All Attractions in Winter Haven

Learn to water ski, tube with friends, ride jet skis, rent a pontoon boat, or go paddle boarding at Winter Haven WaterSports. All these activities are done on Winter Haven’s southern Chain of Lakes. Read more...

If you’re looking for a unique vacation experience, Waldo Wright’s Flying Service will fulfill your expectations. You can join Waldo for flight operations in two locations – Winter Haven and Polk City. Read more...

You TOO can fly a Stearman at Preston Aviation! This Tailwheel Flight School offers introductory flights and tailwheel training in a legendary Piper J3 Cub and Boeing Stearman biplane. Read more...

This speedway welcomes racing enthusiasts of all ages to view weekend stock car competitions. Read more...

Explore the many lakes that make up Winter Haven’s Chain of Lakes during a tour with The Living Water Boat Cruises. Read more...

Unleash your creative side with Painting with a Twist. Bring your favorite beverage, possibly a snack and relax. The talented team at Painting with a Twist guides you step by step through the night’s featured painting. Reservations required. Read more...

We are a Mobile paddleboard business that gives us access to several beautiful launch locations on Winter Haven’s Chain of Lakes. We provide Tours which include a lesson for beginners and those who just want to learn more about the sport and the history of the area. We also provide rentals for the experience paddlers and both new and used Read more...

Kayak Equipment Rentals on the Chain of Lakes Read more...

The Cypress Gardens Water Ski Team was started by former waterskiers from Cypress Gardens Theme Park who want to pass on their show skiing legacy to the next generation. Before Walt Disney World and the rest of Central Florida’s sprawl of tourist destinations there was a family-owned theme park known as Cypress Gardens. Cypress Gardens’ founder, Dick Pope, filled the Read more...