Updated: Jul 14, 2021
Skip the stress of planning the perfect date and check out our unique list of ideas that are guaranteed to make it memorable.
Do you opt for plans that are tried and true or do you try to impress with something new and bold? There's so much to do in downtown Oakville. How do you narrow it down for the perfect date? Take the pressure off the next time it's your turn to plan by scanning our suggestions of the best date ideas in Town. We think there's a little something for everyone here. Enjoy!
Catch a sunset
There is no booking or equipment needed to enjoy a beautiful Oakville sunset. Take a stroll out on the pier toward the Oakville Lighthouse. Experience the picturesque background and walkway which includes a number of benches to sit and snuggle while taking in the spectacular views of sailboats along the lake.
Take me there: 99 Forsythe St.
Dine on a patio
Experience a slice of Italy while indulging in fresh pasta, pizza or salad on Buca di Bacco’s outdoor patio oasis. With plenty of shade provided by the surrounding trees during the day and fairy lights adding a warm glow to the evening, the patio is a perfect backdrop for a memorable date experience. Check out our patio guide for more downtown dining options.
Price: $$-$$$ Take me there: 130 Thomas St.
Reservations: Call 905-845-7396
Enjoy a romantic picnic
Take advantage of the many lakeside parks and greenspaces located in Downtown Oakville. If it’s a nice day, head over to Dingle Park or Lakeside Park and enjoy your picnic favourites for brunch, lunch or dinner. Price: $
Get frisky at The Lovers Boutique
If you’re feeling bold and want to try something new and exciting, spice up date night with a trip to the Lovers Boutique. The Lovers Boutique is stocked with everything from lingerie to sex toys and bondage equipment. Whatever your preference, there’s something for everyone to enjoy.
Take me there: 300 Lakeshore Rd. E
Grab a coffee and go for a walk
Grab a coffee or tea at Aroma Espresso Bar and walk up Reynolds St. toward George’s Square. The mini park is fitted with lots of benches and seating areas if you’d like to slow things down and take a break.
Take me there: 321 Lakeshore Rd. E
Indulge in some ice cream
Chill out and treat your date to ice cream or other frozen treats at Chocolato + Tommy Café. While enjoying your ice cream, go for a walk along Lakeshore and window shop.
Price: $ Take me there: 236 Lakeshore Rd. E
Relax at Leela Eco Spa
Looking for an intimate, relaxing experience you and your partner can enjoy together? Leela Eco Spa offers a variety of couples packages to give you and your special someone a chance to get away from the daily hustle and bustle and sink into tranquility and relaxation.
Take me there: 210 Lakeshore Rd E.