Winter Haven: Chain of Lakes Wildlife & History Pontoon Tour

Summary

Chain of Lakes wildlife, Cypress Gardens nostalgia and lakeside stories

You’ll glide past five or more historic lakes in Winter Haven’s famous Chain of Lakes, spotting wildlife like herons and turtles while your local guide shares stories about Cypress Gardens and legendary waterskiers. Expect small surprises—a sudden osprey dive or echoes of old Florida—plus bottled water and flexible lunch options if you want to linger longer by the shore.

What’s the experience like?

“You ever seen an anhinga dry its wings?” That’s how our guide, Mike, started as we drifted away from the dock in Winter Haven. He’s got this way of talking—like he’s letting you in on a family secret. The pontoon boat was new but smelled faintly of sunscreen and lake water (not bad, just Florida). We passed the old Chain of Lakes Park where apparently the Red Sox used to train—hard to picture now with the herons gliding low over the reeds. I tried to snap a photo but mostly just caught my own reflection in the window.

The best part? Mike didn’t rush us. He pointed out turtles sunning themselves on half-sunk logs and slowed down for a blue heron that looked like it owned the place. Sometimes he’d pause mid-story—like when we floated by what’s left of Cypress Gardens—and just let us listen to the water lapping against the hull. You could almost imagine those southern belles standing on that old bridge, all pastel dresses and polite waves. I didn’t expect to feel nostalgic about a place I’d never been before.

I think my favorite moment was spotting an osprey diving for fish, right as Mike was telling us about Elvis Presley skiing here (apparently he wiped out more than once). There was this warm breeze, not too hot yet, and someone behind me quietly munching on chips they’d brought along. It felt relaxed—nobody performing for tourists or anything. Just real Florida: gators lurking near the banks if you looked close enough, otters if you were lucky (we weren’t), and that mix of wildness and old stories you only get on these lakes. I still think about that view across the water when everything went quiet except for some distant laughter from another boat.

Step-by-step itinerary

Day 1 — Explore Chain of Lakes history and wildlife

• Cruise by Chain of Lakes Park
• Pass historic Cypress Gardens and pool
• Explore Winter Haven's famous lakes

Top questions

How long is the Chain of Lakes pontoon tour?

The tour lasts approximately 2 hours.

Is bottled water included on the tour?

Yes, bottled water is provided for all guests.

Can I bring my own food or drinks?

Yes, guests are welcome to bring anything they’d like to eat or drink onboard.

Are there lunch or dinner options after the tour?

You can request reservations at Harborside restaurant for lakeside dining after your tour.

Is this Winter Haven boat tour suitable for kids?

Yes, infants and small children can join; strollers are allowed onboard.

Is wheelchair access available?

Yes, but only one non-transferrable wheelchair guest per tour; call ahead to arrange special pickup location and availability.

What kind of wildlife might we see?

You may spot alligators, otters, blue heron, turtles, osprey, anhingas, and more along the lakeshores.

When is the best time to book for wildlife viewing?

Mornings from late May to September are best—the wildlife is most active then and it’s cooler before afternoon rains.

What’s included

Your day includes a two-hour guided pontoon cruise through Winter Haven’s Chain of Lakes with a local expert sharing stories along the way; bottled water is always provided onboard so you can relax and enjoy spotting wildlife or snapping photos. If you want to extend your experience with lunch or dinner by the lake at Harborside restaurant, just let them know—they’ll help set up reservations for you too.