Winter Haven, FL 4-6
Winter Haven lives up to its name as the perfect haven from harsh northern winters and a delightful destination year-round. Known as the “Chain of Lakes City,” Winter Haven boasts over 50 lakes within or bordering its city limits, earning it the well-deserved title of “Water Ski Capital of the World.”
Notable Attractions
The crown jewel of Winter Haven’s attractions is LEGOLAND Florida Resort, a vibrant theme park built on the historic grounds of Cypress Gardens. With over 50 rides, shows, and attractions, plus a water park designed specifically for children ages 2-12, it’s a must-visit destination for families. Nearby, the world’s first Peppa Pig Theme Park delights preschoolers with themed rides and shows.
Nature enthusiasts will appreciate the city’s extensive Chain of Lakes, where 24 lakes are connected by navigable canals. Visitors can experience this unique aquatic network through pontoon boat cruises with The Living Water Boat Cruises, paddleboarding adventures with Paddleboard Winter Haven, or kayak rentals from Off the Chain Kayak Co. See another article.
Cultural and Historical Sites
Winter Haven’s rich cultural scene centers around its restored historic downtown district. The Historic Ritz Theater serves as a cultural hub, while Gram Parsons’ Derry Down preserves the musical legacy of this influential artist with regular live performances.
Theatre Winter Haven, acclaimed as “one of the best community theaters in America,” offers high-quality productions from September through April, featuring exceptional local and sometimes nationally-recognized talent. History buffs should visit the Museum of Winter Haven History to explore the city’s past, including its significance in the development of water skiing.
Art lovers can explore various galleries and the vibrant street murals throughout downtown, while the Polk State College Winter Haven Art Gallery showcases rotating exhibitions from established and emerging artists.
Dining and Shopping
Winter Haven’s dining scene offers something for every palate. Lakeside dining is a specialty, with restaurants like Harborside Restaurant serving up fresh seafood with water views. Harry’s Old Place is a local favorite for pecan-crusted grouper, while Andy’s Igloo, a family staple since 1951, offers classic burgers and their famous “Garbage Can” milkshakes.
Beer enthusiasts shouldn’t miss Grove Roots Brewing Co. for locally crafted beers inspired by the area’s citrus heritage, or Union Taproom, featuring 40 rotating taps of craft beverages. Coffee lovers can enjoy freshly roasted beans at Haven Coffee Roasters, Richard’s Fine Coffee, or Honeycomb Bread Bakers.
Downtown shopping includes unique boutiques like Andy Thornal Company, offering high-quality outdoor gear and apparel, and Sherman’s Antiques, which houses thousands of square feet of treasures and even a specialized doll hospital.
Popular Events and Activities
Winter Haven hosts numerous community events throughout the year, including concerts in Central Park, family festivals, and downtown craft beer crawls. A highlight is watching the original Cypress Gardens Water Ski Team perform on Lake Silver on the third Saturday of each month, continuing the city’s storied water skiing tradition.
For a unique perspective on the city’s culinary landscape, Winter Haven Food Tours offers guided tasting experiences through local restaurants and food establishments.
Recommendations for First-Time Visitors
First-time visitors should begin with a boat tour of the Chain of Lakes to appreciate Winter Haven’s unique geography. Next, spend a day at LEGOLAND Florida Resort, making sure to visit the historic Cypress Gardens area and sit under the famous Banyan tree planted as a seedling in 1939.
Explore downtown Winter Haven on foot, stopping at local shops, restaurants, and cultural venues. End your day with a lakeside dinner, watching the vibrant sunset while enjoying local cuisine and craft beverages.
Winter Haven’s central location makes it an ideal base for exploring other Central Florida attractions—it’s just 30 miles from Walt Disney World and 18 miles from Bok Tower Gardens in Lake Wales.
With its perfect blend of natural beauty, family-friendly attractions, cultural richness, and small-town charm, Winter Haven truly offers something for everyone who wants to stay, live, play and explore.
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POI #1 – Jarrett-Gordon Ford Winter Haven Service, 3015 Lake Alfred Rd, Winter Haven, FL 33881
POI #2 – New Beginnings High School Winter Haven, 3425 Lake Alfred Rd, Winter Haven, FL 33881