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, the first week of August, and Labor Day. Also, the Verizon 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 on Saturdays. Finding a place to eat on the weekend can also be a hassle if you do not have reservations, so either buy food in advance or get take-out/delivery.

Though there are more activities and events planned for the summer, it may not be the best to visit, as the island is crowded and prone to summer storms, which may range from an afternoon rainburst to a severe hurricane. Go during the early fall if possible, as the weather is still warm and restaurants are uncrowded. Spring is also a good time to visit, though the ocean will probably still be too cold for swimming. However, be aware that events are more likely to be rescheduled or cancelled during the low season between Labor Day and Easter. Do not go during the winter, as many businesses and activities shut down between Thanksgiving and mid-February.