Winter Haven is home to LEGOLAND® Florida Resort and more. From paddle board tours and lakeside dining on the Chain of Lakes to its award winning community theatre, Winter Haven is the perfect vacation destination for everyone in your travel party.

Winter Haven's Central Avenue
Winter Haven's Central Avenue

Winter Haven

Winter Haven has many meanings to many people. For some it's as literal as it sounds . . . it's the perfect haven from the harsh Winter months up North. To others, Winter Haven means experiencing the lakeside lifestyle, with over 55 lakes to ski, wakeboard, paddleboard, kayak, flyboard, jet ski or simply watch the vibrant orange and pink sunsets from the dock while sipping on a glass of wine or a Winter Haven brewed craft beer.

Click the button below to view our Winter Haven Chain of Lakes Map. 

Chain of Lakes Map

To children, or even just the child within, Winter Haven is home to the most beautiful, entertaining and interactive theme park, hotel and beach resort in the world, LEGOLAND Florida Resort, LEGOLAND Hotel and LEGOLAND Beach Retreat. And yet to others, Winter Haven is a place of varied arts and cultural experiences from multiple art galleries and interactive artistic experiences, locally-owned artisanal restaurants and shopping, a restored historic downtown business district and the revival of locally-grown music at the Derry Down and the historic Ritz Theatre. It's also home to the one of Florida's best community theaters, Theatre Winter Haven.

Poster Image for Florida Travel: Experience Lakeland & Winter Haven in 60 Seconds

Winter Haven can truly become the "something-for-everyone" destination to visit, play and stay!

Our Top 20 Things To Do in Winter Haven

  1. Spend a day or two at LEGOLAND® Florida Resort, a 150-acre interactive theme park with more than 50 rides, shows and attractions, restaurants, and shops. And even if you don’t have kids in your travel party, Miniland USA is a sight to behold for all ages.
  2. Go fly-boarding and learn to water ski with Winter Haven Watersports.
  3. Watch the original Cypress Gardens Waterski Team perform on Lake Silver on the third Saturday of each month.
  4. Stay and play at one of the two accommodations at LEGOLAND® Florida Resort: LEGOLAND® Hotel and LEGOLAND® Beach Retreat.
  5. Enjoy an afternoon of lakeside dining at Harborside Restaurant. We dare you to eat their entire Harborside Fish Sandwich in one sitting.
  6. Enjoy some of the best craft beer Central Florida has to offer at Grove Roots Brewing Co.
  7. Find a unique gift for yourself or a favorite BFF at Winter Haven’s newest boutique, The Shop.
  8. Go to the theatre! Nationally and internationally acclaimed, Theatre Winter Haven has been called “one of the best community theaters in America.” Stars have been among their ranks including Tony Award winner Karen Olivo. Their season runs from September through April.
  9. If you have a few HOURS and love to shop, head straight to Sherman’s Antiques. Open seven days a week, Sherman’s Antiques has 5,000 square feet of antiques AND a doll hospital.
  10. Fly a Stearman! Preston Aviation offers 15-minute and 30-minute biplane rides in their Stearman Biplane. You can even take control and fly the plane yourself if you dare – no flying experience required.
  11. Tour the Chain of Lakes with Paddleboard Winter Haven. Owner Kami will meet you at the lake of your choice with boards, paddles, personal flotation devices, instruction, interesting information about the area, and BIG SMILES.
  12. Find a cute new outfit at M. Marie, Winter Haven’s boutique that is described as “California girl meets Florida girl, a splash of hippy chic and a lot of love.”
  13. Watch your kids splash around all day at LEGOLAND® Florida’s Water Park, a water park designed specifically for kids ages two to twelve.
  14. After a morning of shopping downtown, stop in Fire Restaurant and eat one of the best hamburgers in all of Central Florida. If you’re really hungry, start with their fried green beans.
  15. Join the locals for dinner at Harry’s Old Place and chow down on pecan-crusted Grouper – find “Harry’s In a Bag” on the menu.
  16. Shop for a pair of Chaco’s or a new Orvis fly rod at Andy Thornal Company, which happens to be the boutique version of REI right in the heart of Downtown Winter Haven.
  17. Sit under the Banyan tree originally planted as a seedling in 1939 in Cypress Gardens at LEGOLAND® Florida Resort.
  18. Hide behind inflatable bunkers, shoot your friends and family with paintballs, and get the adrenaline rush that comes from an afternoon at Action Paintball.
  19. Rent a pontoon boat from Marine Supply and cruise many of the lakes on Winter Haven’s Chain of Lakes.
  20. Paddle, ski or float across Lake Eloise to watch LEGOLAND® Florida Resort's action-packed Live Water Ski Show at Pirates' Cove.

The Greater Winter Haven Chamber of Commerce can provide additional information about the area.