Maui Private Sightseeing Tours

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Maui Activities

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Haleakala Private Sunset Tours
Likely to Sell Out
Likely to Sell Out
5.0 (7)

Haleakala Private Sunset Tours

Here’s what you’ll see and do: Scenic Drive Through Upcountry Maui You’ll start your journey with a relaxing ride through Upcountry Maui, passing charming towns...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (7)
from
$555
The Ultimate Road to Hana Slingshot Adventure from Kihei Maui
5.0 (6)

The Ultimate Road to Hana Slingshot Adventure from Kihei 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 (6)
from
$541
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
Private Road To Hana Tour with Professional Photos Included
5.0 (19)

Private Road To Hana Tour with Professional Photos Included

Not only will you get professional photos and videos, but you will get a guide who wants to show you the real jungle. Get past...

8 to 10 hours • Free Cancellation
5.0 (19)
from
$525
Maui Haleakala Volcano Summit Slingshot Tour from Kihei
5.0 (1)

Maui Haleakala Volcano Summit Slingshot Tour from Kihei

Embark on an unforgettable adventure with our Maui Haleakala Volcano Summit Slingshot Tour from Kihei! Feel the thrill as you drive the powerful and fun...

1 day • Free Cancellation
5.0 (1)
from
$524
Private Road to Hana Tour with Pickup-Ultimate Package, Backside
5.0 (4)

Private Road to Hana Tour with Pickup-Ultimate Package, Backside

We are proud to offer guests this option to experience the rarely-traveled "backside" of the Road to Hana- including the amazing landscapes of Kipahulu, Kaupo,...

9 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$500
Maui Coast Slingshot Tour from Kihei
5.0 (4)

Maui Coast Slingshot Tour from Kihei

Get ready for an exhilarating adventure along the narrow and winding Maui North Loop Coast Cruise. This tour takes you to some of Maui's most...

8 hours • Free Cancellation
5.0 (4)
from
$496
Maui Coast Slingshot Private Tour from Lahaina
5.0 (1)

Maui Coast Slingshot Private Tour from Lahaina

Get ready for an exhilarating adventure along the narrow and winding Maui North Loop Coast Cruise. This tour takes you to some of Maui's most...

8 hours • Free Cancellation
5.0 (1)
from
$485
Private Tour Maui Pineapple Farm in Haliimaile

Private Tour Maui Pineapple Farm in Haliimaile

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to...

4 hours • Hotel pickup offered
from
$454
Maui Circle Island-PRIVATE-Air Tour for 2-5: Waterfalls & Lava!
5.0 (243)

Maui Circle Island-PRIVATE-Air Tour for 2-5: Waterfalls & Lava!

You’re worth Maui’s #1 Ranked Outdoor Activity and ONLY Private Air Tour! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day is just...

80 to 90 minutes • Free Cancellation
5.0 (243)
from
$452
Island of Maui Customized Half Day Tour
Likely to Sell Out
Likely to Sell Out
5.0 (5)

Island of Maui Customized Half Day Tour

Tailored to You No cookie-cutter itineraries here. We design each tour around your group's interests, pace, and energy level Insider Access With a local guide...

6 hours • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$450
Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!
5.0 (268)

Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!

As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day is just a Click Away!  Enjoy Maui's Most Affordable Aerial Activity: Your Spectacular, Once-in-a-Lifetime,...

1 hour • Free Cancellation
5.0 (268)
from
$420
Maui Whale Watching -PRIVATE- Air Tour: (2-5 People): SEE WHALES!
5.0 (63)

Maui Whale Watching -PRIVATE- Air Tour: (2-5 People): SEE WHALES!

Enjoy Maui’s #1 Ranked Outdoor Activity and ONLY *Private* Air Tour! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day is just a...

1 hour • Free Cancellation
5.0 (63)
from
$420
Maui-PRIVATE-Air Tour: SKY-ROAD to HANA: Lava+ Jungle Waterfalls!
5.0 (31)

Maui-PRIVATE-Air Tour: SKY-ROAD to HANA: Lava+ Jungle Waterfalls!

Explore the stunning landscapes of Maui on a private air tour, soaring over dramatic volcanoes, lush jungles, and captivating waterfalls. This exclusive experience allows you...

1 hour • Free Cancellation
5.0 (31)
from
$420
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
Maui Road to Hana VIP Private Tour in Convertible Bronco or Jeep
5.0 (55)

Maui Road to Hana VIP Private Tour in Convertible Bronco or Jeep

Book a private, custom Maui adventure of a lifetime. Our most popular experience is the Reverse Road to Hana Loop—a breathtaking full-circle journey that begins...

6 to 9 hours • Hotel pickup offered • Free Cancellation
5.0 (55)
from
$400

Frequently Asked Questions

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

Recent activity reviews
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
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
Stunning !
New York City
Maui Circle Island-PRIVATE-Air Tour for 2-5: Waterfalls & Lava!
Z3880SGamera, Sep 2026
Stunning !
This was an amazing experience with stunning views!
Read more
Breathtaking🤍
New York City
Maui Circle Island-PRIVATE-Air Tour for 2-5: Waterfalls & Lava!
Cosmo672, Sep 2026
Breathtaking🤍
This is the only way to see Maui. This was real nice tour of the entire island!
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
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
Jill (JJ) was fantastic!!...
New York City
Maui Road to Hana VIP Private Tour in Convertible Bronco or Jeep
Leslie_M, Aug 2026
Jill (JJ) was fantastic!!...
Jill (JJ) was fantastic!! Learned so much from her. She would go wherever you wanted to go. Definitely made a friend!❤️
Read more
An experience almost too magical for words.
New York City
Haleakala Private Sunset Tours
Brian_W, Aug 2026
An experience almost too magical for words.
This was the perfect romantic sunset experience. The views were incredible. Vic is an amazing guide, I'd hire him for any type of Maui tour. A great and knowledge guide who got us in the absolute best spot to witness the sunset. He promptly answered any questions we had before the tour. We asked about what to wear in advanced and he provided us with hoodies and a warm blanket to watch a magical sunset. Vic took many photos throughout the experience for us so we could focus on watching the sunset with each other. Vic is an extremely good/safe driver. He knew so much about Maui. I'd book him again for any kind of tour on the island. I firmly believe this is the best Haleakala Private Sunset Tour you can book. I would recommend this tour to anyone going to Maui. You'll remember it for the rest of your life.
Read more
The absolute highlight of a great Maui trip.
New York City
Haleakala Private Sunset Tours
D4541FLbrianw, Aug 2026
The absolute highlight of a great Maui trip.
I have traveled many places with tour guides, NONE have been as good as Vic. I would consider booking him for anything on Maui. However, this tour was absolutely incredible. The tour was the number highlight of my girlfriend and I's trip to Maui. Before the tour, I inquired about what to wear as we did not pack anything for cold weather on Maui. Vic was ready with 2 hoodies and a warm blanket. The tour started with him picking us up at our hotel. Immediately he provided us with his mother's incredible homemade banana bread and offered us beverages. We then began the drive, throughout the drive he pointed out interesting things along the way. His driving was A+. Multiple times we got out and he took pictures for us at incredibly scenic spots. Eventually, Vic got us to the summit in a great parking spot. He then helped us to the perfect spot to view the sunset, protected from the wind by rocks. Again, he took more photos for us while we prepared to watch an incredible sunset. The view was unlike anything I'd seen before. Despite his excellent photography, I still felt compelled to snap a few pictures with my phone. As some groups started to leave, Vic said just wait because the colors are only going to get better. I am glad we did, photos do not do the sunset justice. The experience was absolutely magical. After all was said and done, I felt lucky to have booked with him. I truly believe this is the best sunset tour and guide you could possibly find on Maui. Anything we needed help with, he was able to assist. He has a great sense of humor and a perfect laid back vibe. More importantly, he is a good person. The next time I am fortunate enough to visit Maui, I will absolutely book with him/Aloha Wild Tours again. I cannot stress how great of a local guide Vic was. A couple days later, he sent us a video of different moments he recorded set to perfect music. I'll always treasure that video of my girlfriend and I from the sunset tour. If you book this tour, you will be treated with the best views of your life and learn a lot about Maui. It was more than just a tour, in the end we made a good friend while seeing the best sunset of our lives. If you are still reading this, stop and book your tour already. You will not regret it.
Read more
Jill was amazing. It was...
New York City
Maui Road to Hana VIP Private Tour in Convertible Bronco or Jeep
Carolyn_I, Aug 2026
Jill was amazing. It was...
Jill was amazing. It was our first time on Maui and she made sure to steer us towards truly unique experiences and away from some tourist traps. The ride in the Bronco truly provided an immersive experience of being in the rainforest and her skill in navigating the road in on/off rainy conditions left us able to take it all in. Black and red sand beaches, turtles, George, Huli Huli chicken, waterfalls, you name it! Truly unforgettable experience!
Read more
Lovely experience!
New York City
Maui-PRIVATE-Air Tour: SKY-ROAD to HANA: Lava+ Jungle Waterfalls!
P2090TYdominiqueb, Jul 2026
Lovely experience!
Me and my family were very happy with our guide. He made it even more entertaining and helped me feel more comfortable while I was nervous.
Read more
Husband birthday gift.
New York City
Maui-PRIVATE-Air Tour: SKY-ROAD to HANA: Lava+ Jungle Waterfalls!
cesarinak2023, Jul 2026
Husband birthday gift.
Best experienced ever. My husband always wanted to ride a helicopter. So for his 49th birthday i surprise him witha hands on tour. 100% recommend this tour our pilot Erick was awesome.
Read more
Sunset flight
New York City
Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!
J1524TFtammyr, Jul 2026
Sunset flight
We had an amazing flight, gorgeous views!!!
Read more
Awesome
New York City
Romantic Sunset Champagne -Private- Maui Air Tour: Intimate & Spectacular!
O3767QSleem, Jul 2026
Awesome
O flew on this awesome tour and the views were amazing
Read more
A stress free trip to Hāna and the backside.
New York City
Private Road to Hana Tour with Pickup-Ultimate Package, Backside
K4083WMericw, Jun 2026
A stress free trip to Hāna and the backside.
My wife and I went on the road to Hāna ultimate trip which included returning via the backside. Eugene is a small business owner, who was great. He is extremely knowledgeable. The trip is customized to your likes and speed. You get to go to places that larger vans don’t go to. I’m glad I did not drive the roads myself. Lots of hairpin turns, single lane roads and bridges. You get to sit back and enjoy the scenery rather than focus on driving. Eugene knew that the backside road would be closed while they worked on shoring up the cliffs and that it wouldn’t open until the afternoon, so he planned the trip accordingly. A sign also said local traffic only.
Read more
Private Half Day Maui Tour
New York City
Island of Maui Customized Half Day Tour
Ryan_W, Jun 2026
Private Half Day Maui Tour
Shelby was great, we did the half day tour and she made sure to pack in as many sites and activities as we could! She made things easy and customized the tour based on our preferences/what we wanted to do. We were able to explore the lava fields, South Maui, Oneuli Beach, and the inland waterfalls. We even got to see some neat wildlife along the way as well. Would highly recommend for anyone staying in Maui looking for a customized tour of the island!
Read more
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