As with most of Hawaii, Kihei has a fascinating history. According to legend, two cloud warriors, one from the north and one from the south, battled one another until a truce was called. When the warriors separated, the piece of blue sky left between them was called Alanui o Lani (Highway to Heaven), and the area beneath that sky is now known as Kihei.
Wailuku has great historical value and a vibrant cultural legacy that runs deep. From Kamehameha’s victory at Iao Valley to the birthplace of the powerful sugar industry, Wailuku played a large role in the island’s history and made a strong impact on the state of Hawai‘i.
The birth of the town can be traced back to the opening of the Paia Store in 1896. The real roots however, go further back to the creation of the plantation camps which housed workers of the Paia Sugar Mill which up until 2000 was Maui's oldest operating plantation.
Lahaina served as a major whaling port and fishing town in the 1800s due to its prime location on whale migration routes, calm ocean conditions and endless days of perfect sunshine. With as many as 400 ships at a time docked in the harbor, Lahaina soon became a sailor's dreamland. When Kamehameha II gave permission for missionaries to begin settling in the islands, they too were attracted to the weather, beauty and importance that Lahaina offered, causing tension with the hard partying sailors.
Another major event that took place at Ka‘anapali long before the age of contact was the Battle of Koko ‘O Na Moku. Two brothers who vied for the coveted royal crown met on this field where the first hole of the Ka‘anapali North Course is now. The bad blood that ran between these two brothers soon ran on the field as thousands of warriors met in a fierce battle.
Maui was a part of a pivotal change in Hawaii's history: After conquering Maui in 1795, Kamehameha united all of the islands into one kingdom. It started in 1759, when yet another battle over land was going on. This time Kalaniopuu, a chief from the Big Island, had captured Hana from the powerful Maui chief Kahikili.