Enjoy free skating at Nathan Philips Square in downtown Toronto this winter

Best Winter Weekend Getaways From Toronto

Published: January 12, 2023

It’s time to pack your bags and head out on a winter weekend getaway! Break up your winter routine with a short break, whether that means hitting the slopes for a ski weekend, a girls’ weekend shopping trip to a big city or soaking up some sun down south with the family, there is a perfect winter break for everyone and we’re here to help you make the most of your winter travel plans.

Connecting Toronto Pearson Airport and downtown Toronto in 25 minutes with two convenient stops in between, UP Express offers a comfortable onboard experience with ample luggage storage, free Wi-Fi, and savings on fares for adults, seniors, post-secondary students and youth with PRESTO. Plus, kids under 12 always travel for free!
Get inspired with our top winter weekend travel picks.

Winter Weekend Getaways In Ontario

Winter weekend getaways in Ontario include Prince Edward County

Ontario has it all when looking for a winter weekend getaway that works with any budget, no matter if you are travelling solo, as a couple, with friends, or with family. Grab your BFFs for a girls’ weekend at Blue Mountain in Collingwood where you can indulge in some skiing or sit back and soak in the après ski ambiance for a little solo relaxation in a hot tub at the Scandinave Spa. Couples looking for a little romance should head to Prince Edward County for cozy and snowy wine tastings in the country with an Instagram-worthy stay at the Drake Devonshire Hotel, the cozy and hip PEC outpost of downtown Toronto’s Drake Hotel.
There is no better place to take the family than Niagara Falls. Equally fun for the young and young-at-heart, Niagara Falls is pure magic in the winter as the mist from the mighty waterfalls coats everything in a sheet of ice that sparkles. But it’s not just the wondrous natural sights here, warm up along the family-friendly fun houses and museums that line Clifton Hill, take a ride on the Niagara SkyWheel for spectacular views or simply spend the day at Great Wolf Lodge, Niagara’s premiere indoor family waterpark resort. GO Transit services Niagara Falls all-year round, making connections from downtown Toronto’s UP Express Union Station a breeze.

Of course, there’s always plenty to see and do in Toronto in the winter – from ice skating and shopping to museums, sporting events, nightlife, and incredible restaurants and neighbourhoods to explore – there is a Toronto vacation for everyone!

Weekend Trips In Canada During Winter

Enjoy free skating at Nathan Philips Square in downtown Toronto this winter

Sometimes you want to get even further out of town. Canada has lots to explore during the winter, especially if you’re ready to bundle up!
Just an hour and a half by shuttle bus from Vancouver International Airport in British Columbia, you’ll find the picturesque village of Whistler Blackcomb. Perched at the base of two mountains, there are lots of ways to keep busy here – even if you don’t ski! From outdoor spa experiences to fine dining, be sure to experience the Peak 2 Peak gondola for the most incredible views of the snowy mountainside between Whistler and Blackcomb mountains. If a true weekend ski vacation is what you’re after, skiing at Banff and Lake Louise in Alberta and Mont Tremblant in Quebec have some of the best snow-filled weekend experiences for skiers and snowboarders, welcoming all ages and skill levels.
From Ontario, head east to Nova Scotia where the winter weather doesn’t put a damper on outdoor fun the whole family can enjoy. Snowshoeing the Franey Trail in Cape Breton Highlands National Park offers stunning 360-degree views of the Atlantic coastline or head to Sugar Moon Farm where you can explore over 30 km of winter hiking trails before warming up at their maple syrup camp. For those who aren’t afraid to get a little wet, get on a board with the locals who surf the winter swells at Lawrencetown Beach outside of Halifax – even in the middle of winter. The water here typically hovers around 0 degrees Celsius and the friendly locals are always happy to welcome newbies who want to test out the surf.

U.S. Weekend Getaway Destinations

Take a winter weekend trip to New Orleans during Mardi Gras in February 2023

Head south of the boarder for a weekend getaway from Toronto! The possibilities are endless with U.S. weekend destinations just a few hours away by flight. See the sights in New York City with a weekend full of shopping, Broadway shows, and some of the country’s top dining experiences. The hustle and bustle of the city also makes it a great trip for solo travellers who can keep busy exploring all the museums and landmarks the city has to offer. Those looking for some winter excitement can plan a weekend of live music and tasty seafood po’boys in historic New Orleans, Louisiana where it’s always a party on Bourbon Street. Time your weekend trip around Mardi Gras as the city welcomes revellers from around the world to their famous celebrations culminating in the bead-filled parade on February 21, 2023.

Warm weather weekend destinations like Miami offer fun in the sun

Trade the winter weather for some sun and fun in Miami, Florida where you can hit the beach during the day and snap Insta-worthy pics of the colourful historic Art Deco buildings before dancing the night away at one of Miami’s hottest dance clubs. Just a two-hour flight from Toronto, Nashville, Tennessee makes for the perfect girls' weekend getaway for music-lovers with its honky-tonks, live music venues, museums, and more! A long weekend is plenty of time for a friends’ trip to check out the sights in Los Angeles, California and rub elbows with the stars with a shopping trip to Rodeo Drive or the newly-opened Academy Museum where you can get up-close-and-personal with an Oscar. The City of Angels may be full of glitz and glamour, but outdoor enthusiasts will also love hiking Runyon Canyon for spectacular views and strolling along the nearby beaches.

Let your vacation start the moment you step on board UP Express! Skip the traffic and relax in comfort on your journey to and from Toronto Pearson Airport. With roomy cabins and plenty of luggage storage on board every train, we’ll help you keep your trip on track with frequent and convenient service between downtown Toronto and Pearson Airport, seven days a week.

International Destinations For A Short Winter Break

The winter months are the perfect time to take a weekend break in Iceland. With direct flights from Pearson International Airport, Iceland is a year-round destination that truly shines in the winter months. Though daylight may be limited, the Northern Lights make for spectacular winter viewing while the natural hot springs at the world famous Blue Lagoon are a welcome and relaxing spa treat for couples to cozy up.

If sunshine and warmth is what you’re after, there are many Caribbean beaches and sunny spots under a five-hour flight from Toronto. Sit on the soft white sands and get up-close-and-personal with stingrays in the Cayman Islands or experience Tulum, Mexico to find out why this picturesque spot has become a must-visit for Canadians. With its many luxury resorts, the breezy Bahamas make a great upscale break on a winter weekend for couples looking for a short getaway.
Want the sun but not the sand? Consider Havana, Cuba for a short weekend trip where you can feast on classic Cuban cuisine like arroz con pollo, yucca fries, and flans, perfectly paired with a café con leche – or spicy rum. And if you decide you need a beach, you’ll find a number of public beaches right at the edge of the city.
No matter where your winter weekend getaway takes you, UP Express will help you start and end your trip with ease. Featuring convenient and frequent service, it takes just 25 minutes from Pearson Airport to downtown Toronto’s Union Station where you can connect with GO Transit, a local subway or streetcar, or other inter-city train services like VIA Rail to discover new and interesting destinations in and out of the city. The possibilities are endless!