Winter Haven, FL 4-9
Known as the “Chain of Lakes City,” Winter Haven has evolved from humble beginnings to become one of Florida’s most distinctive destinations. It stands as a unique blend of natural beauty, family entertainment, and small-town Florida charm.
A Rich History
Winter Haven’s story began in the late 19th century when the arrival of the South Florida Railroad in the 1880s spurred development in the area. The city was officially incorporated in 1911, but its transformation truly accelerated when Dick Pope Sr. established Cypress Gardens in 1936. This botanical wonderland, famous for its stunning gardens and water ski shows, put Winter Haven on the tourism map and earned the city its reputation as the “Water Ski Capital of the World.”
For decades, Cypress Gardens attracted visitors from around the globe, featuring elaborate Southern belle costumes, botanical displays, and world-class water ski performances that broke numerous records. Though the original attraction closed in 2009, its legacy lives on as part of LEGOLAND Florida Resort, which preserved many of the historic gardens including the iconic Banyan tree planted as a seedling in 1939. Read more.
Natural Splendor
Winter Haven’s most distinctive feature is its impressive system of lakes. With 50 lakes within or bordering the city limits, the interconnected Chain of Lakes offers endless opportunities for recreation and relaxation. The Southern Chain connects 16 lakes via canals, creating a waterway paradise for boaters, anglers, and water sports enthusiasts.
These pristine waters provide the perfect setting for activities like pontoon boating, kayaking, paddleboarding, wakeboarding, and fishing. Local businesses like Off the Chain Kayak Co., Paddleboard Winter Haven, and The Living Water Boat Cruises offer various ways to explore these natural treasures. Bass fishing enthusiasts particularly prize these waters for their abundant catches.
Modern Attractions
Today, Winter Haven is perhaps best known as home to LEGOLAND Florida Resort, which opened in 2011 on the former Cypress Gardens site. This 150-acre interactive theme park features more than 50 rides, shows, and attractions designed specifically for families with children aged 2-12. The resort has expanded to include three accommodation options: LEGOLAND Hotel, Pirate Island Hotel, and LEGOLAND Beach Retreat.
In 2022, the Peppa Pig Theme Park Florida opened adjacent to LEGOLAND, offering young children and their families another exciting attraction. These theme parks, combined with Winter Haven’s proximity to Walt Disney World (just 30 miles away), make it an ideal base for a family vacation centered around Florida’s famous attractions.
Cultural Scene
Beyond its natural beauty and theme parks, Winter Haven boasts a thriving cultural scene. The historic downtown district has undergone a renaissance in recent years, featuring restored buildings that now house art galleries, boutique shops, and local restaurants.
The city’s artistic spirit is evident at venues like the Historic Ritz Theater, which hosts various performances, and Theatre Winter Haven, nationally acclaimed as “one of the best community theaters in America.” Music lovers appreciate Gram Parsons Derry Down, a venue celebrating the legacy of the influential musician who grew up in Winter Haven.
Neighborhoods and Community
Winter Haven encompasses various neighborhoods, each with distinct character. The historic downtown area features charming bungalows and Mediterranean revival homes, while lakefront communities like Lake Eloise and Lake Howard offer stunning water views. Southeast Winter Haven includes newer developments with modern amenities, while the Chain of Lakes area remains highly desirable for its access to water recreation.
The city hosts numerous community events throughout the year, including the annual Smoke on the Water BBQ competition, holiday celebrations, and regular water ski shows performed by the Cypress Gardens Water Ski Team, continuing the tradition that made Winter Haven famous.
Culinary Delights
The local food scene offers everything from waterfront fine dining to nostalgic favorite spots. Harborside Restaurant provides lakeside dining with fresh seafood, while Andy’s Igloo has served burgers, fries, and their famous “Garbage Can” milkshakes since 1951. The craft beverage scene thrives with Grove Roots Brewing Co. and Union Taproom offering local flavors, while coffee enthusiasts can enjoy freshly roasted beans at Haven Coffee Roasters.
For visitors wanting to sample the local fare, Winter Haven Food Tours provides culinary experiences highlighting the city’s diverse offerings.
Winter Haven effortlessly combines Florida’s natural beauty with family entertainment, cultural experiences, and community charm. Whether exploring its lakes, enjoying theme park thrills, or simply relaxing in its old-Florida atmosphere, this Central Florida gem offers a distinctive experience that keeps visitors returning season after season.
POI #1 – Ripley’s AUTOMOTIVE LLC., 2706 Avenue G NW, Winter Haven, FL 33880
POI #2 – Jan Phyl Village Park, 50 Coleman Rd, Winter Haven, FL 33880