FlexPay
Vik Hotel Arena Blanca
All-InclusivePunta Cana
Dominican Republic
From Toronto (YYZ)Transat Holidays · Direct flightDeparts Tue, Nov 3
- 7 nights
- Room Gardenview
- Flights incl.
From
$1,061
per person · taxes incl.
or $88/mowith FlexPay
Eurostars Grand Cayacoa
All-InclusiveSamana
Dominican Republic
From Toronto (YYZ)Sunwing Vacations · Direct flightDeparts Sat, Sep 12
- 7 nights
- Deluxe Oceanview Room
- Flights incl.
From
$1,095
per person · taxes incl.
or $91/mowith FlexPay
The Fives Downtown Hotel Residences
Room OnlyRiviera Maya
Mexico
From Toronto (YYZ)Transat Holidays · Direct flightDeparts Mon, Oct 26
- 7 nights
- Superior Room
- Flights incl.
From
$1,178
per person · taxes incl.
or $98/mowith FlexPay
Viva Heavens By Wyndham
All-InclusivePuerto Plata
Dominican Republic
From Toronto (YYZ)Sunwing Vacations · Direct flightDeparts Fri, Oct 2
- 7 nights
- Bliss Room
- Flights incl.
From
$1,183
per person · taxes incl.
or $98/mowith FlexPay
Blue Bay Villas Doradas
All-InclusivePuerto Plata
Dominican Republic
From Toronto (YYZ)Transat Holidays · Direct flightDeparts Wed, Sep 9
- 7 nights
- Promo Room
- Flights incl.
From
$1,188
per person · taxes incl.
or $99/mowith FlexPay
Hotel Marina El Cid Spa And Beach Resort
All-InclusiveRiviera Maya
Mexico
From Toronto (YYZ)Sunwing Vacations · Direct flightDeparts Thu, Sep 10
- 7 nights
- Luxury Room
- Flights incl.
From
$1,205
per person · taxes incl.
or $100/mowith FlexPay
Transparent pricing
Book with confidence
Real people, real support
Escape the Canadian winter
Swap short, cold days for warm sunshine. A winter vacation gives you the mid-season reset that makes the rest of winter easier.
Choose your kind of escape. Unwind at an all-inclusive resort, explore a new city or settle into a beachfront hotel with nothing on the schedule.
Packages keep planning simple. Bundle your flight and hotel in one booking, with options for different budgets, travel dates and departure cities.
Where to go for winter sun
Mexico and the Caribbean are classic winter favourites for good reason: warm weather, beautiful beaches and convenient flights from Canada. Choose Cancun or Riviera Maya for resorts and nightlife, Punta Cana for long beaches and easy all-inclusive stays, or Cuba and Jamaica for laid-back island time. For something different, look to Florida, Costa Rica or destinations farther south where summer is just beginning.
More seasonal getaways
Winter vacations FAQ
Where is the best place to vacation in winter?
Mexico, the Dominican Republic, Cuba and Jamaica are among the most popular warm-weather winter destinations for Canadians. The best choice depends on your budget, departure city and whether you prefer beaches, activities, nightlife or a quiet resort.
When should I book a winter vacation?
For the best selection, book three to six months before departure. Christmas, New Year and March break dates sell quickly, while travellers with flexible dates may find last-minute offers outside peak periods.
What is included in a winter vacation package?
Most packages combine round-trip flights and hotel accommodation. All-inclusive packages may also include meals, drinks, resort activities and airport transfers, but inclusions vary, so review the package details before booking.
What is the cheapest month for a winter vacation?
January after the holiday rush and parts of early December can offer better value. Prices are usually highest over Christmas, New Year, family day weekends and provincial March break periods.
How can I find the best winter vacation deal?
Compare several destinations, keep your departure dates flexible and check nearby airports when practical. Booking early gives you more choice, while last-minute deals can work well if your dates and destination are flexible.