Several companies on Maui offer horseback riding that's far more appealing than the typical hour-long trudge over a dull trail with 50 other horses.
Mendes Ranch. Family-owned and run, Mendes operates out of the beautiful ranchland of Kahakuloa on the windward slopes of the West Maui Mountains. Morning and afternoon trail rides lasting 1½ hours ($99) are available. Cowboys take you cantering up rolling pastures into the lush rain forest, and then you'll descend all the way down to the ocean for a photo op with a dramatic backdrop. Don't expect a Hawaiian cultural experience here—it's all about the horses and the ride. 3530 Kahekili Hwy., Wailuku, HI, 96793. 808/244–7320 or 800/871–5222. www.mendesranch.com.
Piiholo Ranch. The local wranglers here lead you on a rousing ride through family ranchlands—up hillside pastures, beneath a eucalyptus canopy, and past many native trees. Two-hour rides ($120) are offered twice daily. Their well-groomed horses navigate the challenging terrain easily, but hold on when axis deer pass by! You must be at least eight years old and in good physical condition to participate. Small groups (no more than six riders) make it a more personal experience. End of Waiahiwi Rd., Makawao, HI, 96768. 808/270-8750. www.piiholo.com.
Pony Express Tours. This outfit offers horseback journeys into Haleakala Crater. The half-day ride, which descends into the crater floor for a picnic lunch ($188), is a great way to experience the majesty of the volcano without having to hike. Prior riding experience is highly recommended, as you're on horseback for at least 4 hours. The company also offers 1½- and 2-hour rides ($95 and $110) on the slopes of the Haleakala Ranch. Kula, HI, 96790. 808/667–2200. www.ponyexpresstours.com.