Winter Haven is a car-dependent city. There is no local bus network of practical use to visitors, and distances between attractions — LEGOLAND, the downtown historic district, the lakefront parks — are too spread out to walk between comfortably.
A rental car is the simplest option, and the chain of US-27, SR-17, and Avenue C NW covers all the main areas. Traffic is light by Florida standards; only the LEGOLAND entrance road backs up on busy days.
The Chain of Lakes Trail, a 4.7-mile paved path, connects several lakefront areas and is suitable for cycling. Bike rental is available at a handful of points downtown and near the lakefront. This is the best option for exploring the lakes and downtown on foot or by wheel without needing to drive.
Ride-hailing (Uber and Lyft) operates in Winter Haven and is reliable enough for getting between downtown and LEGOLAND, though surge pricing applies on peak park days.