Paddle Pirates Woodbine & Cherry Beach

Paddle Pirates operates paddleboard and kayak sessions at both Woodbine Beach and Cherry Beach along Toronto's eastern waterfront. They offer guided group outings, lessons, and rentals that work well for families with older kids who are ready for a real water sport experience.

The company provides all equipment — paddleboards, kayaks, paddles, and life jackets. Each session begins with a land-based lesson covering balance, paddling technique, and water safety. Then you're out on Lake Ontario with a guide who stays with the group. The water near both beaches is relatively calm and sheltered, making it manageable for beginners.

Kids should be at least 8 years old and comfortable in the water. Younger children lack the strength and balance for stand-up paddleboarding, and the sessions run long enough that little kids would lose interest. Tweens and teens are the sweet spot — they have the coordination to pick up the technique quickly and the attention span to enjoy 90 minutes on the water.

Woodbine Beach sessions put you close to the boardwalk and all the amenities of The Beaches neighbourhood. Cherry Beach is quieter and more rugged, with a more open-water feel. Both locations offer free parking, though Woodbine lots fill up on hot summer weekends.

Paddle Pirates runs from roughly late May through September, weather-dependent. Sessions can be cancelled for high winds or storms. Book at least a week ahead for weekend slots during July and August.

After your session, Woodbine Beach has the advantage of being right next to cafes, ice cream shops, and restaurants along Queen Street East. Cherry Beach is more isolated — bring your own snacks.