Sandwiched Between Orlando And Sarasota Lies Florida's Iconic 'Water Ski Capital Of The World'

Driving through downtown Winter Haven, Florida — which is on the National Register of Historic Places — you'll see a water tower proclaiming this city "the water ski capital of the world." Florida's first theme park, Cypress Gardens, and its biggest supermarket chain, Publix, both originated here. Winter Haven is also nicknamed the Chain of Lakes City, since there are over three dozen lakes under its jurisdiction, many of them connected by navigable canals. For tourists, Winter Haven is perhaps best known as the place where you can travel back to your childhood at Legoland. However, history buffs may be drawn more to the park's Cypress Botanical Gardens area than any of its kiddie rides.

The water ski shows at Cypress Gardens, performed on Lake Eloise, were once the world's longest continued daily entertainment production. These shows pioneered the ramp jump, the swivel ski, barefoot water-skiing, and kite-flying and human pyramids on skis. They helped popularize water-skiing internationally, putting it on the cover of Sports Illustrated and attracting TV stars like Johnny Carson and Carol Burnett in the 1960s. Today, the Cypress Gardens Water Ski Team still performs free shows once or twice a month (always on the third Saturday) on Lake Silver in Winter Haven.

Originally showcased at the American Water Ski Association's headquarters in Winter Haven, the USA Water Ski and Wake Sports Hall of Fame is now located in nearby Davenport in the Visit Central Florida information center. You'd pass it just before you hit I-4 on a theme park run from Legoland Florida to Disney World. Winter Haven itself is almost equidistant between Orlando International Airport and Tampa International Airport. It's about an hour's drive both ways, which makes the city a convenient stopover on a trip to Orlando or Tampa and Sarasota.

Theme park history in Florida goes back to 1936 when Cypress Gardens opened on the site now occupied by Legoland. The park's founder, Dick Pope, has been called the "Father of Florida Tourism" for the publicity he brought to the state while promoting Cypress Gardens. According to The Palm Beach Post, Pope was the one who invited Walt Disney to the Sunshine State, having him stand at the entrance to Cypress Gardens with a counter and tally visitors to show how many you could get streaming into a Florida theme park.

In its '60s heyday, before Disney World opened — with Pope receiving the first lifetime pass — Cypress Gardens tied with the Grand Canyon as America's number one tourist attraction. The park's first water ski show was performed in 1942, and it was named for a cypress growers' association that provided materials for the botanical gardens (which started with $300 worth of azaleas and camellias, per the Post). In 2011, 75 years after the debut of Cypress Gardens, Legoland took its place, continuing the shows until 2024, when they finally ended and the water ski team moved outside the park to Lake Silver.

Legoland's Cypress Botanical Gardens section preserves part of the original park, allowing it, like downtown Winter Haven, to remain on the National Register of Historic Places. Walking under the sprawling branches and aerial roots of a banyan tree planted in 1939 is one highlight of Cypress Botanical Gardens. You can also see Lego versions of the park's famous Southern Belles, who would stroll the gardens in hoop skirts, greeting visitors. At the highest point in the gardens, you'll see the Chapel Gazebo, constructed out of a World War II radar dish and pillars from a factory in the cigar capital of the world, Ybor City.

In the downtown Winter Haven historic district, which includes the landmark Ritz Theatre, you'll find two plaques showing where the Publix supermarket chain started. The first plaque, commemorating the original Publix's site in 1930, is located along the storefronts in the town square, surrounding Central Park. Two blocks over, outside a building that's now a Catholic thrift and gift shop, you'll see the second plaque. It marks the spot where Publix transitioned from a store to a supermarket with frozen food cases in 1940.

Winter Haven is about a 15-mile drive from the pretty landscapes and hidden trails of Lake Wales. Some of those trails wind through Bok Tower Gardens, where you can hear the bells of a 205-foot musical instrument chime from the Singing Tower. Surrounded by orange groves, Bok Tower Gardens is a few miles past the headquarters of Florida's Natural, which used to advertise itself as the "one national orange juice brand that can proudly claim to use only 100 percent American oranges." The Grove House visitor center at Florida's Natural, which operates seasonally, is scheduled to reopen in October 2026.

For those traveling by rail, Winter Haven has an Amtrak station connecting it with Orlando, Tampa, and other major cities via the Floridian and Silver Meteor/Palmetto trains. The station is just down the road from the waterfront restaurant Harborside, where you can dine on fried gator tail and enjoy views of Lake Shipp. To see more of the Chain of Lakes City, you can link up here with The Living Water Boat Cruises, which has pontoon boat tours departing from the restaurant's dock. Cypress Gardens Boulevard ends near the lake and railroad tracks, and from there, it's a straight shot of around five miles to Legoland.