Windward Bay Beach, being a cove, generally offers calmer waters compared to more exposed beaches, making it suitable for swimming. The sheltered nature often means clearer conditions, ideal for snorkeling. However, as with any natural environment, it's always wise to assess conditions upon arrival and be mindful of any currents, especially near the headlands. There are typically no lifeguards on duty, so swim with caution.

To experience Windward Bay Beach at its most tranquil, visiting during the shoulder seasons or early mornings/late afternoons is recommended. As it's often overshadowed by Galleon Beach, it naturally sees fewer visitors. Avoiding peak tourist season, typically December to April, will further enhance the quiet, secluded atmosphere. Weekdays are generally less busy than weekends.