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Exterior and entrance of LEGOLAND Hotel at LEGOLAND Florida Resort in Winter Haven, FL

Things to Do in Winter Haven

Winter Haven is home to LEGOLAND® Florida Resort and more. Get on Winter Haven’s Chain of Lakes or experience the city’s award winning community theatre, lakeside restaurants and local(kid-friendly) brewery – Grove Roots Brewing Co.

Places to Go and Things to See in 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 – pontoon boat tours, paddle-boarding, wake-boarding, water skiing, kayak tours and fishing.

Then there’s the more relaxed way of enjoying our lakes – watch vibrant orange and pink sunsets from a dock while sipping on a glass of wine or a Winter Haven brewed craft beer.

LEGOLAND Florida Resort

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, Pirate Island Hotel, LEGOLAND Hotel and LEGOLAND Beach Retreat.

Arts & Culture

To others, Winter Haven is a place of varied arts and cultural experiences from multiple art galleries and interactive artistic experiences, locally-owned artisan restaurants and shopping, a restored historic downtown business district and the revival of locally-grown music at Gram Parson’s Derry Down and the historic Ritz Theatre. It’s also home to the one of Florida’s best community theaters, Theatre Winter Haven.

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

Winter Haven Activities

  1. Experience Winter Haven’s Chain of Lakes during a pontoon boat cruise with Living Water Boat Cruises.
  2. Enjoy an afternoon of lakeside dining at Harborside Restaurant. We dare you to eat their entire Harborside Fish Sandwich in one sitting.
  3. Watch the original Cypress Gardens Waterski Team perform on Lake Silver on the third Saturday of each month.
  4. Rent kayaks from Off the Chain Kayak Co. and explore the Chain of Lakes.
  5. Enjoy some of the best craft beer Central Florida has to offer at Grove Roots Brewing Co.
  6. Find a unique gift for yourself or a favorite BFF at Winter Haven’s newest boutique, The Shop.
  7. 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.
  8. 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.
  9. Take flight in an open cockpit biplane with Waldo Wright’s Flying Service.  You can even take control and fly the plane yourself if you dare – no flying experience required.
  10. 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.
  11. Go fly-boarding and learn to water ski with Winter Haven Watersports.
  12. Watch your kids splash around all day at LEGOLAND® Florida’s Water Park, a water park designed specifically for kids ages two to twelve.
  13. Take the entire family to Andy’s Igloo for burgers, fries and a Garbage Can milkshake.
  14. 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.
  15. 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.
  16. Sit under the Banyan tree originally planted as a seedling in 1939 in Cypress Gardens at LEGOLAND® Florida Resort.
  17. Rent a pontoon boat from Marine Supply and cruise many of the lakes on Winter Haven’s Chain of Lakes.
  18. Paddle 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.


Spend a Weekend in Winter Haven

Spend a Weekend in Winter Haven

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family of four on pontoon boat during tour with The Living Water Boat Cruises in Winter Haven, FL

The Living Water Boat Cruises

Explore the many lakes that make up Winter Haven's Chain of Lakes with Living Water Boat Cruises. We highly recommend…

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kayaks being transported on trailer and in back of a black truck with lake in background

Off the Chain Kayak Company

Paddle around Winter Haven's Chain of Lakes with friends and family when you rent from Off the Chain Kayak Company.

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