Visible over the sea from Lahaina in Maui, Lanai is small, relatively secluded and rewardingly undeveloped. Once the biggest pineapple supplier in the U.S., modern Lanai is today home to only 3,200 residents and some of the best snorkeling in the Hawaiian Islands. White sand beaches stretch around large sections of shoreline on this small island, contrasting sharply with the steep black cliffs that frame Kaumalapau Harbor and Manele Bay, dropping down to craggy rock formations and pools at Palaoa Point in the south.
There are only limited stretches of paved road, and many of the sites on Lanai require 4WD, unless you intend to cover the island on foot. Only 18 miles wide and 13 miles long, the main roads run from the northwest through the center to Lanai City and down to Kaumalapau Harbor in the southwest and Manele Bay in the southeast. Rent a 4WD vehicle in town and head for the Munro Trail, navigating the trail up to Lanaihale, where at 3,370 feet you are rewarded for the drive with stunning views out over the island. On the north end of Lanai, a 4WD-only road leads to the Garden of the Gods—a barren and otherworldly spot liberally punctuated with odd piles of rocks. Beyond, further down the rough road, is Polihua Beach. Here you'll find a lot of sand, a lot of sea but not a lot of people, so if you're after isolation this is it.
Lanai boasts some of the best dive spots in Hawaii, so if you're after time under the water rather than just wandering along at water's edge, Hulopoe Bay is a great place to put on your mask. Book a guided tour or rent gear in Lanai for beach dives. Pitch your tent at the only campground open to visitors on Hulopoe Bay for views south across the sea when you've worn out your snorkeling muscles.
For top-rate Hawaiian beach-combing, Shipwreck Beach is where you go to find treasures washed up from the sea. The hulking mass of an old World War II ship is impossible to miss, marooned on an offshore reef—one of many that have gotten hung up on the reefs in the area. Just don't swim here—conditions are dangerous. For some further Hawaiian history, check out the petroglyphs near the west end of Shipwreck Beach or the Luahiwa Petroglyphs closer to Lanai City.
Head in to the comparative civilization of Lanai City if you have problems catching your own dinner on one of the beaches locals fish from. Or, improve your chances by heading out to sea with a charter boat and cast off for marlin, tuna and swordfish.
Ferries cross to Lanai several times a day from Lahaina, Maui and there are daily flights to Honolulu and less-frequent flights to Maui and Molokai.