MORNING Pick up the famed 42-mile Hana Highway—a series of some 600 odd hairpin turns among cliffs, waterfalls, and primordial trees—just past the boho town of Paia; Maui. It's about three hours east to time-stands-still Hana, where Oprah goes to chill.
AFTERNOON Don't miss Maui's only black-sand beach, at Wai'anapanapa State Park; Hawaii State Parks.
EVENING Stay for dinner at the luxe Travaasa Hana, and crash in a sea-ranch cottage. Rooms from $800, with meals; Travaasa. Or drive to Paia (the return goes quicker—about two hours) and check into the wallet-friendly Inn at Mama's Fish House. Rooms from $175; Mama's Fish House.