Maui Private Sightseeing Tours

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Maui Activities

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Maui Classic Road to Hana Self-Guided GPS Audio Driving Tour
4.8 (248)

Maui Classic Road to Hana Self-Guided GPS Audio Driving Tour

Experience Maui’s iconic Road to Hana at your own pace on a self-guided GPS audio driving tour through lush rainforest, waterfalls, coastal viewpoints, and historic...

12 to 13 hours • Free Cancellation
4.8 (248)
from
$25
Ultimate Self-Driving Audio Tour of Road to Hana, Maui
4.4 (147)

Ultimate Self-Driving Audio Tour of Road to Hana, Maui

Purchase one tour per car, not per person. Everyone listens together! Explore the Hana Highway, Maui’s top attraction, with this self-guided audio tour! The 65-mile...

2 to 3 hours • Free Cancellation
4.4 (147)
from
$17
Private Road to Hana Tour Black Sand Beach/Waterfalls/Sea Turtles
5.0 (236)

Private Road to Hana Tour Black Sand Beach/Waterfalls/Sea Turtles

Looking for more than just a Road to Hana tour? The Magic of Maui Experience is a 100% private, customized adventure designed entirely around you....

8 hours • Free Cancellation
5.0 (236)
from
$299
Maui: VIP Private Road to Hana Tour with Pick Up
5.0 (1,217)

Maui: VIP Private Road to Hana Tour with Pick Up

Discover the magic of Maui with our exclusive, personalized private tours. Say goodbye to crowded buses and rigid schedules—your adventure is uniquely crafted to suit...

8 to 10 hours • Hotel pickup offered • Free Cancellation
5.0 (1,217)
from
$299
Epic Waterfall Adventure, the Best of Maui
4.9 (351)

Epic Waterfall Adventure, the Best of Maui

Only tour company on Maui that offers optional cliff jumping into Waterfalls, go pro photography, and videography! This personalized experience is great for nature lovers...

3 hours 30 minutes • Free Cancellation
4.9 (351)
from
$179
Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour
4.7 (70)

Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour

Take an adventure and experience an important part of Hawaiian history on this 1-hour canoe tour in Maui. Paddle a traditional Hawaiian outrigger canoe while...

1 hour • Free Cancellation
4.7 (70)
from
$155
Private Road to Hana Tour with Pickup
4.9 (48)

Private Road to Hana Tour with Pickup

One of the most sought-after and scenic drives in the world, you will be amazed at every turn on our Private Road to Hana Tour....

8 hours • Hotel pickup offered • Free Cancellation
4.9 (48)
from
$400
Waterfall, Rainforest, Chocolate Tour & Historical Sites
4.7 (169)

Waterfall, Rainforest, Chocolate Tour & Historical Sites

"VOTED BEST OF MAUI" Fun Easy Mini Waterfall hike, Chocolate Tour, Rainforest Adventure & Ancient Historical Sites at "The Legendary Kings Gardens Maui" * See...

2 hours
4.7 (169)
from
$148
Lanai Snorkeling Half Day with Sea Scooter
Likely to Sell Out
Likely to Sell Out
5.0 (8)

Lanai Snorkeling Half Day with Sea Scooter

Winner of 2018 Travel & Hospitality Award Winner & Certificate of Excellence Cool Hawaii Award for 9 years in a row. Our 50 ft Sanity...

4 hours 15 minutes • Free Cancellation
5.0 (8)
from
$193
Maui -PRIVATE- Air Tour: 5 Islands: (2-5 people): SEE Even MORE!
5.0 (816)

Maui -PRIVATE- Air Tour: 5 Islands: (2-5 people): SEE Even MORE!

Enjoy Maui’s ONLY PRIVATE Air Tour and Cool Hawaii #1 Ranked Outdoor Activity on Maui! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui...

80 to 90 minutes • Free Cancellation
5.0 (816)
from
$536
Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!
5.0 (598)

Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!

Maui’s ONLY *PRIVATE* Air Tour is Cool Hawaii #1 Ranked Outdoor Activity on Maui! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day...

1 hour • Free Cancellation
5.0 (598)
from
$380
Deluxe Halfway to Hana: Private Tour from Kahului
Likely to Sell Out
Likely to Sell Out
5.0 (200)

Deluxe Halfway to Hana: Private Tour from Kahului

This excursion is completely private! Just you and one of us! Receive undivided attention and the space for an intimate experience. Enrich the journey with...

7 to 8 hours • Free Cancellation
5.0 (200)
from
$359
VIP Private Road to Hana Tour in Cadillac Escalade with Pickup
Likely to Sell Out
Likely to Sell Out
5.0 (100)

VIP Private Road to Hana Tour in Cadillac Escalade with Pickup

No other tour comes close to the ultimate luxury and adventure of our tours. Enjoy Ultra VIP style, class & luxury in our new black...

10 to 12 hours • Hotel pickup offered • Free Cancellation
5.0 (100)
from
$258
The Ultimate Road to Hana Slingshot Adventure from Lahaina Maui
5.0 (5)

The Ultimate Road to Hana Slingshot Adventure from Lahaina Maui

Experience Maui's legendary Road to Hana like never before—in an exhilarating Polaris Slingshot from Aloha Motorsports! Forget cramped buses; embrace open-air freedom, tropical breezes, and...

1 day • Free Cancellation
5.0 (5)
from
$584
Private Haleakala Summit & Stroll from Kahului
Likely to Sell Out
Likely to Sell Out
5.0 (69)

Private Haleakala Summit & Stroll from Kahului

Personalized tours ensure a relaxed and easeful day. Let us handle the logistics, you enjoy the ride. Our private setting supports an intimate experience and...

5 hours • Free Cancellation
5.0 (69)
from
$359
Private Road to Hana Waterfalls, Black Sand & Hidden Gems
5.0 (90)

Private Road to Hana Waterfalls, Black Sand & Hidden Gems

This Road to Hana experience is all about having an easy, fun, and unforgettable day with a great guide you’ll actually enjoy spending time with....

9 to 10 hours • Hotel pickup offered • Free Cancellation
5.0 (90)
from
$370

Frequently Asked Questions

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

Recent activity reviews
An amazing day!
New York City
Maui: VIP Private Road to Hana Tour with Pick Up
susancap12, Sep 2026
An amazing day!
What an amazing day! This tour is so worth it to learn about the area and to enjoy the scenery. Ty was a great guide and made the day so easy. Highly recommend.
Read more
Amazing waterfalls adventure
New York City
Epic Waterfall Adventure, the Best of Maui
Rob_S, Sep 2026
Amazing waterfalls adventure
Sirena was an amazing guide, energetic and enthusiastic, she certainly made the adventure memorable and the photos and video footage she took were awesome. Glad we had water shoes with us as the trail was a little mucky and the rocks in the water were slippery. Beautiful trail walk through bamboo forest, crossing fast flowing river to reach two waterfalls where we had the opportunity to swim in the refreshing water, dive from the rocks and swing into the water from a rope swing. Absolutely amazing for us as we managed to have the top pool/waterfall to ourselves which made it extra special. Got to see the first bit of the Road to Hāna. Highly recommend this trip and Sirena as a guide, mahalo.
Read more
A Maui Must Do REALLY !
New York City
Maui -PRIVATE- Air Tour: 5 Islands: (2-5 people): SEE Even MORE!
leslies383, Sep 2026
A Maui Must Do REALLY !
Purely joyful experience and moving in the way that the colors and scenery were seen. Really a Maui Must Do!
Read more
An Unforgettable Road to Hana Adventure with an Exceptional Guide
New York City
Maui: VIP Private Road to Hana Tour with Pick Up
Relax02100696123, Sep 2026
An Unforgettable Road to Hana Adventure with an Exceptional Guide
Our Road to Hana tour was an unforgettable experience! We enjoyed delicious food and incredible views, saw surfers and sea turtles, visited black- and red-sand beaches, and even swam beneath a waterfall. Of course, I especially loved seeing all the amazing tropical plants! Our guide, Shayne, was exceptional—knowledgeable, entertaining, and so much fun. We had a fantastic day and highly recommend this tour!
Read more
Exhilarating
New York City
Maui -PRIVATE- Air Tour: 5 Islands: (2-5 people): SEE Even MORE!
rrD2756MT, Sep 2026
Exhilarating
Exceeding all expectations by far; a marvelous memory not to be duplicated.
Read more
Beautiful stunning MAUI MUST DO MUST DO!
New York City
Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!
Adventurer593699, Sep 2026
Beautiful stunning MAUI MUST DO MUST DO!
This was the best experience of our lives. Amazing first plane ride of beauty!
Read more
Amazing drive to Hana
New York City
VIP Private Road to Hana Tour in Cadillac Escalade with Pickup
Colo2022, Sep 2026
Amazing drive to Hana
Lorenzo was our private driver and he was amazing. We loved all the stops and food. The vehicle was spacious and comfortable. We probably would not have made to drive on our own.
Read more
Amazing experience!!!
New York City
VIP Private Road to Hana Tour in Cadillac Escalade with Pickup
299mattied, Sep 2026
Amazing experience!!!
We had the best experience with Exclusive! Lance is an amazing guide and by the end of the day you want to invite him to Sunday dinner! So informative about the islands history and culture, very accommodating and is a wonderful driver. We felt very safe. Can’t wait for our next visit so we can book another tour!
Read more
Our honeymoon on the Road to Hana
New York City
Private Road to Hana Tour with Pickup
Garrett_L, Sep 2026
Our honeymoon on the Road to Hana
Travis was amazing! He was able to cater the trip to our own interests and schedule. He’s a very skilled driver and had a lot of knowledge about the history and culture of Maui. We can’t wait to come back to do it again with him!
Read more
Great Aloha Adventure
New York City
Epic Waterfall Adventure, the Best of Maui
Felix_L, Sep 2026
Great Aloha Adventure
It was amazing tour our guide Stevin was great we really enjoyed everything it was amazing adventure thank you Stevin thank you for being a great guide and also very knowledgeable. God bless brother 🙏
Read more
Freaking awesome adventure!
New York City
Maui -PRIVATE- Air Tour FUN: 3 Islands: (2-5 people): SEE it ALL!
U8579KNch, Sep 2026
Freaking awesome adventure!
Freaking awesome. The adventure was freaking awesome!
Read more
The tour was great and...
New York City
Private Road to Hana Tour with Pickup
Curtsher_T, Sep 2026
The tour was great and...
The tour was great and our guide was very informative. I am happy I chose the tour because if I would have driven myself I would have missed a lot and the roads were very curvy. Our guide took us to some very nice places.
Read more
Best way to see Road to Hana with an older couple
New York City
Private Road to Hana Tour Black Sand Beach/Waterfalls/Sea Turtles
139tandyr, Sep 2026
Best way to see Road to Hana with an older couple
This is a wonderful way to get a taste of the natural beauty of Maui, regardless of age! Our guide, Yvonne, was knowledgeable, pleasant, conscientious, and patiently kind with us older folks ( in our 60s and 90s). We saw many hidden gems that would have been missed if we had driven the road ourselves, including hidden waterfalls, rainbow eucalyptus trees, a cacao farm, a delicious ice cream stand, a black sand beach, a red sand beach, and a beach filled with giant sea turtles. What was also impressive was Yvonne’s ability to navigate the narrow roads and single- lane bridges with competent dexterity. All in all, it was a very pleasant and informative day, and we certainly appreciate Maui more now!
Read more
An Unforgettable Road to Hana Experience
New York City
Deluxe Halfway to Hana: Private Tour from Kahului
359melissah, Aug 2026
An Unforgettable Road to Hana Experience
I cannot recommend this tour company enough, and if you have the opportunity to request Yvonne, absolutely do it!Yvonne gave us the most incredible private Road to Hana experience. She had so many interesting stories to share, knew so much about the island, and made the entire day feel personal, authentic, and completely different from a typical sightseeing tour.There are honestly so many special things about this tour that I don’t even want to share because I wouldn’t want to ruin the surprises for anyone else! One particularly meaningful moment was when Yvonne created a beautiful keepsake for me that I was able to bring home. It is something I will cherish forever and will always remind me of our day together.Yvonne didn’t just take us on a tour. She gave us a truly original experience and memories that I will treasure forever.This was a great, great tour and easily one of the highlights of my time in Hawaii. Yvonne is absolutely amazing, and I cannot recommend her or this company enough. If I ever return to Maui, I would choose Yvonne again in a heartbeat! 🌺
Read more
The BEST host!
New York City
Waterfall, Rainforest, Chocolate Tour & Historical Sites
Patina_G, Aug 2026
The BEST host!
Arjuna truly exceeded our expectations on this tour! He was so knowledgeable about the forest and the plants. The chocolate was the best part! He contributed to us feeling safe in an unknown area, he is truly the BEST! I would recommend this tour to anyone as long as Arjuna is leading it!
Read more
A must do!
New York City
Maui Classic Road to Hana Self-Guided GPS Audio Driving Tour
Dawn_F, Aug 2026
A must do!
Loved this tour. So fun. Super detailed. So well done.feel like we got a true Maui history and cultural experience.
Read more
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