This wild, lush and sometimes posh region of Maui is home to an extraordinary concentration of variety. In a half-hour drive, you can ascend from the beaches of the North Shore (including the world’s windsurfing capital) through the jungle of the lower slopes, and break out into open Upcountry hills, where cowboys still roam the range, and farmers work the island’s Garden Belt. Communities change accordingly. The hip surfer town of Paʻia gives way to Makawao’s Old West architecture, which dissolves into a handful of stores in mud-on-boots Keokea, after which the road rolls on to eternity – and maybe, we've heard, to Oprah's house.
The region begs for a lazy country drive, taking in athletic surfers, artsy shops, forest trails, mountain views and organic cafes at your own pace. For the adventurous, there’s plenty of ziplining, paragliding and mountain biking.