Few people, if pressed, can name all of the Hawaiian Islands, but to those for whom it is a known quantity, Lanai, the smallest publicly accessible of the main islands, is a harbinger of old Hawaii. At only 141 square miles with a population of 3,200 people, Lanai has only one main town (walkable Lanai City), one high school, a few lodging opportunities, and nothing approaching the concept of traffic. It's just a short boat trip from Maui, across a channel popular among mating whales. Some of the world's best diving and snorkeling exists in the warm, clear water of its Hulopoe Marine Preserve, on the island's southern coast near a prized beach of the same name, where local spinner dolphins are known to show off acrobatic breaches on a regular basis.
Instead of staying on the island (two of the three hotels are Four Seasons properties, which are excellent, but expensive), we prefer to stay somewhere on Maui and take a full-day catamaran tour offered by the family-owned company Trilogy, the only people with permission to escort visitors to the aforementioned preserve and beach. Trilogy has been offering this exclusive tour from Lahaina Harbor since 1973 and has deep ties to the Lanai community, so when you're done with your exhilarating boat ride and expert-guided reef snorkels, you get a tour of a Lanai plantation town given by one of the town's matriarchs as well as a home-cooked BBQ featuring stellar recipes from the homes of locals. There's a drive over dirt roads through the old pineapple fields as well, and, if you have time to break away from the group, some phenomenal cliffside hikes before you return to Maui on the catamaran for another chance to see tail-flapping whales.
Lanai maintains such a treasured peaceful spirit that many well-known personalities flock to the island: Bill Gates got married here, for example, and Oracle CEO Larry Ellison just bought 98% of the rock from the company that had owned it since its halcyon pineapple days. What the wealthy tech maven plans to do with the place remains unknown, but it won't likely change its refreshingly simple qualities. Even if it eventually does, it won't happen overnight; you still have plenty of time to experience what living on Hawaii used to be like.
More information: Trilogy Lanai Tour, $169 for adults; sailtrilogy.com.