Retired teacher looks to make waves with pontoon boat tours

When the Island Princess left Orillia’s waterfront and headed to Barrie, it created a void that many residents and visitors alike quietly felt.

No tour boats were cruising the shores of Lake Couchiching, offering relaxing rides and stories of the region’s natural beauty. But now, a small pontoon boat with a big personality is making waves, thanks to the passion and vision of Kelly Lassaline.

Lassaline, a recently retired teacher, is the owner and operator of Orillia Boat Tours, a one-woman operation offering private scenic tours aboard a 20-foot pontoon boat.

The venture began as a pilot project in 2023, but after a successful first season and her official retirement this June, Lassaline decided to bring it back full-time.

“I knew I would be bored silly if I didn’t have a side gig,” Lassaline said with a laugh. “My kids are grown, my 85-year-old BFF had a stroke, my dog died — I had no one to go out on the boat with me anymore. But if I hang up a sign and tell people it’s $100 a ticket, suddenly everyone’s tripping over themselves to come on a boat ride with me.”

Lassaline’s motivation to launch a boat tour business stemmed not only from a desire to stay busy post-retirement, but from a lifelong love of the water.

Growing up in Parry Sound, she was raised on Georgian Bay, steering boats from a young age and developing a deep respect for Ontario’s waterways.

“I’ve driven boats ever since I was a kid,” she said. “But when I moved to Orillia, it was a bit of a transition. Georgian Bay has depths of 300 feet or more. Here on Lake Couchiching, there are spots just five feet deep. It takes some getting used to.”

What Lassaline offers is more than just a boat ride. It’s a personalized, story-filled adventure where passengers can relax, explore, and learn about the region’s hidden gems.

Orillia Boat Tours offers two-hour private excursions for up to four guests at $100 per person. Lassaline notes that this setup is designed for comfort, affordability, and intimacy.

“While I’m happy to let people pick where they want to go — especially if they want to fish or swim — I also have a scenic route I love to share with newcomers,” she said.

“We travel along Bay Street, around Chief’s Island, through the Narrows into Lake Simcoe, circle Grape Island, and then head back along the Orillia shoreline. It really showcases the best of both lakes.”

And for those looking for a full-day experience, Lassaline offers a signature trip through the Trent-Severn Waterway.

“We leave the Port of Orillia at 8 a.m. to make the 9 a.m. opening of Lock 42 in Washago. From there, we cruise through the beautiful, forest-lined Swift Rapids, making our way to Big Chute.

“If time allows, we watch other boats ride the marine railway before turning around,” she explained. “There are restaurants along the way where we can stop, and the trip usually ends with a swim. It’s a full day on the water, and people love it.”

Lassaline emphasized that her tours are completely customizable. Whether a family wants a quiet cruise, a group of friends wants to explore the Narrows, or a couple wants a private anniversary getaway, she adapts each experience to her passengers.

“It’s their time, their day,” she said. “I’m just the captain.”

Unlike large tour boats that offer scheduled routes and crowded seating, Lassaline’s operation is about creating a personal, relaxed, and interactive atmosphere. Every guest has her full attention, and she encourages conversation, questions, and connection.

“You’re not one of a hundred people. You’re one of four, tops,” she said. “That means if you want to stop for a swim, you can. If you want to explore a certain area, we do that. It’s not a rigid experience. It’s yours.”

And while it might cost more than hopping on a big tour boat, Lassaline said the experience is worth every penny.

“You’re basically getting your own boat, your own captain, and a private experience,” she said. “There’s no need to get your boater’s licence, worry about slip fees, gas, or insurance. Everything is taken care of.” 

Orillia Boat Tours operates with full insurance and commercial registration, and Lassaline has taken every step to ensure safety and professionalism.

Alcohol, smoking, vaping, and drugs are strictly prohibited, and guests are required to sign a waiver prepared by her lawyer.

Life jackets are provided, and although she doesn’t serve food, guests are welcome to bring their own snacks and beverages.

“I want people to feel safe and comfortable,” she said. “This is a licensed, insured operation. I take that seriously.”

Lassaline admits that the weather can be a challenge, especially with this spring’s damp and unpredictable conditions.

“I don’t go out in poor weather. Safety is my top priority,” she said. “If the forecast looks bad the day before a booking, we simply reschedule. Nobody wants to be out in a storm.” 

Now that she’s officially retired, Lassaline is looking forward to extending the season well beyond the traditional summer months.

“September is beautiful on the lake, and all the cottagers have gone home. It’s peaceful and calm,” she said. “I’m hoping to keep the tours going well into the fall.”

For Lassaline, Orillia Boat Tours is more than just a business — it’s a way to share her love of the water, connect with people, and enjoy retirement on her own terms.

“I don’t want to stop everything just because I’m retired,” she said. “I still want to be busy, but on my terms. This keeps me active, social, and surrounded by the thing I love most, the lake.”

Orillia Boat Tours is currently accepting bookings for the 2025 season. For more information or to plan your custom excursion, click here.