7 days in Maui Itinerary

Wailea is a census-designated place (CDP) in Maui County, Hawaii, United States. Escape the urban bustle at Kapalua Beach and Ho'okipa Beach Park. Explore Wailea's surroundings by going to Zipline (in Haiku) and Lahaina (Kayaking & Canoeing & River Rafting & Tubing). The adventure continues: look for all kinds of wild species at Honolua Bay, kick back and relax at Kamaole Beach Park III, tour the pleasant surroundings at Ulua Beach, and get some jogging in at Wailea Beach Path.

To find other places to visit, where to stay, ratings, and other tourist information, read our Wailea trip itinerary planner.

Chicago to Wailea is an approximately 11.5-hour flight. The time zone changes from Central Standard Time to Hawaii Standard Time, which is usually a -4 hour difference. Expect a bit warmer temperatures when traveling from Chicago in May; daily highs in Wailea reach 86°F and lows reach 68°F. Wrap up your sightseeing on the 21st (Mon) to allow time to travel back home.