Explore Maui’s hidden gems with Jack “the Legend” on a private Upcountry tour. Discover secret spots, historic towns, and breathtaking landscapes.
Explore Maui’s hidden gems with Jack “the Legend” on a private Upcountry tour. Discover secret spots, historic towns, and breathtaking landscapes.
- Alii Kula Lavender - A stunning lavender farm located in the higher elevations of Maui.
- MauiWine - Visit the summer residence of Hawaii’s 7th Monarch, savor wine made from local grapes, and relish a delightful lunch at the Ulupalakua Ranch Store.
- Historic Makawao Town - Wander through the historic Upcountry town of Makawao, a genuine…
- Alii Kula Lavender - A stunning lavender farm located in the higher elevations of Maui.
- MauiWine - Visit the summer residence of Hawaii’s 7th Monarch, savor wine made from local grapes, and relish a delightful lunch at the Ulupalakua Ranch Store.
- Historic Makawao Town - Wander through the historic Upcountry town of Makawao, a genuine cowboy town featuring store-front hitching posts for horses. Explore the unique, locally-owned shops and galleries.

- Private transportation
- Pick-up & drop-off service at all the major hotel resorts & condos on Maui
- In-vehicle air conditioning
- Breakfast
- Lunch
- Snacks
- Bottled water
- Carbonated beverages
- Tea and coffee
- Private transportation
- Pick-up & drop-off service at all the major hotel resorts & condos on Maui
- In-vehicle air conditioning
- Breakfast
- Lunch
- Snacks
- Bottled water
- Carbonated beverages
- Tea and coffee
- Sun block
- Sun block
Golden beaches transition into the rolling hills and misty mountains as you journey into Upcountry Maui, situated at the higher elevations around Haleakala – the island’s tallest peak. Let Maui Legend Tours’ most sought-after driver/guide, Jack “the Legend,” offer you a tour from a kama’aina’s (local’s) perspective. He is familiar with all the best-kept…
Golden beaches transition into the rolling hills and misty mountains as you journey into Upcountry Maui, situated at the higher elevations around Haleakala – the island’s tallest peak. Let Maui Legend Tours’ most sought-after driver/guide, Jack “the Legend,” offer you a tour from a kama’aina’s (local’s) perspective. He is familiar with all the best-kept secret spots, from the jungles of Haiku to the lush green and golden hills of Kula. Enjoy a walk through the historic Upcountry town of Makawao, a genuine cowboy town complete with store-front hitching posts for horses. Visit the historic Ulupalakua Ranch and the summer residence of Hawaii’s 7th Monarch, King Kalakaua, and much more! You can find Jack’s 5-star reviews online by searching “jack the legend maui”. Aloha! (Tour duration is approximately 8 hours; Passenger capacity is 4 people)
- No children under the age of 6 allowed
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.