Surprisingly charming, this sweet little island. The perfect compliment to Kauai for some guaranteed sunshine. Don't forget to visit Paia. MAHALO.

Sleep: Four Seasons Wailea, Ritz Kapalua, Hotel Wailea

Eat: Mama's Fish House, Flatbread Company, Nobu

See: Sunrise atop Haleakala, Makawao, turtles at Ho'okipa, surfing at Peahi (look don't touch)