14 Unique Date Ideas in and Around Toronto for May


Has everyone been getting their personality back because the weather is above 10? We don’t even mind rainy date days because the city is alive again, and so are fun events and date ideas to explore!

It doesn’t matter if you’re looking for a casual first date, or a place to celebrate your 10th anniversary – Toronto is full of options for whatever type of date you’re searching for and it’s only getting better from here.

Plus, scope out the perfect event for Mother’s Day! From high tea to creative workshops, there’s something for your dates with the moms and mother figures in your life.

Check out events and date ideas happening this May in Toronto!

KANDL Artistique Mother’s Day Workshops

We’ve said it before and we’ll say it again – if you’re looking for a gift idea and a date idea in one, this spot is the perfect place. Browse the beautiful boutique that carries some of the most gorgeous smelling candles ever (including Drake’s own candles!), and then sip on wine or coffee and tea while creating your own luxury candle.

Lab reservations for Mother’s Day can be made online; there are still spots for the May 6th at 11am and 2pm labs, as well as the May 8th at 11am and 8pm labs!

Where: 88 Avenue Road, Toronto

‘Rhythm & Blooms at St. Regis’ Astor Lounge

This new pop-up in the lobby lounge of the St. Regis hotel in Toronto is the perfect Mother’s Day, or date idea. Equipped with gin cocktails by Whitley Neill Gin, this lounge is prohibition-style (inspired by the founding family, the Astors, who lived through the enchanting era of speakeasies and prohibition).

Enjoy live jazz music, their iconic champagne sabrage Evening Ritual daily, Insta-worthy cherry blossom tree decor, signature spring cocktails, Prohibition Afternoon ‘Iced-Tea’, and spring-inspired bites!

All you have to do is make your reservation via Opentable for the Astor Lounge!


Evening jazz music Fridays & Saturdays 6 – 9pm

Evening Sabrage Ritual 6pm daily

Afternoon Tea on Saturdays & Sundays

Where: Astor Lounge, lobby of St. Regis Hotel at 325 Bay St., Toronto

Princess Diana – Accredited Access Exhibition

For the first time, world famous Royal Photographers, Anwar Hussein and his two sons Samir and Zak share collections of their original images and the personal, exclusive and never-before-told stories behind them. The Husseins collectively spent four decades working side by side with the iconic Princess and her family and will reveal what they witnessed first-hand, both in public and private moments.

When: On until June 12th, 2022

Where: Casa Loma, 1 Austin Terrace, Toronto

The Porch & Rock n Horse Saloon Cinco de Mayo Party

What kicks off patio season better than Cinco de Mayo festivities in the city? The Porch has partnered with Jose Cuervo to put on the biggest Cinco de Mayo party in the city, they say. What you can expect? A live DJ, Mexican eats, and a specialty tequila drink menu curated by Jose Cuervo.

When: May 5th starting at 5pm

Where: Two-level party, The Porch and Rock n’ Horse Saloon at 250 Adelaide St. W., Toronto

Sip & Sizzle

During each of the four weekends in May, you can head to the wineries of Niagara on the Lake for wine and food pairings created by each and every one! This event is an amazing date idea, and NOTL is the perfect place for a day trip or romantic weekend getaway in Ontario’s own wine country.

Purchase an individual passport, or a couple’s passport and enjoy one wine sample and food pairing at each winery. The catch it, you can only visit each winery for the pairing once, and you can only visit eight max. per day, but trust us, that’s more than enough winery visits for one day!

Since NOTL is so close, you can head down more than once to tackle even more wineries throughout May’s weekend. Might we suggest booking a bike rental with a local company to bike through the vineyards from tasting to tasting?

As always, wine taste responsibly. For the breakdown of wineries and pairings, click here.


Weekend One – May 6-8, 2022

Weekend Two – May 13-15, 2022

Weekend Three – May 20-22, 2022 (does not include Victoria Day Monday)

Weekend Four – May 27-29, 2022


16 wineries across Niagara on the Lake including Chateau de Charmes, De Simone Vineyards, Inniskillin, Jackson-Triggs, Konzelmann Estate Winery, Lakeview Wine Co., Marynissen Estates Winery, Niagara College Teaching Winery, Palatine Hills, Peller Estates, Pillitteri Estates Winery, Queenston Mile Vineyard, Reif Estate Winery, Riverview Cellars Estate Winery, Trius Winery, Wayne Gretzky Estates

Gin High Tea Sundays at Reid’s Distillery

If gin and high tea sound like your kind of Sunday Funday, you can head to Reid’s Distillery off of Lakeshore Rd E., in the Studio District for gin cocktail teapots, towers of finger sandwiches, scones, smoked salmon, and pastries!

When: Starting Mother’s Day (May 8th) and then every Sunday at 3pm

Where: Reid’s Distillery, 32 Logan Ave., Toronto

EATALY AYCE Springfest

All you can eat Italian food, an open bar, and a gorgeous store? Count us in! This dream date is happening at Eataly Toronto. On Friday, May 13 from 6-11 p.m., they’re shutting down the entire store to the public and will host their first ever all-you-can-Eataly event spanning across all 3 levels.

Once you have your ticket, you have access to unlimited drinks at 5+ open bars including Italian wines, cocktails, and craft beer; unlimited food at more than 20 tasting stations with pizzas, pasta, salumi, formaggi, and sweets; a live band all night long; pasta making demonstrations, oyster-shucking and even more! Tickets are $165/person.

We’re dreaming of it already.

When: Thursday May 13th, starting at 6pm until 11pm. Staggered entry times.

Where: Eataly Toronto, Manulife Centre, 55 Bloor Street W., Toronto

Meadow Installation and Picnic at Post Creative

At the iconic Post Creative studio, just east of the DVP, enjoy a morning brunch, mid-day snack or evening date in the meadow. You and your date will be surrounded by pillows, candles, blankets, flora – and refreshments and snacks.

This setup includes two bottles of sparkling and citrus juices, a selection of light to dark roast coffee, fresh fruit, and local freshly baked bread with a side of olive oil + balsamic vinegar, all arranged around a custom low table top and pillow filled seating area. You can also bring your own snacks, bevvies and details to make it especially you! This would be a perfect spot for a proposal, no?

Couples and brands have flocked to this studio for gorgeous photos and stepping into the space will make you feel like you’re having a date night in a painting.

Click here to check out more and book the studio!

When: Now until June 30th

Where: Post Creative Studio, 1243 Milky Way, Toronto (Parkdale area)


From the people behind Toronto’s Festival of Beer comes the FizzFest that celebrates all things seltzers, ciders, premixed drinks and cocktails. It’s not doubt that the world of seltzers has taken over when it comes to refreshing date night drinks (and they’re not just for summer beach sippers anymore)!

What you can expect at FizzFest is delish cocktails to sample from partners like Ace Hill Vodka Soda, Bangarang Hard Seltzer, Corona Tropical, Bud Light Seltzer, Founder’s Original, Brickworks, Peller Wines, Cottage Springs, and so much more.

You’ll also be able to get food from vendors including Poutine Supreme, Hotdog Al, Meltwich, and Oyster Boy.

When: Saturday May 21st – Sunday May 22nnd 12pm to 6pm

Where: Fort York Garrison Commons. 100 Garrison Rd., Toronto

Her Time by Shelter Movers

Have a date night in and support a local cause. Shelter Movers Greater Toronto invites local supporters to attend Her Time, a curated virtual wine experience hosted by sommelier Lauren Power and a guided culinary experience led by Carolyn Cohen.

The food menu includes one-skillet Thai Coconut Curry with Lemongrass and Ginger, and Double Chocolate Salted Tahini Skillet Brownie Cookie.

Your support will ensure Shelter Movers Greater Toronto is able to continue serving survivors of gender-based violence in our community by providing free moving and storage services. 

Ticket options include the wine and a recipe card, or a full food delivery for a full date night in!

For more information and tickets, click here.

When: Thursday May 26th 6:30pm-8:15pm

Jungle Brunch or Dinner Dates at Chotto Matte

Whether you’re looking for a creative Mother’s Day date, or an intimate date night with sharing plates, you’ll have to experience Chotto Matte. Go for the cool decor and amazing recommendations and stay for their Pisco Sours, sashimi plates, and Robata Grill.

The Nikkei menu is the perfect fusion of Peruvian tapas and Japanese bites, and the Jungle Brunch opens your eyes to a new world of morning meals entirely with entertainment, unlimited small plates, and even an option for unlimited cocktails!

100 points to the date that brings you for delish unlimited brunch and drinks, just saying.

When: Jungle Brunch happens every Saturday from 12.00 pm, on. Happy Hour takes place Monday to Thursday 4-6pm.

Where: 161 Bay St., Toronto

TASC Tulip Festival

Get whisked away to a field that looks like you’re in Europe. Tulip season might be one of the most beautiful in Ontario and TASC Tulip Farm is letting you experience it!

Tulip’s aren’t in season very long, and you only have until May 22nd to check it out and get the most Instagrammable pictures of the season. When you go to TASC, 10 tulips are included in your ticket so you and your date can have the cutest take-home momento.

When: Limited tickets are available between now and May 22, open daily

Where: TASC Tulip Farm, 1415 Balfour St., Fenwick

Lindeman‘s Sunshine Station at Stackt Market

Who doesn’t love wine tasting in the middle of the city for date night? Lindeman’s is brightening up your trips to Stackt Market with their Sunshine Station tasting experience. You can’t miss their bright yellow booth.

 The pop-up at Stackt Market will consist of visitors having the opportunity to sample Lindeman’s wine paired with food being served at the Stackt Marketplace, served from a sustainable, wrapped cocktail box. Other activities include calculating carbon footprint, while experiencing the full bloom of spring with various mixed media throughout the space. 

Lindeman’s is celebrating reaching 100% carbon neutrality and is working towards their goal of using 100% renewable energy by 2024.

When: Now until May 31st; Tues. – Fri: 4pm-9pm, Sat: 12pm-9pm, Sun: 12pm-6pm , Mon (after May 24th): 4pm-9pm

Where: Stackt Market, 28 Bathurst St., Toronto

Canada’s First Halal Food Tour with Nightmarket TO

Nightmarket TO has partnered with Tourism Mississauga, MetalWorks Production Group, Al-Ahad Foods, Knorr, and Islamic Relief, for eight various weekends. They’ll be bringing their Halal Food Festival to various cities around Ontario all season long!

On Sundays you you can have a doggy date and “Bring a Pup” to take some professional photos with the market mascot Professor Wrinklez.

You’ll be able to choose from over 12 delicious vendors that will cater to the muslim community by serving all hand-slaughtered halal meat options including Gourmet Guyz, Donia Donair, Rick’s Good Eats Toro Grill Canada, Heirloom Toronto and many others.

When: Starting May 6th in Mississauga

Fridays 3 pm – 12 am EST
Saturday’s 2 pm – 12 am EST
Sundays 2 pm – 11 pm EST.


  • May 6-8th: Mississauga (Square One Shopping Centre)
  • May 13-15th: Milton
  • May 20-22nd: Kitchener/ Waterloo
  • May 27-29th: London
  • June 3-5th: Burlington
  • June 10-12th: Scarborough
  • June 17-19th: Ajax
  • June 24-26th: Toronto

We have more local, national, and travel date ideas waiting for you, plus free shipping for your datenight game when you use DATENIGHT at checkout!

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