Maui Luxury & Special Occasions

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Maui Activities

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Best of Maui Tour: Sips, Sites and Bites with Lunch
Likely to Sell Out
Likely to Sell Out
4.4 (192)

Best of Maui Tour: Sips, Sites and Bites with Lunch

See the very best of Maui on this experiential sightseeing day trip with your informative local guide. Journey to Haleakala National Park on the east...

9 hours 30 minutes • Hotel pickup offered • Free Cancellation
9 hours 30 minutes • Hotel pickup offered • Free Cancellation
9 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.4 (192)
from
$307
Private Tour of Maui, the Valley Isle
4.9 (33)

Private Tour of Maui, the Valley Isle

Experience the diversity Maui has to offer by customizing your own private tour of Maui, The Valley Isle, with preferred locations and flexibility along the way. Whether...

8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
4.9 (33)
from
$310
Haleakala's Best Sunset Tour with Dinner
Likely to Sell Out
Likely to Sell Out
4.8 (25)

Haleakala's Best Sunset Tour with Dinner

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

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
4.8 (25)
from
$314
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
8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
4.7 (3)
from
$314
Birds Eye View 30 Minute Maui Helicopter Tour
5.0 (2)

Birds Eye View 30 Minute Maui Helicopter Tour

Explore parts of Maui from a birds eye view! Whether you are a first time flier or a frequent flier folks looking for a shorter...

30 minutes • Free Cancellation
30 minutes • Free Cancellation
30 minutes • Free Cancellation
5.0 (2)
from
$316
Haleakala Sunrise Best Guided Bike Tour with Bike Maui
4.7 (279)

Haleakala Sunrise Best Guided Bike Tour with Bike Maui

Experience one of nature's most memorable moments: Sunrise atop Haleakala! After sunrise, you begin the guided biking adventure at 6,500 ft. elevation just outside of...

8 hours • Free Cancellation
8 hours • Free Cancellation
8 hours • Free Cancellation
4.7 (279)
from
$318
Maui: Molokini and Turtles Luxury Yacht Snorkel
5.0 (621)

Maui: Molokini and Turtles Luxury Yacht Snorkel

We are a family-owned Maui company with over 40 years of experience on Hawaiian waters. Our expert Captains and crew bring decades of combined local...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (621)
from
$318
Private Unique Road to Hana Adventure
Likely to Sell Out
Likely to Sell Out
5.0 (90)

Private Unique Road to Hana Adventure

We're called Unique for a reason... This is not your standard Hana tour. We'll take you on a full day adventure all the way to...

10 to 11 hours • Hotel pickup offered
10 to 11 hours • Hotel pickup offered
10 to 11 hours • Hotel pickup offered
5.0 (90)
from
$319
Road to Hana Tour - Best of Maui
Likely to Sell Out
Likely to Sell Out
4.9 (137)

Road to Hana Tour - Best of Maui

Excitement, Adrenalin, Refreshing Waterfalls, and mesmerizing cliffside views. Everything about our road to Hana adventure is epic, personalized, photographed, videographed, and unforgettable. We’ll take you...

6 to 9 hours • Free Cancellation
6 to 9 hours • Free Cancellation
6 to 9 hours • Free Cancellation
4.9 (137)
from
$333
Private Road to Hana Tour
5.0 (64)

Private Road to Hana Tour

We take you places the large tour companies don't for an unforgettable experience driving around Haleakala Volcano through the rainforest of East Maui with a...

9 hours 30 minutes • Hotel pickup offered • Free Cancellation
9 hours 30 minutes • Hotel pickup offered • Free Cancellation
9 hours 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (64)
from
$340
Road To Hana Captured In Photography and Video
5.0 (2)

Road To Hana Captured In Photography and Video

A visit to Maui would be incomplete without doing the Road to Hana. However, most visitors don't get the best experience because they waste time...

9 hours • Hotel pickup offered • Free Cancellation
9 hours • Hotel pickup offered • Free Cancellation
9 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$345
Private Road to Hana - Waterfalls, Red Sand & Hidden Gems
5.0 (1)

Private Road to Hana - Waterfalls, Red Sand & Hidden Gems

Experience the legendary Road to Hāna through the eyes of a local guide who shares insider stories, hidden gems, and the cultural roots of this...

7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
5.0 (1)
from
$345
Road To Hana: Maui Waterfall Hiking Tour in Private Jeep
Likely to Sell Out
Likely to Sell Out
4.9 (368)

Road To Hana: Maui Waterfall Hiking Tour in Private Jeep

This jeep, waterfall, bamboo forest, hiking tour on the Maui Hana Highway is unique because they are private! Yup, that's right. Just you and your...

8 hours • Hotel pickup offered
8 hours • Hotel pickup offered
8 hours • Hotel pickup offered
4.9 (368)
from
$349
Full-Circle "Reverse" - Luxury Road to Hana Tour from West Maui
4.8 (96)

Full-Circle "Reverse" - Luxury Road to Hana Tour from West Maui

#1 We go ALL THE WAY AROUND THE MOUNTAIN so you don't see the same thing twice! #2 We do it in REVERSE, the way...

8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
4.8 (96)
from
$350
Full-Circle "Reverse" - Luxury Road to Hana Tour from South Maui
4.8 (48)

Full-Circle "Reverse" - Luxury Road to Hana Tour from South Maui

#1 We go ALL THE WAY AROUND THE MOUNTAIN so you don't see the same thing twice! #2 We do it in REVERSE, the way...

8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
8 to 10 hours • Hotel pickup offered • Free Cancellation
4.8 (48)
from
$350
Deluxe Halfway to Hana: Private Tour from Kahului
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
7 to 8 hours • Free Cancellation
7 to 8 hours • Free Cancellation
5.0 (200)
from
$359

Frequently Asked Questions

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

Recent activity reviews
Fantastic, comfortable...
New York City
Maui: Molokini and Turtles Luxury Yacht Snorkel
Sherveen_Z, Sep 2026
Fantastic, comfortable...
Fantastic, comfortable and engaging experience. The boat was amazing and clean. The captain and crew were very friendly and knowledgeable. Couldn’t ask for a smoother trip.
Read more
'ELUA is to go for Luxury Yacht!
New York City
Maui: Molokini and Turtles Luxury Yacht Snorkel
Josh_E, Sep 2026
'ELUA is to go for Luxury Yacht!
All the crew were so nice, professional, helpful, and fun to talk to! The boat was beautiful and very clean. We loved our snorkeling experience! Mahalo to Capt. Justin and co-Captain(forgot her name, sorry), Sam, Emily, and Ana! Keep up the great work! Until next time! 🌺⛵️🤙🏽-The Ehlers.
Read more
Get off the beaten path with Alec
New York City
Road To Hana: Maui Waterfall Hiking Tour in Private Jeep
H619GAsharonk, Aug 2026
Get off the beaten path with Alec
If you want a private our that is fun and different, book Alec. He made our day so much fun. We went off the beaten path to see amazing views and stopped at some fun spots along the way for treats. Alec has been doing this tour for 30 years. He knows his stuff. Can’t go wrong with this one!!
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
Ani on the Road to Hana
New York City
Road to Hana Tour – Best of Maui
Gigi_L, Aug 2026
Ani on the Road to Hana
Our tour guide, Ani, was amazing! She made sure that we hit all of the “spots” and spent so much extra time with us. She played great tunes all day and she’s also a great singer. I can’t say enough wonderful things about her. ❤️
Read more
Bucket list
New York City
Best of Maui Tour: Sips, Sites and Bites with Lunch
jeromepU7964FW, Aug 2026
Bucket list
Preston our tour guide did a FANTASTIC job. He made it fun and very informative.
Read more
Good trip
New York City
Best of Maui Tour: Sips, Sites and Bites with Lunch
jos_danielr662, Aug 2026
Good trip
Good trip was awesome i can repeat it
Read more
Breathtaking of Maui
New York City
Birds Eye View 30 Minute Maui Helicopter Tour
Jenise_H, Aug 2026
Breathtaking of Maui
Very knowledgeable, friendly, and professional! Great views of water falls and the mountains! Breathtaking views!
Read more
Sunset tour gets back...
New York City
Haleakala’s Best Sunset Tour with Dinner
Sophia_K, Aug 2026
Sunset tour gets back...
Sunset tour gets back little late but great experience. The views and scenery amazing throughout . Enough stops for restroom and food/snacks. Our tour guide Mike was extremely knowledgeable of history of Hawaii especially Maui and the volcano.
Read more
Great family experience
New York City
Haleakala Sunrise Best Guided Bike Tour with Bike Maui
Adam_H, Aug 2026
Great family experience
Very friendly and knowledgeable staff, made sure that we all felt very comfortable. Despite the varied level of biking skills, catered to all our needs. Loved the share of Hawaiian culture and vegetation.
Read more
Haleakala Sunsets Rock!
New York City
Haleakala’s Best Sunset Tour with Dinner
milap601, Aug 2026
Haleakala Sunsets Rock!
See all the beautiful colors without getting up at 2 AM! Michael was a wonderful guide who was truly passionate about Haleakala National Park. The views on the way up are spectacular and not driving allowed us all the ability to enjoy them. The sunset was amazing but what we most enjoyed was seeing the stars. Breathtaking! It was nice having a choice from a menu for dinner. Also, there were plenty of bathroom spots. Getting a chance to talk to the Menehune was fun.
Read more
The sunrise was...
New York City
Haleakala Sunrise Best Guided Bike Tour with Bike Maui
Brian_K, Aug 2026
The sunrise was...
The sunrise was beautiful. Well worth dealing with the wind and the cold. We brought layers but we still used their jackets and that helped a lot. Russel was great. I didn't expect to learn so much about the history and plant life of the mountain on our bike ride. We felt very safe during the guided tour. You had a vehicle behind the group so cars would only pass when we pulled over to stop for a quick break. Otherwise, you had the whole right side of the road to yourself.
Read more
A unique and unforgettable excursion
New York City
Road to Hana Tour – Best of Maui
Michael_D, Aug 2026
A unique and unforgettable excursion
It was truly a unique and wonderful experience. The tour guide, Mike, was extremely knowledgeable about the area and had a lot of great surprises and cool stops along the way. Mike knew all the local hidden spots and showed us a great time. We will never forget it!
Read more
Best day ever!
New York City
Deluxe Halfway to Hana: Private Tour from Kahului
J5769TIbriannaf, Jul 2026
Best day ever!
Amazing experience! The guide was amazing and very knowledgable about the island, made for a really fun day! 100% recommend!
Read more
Stop scrolling, pick this tour, ask for Travis
New York City
Private Unique Road to Hana Adventure
j_foster1234, Jul 2026
Stop scrolling, pick this tour, ask for Travis
Our tour guide Travis was amazing. Funny, knowledgeable and very good at offering options specific to our family and how we felt in the moment. The roads are very windy (600 switchbacks) but I never felt like we were in an unsafe situation, even when he had to back up or maneuver in tight circumstances - I felt that my family and I were very safe. Ask for Travis. He also knows a lot about Hawaiian culture, my husband, teen and 20 year old really enjoyed themselves. And so did I!
Read more
AMAZING TOUR!!!
New York City
Road To Hana: Maui Waterfall Hiking Tour in Private Jeep
A794CFamyv, Jul 2026
AMAZING TOUR!!!
This was an amazing experience. Our guide knew the road so well. We wouldn't have experienced the Road to Hana if we had driven it on our own. SO many beautiful stops. HIGHLY RECOMMEND!!!
Read more
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