Things To Do Near Winter Park
The best things to do in Winter Park, Florida: clear kayak tours on the chain of lakes, Park Avenue food tours, ghost walks and more, plus hotels.
Winter Park, just north of Downtown Orlando, feels like a different world from the theme parks: brick streets, oak-shaded parks, the boutiques and cafes of Park Avenue, and a chain of lakes linked by narrow canals lined with historic homes.
This page ranks the bookable experiences in and around Winter Park by traveler ratings and review volume, led by some of the highest-rated kayak tours in the Orlando area, and adds the town's best free highlights.
- 12 options compared
- From $14.99
- Avg rating 5.0 (623 reviews)
- Typical length 2 hours
- 9 with free cancellation
Prices and ratings updated .
Our quick picks
Compare the top 9
| # | Experience | Rating | From | Length |
|---|---|---|---|---|
| 1 | Winter Park Chain of Lakes Day Time Clear Kayak Paddle | 5.0 (249) | $69 | 2 hours |
| 2 | Clear Kayak Sunset Tour through The Winter Park Chain of Lakes | 5.0 (202) | $80 | 2 hours |
| 3 | Paddleboard the scenic Winter Park Chain of Lakes | 5.0 (16) | $75 | 2 hours |
| 4 | Ghosts of Winter Park - A Chilling Walking Tour! | 5.0 (5) | $42 | 1 hr 30 min |
| 5 | Flavors of Winter Park Foodie Walking Tour | 4.5 (46) | $66.84 | 2 hr 30 min |
| 6 | Winter Park Arts & Culture Walking Tour | New | $50 | 2 hours |
| 7 | An Epic Bar Crawl in Winter Park | New | $14.99 | 1 hr 30 min |
| 8 | Peacocks, Presidents and Puzzles - The Winter Park Walking Tour | New | $42 | 1 hr 30 min |
| 9 | Wacky Winter Park Scavenger Hunt | New | $29 | 2 hours |
What is on this list
1. Winter Park Chain of Lakes Day Time Clear Kayak Paddle
Take a 2 hour guided tour in our 100% clear kayaks while exploring the Winter Park Chain of Lakes. Winding through the Venetian style canals you’ll find the picturesque city is laced with history and lined with some of Florida’s finest flora and fauna.
Why it made our list
- Rated 5.0 out of 5 by 249 travelers
- Small group experience
- Private option for your group only
- Takes about 2 hours
2. Clear Kayak Sunset Tour through The Winter Park Chain of Lakes
Be ready for a paddling excursion that will showcase Winter Park’s natural beauty from the water and lead guests up to a breathtaking sunset. We’ll guide the way through narrow Venetian style canals laced with history and lined with some of Florida’s finest flora and fauna.
Why it made our list
- Rated 5.0 out of 5 by 202 travelers
- Small group experience
- Private option for your group only
- Takes about 2 hours
3. Paddleboard the scenic Winter Park Chain of Lakes
Discover the allure of Winter Park on our exclusive paddle tour! Immerse yourself in the historical charm and lush tropical beauty that adorn the canals connecting the Winter Park Chain of Lakes.
Why it made our list
- Rated 5.0 out of 5 by 16 travelers
- Free cancellation available
- Small group experience
- Takes about 2 hours
4. Ghosts of Winter Park - A Chilling Walking Tour!
Winter Park has seen many famous business leaders, US President and celebrities pass along its cobble stone streets along and near famous Park Avenue. We'll tell you a little but about their time in this village, mostly about the ones who apparently never left!
Why it made our list
- Rated 5.0 out of 5 by 5 travelers
- Free cancellation available
- Takes about 1 hr 30 min
5. Flavors of Winter Park Foodie Walking Tour
Take a bite out of the best of Winter Park and stroll down Park Avenue on our unique Flavors of Winter Park Foodie Walking Tour! Park Avenue is home to many internationally themed and locally owned boutique restaurants who are thrilled to share samples of their cuisine with you!
Why it made our list
- Rated 4.5 out of 5 by 46 travelers
- Free cancellation available
- Flagged by Viator for excellent quality
- Private option for your group only
6. Winter Park Arts & Culture Walking Tour
Winter Park has some of the finest art museums clustered together in close walking distance. Join us for a guided historical tour of this breath-taking village as we explore art and historical museums and share a brief history of the town and its buildings while traveling from location to location.
Why it made our list
- Free cancellation available
- Private option for your group only
- Takes about 2 hours
7. An Epic Bar Crawl in Winter Park
Dive into adventure, your go-to for the ultimate app-led adventure hunts! Step into a world where every landmark and hidden gem is waiting to be discovered.
Why it made our list
- Free cancellation available
- Takes about 1 hr 30 min
8. Peacocks, Presidents and Puzzles - The Winter Park Walking Tour
Welcome to one of Florida’s best-kept secrets, the lovely city of Winter Park! Chartered in 1887, Winter Park is more than 100 years old and has the pedigree to prove it.
Why it made our list
- Free cancellation available
- Private option for your group only
- Takes about 1 hr 30 min
9. Wacky Winter Park Scavenger Hunt
Our very unique, immersive adventures are the only ones of their kind. We provide your very own remote, interactive, live host to assist and encourage you along through your phone.
Why it made our list
- Free cancellation available
- Takes about 2 hours
Free and local highlights in Winter Park
- Park Avenue: Boutiques, cafes and restaurants along Central Park, perfect for an afternoon stroll.
- Winter Park Farmers' Market: Saturday mornings at the historic train depot.
- Kraft Azalea Garden: A lakeside garden on Lake Maitland with huge cypress trees and sunset views.
- Hannibal Square: A walkable dining district just west of Park Avenue.
How to choose
See the lakes from the water
Clear kayak and paddleboard tours glide through the canals and past lakefront estates. The narrated Scenic Boat Tour, running since 1938, is the relaxed alternative.
Taste Park Avenue
A walking food tour is a great introduction to the local restaurants before you pick a spot for dinner.
Time it for sunset
Sunset and glow-in-the-dark paddles are Winter Park's most romantic experiences and sell out early.
Good to know before you book
- Winter Park is 30 to 40 minutes from the major theme parks.
- SunRail stops in the middle of town, a short walk from Park Avenue.
- Parking on Park Avenue is limited on weekends; arrive early.
- The Charles Hosmer Morse Museum, home to a famous Tiffany collection, is on Park Avenue.
How we rank
We compare every matching experience listed on Viator for the Orlando area and rank them with a weighted score that balances the average traveler rating with the number of reviews, so a few perfect scores cannot outrank thousands of consistent ones. Transport-only services and listings Viator flags as inactive are left out, and near-duplicate listings are grouped. Prices and ratings refresh each time we update our data. We may earn a commission when you book, which never affects the ranking. See our disclosure.
Frequently asked questions
How much do tours and attractions near Winter Park cost?
The 12 options we track start from $14.99 per person, with a typical starting price of about $66.84. Prices change by date and group size, so check the booking page for your dates.
What is the best-rated option on this list?
Right now it is Winter Park Chain of Lakes Day Time Clear Kayak Paddle, rated 5.0 out of 5 by 249 travelers, from $69.
Can I cancel if my plans change?
9 of the 12 options here offer free cancellation, usually up to 24 hours before the start time. The exact policy is shown on each booking page.
Is Winter Park worth visiting from Orlando?
Yes. It is one of the prettiest places in Central Florida, with great food, shopping and some of the best-rated kayak tours in the area. It is an easy half day from anywhere in Orlando.
What is Winter Park, Florida known for?
Park Avenue, the chain of lakes and its Scenic Boat Tour, Rollins College, the Morse Museum's Tiffany collection and a charming small-town feel.