ORLANDO · DESTINATION
Central Florida’s best days out.
The 15 top-rated winter park & chain of lakes tours in and around Orlando. Real prices, real run times and the operator behind each one, so you can lock in the right day out in a couple of minutes.
A 2-hour pontoon cruise through Winter Haven’s Chain of Lakes with local history, wildlife spotting, and photo-friendly stops.
Most Popular“Besides it being a beautiful day to be outdoors, Rue with his knowledge of the area made it perfect.”
90-minute St. Cloud sunset cruise on East Lake Toho with a covered accessible deck, onboard music and games, and a bar for drinks.
“We had a very relaxing time on the riverboat. The captain and staff were very welcoming and friendly. The saxophone player was great and added a nice touch to the cruise. We bought the tickets the day of the cruise. So glad we did. We’ll do it again in the future.”
Paddle clear kayaks through Winter Park’s chain of lakes and canals with a local guide—small group, about 2 hours.
“This activity was off the hezy my peezees! Straight up, on a kayak solo or with a #2 for 2 hours rowing that slick, see through around lakes and 2 canals hearing about the area. I got so much info I'll never remember but it made the event lively. Had a mishap and sunk the…”
Paddle a clear kayak at sunset through Winter Park’s Chain of Lakes canals, with small-group coaching, wildlife, and local stories.
“Had a wonderful time with Rosa as our guide. We had a small overnight getaway to Winter Park and this sunset kayak was the perfect way to end the day. We will definitely be back. It was beautiful through the canals and Rosa gave us a great history of area.”
Cruise Winter Haven’s Chain of Lakes on a small pontoon for wildlife spotting and local history in about one hour for $26.50.
“What a magnificent tour! Our guide, Rue, was super. He was knowledgeable and very kind. Fabulous afternoon on the water seeing lots of wildlife, osprey, gator, turtles. Etc. Highly recommend.”
Beginner-friendly horseback ride through Lake Louisa State Park’s quieter trails, with safety gear, small-group guides, and scenic photo spots.
“Best experience ever. The horses were so calm. The trail was relaxing and serene. The trainers were very fun and upbeat super nice and professional. Definitely will do this every time I come back to visit Florida.”
Pontoon pub crawl on Winter Haven lakes: 5 lakefront stops by boat with a friendly captain, cooler/ice available, and a sunset cruise.
“Absolutely phenomenal! Captain Dave ran a great show, and our trip was better than what we asked for. We had a ton of laughs, and Capt. Dave had great recommendations at each stop. Definitely want to come back!”
Paddle a glow-lit clear kayak on Winter Park lakes and canals—easy for beginners, taught by your guide, with mansion and wildlife views at night.
“Chris was a great guide, although at times it was a bit hard to hear him. That tiny thing aside, we so enjoyed this. We are NOT young or athletic, and came with minimal kayaking experience. He was helpful and patient. We saw a lovely sunset and ended with moonlight and stars. It was peaceful…”
Private Lake Tohopekaliga fishing charter near Orlando. Guided trophy bass on a 21' boat, all gear included, up to 4 anglers, 4 hours.
“We had a good time fishing with our guide. We caught a few, missed a few, but did catch a 7lb bass. Only negative was not getting the full 3 hours, probably got shorted a good 30 minutes.”
Private Orlando bass fishing on the Butler Chain of Lakes with a licensed captain, modern 21-foot boat, gear, safety, and 4–12h options.
“He was patient and helpful. Knew the area very well and put us on good fishing immediately. Would recommend for others looking for fishing trips.”
A small-group Winter Park walk with 6 food-and-drink samples, Park Avenue history, and discounts that help you stretch the day.
“Learning the history of winter park and eating some good food!! We had a great time. The tour leaders very knowledgeable!”
Private 6-hour fishing charter on Orlando’s Butler Chain of Lakes with gear, instruction, and a pro captain—great value for two.
“John leach was a great tour guide we caught plenty of bass. My stepson and I were both very happy for this experience.”
Cruise Kissimmee’s lakefront to St. Cloud on an all-electric trike for 4 hours, with a beach, splash pad, wildlife, and a 360 pavilion.
“My husband and I did the entire route and then went into the town and had lunch. We had the best time, we are seniors. I am 80 yrs old so don't be afraid of your age - get a bike!”
Paddle Winter Park’s Chain of Lakes on a small-group board tour with safety coaching, a dry bag, and photo/video. From $59 for ~2 hours.
“So peaceful on the canals! This experience is a hidden gem! And you don’t Have to stand up…. Our guide was fabulous.”
Private pontoon fishing on Lake Tohopekaliga near Orlando: calm ride, gear and lures included, casting lessons, eagles and alligators.
“Caught 14 nice sized largemouth in a fun day. Captain Bill did a great job with my 3 grandchildren ages 4, 6 8.”
Every corner of Central Florida, and every way to see it.
