Taking a Maui horseback riding tour is an enjoyable, at times thrilling experience. Often there are views of Maui unreachable any other way, and if you’re interested in more than reading about Hawaii’s paniolo heritage, visiting a ranch and striking out on horseback is the way to do it. Though there are plenty of guided tours available, each one differs fairly significantly in the type of terrain, riding, and overall experience offered.
The most well-known horseback riding outfit on this side of the island is Mendes Ranch (3530 Kahekili Hwy., 808/871-5222), a family-run operation on the road to Kahakuloa. Just before the seven-mile marker on Kahekili Highway, often you will smell Mendes Ranch before you see it. That’s what happens when you have a fully operational ranch with more than 300 head of cattle, but it’s all part of the paniolo experience. While group sizes can be large and the 1.5-hour rides run $110/person, what separates Mendes from all the other ranches is that you can actually run the horses. You can gallop at Mendes, so there’s no nose-to-tail riding here. The ride itself goes from the family ranch house down the bluffs to the windswept shoreline, and lunch can be included with some of the tours. Expect afternoon rides to be windy and the morning rides to be clearer and calm. The coastal views here aren’t accessible by any other means, and Mendes Ranch is a fabulous option to see them.
Much closer to the main resort areas is the central Makani Olu Ranch (363 W. Waiko Rd., 808/870-0663), another working cattle ranch set back in the Waikapu Valley. Only 25 minutes from Wailea and 35 minutes from Ka‘anapali, Makani Olu maintains a herd of 100 longhorn cattle and caps the trail rides at only four riders. The two-hour, $125 ride takes guests across Waikapu Stream into the forest behind the Maui Tropical Plantation and eventually turns inland and works its way up the valley. The views from this part of the trail look back at Haleakala and the green central isthmus, and this is the only way you can gain access to this remote part of the island. All tours are at walking pace only, which makes them a better option for novice riders. A lunch option is available with the ride, and experienced riders can opt for a $150, private or semiprivate ride that includes 45 minutes in a round pen working on skills. While this is a nice option for families, all riders must be over 10 years old and under 220 pounds.
Makena and Beyond
The only horseback riding in South Maui is found way down south at the end of the road at Makena Stables (8299 South Makena Rd., 808/879-0244), a family-run outfit that has been leading horseback riding tours since 1983. The trails here meander over Ulupalakua Ranch land only accessible via a private tour. Along the way there’s a good chance of spotting axis deer or wild goats that clamber across the jagged a‘a lava. This is one of the few horseback riding operations on the island with the possibility of riding your horse directly along the shoreline. The only other way you can access this stretch of coastline on horseback is if you take a tour from Triple L Ranch beginning in Upper Kanaio. Since Triple L is 40 miles from Wailea, however, and Makena Stables is only seven, this is the obvious choice if your vacation is based in South Maui.
Not only do the views stretch out over the waters of La Perouse Bay to the island of Kaho‘olawe in the distance, but you ride directly through the island’s most recent lava flow, taking time to stop at Kalua O Lapa, the volcanic vent from which Madame Pele leaked her fiery liquid only a few centuries ago. Group sizes are capped at six, and riders must be under 205 pounds. To escape the brutal South Maui sun, take a sunset ride during the coastline’s most artistic and romantic hour.
Sprawling across 800 acres, Pi‘iholo Ranch (808/270-8750, 8:30am-1pm Mon.-Sat.) is a working cattle operation set back in the pastures above Makawao. One-hour ($75), two-hour ($120), and private rides are available for journeys across open ranchland 2,000 feet up on the mountainside. Groups are capped at six people and the one-hour and two-hour rides go at a mellow pace. Coffee is provided for the early morning rides (8:30 and 9am), and every Tuesday and Thursday at 4pm there are free roping sessions open to the public to come and enjoy. To reach Pi‘iholo Ranch go 1.5 miles up Pi‘iholo Road before branching left on to Waiahiwi Road. Follow this for 0.5 mile, and the sign for the ranch will be on the left.
In addition to offering rides across the pastureland of Haleakala Ranch ($95-110), Pony Express (18303 Haleakala Hwy., 808/667-2200) is the only operation on the island that takes you down inside the crater on horseback. Saddling up from the 9,800-foot level near the summit, riders depart down Sliding Sands Trail before eventually reaching the crater floor over 2,500 vertical feet below ($182). Over the course of this 7.5-mile, four-hour excursion, you’re able to descend into the backcountry of Haleakala National Park and a realm accessible only by trail. It can be cold and breezy up here, but riding in the saddle as you crunch your way across an otherworldly panorama of cinder is a riding experience unlike any other on the island.
Keokea and Ulupalakua
If you want the feeling that you’re riding with a genuine ranching family in their scenic backyard, then book an excursion with the folks at Thompson Ranch (Middle Rd., 808/878-1910). The rides take place in the pastures of a working cattle ranch, and there isn’t one thing about this ride that feels “touristy” in any way. You meet Jerry and Toni Thompson at their ranch house and then hitch a ride with them up to the horse stables where you are introduced to your steed for the next two hours ($100). Once saddled up, you climb up toward the uppermost edge of the ranch where the pasture bumps into the edge of the Polipoli forest. Since this is all private land—and there is no other way to access this section of the mountain—riding across these pastures provides a glimpse into one of the only places in the United States where you can ride near forests of native koa and sandalwood trees and gaze down on the clear blue Pacific. This is a fantastic ride for couples or families looking for an off the beaten path riding experience.
To ride across the back of a dormant volcano on horseback, head to Triple L Ranch (15900 Pi‘ilani Hwy., 808/280-7070, 8am-6pm daily). While one-hour and two-hour rides are offered for $125 and $150 (and include a voucher for a free Bully’s Burger), the real reason to choose this ranch over any other is the chance to book either a half-day ($285) or full-day ($375) ride down to a rocky beach completely inaccessible from anywhere else on the island. Centuries ago this section of mountain sported a large native Hawaiian population, and along the way the guides will point out archaeological sites dating to the days of ancient Hawaii. Furthermore, if you are an advanced rider and want to trot, canter, or gallop your horse, there isn’t anyone who’s going to stop you. Four miles past the Tedeschi Winery in Ulupalakua, this is truly the “last frontier” out here, a place of rugged beauty, relentless sun, and genuine guides who have been ranching this land for more than 50 years.