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.
“It was a fun, pretty kayaking session with no fears of getting attacked by a gator. The tour guides are super knowledgeable”
Glide through Winter Park canals in a glow kayak, see fish below the surface, spot mansions, and learn paddling in 1.5 hours.
“Fabulous experience! A warm, calm evening… friendly and knowledgeable guide… safe and well maintained kayaks. We paddled through canals connecting three lakes, each with interesting stories, homes, views. The time flew!”
2.5-hour Winter Park foodie walk with 6 tastings, Park Avenue history, drink stops, and 10% discounts after the tour.
“This was such a fun tour. Lots of food and good drinks! Great conversations also! Book now! Great way to find awesome eats.”
Paddleboard the Winter Park Chain of Lakes in 2 hours with safety gear and an included photo/video package for $59.
“We had a great time kayaking on the lakes. The day was perfect and the guides where very welcoming. Highly recommended.”
Winter Haven guided brunch walk with coffee, pancakes, olive oil tastings, and pour-your-own drinks, plus the Ritz and original Publix site.
“Amada was wonderful, great stories and conversations! Food was delicious and Winter Haven is quaint. Very easy to walk around ( my husband and I both use canes ).”
3-hour guided Flavors of Winter Haven food tour with tastings from BBQ, Thai, coffee and gelato, plus lunch included.
“Our host was very nice and knowledgeable about Winter Haven. The food was good and we learn a lot about Winter Haven”
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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