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Upcountry Maui Tour

Specializing in Exclusive Private Tours on Maui, including Road to Hana Tours, Beach Tours, Haleakala Tours and West Maui Tours.

Upcountry Maui Tour

Golden beaches give way to the rolling hills and misty mountains as you ascend into Upcountry Maui, which is located on the higher elevations surrounding Haleakala – the island’s highest peak. Since early times, Hawaiians have farmed the volcanic soil of the upper slopes, growing taro and sweet potato. Upcountry is also the original stomping ground of the paniolo, or Hawaiian cowboys – a culture that arose in the 19th century when King Kamehameha III invited vaqueros from California to teach islanders to wrangle cattle. From high above, the 10,023-foot Haleakala presides over the “Valley Isle”, with epic sunrises and otherworldly landscapes that feel more like the moon or Mars than Maui. 

Let Maui Legend Tours show you around from a kama’aina’s (local’s) point of view. We know all the best places to go, from the jungles of Haiku to the rolling green and golden hills of Kula. Take a stroll through the historic Upcountry town of Makawao, an authentic cowboy town that even has store-front hitching posts for horses. See the historic Ulupalakua Ranch, formerly the Rose Ranch, and the summer home of Hawaii’s 7th Monarch, King Kalakaua. Observe Haleakala Volcano’s last lava flow while looking down on La Perouse Bay, where the first westerner set foot upon Maui. Upcountry boasts a wide variety of scenic vistas, some of the most stunning in the world. 

Stops and locations along the way include:

  • Paia/ Ho’okipa Beach Park (Continental breakfast)
  • Haiku
  • Makawao (half hour stop)
  • Olinda/ Upper Haleakala Highway
  • Kula
  • Crater Road (4,500 ft. elevation)
  • Botanical Gardens 
  • Lavender Farm
  • Rice Park
  • Kea Kea/Grand Ma’s Coffee House*
  • Ulupalakua – Winery/General Store*
  • South Maui/Kaupo

*There will be additional unscheduled stops and photo opportunities

Cost: $999.99

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  • Private Tour Seating Capacity:  6 passengers
  • Inclusions:  Delicious farm-to-table breakfast and lunch (see menu); Snacks & beverages
  • Exclusions:  Restaurant Tipping; Driver Gratuity (8%- 10% recommended)
  • Transportation:  Honda Odyssey Touring Series luxury vehicle. Pickup and drop-off service provided for all the major hotel resorts and condos on-island


Upcountry Maui Gallery