You’re a little sweaty and hungry. The kids are hyped up on cinnamon sugar-dusted apple fries from LEGOLAND Florida. It’s only 5 o’clock.

So you’ve got some extra time to explore Winter Haven, Florida, and the surrounding area.

“We hope people do stay around,” said Kelly Rote, communications specialist for Visit Central Florida.

Without having to travel far, you and your children will get a kick out of these out-of-the-ordinary places and Winter Haven activities.


Andy’s Drive-In Restaurant

Travel to 1951 with a trip to Andy’s Drive-In Restaurant. Don’t pass up the Steakette Burger or Half Pounder, paired with a Fruit Salad Milkshake, featuring chunks of fresh peaches, pineapple, cherries and bananas. The family diner has a Sunday walk-up ice cream window, where 20 flavors of milkshakes come in small, regular and Big Daddy sizes. “There’s nothing fancy. The atmosphere is very casual,” said third-generation owner Popi Nouaros. And the prices are casual too, with the most expensive burger selling for $5.45.

What to do in Winter Haven - Grab a Bite at Andy's Drive in

Andy's Drive-In

- Scott Audette for VISIT FLORIDA



Still need something sweet?

Webb's Candy

You haven’t tasted fudge until you’ve tried the goat’s milk fudge at Webb’s Candy. “It’s a whole lot richer and creamier,” said Sharon Passmo, who has worked at the Davenport candy shop since 1976. Watch fudge being made, try samples of citrus candy and hang out in the Florida-centric gift shop. Goat’s milk fudge sells for $12.95/pound.

Winter Haven Activities - Dessert at Webb's Candy

Stop by for a sample

- Scott Audette for VISIT FLORIDA



Chain of Lakes: Fish & Wildlife 

While watching the ski show at LEGOLAND Florida, you were looking out on the Chain of Lakes. A collection of 12 canal-connected freshwater lakes, Chain of Lakes is open to skiing, boating and fishing

“We’ve got plenty of wildlife here,” said Tricia Gurr, vice president at Marine Supply, which rents a pontoon boat ($195 for four hours and $295 for eight hours). “We always meet at least four gators when we’re out, and there are plenty of beautiful birds on the lakes.”


Winter Haven activities

Chain of Wakes

- Scott Audette for VISIT FLORIDA

The lakes also are filled with bass and brim, but make sure you have a Florida fishing license.  

For a closer look at herons, egrets, frogs and crawfish on the Chain, book an ecotour via paddleboard, kayak or pontoon boat (863-412-7100). Binoculars and casting nets are supplied.

In addition to critters, you’ll run across parks and playgrounds and three boat-up restaurants on the lakes, including Frank and Manny’s Harborside, where a screened-in downstairs dining area was created specifically for flip-flops-clad boaters hungry for some shrimp scampi.

Explore Downtown Winter Haven

Kids can let some energy go at Central Park, where a giant fountain changes colors to celebrate holidays and different commemorations. Benches and picnic tables dot the park, and strands of lights and lampposts light the park at night. The first Saturday of every month brings approximately 20 classic vehicles to the area, along with doo-wop tunes played by a local radio station. You can grab a bite at a handful of pizza and sandwich places.

what to do in Winter Haven FL

Art in Downtown Winter Haven

- Scott Audette for VISIT FLORIDA


Wander into Andy Thornal Company

With all the big-box sports retailers around the country, you don’t see many independent outdoors stores anymore. At Andy Thornal, around since 1945, you’ll find gear for hunting, hiking and fishing (day-long fly fishing schools are offered for $125.) mixed in with a nature-art studio and travel accessories.

Try Wakeboarding

For $75, participate in adventurous Winter Haven activities with some wakeboarding lessons. Beginners welcome at Chain of Wakes. Ask for Head Coach and United Kingdom wakeboarding champ Stewart Mackie.

Fun for Grownups

If you’re lucky enough to have a babysitter or grandparent along on the trip, tuck the kids into bed and head out for some adult time. Travel down the street to wine bar Grape Expectations. Arabellas Ristorante in downtown Winter Haven offers fine Italian and Mediterranean cuisine and an impressive wine list amid live piano serenades ($30-$50 price range).




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