As Hilton Head markets itself as a tourist destination, it is not surprising that the busiest times of the year are Easter, Fourth of July, and Labor Day. Also, the Heritage golf tournament, which is part of the PGA Tour, is held in early or mid-April every year.  During these weeks, expect crowded stores, full hotels and long waits at restaurants. If you plan to visit during one of these times, keep in mind that the traffic can get very bad, especially coming on the island on Saturdays between 4pm and 7pm. Finding a place to eat on the weekend can also be a hassle if you do not have reservations.

There are more activities and events planned for the summer. The ocean water is warm, the ocean breezes cooling. During the fall the weather is still warm, the ocean stays warm till mid October,golf courses and restaurants are uncrowded. Spring is also a good time to visit, though the ocean will probably still be cool. Keep in mind the water temperatures even in January may be warm compared to the Jersey shore or Northern California. However, be aware that events are more likely to be rescheduled or cancelled during the low season between Labor Day and Easter. During the winter some businesses and activities curtail events and activities between Thanksgiving and mid-February. Prices are much lower in the winter season, the weather snow free, and some properties will give special long term discounts to snow birds.