Go on a fun-filled date in Toronto’s west end, where photo shoots, flowers and cocktails are just a few of the romantic weekend getaway activities you can enjoy together.

Toronto can be the backdrop to a pretty incredible date — just ask the people behind The Bachelor, who featured Toronto as a setting to a date in a recent episode! Whether it’s with a romantic love interest, a friend or even a solo date to reconnect with yourself, this is a Toronto date itinerary in the city’s west end that’s sure to wow.

Toronto’s westside is a lively alternative to its more widely-known downtown counterparts. Each stop on this date itinerary is located in a different neighbourhood with its own unique energy and character. Between the community feel of Little Italy, the bustle of Koreatown, the trendy energy of West Queen West and the personality of Parkdale, there is something for everyone. These are my personal picks for a romantic time.

Olivia’s Garden

Fueling up for your Toronto date adventure means stopping for some java and treats at one of Toronto’s many independent cafés. Located in Little Italy, Olivia’s Garden provides the perfect backdrop to your date’s first stop, with a delightful light-filled café that also houses a floral studio in the same space. 

You and your date can catch up over sips of espresso-based beverages (or one of their signature pink drinks) and can then browse through their floral offerings. Whether you choose a single stem or a bespoke bouquet, starting your date off with coffee and flowers is sure to impress.


You know what they say: photos or it didn’t happen! Have a unique experience and leave with a printed photo memento of your date at Monography Studio in Koreatown, North America’s first self-portrait studio. 

Arrive at the studio early to change or freshen up and capture your most natural self in their private photo studio for 25 minutes of fun! The Monography staff can assist you with camera orientation during the photoshoot, but otherwise, the experience is self-guided. 

After your photoshoot fun is complete, select four of your best photos to be retouched and printed within 15 minutes (you can also have them mailed to your home if you’re tight on time.) Reservations are needed, and sessions can be done in both black and white, and colour. Make sure to book ahead!

Bar Poet

By now you and your date have likely worked up an appetite, so a meal to experience Toronto’s acclaimed restaurant scene is on the menu. Bar Poet is a West Queen West staple, serving scratch-made pizza under a tree-lined cascade of twinkle lights in a very fun and approachable environment. 

What makes Bar Poet so special, apart from the almost enchanted decor and delicious food, is their downstairs area that has a skeeball machine and unlimited arcade games. A great spot for a day date or even a late-night affair with last call at 2 a.m.

The Shameful Tiki Room

To cap off a fun date in Toronto, jetting off to a tropical paradise would be a way to leave an impression. If spontaneous plane travel isn’t in the cards, the next best thing is visiting The Shameful Tiki Room

Located in Parkdale, The Shameful Tiki Room pays homage to mid-century American tiki bars and crafts eclectic tropical cocktails served in tiki mugs. The atmosphere will have you forgetting what city you’re truly in; think rattan furniture, tropical plants and artifacts that will make you feel like you’re in Hawaii. 

There are no windows in this neighbourhood haunt, so prepare to get cozy with your date in the mellow atmosphere. The Shameful Tiki also serves a Polynesian-inspired menu, so you and your date can graze as you sip the night away. 

You may also like: 12 Unique Toronto Date Ideas