Maui Outdoor Activities

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Maui Activities

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Hana Tour Private
5.0 (1)

Hana Tour Private

Our Road to Hana tour is completely custom tailored to you with many activities to explore depending on your desires, the weather and your energy...

7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
5.0 (1)
from
$1,000
Private Road to Hana Tour in Maui with SUV
5.0 (1)

Private Road to Hana Tour in Maui with SUV

Enjoy the Road to Hana in a comfortable small-group SUV experience with a maximum of 4 travelers. This tour is designed to feel more personal...

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$1,000
Private Hana Highway Highlights
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Private Hana Highway Highlights

PRIVATE TOUR: PRICE IS PER VEHICLE - HOLDS 1-6 PASSENGERS: CRUISE SHIP PASSENGERS - KAHULUI PORT PICK UP HOTEL GUESTS - Tour picks up from...

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$1,100
Private Full Day Hana Jeep Tour
4.6 (7)

Private Full Day Hana Jeep Tour

My name is Kai Funes Smith, I am a 5 star rating tour driver on the island Maui. What makes my tour unique is I...

8 to 9 hours • Hotel pickup offered • Free Cancellation
8 to 9 hours • Hotel pickup offered • Free Cancellation
8 to 9 hours • Hotel pickup offered • Free Cancellation
4.6 (7)
from
$1,159
Experience the soul of Maui: Tours led by Maui's own!

Experience the soul of Maui: Tours led by Maui's own!

Escape the crowds and experience the legendary Road to Hāna like never before! As a Hawaiian-owned private tour company, we offer an exclusive, immersive, and...

7 to 9 hours • Hotel pickup offered • Free Cancellation
7 to 9 hours • Hotel pickup offered • Free Cancellation
7 to 9 hours • Hotel pickup offered • Free Cancellation
from
$1,334
Road to Hana Halfway Tour
Likely to Sell Out
Likely to Sell Out

Road to Hana Halfway Tour

Your adventure begins with complimentary round trip transportation from the lobby of your resort. Sit back, relax and enjoy the comfort of your air-conditioned luxury...

6 to 7 hours • Free Cancellation
6 to 7 hours • Free Cancellation
6 to 7 hours • Free Cancellation
from
$1,356
Private Upcountry Hiking Tour

Private Upcountry Hiking Tour

Venture into the serene upland forests of Maui, where the vibrant coastlines give way to the cool embrace of majestic trees and lush greenery. This...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
from
$1,356
3-Day Private Kiteboarding Course at Kanaha Beach in Kahului
5.0 (2)

3-Day Private Kiteboarding Course at Kanaha Beach in Kahului

This 3-lesson course includes 9.0 hours of private kiteboarding instruction spread over three days. This is a discounted package. This course is the fast track...

3 days • Free Cancellation
3 days • Free Cancellation
3 days • Free Cancellation
5.0 (2)
from
$1,371
Private Road to Hana Maui Open-Air Jeep Tour
5.0 (40)

Private Road to Hana Maui Open-Air Jeep Tour

Embark on an unforgettable journey along the iconic Road to Hana in our open-air Jeeps, where adventure meets luxury! Experience the breathtaking beauty of Maui's...

7 to 8 hours • Hotel pickup offered • Free Cancellation
7 to 8 hours • Hotel pickup offered • Free Cancellation
7 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (40)
from
$1,399
Private Half Way to Hana Tour with Local Guide
Likely to Sell Out
Likely to Sell Out

Private Half Way to Hana Tour with Local Guide

Explore the stunning scenery of the Road to Hana on this private tour. Enjoy personalized attention from your local guide as you visit iconic spots...

5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
from
$1,399
Maui to Big Island : Big Island Volcano Helicopter Tour & Ground Tour
5.0 (1)

Maui to Big Island : Big Island Volcano Helicopter Tour & Ground Tour

This is the best way to see the most active volcano in the world. This tour will fly you over to the Big Island for...

11 hours
11 hours
11 hours
5.0 (1)
from
$1,400
Private Pipiwai Trail Maui Open-Air Jeep Tour

Private Pipiwai Trail Maui Open-Air Jeep Tour

Discover the breathtaking beauty of Maui on our exclusive open-air Jeep tour of the iconic Road to Hana and the stunning Pipiwai Trail! This luxurious...

6 to 8 hours • Hotel pickup offered • Free Cancellation
6 to 8 hours • Hotel pickup offered • Free Cancellation
6 to 8 hours • Hotel pickup offered • Free Cancellation
from
$1,400
Private Luxury Hana Tour in 7 Passenger SUV
5.0 (1)

Private Luxury Hana Tour in 7 Passenger SUV

My name is Kai Funes Smith, I am a 5 star rating tour driver on the island Maui. What makes my tour unique is I...

7 to 8 hours • Hotel pickup offered • Free Cancellation
7 to 8 hours • Hotel pickup offered • Free Cancellation
7 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$1,450
Private East Maui Hiking Experience
Likely to Sell Out
Likely to Sell Out

Private East Maui Hiking Experience

Nestled along the renowned Hāna Highway, escape into Maui’s untouched rainforest. As you journey to this serene trail, watch the landscape shift into a world...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
from
$1,461
Private Maui Redwood Hiking Experience
Likely to Sell Out
Likely to Sell Out

Private Maui Redwood Hiking Experience

Escape to the Wilderness of Maui’s Hidden Highlands Venture high into the slopes of Haleakalā, where the landscapes transform into an unexpected forest retreat. This...

5 to 6 hours • Free Cancellation
5 to 6 hours • Free Cancellation
5 to 6 hours • Free Cancellation
from
$1,565
Private Redwood Forest Hiking Tour
Likely to Sell Out
Likely to Sell Out

Private Redwood Forest Hiking Tour

Discover the serene beauty of Maui on an exclusive private tour of the Sequoia Redwood Forest. This luxurious journey includes round-trip transportation from Kahului Park...

6 hours • Free Cancellation
6 hours • Free Cancellation
6 hours • Free Cancellation
from
$1,565

Frequently Asked Questions

These answers are based on answers previously given to Cool Hawaii customers' questions.

Recent activity reviews
Magical Maui tour
New York City
Private Road to Hana Maui Open-Air Jeep Tour
naomifR1588LE, Sep 2026
Magical Maui tour
We did two tours with Vicente, and it were the best tour experiences we ever had.Vicente shared history, background information and fun facts during the tour with us. He showed us all kinds of flowers and plants while passing by on the road to Hana. He knows where are delicious lunch and dinner places. He is super professional, thoughtful in every way and a fantastic, versed driver. We felt welcomed, safe and in good hands all time.
Read more
Safe and Enjoyable on the Road to Hana
New York City
Private Road to Hana Tour in Maui with SUV
Jerome_B, Aug 2026
Safe and Enjoyable on the Road to Hana
Our driver, Kellen (substituting for Jonas), gave us a safe trip to Hana and back, with fun stops along the way and a comprehensive description of what we were seeing. It was a great day.
Read more
Great tour experience! 10/10
New York City
Private Full Day Hana Jeep Tour
724angelinaa, Jul 2026
Great tour experience! 10/10
My family of three were picked up from our hotel in Lahaina by our driver/tour guide, Lyman. Lyman was personable, funny, super knowledgeable of the area and island, and a great driver! He was mindful of our interests, needs and comfort. We had snacks and lunch at some local spots and developed a newfound appreciation for the nature and beauty that Maui has to share! The tour was about nine hours long, but time flew by and we hardly noticed how long we had been driving around from start to finish.
Read more
Amazing
New York City
Private Road to Hana Maui Open-Air Jeep Tour
Jonathan_P, Jul 2026
Amazing
Andrea was amazing and really showed us everything. Amazing time was had by all and the memory will last a lifetime
Read more
One of the best days of our lives
New York City
Private Full Day Hana Jeep Tour
H2931PRlukeh, Jun 2026
One of the best days of our lives
We had an incredible experience with Lyman. We felt privileged to get the Hana experience from a true local . Lyman is a funny and special person that was generous with his time, energy, and effort. Hope we can do it again in the future!
Read more
Must do! Amazing
New York City
Private Hana Highway Highlights
cbig, Feb 2026
Must do! Amazing
Thank you Nick for picking us up directly from our condo and showing me and my husband all the beautiful sites on the Hana road. You really are a wealth full of knowledge with the area and all the plants. Especially love the painted eucalyptus trees and hike to the water fall was a blast!
Read more
Awesome trip to Hana
New York City
Private Luxury Hana Tour in 7 Passenger SUV
lana_r, Dec 2025
Awesome trip to Hana
Kai was an exceptional guide and host. He kept us entertained the whole trip. He is kind, funny and informative. Book it!
Read more
Amazing helicopter views
New York City
Maui to Big Island : Big Island Volcano Helicopter Tour & Ground Tour
Donna_M, Oct 2023
Amazing helicopter views
It was our first time in a helicopter and it was amazing. Great pilot and all the crew through Big Hawaiian Helicopters were amazing. Very accommodating too.
Read more
Amazing Tour and Great Service!
New York City
Hana Tour Private
tsharp20, Sep 2022
Amazing Tour and Great Service!
Kekoa is an awesome guy - he pulled my partner and I into his store with a comment on my shirt. We spent almost 45 minutes talking about himself and his family, Hawaii, and local history and politics before he even mentioned that he runs a business booking activities if we were interested. We ended up booking a trip for our whole family (9 people total) on a Road to Hana tour with Chase.Chase was a phenomenal tour guide. He went above and beyond at stops to point out indigenous plants and stopped at local shops to support those businesses. He shared his experiences living on Maui, how he went to the high school the lights the big L on the side of the mountain on fire at graduation.If you are in downtown Lahaina by the banyan tree, you have to at least stop in and talk to Kekoa!
Read more
The real Maui!
New York City
Private Hana Highway Highlights
Clare_S, Jan 2022
The real Maui!
Was by far the best experience on Maui. Our guide, Nick was second to none. The tour was all about what we wanted to get out of it with plenty of stops.
Read more
Awesome instructions
New York City
3-Day Private Kiteboarding Course at Kanaha Beach in Kahului
Windandocean, Dec 2019
Awesome instructions
Gonzo provided extremely thorough instruction through the entire course. He stuck to his plan so that I could successfully complete each skill before moving onto the next…although I wanted to skip to the final step right away. It was super well planned out.
Read more
5 days of private instruction with Gonzo
New York City
3-Day Private Kiteboarding Course at Kanaha Beach in Kahului
SF_Eric, May 2018
5 days of private instruction with Gonzo
Organizing: Suzie answers the phone, is responsive on text, email etc. and provided a quick and easy painless process for organizing private lessons. I arranged it a couple weeks in advance and just connected with her when I arrived to check the conditions.Lessons: Gonzo was my instructor for all five days. (I had a lesson from another company two seasons ago and was not impressed - the instructor was pretty fast and loose with instruction and was more concerned about a tip then my progress.) Gonzo was exactly the opposite - very down to earth, cool guy and provided a good level of instruction the entire time. The conditions at kite beach are quite a bit different than I am used to in the bay area and he was able to adjust his instruction greatly to the conditions and my progress. I have about as long of a learning curve as anyone I know, and he got from my current point to riding consistently upwind. I highly recommend this company, and Gonzo in particular, although the other instructors at the truck seemed equally helpful.
Read more
An Unforgettable Day
New York City
Private Road to Hana Maui Open-Air Jeep Tour
Mark L, Apr 2026
An Unforgettable Day
Ed was the best! A Maui native with a deep love for Maui. He gave us a real sense of what it was like growing up on the island throughout the day. We saw so many cool places and amazing vistas, swam in waterfalls, ate banana bread, hiked bamboo forests, ate at the food trucks in Hana Town, explored caves, saw goats near and far, and bought some fresh fruit from the side of the road. It was an amazing day that my family will never forget, Mahalo Ed!
Read more
highlight of our Maui trip
New York City
Private Full Day Hana Jeep Tour
ghaffaarc, Feb 2026
highlight of our Maui trip
This was everything we could have asked for. He could adjust the trip to our preferences and knew about every little thing. Just me, my wife and our guide, who lives in Hana and showed us the neighborhood he lived in. I was a great way to both learn from the actual people that live there and support the local community as well. It much better to hire a guide, because then you can just focus on enjoying and making the most out of the time.
Read more
The HIghlight of Our Trip
New York City
Private Full Day Hana Jeep Tour
801gretab, Sep 2025
The HIghlight of Our Trip
Kai is an amazing tour guide. He picked us up at our condo and then tailored the tour the way that WE wanted. He was funny, knowledgable and FUN! His stories about the history of the people and islands helped me to learn much about the beauty of Hawaii and the Hawaiian people. If anyone would ask me, I would tell them that this tour is WELL worth it. Mahalo Kai for the best adventure of our trip to Maui.
Read more
This tour was the best of the best!
New York City
Private Road to Hana Maui Open-Air Jeep Tour
cjr988, Aug 2025
This tour was the best of the best!
We spent the day with Vincente! We travels the road to Hana and it was simply AMAZING! Vincente, understood the assignment as we did not know what or where this tour would not should take us! Our guide is a supporter of all things local and it was our absolute pleasure to eat and drink at local establishments! We also learned some incredible information about the island and its vegetation. One thing I must mention is that Vincente is safe and courteous. If you are trying to decide which local company to travel with once you exit the ship, you simply must go with our guy Vincente!
Read more
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