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Explore hand-picked winter packages to warm-weather favourites across Mexico, the Caribbean and beyond.
Live packages by departure city — flights, hotel and transfers in one price.
Punta Cana
Dominican Republic
Sunwing Vacations · Direct flight
Cancun
Mexico
Sunwing Vacations · Direct flight
Punta Cana
Dominican Republic
Air Canada Vacations · Direct flight
Punta Cana
Dominican Republic
Transat Holidays · Direct flight
Puerto Vallarta
Mexico
Air Canada Vacations
Riviera Maya
Mexico
Transat Holidays · Direct flight
Puerto Plata
Dominican Republic
WestJet Vacations · Direct flight
Puerto Vallarta
Mexico
Air Canada Vacations · Direct flightChosen and checked by shoptravel travel advisors.
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.
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.
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.
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.
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.
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.
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.
Flight + Hotel
Flights
Cars
Cruises
