
Private Upcountry Maui Tour
Traveler rating
5.0/5
Based on 1 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Upcountry Maui Tour worth booking?
Private Upcountry Maui Tour is a 8-hour experience in Maui, United States, from $1,068 per person. It scores 51 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 1 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 51 / 100
- Rating
- 5/5 (1)
- Duration
- 8 hours
- From
- $1,068 per person
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. Let Maui Legend Tours' most-requested driver/guide, Jack "the Legend" show you around from a kama’aina’s (local’s) point of view. He knows all the best-kept, secret spots, 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 with store-front hitching posts for horses. See the historic Ulupalakua Ranch and the summer home of Hawaii’s 7th Monarch, King Kalakaua, and much, much more! You can check out Jack's 5-star reviews online by Googling "jack the legend maui". Aloha! (Tour duration is approximately 8 hours; Passenger capacity is 4 people)
What you get
About this experience
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. Let Maui Legend Tours' most-requested driver/guide, Jack "the Legend" show you around from a kama’aina’s (local’s) point of view. He knows all the best-kept, secret spots, 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 with store-front hitching posts for horses. See the historic Ulupalakua Ranch and the summer home of Hawaii’s 7th Monarch, King Kalakaua, and much, much more! You can check out Jack's 5-star reviews online by Googling "jack the legend maui". Aloha! (Tour duration is approximately 8 hours; Passenger capacity is 4 people)
What's included
Included
- Private transportation
- Carbonated beverages
- Bottled water
- Snacks
- Lunch
- In-vehicle air conditioning
- Breakfast
- Pick-up & drop-off service at all the major hotel resorts & condos on Maui
- Tea and coffee
Not included
- Sun block
What you'll see and do
Alii Kula Lavender
Beautiful lavender farm in the upper elevations of Maui
30 minutes here · Admission included
MauiWine
See Hawaii's 7th Monarch's summer home, taste locally grown wine, enjoy a delicious lunch at the Ulupalakua Ranch Store.
30 minutes here · Admission included
Historic Makawao Town
Take a stroll through the historic Upcountry town of Makawao, an authentic cowboy town with store-front hitching posts for horses. Enjoy the locally-owned shops and galleries.
30 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 1 travelers per booking
- Operated by
- Maui Legend Tours, LLC
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- No children under the age of 6 allowed
Photos





Traveler reviews
1 verified traveler reviews for Private Upcountry Maui Tour. Ratings and reviews provided by Viator and Tripadvisor.
Road to Hana
Wonderful experience. Jack was very informative and a very helpful guide. Lunch at the food truck for fish tacos was great. Both of us enjoyed the ride as neither of us had to drive. I highly recommend this tour.
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 51
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Upcountry Maui Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Maui.
How much does Private Upcountry Maui Tour cost?
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Prices start at $1,068 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Maui usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Upcountry Maui Tour take?
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Plan for about 8 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Maui is not rushed.
Is Private Upcountry Maui Tour worth it?
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It holds an Outty Ranking of 51 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 1 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Maui, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Upcountry Maui Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Upcountry Maui Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Upcountry Maui Tour?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Maui can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Maui and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Private Upcountry Maui Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Maui within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Maui?
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Maui's three signature days are the Hana road, the Haleakala summit sunrise and the Molokini snorkel sail, and all three are logistics problems as much as experiences. Sunrise summit entry is permit-controlled, Hana is a ten-hour driving day, and Molokini boats vary wildly in size. Our ranking rewards operators who handle permits and keep boat capacity low. On Outty we rank every Maui experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Molokini Crater + South Maui Coast Adventure from Kihei, Maui, West Maui Snorkeling Experience by Boat from Ka'anapali, Maui Eco-Raft Tour: Eye-Level Whale or Dolphin Watching - Lahaina. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Maui?
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April to May and September to October. Whale season runs December to April. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Maui?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Private Upcountry Maui Tour?
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Included: Private transportation; Carbonated beverages; Bottled water; Snacks; and Lunch. Not included: Sun block. Always check the voucher for the final list before you travel.
Does Private Upcountry Maui Tour include hotel pickup?
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Yes, pickup is offered for every traveler from 3 listed pickup locations in and around Maui. You can also enter a custom pickup address when booking.
What languages is Private Upcountry Maui Tour offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Upcountry Maui Tour?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Upcountry Maui Tour wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Upcountry Maui Tour if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
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