Orlando · WINTER PARK TOURS
A chain of lakes joined by narrow canals, with old money on the banks and a brick main street a block away. These 14 cover the scenic boat, the clear kayaks and the food walks, priced and timed.
Cruise Winter Haven’s Chain of Lakes for wildlife, local history, Cypress Gardens, alligators, birds, and a look at Florida’s water-skiing past.
“Bring a hair tie or hat for ladies. Boat was nice and clean. Very knowledgeable guide. Highly recommend.”
Paddle clear kayaks through Winter Park’s lakes and Venetian canals, with a local guide, wildlife, history, and a relaxed two-hour outing.
“Cameron was a great tour guide. The 8am tour had the best weather. He was so knowledgeable and kind.”
Paddle Winter Park’s clear kayaks through historic canals at sunset, with wildlife, local stories, calm water, and hands-on guides.
“Keith was amazing showing us around the lakes. He talked about history, the houses, and stories. We had a great time!”
Cruise Winter Haven’s famous Chain of Lakes by pontoon for wildlife, local history, Cypress Gardens views, and spring-training lore.
“Rich was a knowledgeable tour guide. He was careful to explain all of the interests along the tour - alligators, many birds, social attractions as well as historic homes. The size of the boat was just right for this tour.”
Paddle a clear, light-up kayak through Winter Park’s Chain of Lakes, with wildlife, mansions, local stories, and a calm night on the water.
“Jackson was an awesome tour guide. Highly recommend!! The 9:15 tour was really cool! Would definitely do again!!”
Fish for bass on Orlando’s Butler Chain of Lakes with a private captain, modern boat, gear, water, and flexible trips from 4 to 12 hours.
“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.”
Explore Winter Park through local bites, drinks, history, and six tasting stops on this small-group food walk from $66.84.
“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!”
Trade Orlando’s theme parks for a private six-hour bass fishing charter on Butler Chain of Lakes, with gear, water, and a local captain included.
“John leach was a great tour guide we caught plenty of bass. My stepson and I were both very happy for this experience.”
Paddle Winter Park’s lakes and canals for two hours with a guide, wildlife views, safety gear, and photos included for $59.
“We had a great time kayaking on the lakes. The day was perfect and the guides where very welcoming. Highly recommended.”
Taste Winter Haven through coffee, burgers, barbecue, Thai food, gelato, and local stories on a small-group downtown food tour.
“I want to thank you for creating a memorable and inspiring food tour experience for me and my date. We greatly enjoyed the delectable fruit bruschetta from Obscure Wines, the scrumptious Bami from Bach Lac Bakery, and the divine chocolate expresso gelato paired with samplings of their balsamic vinegars. Unfortunately, we didn't get to indulge in the culinary delights of Temp 1930, El Olivia Mexican Restaurant, and Thai Haven, which was a bit disappointing. However, your passion for the history of Winter Haven made the tour even more fascinating. Additionally, The birthday surprise was a heartwarming touch that made the experience even more memorable.”
Explore Winter Haven on a small-group brunch walk with coffee, pancakes, local history, olive oils, pizza, and a pour-your-own taproom.
“Tour guide knowledgeable and interesting but very disorganized and food samples were poorly presented and took a ridiculous amount of time.”
Review of a private Winter Haven bass fishing charter, with lake choices, pricing, gear, weather rules, and practical booking advice.
“Travelled from Missouri all the way to Orlando on fiancé’s birthday. We drove an hour to get to the charter and arrived to the location 2 hours early only to find out that no one was coming. Called they said they never got the booking even though we had the confirmation number and emails. It sucked because we were super excited for the trip.”
Explore Winter Park after dark on a 90-minute ghost walk filled with haunted sites, pioneer stories, and unsolved mysteries.
“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”
Explore Winter Park on a self-guided scavenger hunt with photo challenges, local landmarks, team play, and app-based clues.
“to far apart to locations, younger ones lost interest fast. Older ones to much walking. Felt intrusive in some areas and some stores did not appreciate groups coming in.”
Pick a gate, a spring run or a stage.
