5 Anniversary Ideas for Ontario Couples

You don’t need to charter a plane or book a five-star resort to have a great anniversary. Ontario’s packed with simple, thoughtful ways to make the day feel different without turning it into a production. 

Here are five anniversary ideas in Ontario that hit the right mix of easy and memorable, with no choreographed candlelight required.

1. A Local Cruise

No planning, no packing, no pretending you’re outdoorsy — just water, sky, and the person you like most. Ontario’s lakes are perfect for low-effort romance, and a dinner or sunset cruise gives you atmosphere for free. 

If you live in or around the Georgian Bay area, Collingwood Charters runs private charters and public cruises where you can eat (dinner), watch the light change (sunset), and remember why you put up with each other’s quirks in the first place.

It’s quiet, it’s simple, and someone else does the driving. Perfect.

2. Weekend in Prince Edward County

Some places feel like they were built for anniversaries, and Prince Edward County is one of them. With its small towns, backroad wineries, beaches, and good food, it’s easy to fill two days without ever feeling rushed.

You could start with a lazy breakfast in Bloomfield, bike through the vineyards, and end the evening at a local inn with a bottle of rosé and not much else planned. It’s practically the definition of a romantic date idea Ontario couples can actually pull off without a travel agent or a five-hour drive.

3. The Outdoors (Minus the Camping Trip)

Not everyone dreams of sleeping in a tent, but being outside together still works. On your Ontario anniversary, try one of these romantic things to do outdoors that won’t destroy your comfort zone:

• Paddle a rented canoe on the Lake of Bays.

• Pack a picnic for Rattlesnake Point.

• Walk to one of Hamilton’s waterfalls, like Tiffany or Webster’s.

• End the day with takeout eaten on a dock somewhere quiet.

You’ll get fresh air, small moments of teamwork, and maybe a few inside jokes about who’s worse with directions.

4. The Unplanned Road Trip

If you’re feeling a little spontaneous, go ahead and skip the itinerary. Pick a direction, start driving, and stop wherever it looks interesting. Small towns like Elora, Perth, or Creemore are perfect for this, as they’re enough to explore, but not enough to stress you out.

You might end up at a bakery, a used bookstore, or a brewery with a live band you’ve never heard of. It’s one of those couples’ activities where the fun comes from the unknown, not the schedule.

5. A One-Night “Getaway” in Your Own City

Book a boutique hotel downtown. Dress up for dinner somewhere new. Walk home like tourists instead of locals. You’d be surprised how much a change in setting resets your brain.

If you’re in a city like Toronto, Ottawa, or London, a quick search for “unique date ideas near me” may just surface some hidden gems, like mixology classes, rooftop patios, or even late-night dessert bars. It’s proof that novelty doesn’t always mean distance.

Take Your Anniversary on the Water

You don’t have to plan the perfect anniversary — just something that feels like you. A cruise, a weekend drive, a quiet hike; it all counts if it gets you off your phones and into the moment. And if the water calls to you, start there. 

Here at Collingwood Charters, we offer private and public dinner and sunset cruises on Georgian Bay that can turn an ordinary evening into something worth remembering. Book your cruise today.