LGBTQ Toronto Itinerary: Laid-Back Weekend

The best thing about Toronto is its diversity – not only in the people it welcomes, but in the experiences it offers. You can come to Toronto for a wild weekend of partying at some of the country’s hottest clubs, or simply share a few laughs with friends at a comedy bar or lounge. Wherever you go and whatever you do, you’re guaranteed to have fun and feel welcomed.

If you’re looking to experience gay Toronto’s nightlife at a more relaxed pace, check out this sample itinerary for a laid-back weekend featuring some of the city’s coolest LGBT-friendly lounges, bars, and attractions.

Day 1: Poolside drinks, comedy, & board games

Start your weekend off in style by basking in the summer sun, drink in hand, at Cabana Pool Bar. Inspired by the top outdoor pool party destinations in Miami and Las Vegas, Cabana Pool Bar is a posh lakeside lounge featuring a crystal clear swimming pool, fully licensed bar, 12 cabanas, 42 deluxe chaise lounges, and 50,000 square feet of enclosed patio space. You’ll feel like you’re in a Florida resort as you chill out by the pool to house tunes and admire the city skyline (and your fellow sunbathers). When you get hungry, order a delicious meal from Cabana’s diverse menu.

As the sun begins to set, catch a cab over to Toronto’s world-famous comedy club, The Second City, for a hilarious evening of sketches and improv. The Second City is one of the most recognizable names in improvisational comedy, having launched the careers of famous comedians like Dan Ackroyd, John Candy, Eugene Levy, and Martin Short. You’ll be laughing out loud as you watch the madness ensue on stage.

What better way is there to wrap up a delightful evening than with board games? Snakes and Lattes, located in the funky and queer-friendly Annex neighbourhood, is Toronto’s original board game café. With a game library consisting of over 2,500 titles, Snakes and Lattes has classics like Risk and Monopoly as well as hidden gems like Creationary and Settlers of Catan. Sip on a latte, cappuccino, or alcoholic beverage as you and your friends keep the laughs going with fierce but friendly competition. When you’re ready to call it a night, head back to your hotel for a good night’s rest.

Day 2: Live music and billiards

Spend the day exploring the city and seeing its many attractions. When evening rolls around once again, head over to Sneaky Dee’s for a Tex-Mex meal in a graffiti-grunge setting. Openly gay-friendly, Sneaky Dee’s is one of the best places in the city to share a plate of nachos or fajitas and wash it down with a pint of beer. Alternately, check out Henhouse – a newer restaurant/bar in Little Portugal that attracts a significant number of ladies who love ladies, as well as other queer and queer-friendly folk.

How about a little bit of live music to jam out to? Just down the street from Sneaky Dee’s, College Street Bar is a cozy, unpretentious hotspot with some of the best live music in the city. Attracting a mixed crowd of gay and straight, young and young-at-heart, College Street Bar features bands from a diverse range of genres. For an evening of smooth jazz, head to The Rex on Queen Street, where there’s a different jazz or blues act every night of the week.

Finally, you can’t visit gay Toronto without making a trip to the Village. Drop by Pegasus for the friendliest atmosphere on Church Street. Shoot some billiards or throw some darts while making new friends. Or, swing over to Zipperz piano lounge and end your evening with sing-along musical cabaret.

A world of possibilities

There’s so much to see and do in gay Toronto, you could never fit it all into a single weekend. Once your weekend getaway ends, you’ll be itching to come back for more. With its friendly vibe and diverse range of activities, Toronto is the place to be for LGBT nightlife of all kinds.