Maui Horseback Riding Vacations
Haleakala Horseback Tours by Pony Express

Join the Family with a Pony Express Trail Ride
From the verdant expanses of Haleakala Ranch to the other-worldly terrain of Haleakala Crater, you’ll see parts of Maui best seen from a horse! Expertly guided and narrated, you’ll feel like you’re seeing Maui with a friend who has horses. This is not your average tour! Specializing in horseback tours on the slopes of Haleakala, Pony Express is proud to offer one of the only horseback rides in the world that goes into a dormant volcano, Haleakala Crater. Located at the 10,000 ft. elevation, rides are limited to small groups and are led by experienced and knowledgeable wranglers who narrate about the geology, legends, and plant life of the crater. We are also able to offer double the riding options with two scenic locations on both Haleakala Ranch and within the crater at Haleakala National Park.

The Hawaiian cowboy (Paniolo) pre-dates the American cowboy by about 50 years, so cattle ranching occupies a significant chapter in Hawaii’s history. Haleakala Ranch comprises a large portion of Maui’s highlands and our Pony Express rides go through the heart of it at the 4,000’ elevation. The panoramic views of Maui and even beyond to Molokai, Lanai, and Kahoolawe at this elevation are breath-taking and Unforgettable; be sure to have your camera and plenty of film. Plan to make an “Upcountry Day” of it; take a Haleakala Ranch Horseback Ride, view the Crater, see the Tedeschi Winery, Maui’s abundant Protea Farms and end up in the historic cowboy town of Makawao for an early supper and some of Maui’s most unique upscale shopping and art galleries!

Four Distinctly Different Haleakala Maui Horseback Tours
Junction Ride - 4 hours
The “Junction Ride” is considered a novice ride, meaning the trail is gentle with no steep drop-offs. We descend from the 10,000 ft. elevation down the Sliding Sands Trail about 2500’. The ride is 3½-4 hours long and covers 7.6 miles of incredible scenery. As we follow the Sliding Sands trail down to the floor of Haleakala Crater, the ride makes several stops along the way. The entire ride will be narrated but during these stops, our knowledgeable Maui Trail Guides are really able to share their love and knowledge of the island with narration on the history of volcanic activity in Hawaii, geography, Hawaiian culture, and flora and fauna unique to the crater. Watch for your glimpse of the rare Haleakala wonder that is the Silversword Plant. View extinct Cinder Cones and immerse yourself in the exotic, almost alien landscape of this majestic dormant volcano. Enjoy a refreshing picnic lunch at the crater floor before we make our way back up to the top. Riders meet at the visitor center parking lot at the top of the crater at 10:00am and return around 2:00pm. This is not a ride for beginners!

Two Haleakala Ranch Rides - 4 hours Pony Express also offer two rides daily across Haleakala Ranch, a private ranch located at the 4,000 ft elevation of Haleakala Crater. The terrain is lush, rolling pasture land with amazing panoramic views of the island, coastline below, and beyond. The air is crisp and usually cool and the fragrance of the Rainbow Eucalyptus that grow upcountry lazily hangs in the air. This is a working cattle ranch so an experienced Maui wrangler will narrate about the paniolo (cowboy) history and plant life of the area, including the ancient Chinese rock walls and the remains of Hawaiian Heiau’s (temples). This ride checks in at the ranch twice daily at 8:45 and 11:30am.

Pony Express Ride - 6 hours
For the more advanced rider, Pony Express offers the Kapalaoa Cabin Ride. As the longest trail ride on Maui, we are able to cover 12 miles of extraordinary scenery with over 5 hours in the saddle. This ride allows you to see all the rarely seen features of the crater floor, including the