Paia, a former plantation town on Maui's north shore, is sort of a vacation spot for people who've been on vacation since 1969. For everyone else, it's the home of the legendary 50-foot wave Jaws – or it's that weird place you pass on your way to Hana or Haleakala volcano.
The vibrant three-block town is a patchwork of stained glass, wheatgrass shots, hemp vendors, and eclectic shops and restaurants. Maybe the only reason it never caught on with the package-deal crowd is because its nearest beaches are pummeled by huge and violent waves (for safe surfing and snorkeling, drive to Tavares Bay right on the edge of town).
Paia's position in the middle of Maui means great inland adventures. A few miles south, rising 10,023 feet into the clouds, is the dormant volcano Haleakala. Haleakala Bike Company will shuttle you to the top in predawn darkness, where you can watch the sun rise over the crater and then bomb the 23-mile, 29-switchback descent all the way back to town, in time for an Ono Benedict at Charley's. Come back to Charley's after hours and you may end up catching a surprise Willie Nelson gig: He has a place a few miles up the road.
More information: Fly to Kahului and grab a shuttle, or drive 15 minutes west. The Paia Inn is boutique-slick in the center of town [From $240; paiainn.com].