Most people visit Maui and only experience one side of the island—resort-lined Wailea. They rent a car and ambitiously try to tackle the Hana Highway in a single day and, sadly, see nothing of the real Hana. Having lived on Maui, I got to experience the island’s many diverse sides, and I always urge friends to divide their stay between different parts of the island if they want to really get to know the island beyond its gorgeous coast. These are 5 tips for getting beneath the surface of Maui.

1. Experience Maui’s Cowboy Culture

Maui is known for its beaches, but head to the heart of the island—”upcountry”—and you’ll get a taste of Maui’s paniolo (cowboy) culture. The rustic little town of Makawao exudes western charm and is a perfect place to spend an afternoon visiting art galleries and independent boutiques. In the past, the only option for accommodations were B&Bs, but now travelers can book a wellness retreat at the stylish upcountry retreat, Lumeria.

2. Spend a Night (or Two) in Hana
Anyone who has tried to drive the 54-mile Hana Highway in a day knows that you end up in a slow line of convertible rental cars, and by the time you reach Hana, you need to turn around and retrace the windy road back home. Get on the road early to beat the traffic, and then plan out your day: stops at Garden of Eden Arboretum and Botanical Garden, Waianapanapa State Park to see its famous black-sand beach, and Red Sand Beach. Most importantly, make time to hike to Makahiku Falls. Spend a night at the Travaasa Hana Hotel, then go for a swim the next morning at ‘Oheo Gulch or surf Hamoa Beach.

3. Hang with Locals in Paia
The hippy town of Paia is full of local character. Spend an afternoon in town and check out cute boutiques such as Imrie, Tamara Catz, and Nuage Bleu. Grab lunch at Café de Amis or Flatbread Pizza, but save room for a scoop of homemade gelato at Ono Gelato Company. I used to get my morning coffee at Anthony’s, where Laird Hamilton and his surf crew could often be spotted.

4. Learn to Fly
Everyone associates Hawaii with surfing, and while there’s some seriously good surf to be had on Maui, the island is really known for its epic windsurf and kite-surf spots. Take a lesson at Kanaha Beach (locally known as kite-surf beach) with the excellent instructors at Kiteboarding School Maui.

5. Get Beyond the Beach Resorts in Wailea
While the resort beaches of Wailea have perks like beach bars, lounge chairs and snorkel equipment, they’re also crowded. When I lived in Maui, I’d bypass these beaches and continue down the road about 15 minutes to Makena Beach State Park. Locals call it Big Beach because of its size, and if you hike over the hill you end up at Little Beach, which is more like a small cove (be warned—on Sundays, Little Beach attracts lots of naked sunbathers).

Want more? Check out our ultimate guide to Hawaii!