Those two islands are very different! Both of them have very small populations--neither island has more than one public high school. Transportation to both of them is a little tricky. You ll need to ride either a prop plane or a ferry to get to either one. The ferry ride to Lanai is shorter, cheaper, and smoother if that makes a difference to you. You start to see the difference when you fly into the airports. LNY is small, but air conditioned and modern. You have to walk down steps when you deplane in either airport, but at MKK, the gate you walk through is literally a chain-link gate. Molokai s airport terminal is little more than a shed, about the length of a high school gym, with four signs hanging on the side: baggage claim, check in, snack bar, and air freight. Plenty of people walk right past the baggage claim on Molokai, maybe because it s a wide concrete bench, maybe because there are usually people sitting on it.98% of Lanai is owned by a company called Castle Cooke. There are two luxury resorts, and almost everybody lives in a small village in the center of the island, all neat and quaint with cute boutiques and cafes. Most of the population of the island is of Filipino descent. The local school benefits from corporate sponsorship when companies like Nike hold executive retreats there. When Bill Gates wanted to get married in a private ceremony, he simply paid for every hotel room on Lanai, and every commercial plane ticket in or out that weekend.Several miles away on Molokai, more than half the total population is of Native Hawaiian descent, and more than three quarters of the schoolkids. The largest tourist attraction is what they used to call a leper colony. A couple dozen Hansen s Disease patients still live on the Kalaupapa penninsula, at the bottom of a thousand foot cliff. Visits to Kalaupapa are tightly controlled, unless you have a sponsor who lives down there.On Topside Molokai, several activist families work hard to chase away anything that looks like mass tourism or overdevelopment--cruise ships for example. Because of their opposition to a proposed luxury residential development that would leave a footprint bigger than the island s largest town, the largest employer on the island shut down the 18-hole golf course, the only movie theater, the hotel with the island s only elevator, and a popular restaurant and bar in 2008. Many of the island s residents make their living through a combination of farming, hunting, fishing, and bartering, and they raise their children to be proud they can live off the land. There is only one hotel on the island, but when you are in the restaurant, looking out to sea, hearing local characters like Uncle Mel and Larry laugh and joke at the bar, watching somebody s auntie get up and dance hula to live music, it seems that the buildings of the Hotel Molokai are the only buildings in the world. Meanwhile, up the hill, among the picnic tables outside the Kualapuu Cookhouse, it s Thursday night: prime rib night. Local folks who still have grease stains on their shirts from work have brought ukuleles and a washtub bass to play music just because they enjoy it. They ve convinced Bruiser to come out of the kitchen and sing a Bruddah Iz song. You ll have to pop across the street to the market to buy a bottle of wine, but the food is fantastic! Which island you prefer will be up to your personal preferences, but visiting either place takes careful planning. Transportation to either island is so limited that a high school sports tournament could prevent you from getting a ticket if you don t make reservations ahead of time.
If you re a scuba diver Lanai is great because it has a famous dive site called the Lanai Cathedrals. It s a series of lava domes you can swim through. If you re not a diver I think Molokai may have more sights to offer.