Featured Dates

  • Outdoor patio with beverages

    Summer Sin: Treats on Queen Street

    If you and your date are big snackers, you'll love this itinerary! Make three stops along Queen Street West grabbing some tasteful bites as you go.

  • Two people walking through a park

    Toronto's Ultimate Night Out: Film, Food, And Beats

    Indulge in comfort food at Gabby's Restaurant & Pub in Toronto. Then, attend the Opening Night feature film "Fancy Dance." After the movie, venture to the Opening Night Party at Steam Whistle Brewery.

  • Woman browsing vinyl music

    Music Lovers: Best Of The Music Scene On Queen West

    A must attend date for any music and vinyl lovers. Hit up the best vinyl shops on Queen West and visit live music venues that make Queen West the centre of Toronto’s music scene.

  • Store with plants

    A Plant-Iful Afternoon: Garden Café + Brunch

    Get ready for a peaceful green afternoon! Start out with some coffee and light plant shopping at Queen Garden, then make your way down to Pasaj for a Turkish breakfast feast.

  • Arcade game controller

    Art And Entertainment: A Date Night In Graffiti Alley And Tilt Arcade Bar

    A romantic evening date night in Toronto with Graffiti Alley and Tilt Arcade Bar.

  • Woman with colourful shadow

    Sweet Illusions: A Date Night Filled With Museum Fun And Sweet Treats

    Learn that there is more than meets the eye by exploring at the Museum of Illusions! Then satisfy your sweet tooth with desserts from Melt n Dip, grab a coffee to go as you head to Berczy Park.

  • Toronto park on the water

    Sweets And Serenade: Dessert From Touti Cafe + Music In The Garden

    Pick up a sweet treat from Touti Cafe, then head to the Toronto Music Garden for a delightful live music performance. End the night with a photo at the iconic Red Canoe at Canoe Landing Park.

  • Castle

    The Ultimate Royal Experience: A Day Of Discovery, Dining, And Delight At Casa Loma

    Explore the grandeur and history of the castle, with a self-guided tour. Enjoy fine dining at the castle's restaurant, savouring the flavours and culinary experience fit for royalty.

  • Woman with rainbow shadow

    Sweet Illusions: A Date Night Filled With Museum Fun And Sweet Treats

    Explore the Museum of Illusions then satisfy your sweet tooth with desserts from Melt n Dip as you head to Berczy Park to check out the fountain.

  • Woman with graffiti wall

    An Artful Afternoon in the Heart of Toronto

    An afternoon of free art, coffee, cocktails and other activities in the Heart of Toronto.

  • Microphone

    The Cabbagetown Experience: Endless Fun on a Beer Budget

    A night in Cabbagetown on a Beer budget!

  • People kayaking

    You're So Humber Baby

    A canoe trip to nowhere in the heart of the city pairs well with hidden culinary gems, independent stores, and festivals on the West End of the city.

  • Modern art gallery

    Experience The Magic Of Islamic Art

    A day to embark on a journey to try middle eastern food, visit a cultural exhibition and attend a soulful performance.

  • Animated man holding passport

    Distillery Daze: Lunch + Live Performance

    Fill your cup with culture and cuisine during this afternoon in the Distillery District!

  • Middle Eastern Odyssey: A Cultural And Culinary Journey With Global Voices Performance

    A day to embark on a journey to explore the charm of the middle east, try middle eastern Arabic cuisine, and attend a global voices performance.

  • An Unforgettable Night of Indigenous Art, Latin Cuisine, and Electronic Pow Wow

    An unforgettable night of Indigenous art and mouth-watering Latin American cuisine at Lena Restaurante.

  • Kayaks on waterfront

    Beach Day: Paddle On Lake Ontario + Picnic On Cherry Beach

    Spend some time in the sun on the water, kayaking or paddle boarding to your heart's desire. Plus enjoy a picnic on Cherry Beach, a true Toronto hidden gem!

  • Interior of restaurant

    Swing Dancin’ Downtown + Latin Coastal Cuisine

    Enjoy a dinner of latin inspired eats at Baro, then learn to swing dance at Drom Taberna.

  • Lounge with couches and plants

    Gin & Jazz At Reid’s Distillery

    Enjoy live jazz and craft gin cocktails at Reid's Distillery.

  • Dimly lit bar

    Best Of King West: Little Sister Dutch Indo + Music At Drom

    Light up the night on King West with dinner at Little Sister Dutch Indonesian Restaurant and live music and the happenin’ Drom Taberna.

  • Assortment of cheese in boutique

    Cheese Lovers: A Kensington Market Cheese Tour

    If you think the way to their heart is cheese, this is the date for you! Tour Kensington Market’s top cheese boutiques and grab drinks at Trinity Common.

  • Woman reading a book in a store

    Storybook Romance: Lover's Book Crawl in The Junction

    Calling all literature lovers! Spend your afternoon book thrifting before heading to the literature themed cocktail bar Famous Last Words.

  • Forested area with water

    A Walk In The Valley: Evergreen Brickworks Trails + Farmer’s Market

    A romantic walk through tall trees and lush foliage, plus a visit to the farmer’s market.

  • Lock installation against brick wall

    Love & Chocolate: Artisan Chocolate Tour in The Distillery

    Chocolate lovers unite! Enjoy a tour of the Distillery District’s best chocolate makers.

  • Record shop

    Music Lovers: Best Of The Music Scene On Queen West

    A must attend date for any music and vinyl lovers. Hit up the best vinyl shops on Queen West and visit live music venues that make Queen West the centre of Toronto’s music scene.

  • People playing board games

    Triple B: Board Games, Brunch & Bumpin’ Tunes

    Enjoy brunch with live music and board games to boot at Bampot Tea House.

  • Person at an arcade

    Game On: Zed*80 Arcade + Ryus Noodle Bar

    A night of fun, games and delicious ramen. Start with dinner at Ryus Noodle Bar and head to Zed*80 for retro arcade games!

  • Candle making

    Stay Cozy: Candle Making Workshop + Italian Cafe

    Get cozy with a candle making workshop and 5 Elements Espresso Bar.

  • Two glasses of beer

    Gallery Hopping Junction Triangle: Breweries + Galleries

    Take in the best of the Junction Triangle while you tour the neighbourhood’s favourite breweries and art galleries.

  • Chickens outdoors

    East End Delights

    Enjoy this super cute outdoor date, start with walking the Riverdale Farm trails and then grab a mouthwatering lunch from Completo Sandwiches.

  • Interior of dimly lit bar

    Opera Pub + Bar Poet

    Start with appetizers and cool cocktails at Bar Poet, then grab a seat at the Drake Hotel for Opera Pub.

  • Record shop

    Music Lovers: Best Of The Music Scene On Queen West

    A must attend date for any music and vinyl lovers. Hit up the best vinyl shops on Queen West and visit live music venues that make Queen West the centre of Toronto’s music scene.

  • Art exhibit with mirrors

    An Afternoon with Art: Infinity Mirrored Room at the AGO + Brunch at Light Cafe

    Hang out in the famous Art Gallery of Ontario and check out the hottest new exhibit then indulge in a delicious brunch at Light Café.

  • Wine poured into glass

    Let's Go Paint the Town: Wine Flights + Music at The Painted Lady

    Take a vino-inspired journey at the Downtown Winery and take in live music at The Painted Lady.

  • Arcade machines

    Game On: Zed*80 Arcade + Ryus Noodle Bar

    A night of fun, games and delicious ramen. Start with dinner at Ryus Noodle Bar and head to Zed*80 for retro arcade games!

  • Flight of beer

    Gallery Hopping Junction Triangle: Breweries + Galleries

    Take in the best of the Junction Triangle while you tour the neighbourhood’s favourite breweries and art galleries.

  • People walking in Kensington Market

    Local Love: Kensington Market

    Explore Kensington Market, one of Toronto’s fav neighbourhoods. Follow this itinerary to discover the best shops and places to eat!

  • Couple skating at Nathan Phillips Square

    Skate Date in The City: Nathan Phillips

    Celebrate winter weather with a skate in Toronto’s most famous rink, followed by board games at a cozy cafe.

  • Snowy storefront

    Local Love: Greektown

    Explore the vibrant neighbourhood of Greektown where you’ll find plenty of markets, home decor stores and top notch restaurants.

  • Suspended disco balls

    Food for the Soul: Retro Tunes & Contemporary Food at Mrs Robinson

    Mrs Robinson is a retro inspired restaurant hosting live music and DJs four nights a week. Come for dinner and stay for the music!