Winter Haven, Florida: A City of Lakes, Legacy, and Water-Borne Culture

Tucked into the heart of Central Florida, Winter Haven is far more than a stop between Tampa and Orlando—it’s a city with a story carved into the water. Nicknamed the “Chain of Lakes City,” Winter Haven is a rare blend of natural beauty, rich history, and a pioneering spirit that helped define an entire sport: waterskiing.

A Brief History of Winter Haven

Founded in the late 19th century and officially incorporated in 1923, Winter Haven began as a modest settlement surrounded by orange groves, cypress swamps, and a patchwork of glimmering lakes. Its name was a deliberate marketing move, chosen to highlight the mild winters and attract northern settlers—an early example of Florida’s tourism magnetism at work.

The arrival of the South Florida Railroad in the 1880s helped Winter Haven flourish, allowing citrus growers to ship their harvests across the country. By the mid-20th century, the citrus industry had become Winter Haven’s economic backbone, and the city was dotted with packing houses and rail yards, all orbiting around its sun-drenched, lake-laced terrain.

But beyond agriculture, Winter Haven was destined to make waves—literally.

The Chain of Lakes: Nature’s Playground

Winter Haven is built around two major chains of lakes—16 in the northern chain and 9 in the southern—that are interconnected by canals dug in the early 20th century. These sparkling freshwater lakes were not just scenic backdrops for suburban life—they were the heart of the community.

The city’s geography is defined by water. Nearly a third of Winter Haven’s area is composed of lakes, offering ample opportunities for boating, fishing, swimming, and, most iconically, waterskiing. Even today, a short walk in almost any direction brings you to a shoreline or canal.

The Birthplace of Waterskiing’s Golden Age

In the world of watersports, Winter Haven holds legendary status. While waterskiing was invented in Minnesota in 1922, it was Winter Haven that turned it into an art form—and a business.

In 1943, the Cypress Gardens theme park opened on the shores of Lake Eloise. Founded by Dick and Julie Pope, Cypress Gardens was billed as Florida’s first commercial theme park. But it wasn’t roller coasters that drew the crowds—it was the water ski shows. With elaborate pyramids, synchronized jumps, and daredevil tricks, Cypress Gardens’ skiers became internationally famous, even performing for presidents and royalty.

The park’s “Aquamaids”—a troupe of graceful, strong female skiers in sequined suits—helped redefine both the sport and women’s roles in athletic performance. It wasn’t long before Winter Haven earned its nickname as the “Water Ski Capital of the World.”

Cypress Gardens served as the backdrop for dozens of movies, TV shows, and tourism campaigns throughout the 1950s and ’60s. It turned waterskiing from a fringe activity into a cultural spectacle.

Culture and Community on the Water

Today, even though Cypress Gardens officially closed in 2009 (and was absorbed into LEGOLAND Florida Resort), the waterski legacy is alive and well. Local teams like the Cypress Gardens Water Ski Team—many of whom are former professionals or second-generation skiers—still perform free shows and train on the same lakes their predecessors once glided across.

Waterskiing has become a rite of passage for many local kids, passed down like a family heirloom. It’s not unusual to see toddlers learning to ski off the back of a pontoon or retirees slaloming at sunrise. The lakes are both community spaces and living history museums—fluid, glistening arenas where tradition meets recreation.

And the lake culture extends beyond sports. Whether it’s weekly fishing tournaments, paddleboarding yoga, or lakeside concerts, Winter Haven’s identity is inseparable from its water. The community’s pace is laid-back but vibrant, reflecting both the serenity of the water and the adrenaline of skiing.

A Modern City with Deep Roots

While the city continues to grow and evolve—with revitalized downtown areas, arts festivals, and an increasingly diverse population—Winter Haven never strays too far from its roots. Citrus still thrives here. So does hospitality. And so does that water-loving spirit that made this small city a global ambassador for a very Floridian way of life.

From its sun-dappled chains of lakes to its barefoot water-skiing veterans, Winter Haven isn’t just a place—it’s a movement on water.