Kaunakakai is Molokai's main settlement, a port town sitting on the flat, dusty plains, and the island's main trading center. A prominent feature is the dockside wharf which extends nearly a half-mile out to sea. Until only recently, this waterfront area was congested with pineapple tractor-trailer trucks and huge barges hauling the ripe fruit off for shipment to Honolulu canneries. At one time the pineapple companies, Libby, McNeil (which was bought out by the Dole Pineapple Company) and Del Monte provided employment for the majority of the people on the island.
Those days are done, however. The high cost of shipping and labor made it hard for the pineapple companies to compete with growers in the Philippines and Taiwan, and the companies phased out production on the island.

In the past few years the island has been trying to ship out export quantities of other agricultural products like sweet potatoes, onions, green beans, watermelons, alfalfa, bell peppers, honey and seed corn.

Before pineapple was king, Kaunakakai was an ancient canoe landing and the site of King Kamehameha V's summer home. Before Prince Lot became king in 1863, he lived on Molokai. During his nine-year reign, he continued to spend his summers on the island and was a sort of unofficial patron to the island. At one time he owned Molokai Ranch, the largest landholding on the island, which was sold to outside buyers after his death.

It was King Lot who planted the nearby Kapuaiwa Grove which originally had 1,000 coconut trees on ten acres of land. There are still several hundred trees in the grove and a sign that warns would-be grove explorers of the danger of falling coconuts.

Across from the coconut grove is Molokai's church row, a line of churches, one after the other. These churches, all of which have at least a partly native Hawaiian membership, are built on land provided by the Hawaiian Homes Commission.

Kaunakakai's Old West-style store fronts are laid out in a three-block grid
and include a general store, a gas station, a drug store, a church, two markets with sparse, overpriced goods, a bakery, a liquor store, a drug store, public library, banks, post office, police station and a number of small shops and businesses and a ballpark next to the community center and fire station.