Travel Tips

Maximize Your Long Weekends – 7 Ideal Getaways from YYZ

August 8, 2018

Tapped out of vacation time for the year? Yea, me too. If Toronto-based microadventures aren’t satisfying your travel itch that just means you have to get creative with managing your calendar to get your wanderlust fix without risking your 9-to-5. What do I mean by that? Maximize your long weekends by looking for destinations are near enough that you aren’t wasting a second longer than necessary and are the best bang for your (limited) buck.

Avoid abusing your sick days and the subsequent wrath of your boss by checking out the best getaways from Toronto to get the most out of stat holidays:

Chicago, Illinois

By: Plane
Duration: 1h 50m
Cost: from $140
Best time to go: April through May, between September and October
Why: Warm weather and plenty of festivals to keep you busy

As if you needed a reason beyond deep dish pizza, Chicago is under a 2-hour flight from Toronto with a modest price tag to boot! The consummate city dweller will love exploring the infamous Windy City – posing at the iconic Cloud Gate sculpture, cruising down the Chicago River, and catching a baseball game at Wrigley Field.


New York, New York

By: Plane
Duration: 1h 47m
Cost: from $110
Best time to go: April to June, September to early November
Why: Mild weather and manageable tourist crowds

The classic choice, New York is only a hop skip and a jump away from The 6ix and great any time of year. In the winter, meander through the Guggenheim, or sing along at a Broadway musical while summer is for outdoor movies in Central Park and strolling along the High Line with delicious treats from Chelsea Market. Don’t forget revelling in the bar scene in the city that never sleeps! Nothing is more quintessentially New York than sipping martinis à la Carrie Bradshaw.


Havana, Cuba

By: Plane
Duration: 3h 25m
Cost: from $210
Best time to go:  December to May
Why: Blue, sunny skies and dry weather dominate

Craving an exotic mini-break but short on vacation time? Havana is a mere 3.5 hours from Toronto so you can leave work at 5pm and be flirting with locals – rum-filled mojito in hand – by midnight. Feel like you’ve been transported back into the 50s as you cruise in a vintage car down the Malecon, leisurely wander the charming streets of Old Havana, and salsa the night away.


Montreal, Québec

By: Train – VIA Rail
Duration: 4h 54m
Cost: from $65
Best time to go: March to May, September to November
Why: The weather is mild and you have your choice of hotel vacancies

This is the ideal getaway that doesn’t require a passport or foregoing your precious data plan. Explore other parts of Canada without breaking the bank by boarding a train in Hogwarts fashion to Toronto’s European-style province known for inventing the national staple – poutine! Eat yourself into a muumuu at the likes of Lawrence or Garde Manger, hike through Mount Royal or join in the weekly drum circle before luxuriating at a spa on a 1950s ferry boat on the St. Lawrence River.


New Orleans, Louisiana

By: Plane
Duration: 2h 51m
Cost: from $280
Best time to go: February to May
Why: Comfortably cool weather and Mardi Gras celebrations are in full swing

Need a quick fix of some southern charm and spicy gumbo? Jet over to New Orleans and soak in the boisterous energy of the city famed for the bacchanalian Mardi Gras celebrations. Start your morning right in the Big Easy with your mouth full of powdered beignets from Cafe Du Monde while you wander the historic French Quarter and listen local street performers play soulful jazz. Partake in an authentic Creole jambalaya before hitting up Bourbon Street for the riotous nightlife.


Miami, Florida

By: Plane
Duration: 3h 8m
Cost: from $160
Best time to go: March and May
Why: Sunny skies and avoiding winter season prices

Toronto weather not co-operating? Get a much-needed dose of vitamin D that is a mere 3-hour plane ride away in the sexiest city in the sunshine state. Work on your tan on South Beach, brimming with barely-there bikinis and bronzed bodies. If abs aren’t your jam, (and actual jam is your jam) throw on your stretchy pants and feast your way through the emerging culinary scene before walking off your meal in the Design District, full of sleek modern architecture.


Nassau, Bahamas

By: Plane
Duration: 3h 5m
Cost: from $310
Best time to go: November to mid-April
Why: Ideal spring break spot despite crowded beaches

It may seem far away, especially when Toronto is in the depths of the harsh winter months, but tropical weather is closer (and more budget-friendly) than you’d think. Snorkel in the clear turquoise waters around a string of islands covering 100 miles that make up the Bahamas. Lounge on palm-fringed white sandy beaches with a vibrant-hued cocktail and indulge in a traditional Bahamian dish of conch fritters.