ORLANDO
Orlando’s best days out.
The 9 most popular winter activities tours in Orlando, with prices, run times and who you book through. The standouts worth building a day around, and what each one actually gets you.
Kayak Winter Park’s Chain of Lakes in a clear kayak with a local guide. Small groups, gear included, about 2 hours from Dinky Dock Park.
Most Popular“Cameron was a great tour guide. The 8am tour had the best weather. He was so knowledgeable and kind.”
Clear kayak sunset tour in Winter Park’s Chain of Lakes. Small-group paddle through Venetian canals, wildlife views, and $80 golden-hour sights.
“Chris was our guide and he was amazing. He was very laid back and helpful. The tour itself was beautiful!!”
Glide through Winter Park canals in a glow kayak, see fish below the surface, spot mansions, and learn paddling in 1.5 hours.
“We had a great time. The light up kayak was beautiful in the water. We could see all the way to the bottom of the lake. Our guide Chris was amazing and knowledgeable of the area. He taught us how to properly kayak and made us feel at ease. I would recommend this to everyone.”
2.5-hour Winter Park foodie walk with 6 tastings, Park Avenue history, drink stops, and 10% discounts after the tour.
“We had never been there before, so that was lovely. We enjoyed the wine tasting as well as the host. Our guides were awesome. Looking forward to returning.”
Paddleboard the Winter Park Chain of Lakes in 2 hours with safety gear and an included photo/video package for $59.
“Rachelle was great, and we had a wonderful experience. The Winter Park Chain of lakes is such a beautiful gem and we are so lucky!”
Winter Haven guided brunch walk with coffee, pancakes, olive oil tastings, and pour-your-own drinks, plus the Ritz and original Publix site.
“We had such a fun time, and she is one of the best toue guides ever! We were the only 2 and she could have easily canceled the tour but didnt and we ended up with our own unoffical private tour! Amazing food, conversation, drinks and good history.”
3-hour guided Flavors of Winter Haven food tour with tastings from BBQ, Thai, coffee and gelato, plus lunch included.
“Amada was patient, knowledgeable and very accommodating, creating a tour specifically for our tastes and interests. It was great!”
Private winter bass fishing in Winter Haven’s chain of lakes. Gear, tackle, and a cooler included. Up to 2 people. Choose AM/PM.
“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…”
A 90-minute Winter Park night walk with ghost stories, unsolved mysteries, and pioneer tales on foot for $42.
“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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