Lahaina Tours & Sightseeing

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Lahaina Activities

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Haleakala Sunset Experience
4.7 (3)

Haleakala Sunset Experience

One of the very best places to view a sunset on Maui is atop the 10,000 ft. summit of Haleakala and your sensational Sunset Tour...

8 hours • Hotel pickup offered • Free Cancellation
4.7 (3)
from
$314
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
5.0 (4)

Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour

Embark on an unforgettable adventure with our Open-Air Jeep tour, starting along the legendary Road to Hana and culminating in a breathtaking sunset at Haleakalā....

8 to 9 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$1,990
Road to Hana Private Tour with Local Guide
3.9 (7)

Road to Hana Private Tour with Local Guide

Let us know where you will be located and we will start this Private Road to Hana Tour. This is an unforgettable drive which takes...

8 hours • Hotel pickup offered
3.9 (7)
from
$783
Private Full-Day of West Maui Guided Sightseeing Tour
5.0 (1)

Private Full-Day of West Maui Guided Sightseeing Tour

In the past, this part of Maui was even considered the capital of the Hawaiian Kingdom. This is where you could find Hawaiian royalty. Today,...

8 hours • Hotel pickup offered
5.0 (1)
from
$693
Private Road to Hana Rainforest & Waterfall Experience from Maui
Likely to Sell Out
Likely to Sell Out

Private Road to Hana Rainforest & Waterfall Experience from Maui

Experience the road to Hana in ultimate comfort in a private luxury SUV for groups of up to 5 or a transit van for groups...

8 to 10 hours • Hotel pickup offered • Free Cancellation
from
$1,200
Full Day Island of Maui Private Tour

Full Day Island of Maui Private Tour

Exclusive Private Maui Tour – The Ultimate Custom Island Experience Why settle for a crowded group tour when you can have Maui all to yourself?...

10 hours • Hotel pickup offered • Free Cancellation
from
$1,450
Private Tour : OAHU, MAUI, KAUAI or BIG ISLAND : Pick any Island

Private Tour : OAHU, MAUI, KAUAI or BIG ISLAND : Pick any Island

You can choose from Oahu, Kauai, Maui and the Big Island. Start when you want and customize tour to your liking. Oahu : Punchbowl, Dole...

7 to 8 hours • Hotel pickup offered
from
$1,499
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
from
$1,334

Frequently Asked Questions

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

Recent activity reviews
Unforgettable!
New York City
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
Steven_I, May 2026
Unforgettable!
We will never forget our day on the road to Hana with Patricia. We saw some breath taking sites. Patricia knew exactly where to stop and was extremely knowledgeable. We got many beautiful pictures and many cherished memories. Banana bread, coffee, ice cream and huli huli chicken were great! After a long day in the road to Hana we ventured up to the top of Haleakala. We had never seen a sunset as beautiful as that, it was almost spiritual. We spent 12 hours together and Patricia was amazingly patient, knowledgeable and charismatic. This was an amazing day. We highly recommend this tour and our tour guide Patricia.
Read more
Awesome
New York City
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
Naveen_S, May 2026
Awesome
No Brainer , just go for it . Patricia is excellent , very knowledgeable and plan the itinerary based on what we wanted to visit.
Read more
Awesome Sunset Experience
New York City
Haleakala Sunset Experience
Richard_K, Mar 2026
Awesome Sunset Experience
Our trip to the Haleakalā summit was as fantastic as the Sunset we experienced. Mike made the trip up and down the volcano with interesting commentary on the places we passed and Hawaiian history and culture. We stoped at a fruit stand, several viewpoints and the Menehune forest. Good choices for a tasty dinner. Dress in layers as it’s cold up on summit. Very, very enjoyable tour. I would definitely recommend instead of sunrise. Thanks Mike for a great time.
Read more
Worth the wake up time!
New York City
Haleakala Sunset Experience
Friedrac, Feb 2026
Worth the wake up time!
Worth the early wake up. Our guide, Cory, shared info on the constellations, geography, history, and culture. All this and a glorious sunset above the clouds.
Read more
AMAZING AUTHENTIC EXPERIENCE
New York City
Road to Hana Private Tour with Local Guide
Heather F, Oct 2023
AMAZING AUTHENTIC EXPERIENCE
One of the best experiences hands down! Our guide was so lovely and pleasant. We learned a lot about the island and she helped us avoid tourist mistakes. Showed us the island way and even stopped to meet some amazing local people!!
Read more
Awesome tour
New York City
Road to Hana Private Tour with Local Guide
CarlosAdrian_A, Aug 2021
Awesome tour
Excellent trip!!! Joshua the guide is the best!! Totally recommend!!! Perfect explain…definitely will contact them again.
Read more
Experience
New York City
Private Full-Day of West Maui Guided Sightseeing Tour
vineethkumar_k, Dec 2020
Experience
Tour guide Is so good and it has been best ride. He showed us all places. So cooperative. Explained about every place.
Read more
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
New York City
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
E1204JXterrya, Oct 2025
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
Great tour , highly recommended - 5 Star . Very professional and knowledgeable. Great being able to chat with someone who knows their stuff. Karen & Terry.
Read more
Perfect Private Sunset Trip
New York City
Road to Hana and Haleakala Sunset Open-Air Jeep Private Tour
Kimm C, Aug 2025
Perfect Private Sunset Trip
From the moment Patricia picked us up at the hotel, every detail was meticulously planned. She shared her knowledge of Maui, Hawaii and Haleakala with us and made the trip thoroughly entertaining. She provided extra service accommodating our requests and even found the perfect “hidden spot” to watch the Sunset. I cannot recommend this trip more! It was the definition of a 5-Star experience.
Read more
Road to Hana
New York City
Road to Hana Private Tour with Local Guide
Richard_B, Jul 2021
Road to Hana
Our guide did a great job. He was very knowledgeable as he grew up in the area. He gave great recommendations. It’s a very winding road and would highly recommend using a guide.
Read more
It was a great day!
New York City
Road to Hana Private Tour with Local Guide
hollyv821, Jun 2021
It was a great day!
We saw turtles, took a bamboo hike, waterfall swimming, black sand beach, giant wave swimming, cool lava fields. We saw it all! Brandon was a great tour guide who picked us up promptly, drove us around safely and made it a great day!
Read more
Good tour. Organizational problems.
New York City
Haleakala Sunset Experience
Matthew_B, Feb 2026
Good tour. Organizational problems.
Good tour. Good guide. Experienced company. Pickup communication could be better. Company did not notify us bus was late until we had already arrived at the pickup spot. Then the still 15 minutes later that revised schedule. Left us standing in a grocery parking lot for 35+ minutes wondering where our tour was. Original date choice canceled without explanation causing scheduling frustration. Having Cool Hawaii as a middleman seemed to block understanding of real schedule options, pickup options and the overall tour process process. This cost the review a point.More details. Tour guide was a wealth of information. Good number of stops at appropriate places (bathrooms and views). Tour guide was great at taking photos with the perfect background. Hot chocolate after stargazing was greatly appreciated. Dinner was only mediocre.
Read more
Great Day!
New York City
Road to Hana Private Tour with Local Guide
Holly_V, Jun 2021
Great Day!
Great Day! Turtles, bamboo hike, waterfalls, black sand beach, big waves, lava fields. We saw it all! Brandon was an awesome tour guide!
Read more
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