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a family trip to Hilton Head Island Another fun-filled family trip to Hilton Head Island. Hilton Head was a great family destination when we were younger, and it's fun to return now that we're all older and partake in the same activities - golf, tennis, swimming at the pool or at the beach, riding along the bike paths, or just sitting in the air conditioning escaping the humidity! This time we even rented a little motorboat and cruised along the waters between the island and the mainland.