The 9 Best Winter Park Chain of Lakes Tours

1.2 Hour Historical Wildlife Tour of the Chain of Lakes

★★★★★★★★★★5.0 · 293 reviews · 2 hours (approx.) · from $41Our pick

Join Living Water Boat Cruises for a two-hour pontoon trip through Winter Haven’s connected lakes and canals. Captains such as Rue, Randy, Bryce, Saige, and Darrell point out birds, alligators, historic sites, celebrity ski spots, Cypress Gardens, and the famous Florida-shaped pool.

“Great afternoon spent on the water and so relaxing. We would highly recommend this to anyone!! Bryce was kind and very educational!”

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2.Winter Park Chain of Lakes Day Time Clear Kayak Paddle

★★★★★★★★★★5.0 · 216 reviews · from $69

Spend about two hours in a clear kayak on Winter Park’s Chain of Lakes, passing Venetian-style canals, grand homes, and natural areas. A guide such as Cameron, Rosa, Keith, Chad, or Ryan leads the small group, with paddles, life jackets, and instruction included.

“Rosa was amazing tour guide. Very welcoming and took us all at a nice pace. Would go again in a minute.”

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3.Clear Kayak Sunset Tour through The Winter Park Chain of Lakes

★★★★★★★★★★5.0 · 198 reviews · 2 hours (approx.) · from $80

Paddle a clear kayak through Winter Park’s Venetian-style canals and connected lakes as the light softens. A guide such as Kally, Keith, Chad, Rosa, Chris, or Jackson leads the way, sharing local history, houses, wildlife, and practical paddling help. The two-hour tour returns to 410 Ollie Ave.

“Great experience, loved the tour. If you’re into learning about a little bit of history/house prices and just seeing a nice sight, you’ll like this tour. The guide was awesome. Was a little bit longer than two hours but that’s because we weren’t the strongest paddling group. If you are not used to kayaking lots, you may be a little sore after. I would definitely recommend the tour though. Chad did a great job guiding us.”

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4.1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

★★★★★★★★★★5.0 · 141 reviews · 1 hour (approx.) · from $26Best value

Board a private pontoon at Harborside in Winter Haven for a one-hour cruise through connected lakes. Guides such as Rue, Randy, Saige, and Darrell share local history while you watch for alligators, turtles, ospreys, herons, eagles, and other birds.

“Oh! We had a great captain, Randy who was exciting, fun and a great educator. We had a absolute ball with him. I just moved here to the Chain of lakes area and had family in visiting. Captain Randy educated me on the birds and the Lakes my family was very impressed. Thank you Captain Randy.”

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5.Clear Kayak Glow in the Dark Tour Through Winter Park

★★★★★★★★★★5.0 · 102 reviews · 1 hour 30 minutes (approx.) · from $90

Paddle a clear, light-up kayak through Winter Park’s Chain of Lakes near Rollins College. Guides such as Chad, Chris, and Jackson teach beginners, share local stories, and point out mansions, fish, birds, and underwater plants during this 90-minute evening outing.

“Chad was an excellent guide. Pointed out many cool homes on the lakes. We had an amazing time on this experience. The glow lights in the night were really cool.”

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6.Private Orlando Fishing Charter on Butler Chain of Lakes (4, 6, 8, or 12-Hours)

★★★★★★★★★★5.0 · 43 reviews · 4 hours (approx.)

Meet your licensed local captain at R.D. Keene Park and fish the Butler Chain from a 21-foot boat. Choose four, six, eight, or 12 hours. Rods, tackle, safety gear, ice, and water are included. Steve may be your guide, though captain assignments can vary.

“Steve was great friendly helpful the area is so clean and beautiful the restaurant was really nice and staff were friendly”

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7.Flavors of Winter Park Foodie Walking Tour

★★★★★★★★★★4.5 · 42 reviews · 2 hours 30 minutes (approx.) · from $66

Walk Winter Park’s Park Avenue with a guide, sampling food and drinks at about six local stops while hearing stories about the town, peacocks, celebrities, and dignitaries. The 2.5-hour tour starts at 10:45 a.m., includes discounts, and ends where it began.

“Great variety of stops! Lots of local history! Nice being able to meet in the Visitor Center! Wine tasting at the end was a nice touch!”

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8.Private 6-Hour Butler Chain Of Lakes Fishing Charter Near Orlando

★★★★★★★★★★5.0 · 33 reviews · 6 hours (approx.)

Start at 7 a.m. in Windermere for a private six-hour bass-fishing charter on the Butler Chain of Lakes. Your licensed captain provides a modern 21-foot boat, rods, tackle, safety gear, cooler, ice, and water. No experience is needed, and Captain John Leech may be your guide.

“John leach was a great tour guide we caught plenty of bass. My stepson and I were both very happy for this experience.”

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9.Ghosts of Winter Park – A Chilling Walking Tour!

★★★★★★★★★★5.0 · 4 reviews · from $42

Meet at 401 S Park Ave at 7:30 pm for a guided walk through Winter Park’s old brick streets. You’ll hear tales of a vanished actress, German prisoners of war, and an artist who never finished his work. The tour runs about 90 minutes to two hours and returns to the meeting point.

“We visited a couple weeks ago and had a great time. Luckily for us it was only me and my boyfriend on the tour so it was so private which I liked. The two tour guides were very knowledgeable and nice. We had a fun and spooky time”

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