5 Great Reasons to Spend a Weekend in Winter Haven

By: Jessica Roberts

Ready to book a family-friendly weekend getaway? Here’s a list of 5 exceptionally fun things to during weekend in Winter Haven.

Visiting Winter Haven with Your Family

The city is home to LEGOLAND® Florida Resort and offers a wide range of kid-friendly activities. Explore the city’s popular Chain of Lakes and indulge in amazing meals from our many locally owned restaurants.

father and son on Great LEGO Race roller coaster at LEGOLAND in Winter Haven, FL

LEGOLAND® Florida Resort

LEGOLAND® Florida Resort features a theme park, water park and three onsite hotels – all built specifically for kids ages 2-12. Between the theme park and water park, visitors enjoy more than 50 rides, shows and interactive attractions. Read more through the links below.

1 LEGOLAND Way, Winter Haven

Grove Roots Brewing Co.

Downtown Winter Haven is home to one of the best breweries in Central Florida – Grove Roots Brewing Co. Not only is the beer amazing but the brewery is children and dog friendly. Kids can choose from a variety of sodas, juices and sparkling waters. In addition to yard games, Grove Roots has a variety of board games that can be borrowed through staff.

302 3rd St SW, Winter Haven

family playing Jenga at Grove Roots Brewing Co. in Winter Haven, FL

The Living Water Boat Cruises

No weekend in Winter Haven is complete without exploring the many lakes that make up Winter Haven’s Chain of Lakes.  We highly recommend you book a tour with The Living Water Boat Cruises during your visit. Living Water offers 10 different types of boat tours including a Sunset Cruise, a Day Tour with Lunch, or a 2 Hour Tour.

Tours depart from various location in Winter Haven.

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


This great restaurant is on Winter Haven’s Chain of Lakes so you can expect incredible sunset views if you choose to dine here for dinner. Harborside offers fresh seafood as well as steak and pasta dishes. The kids menu includes Jumbo Fried Shrimp, Cheese Quesadilla, Chicken Tenders, Fettuccine Pasta and Cheddar Mac & Cheese.

2435 7th St SW, Winter Haven

Harborside Restaurant is a great option for waterfront dining in Central Florida, located on Winter Haven's Lake Shipp

Andy’s Igloo Drive In Restaurant

Last, but certainly not least, we feature Andy’s Igloo Drive In Restaurant. Not only is the building retro and super cool, but the ice cream sundaes and milk shakes are out of this world. If you don’t believe us, check out all their great reviews on TripAdvisor.

703 3rd St SW, Winter Haven | CASH ONLY

Family of 4 eating milkshakes at counter inside Andy's Drive-In Restaurant & Igloo in Winter Haven, FL

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