Hawaii’s first planned resort town, Kaanapali is a consistent favorite with visitors, with numerous hotels and condominium complexes sharing the prime waterfront location along Kaanapali Beach. Once named America’s Best Beach, the spot offers three miles of sand and warm, swimmable water. Families play on the shores, keeping eyes open for a possible whale swimming in the distance. Tour boats depart directly from the sand during whale-watching season, which runs through the winter.
Along with numerous restaurants, there are a variety of stores located in Kaanapali’s open-air Whalers Village shopping mall. Throughout the day, free Hawaiian entertainment, like hula dancing and lei-making lessons, are offered to guests. A walkway runs in between the beach and the line-up of resorts and businesses, making it easy to forget about the car and stroll from one spot to the next. There’s always a fun crowd of folks moving about.