Maui Luxury & Special Occasions

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Maui Activities

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Half Day Private Road to Hana Tour with Pickup
4.6 (7)

Half Day Private Road to Hana Tour with Pickup

For groups looking to experience the adventure of the Road to Hana, but not wanting to devote an entire day towards the full journey, we...

5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
5 hours • Hotel pickup offered • Free Cancellation
4.6 (7)
from
$300
Halfway to Hana Adventure
5.0 (5)

Halfway to Hana Adventure

Our Halfway to Hāna Adventure is a half-day tour that takes you partway along the Road to Hāna, offering waterfalls, rainforest scenery, and coastal views...

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
5.0 (5)
from
$180
Private Guided Waterfall Hike Rainforest Adventure
5.0 (4)

Private Guided Waterfall Hike Rainforest Adventure

This is a waterfall hike you don't want to miss. It is a moderate hike in difficulty but you will be blown away by the...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (4)
from
$150
Historic Walking Tour in Kihei Maui with Local Guide
5.0 (6)

Historic Walking Tour in Kihei Maui with Local Guide

This Kihei historic walking tour helps visitors experience Maui beyond its beaches by exploring South Maui's rich history, culture, and community stories. Each tour is...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (6)
from
$12
West Maui Self-Guided Audio Tour
4.3 (13)

West Maui Self-Guided Audio Tour

Take a trip around the West Maui Mountains. Drive through the historic town of Lahaina, the famous resorts of Ka'anapali and Kapalua, before checking out...

6 to 12 hours • Free Cancellation
6 to 12 hours • Free Cancellation
6 to 12 hours • Free Cancellation
4.3 (13)
from
$20
Epic Surf Safari - Best of Maui
5.0 (4)

Epic Surf Safari - Best of Maui

This tour can be done on any hour, just message us and we will accommodate you! Our surf guides are out of this world, EPIC....

2 to 3 hours • Free Cancellation
2 to 3 hours • Free Cancellation
2 to 3 hours • Free Cancellation
5.0 (4)
from
$195
Personalized Retreat day
5.0 (4)

Personalized Retreat day

Renew, Revive and Nourish Yourself, you deserve it! This is a one of a kind Hawaiian Cultural Experience. You will visit sacred Hawaiian sights, Get...

3 to 5 hours • Free Cancellation
3 to 5 hours • Free Cancellation
3 to 5 hours • Free Cancellation
5.0 (4)
from
$655
Maui Beach Parks Self-Guided Driving Tour
4.7 (6)

Maui Beach Parks Self-Guided Driving Tour

Explore paradise with this self-guided audio tour of Maui’s most incredible beaches. Lounge seaside, wade into the crystal-clear waters, or even pick up a surfboard...

1 to 2 hours • Free Cancellation
1 to 2 hours • Free Cancellation
1 to 2 hours • Free Cancellation
4.7 (6)
from
$15
Hana Rainforest Scenic Helicopter Tour
5.0 (3)

Hana Rainforest Scenic Helicopter Tour

A wonderful exploration of some of the most popular points of interest on the North Shore and East side island including Paia and Maui's famous...

45 minutes • Free Cancellation
45 minutes • Free Cancellation
45 minutes • Free Cancellation
5.0 (3)
from
$499
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
Full Day Private Maui Waterfall, Beach & Hana Tour
5.0 (4)

Full Day Private Maui Waterfall, Beach & Hana Tour

Explore enchanting sights on the MAUI Island during this shore excursion exploring Volcanoes National Park, waterfall, black sand beach, and more. Spend your day exploring...

8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$850
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
8 hours • Free Cancellation
8 hours • Free Cancellation
5.0 (4)
from
$496
Private Charter Humpback Whale Watching & Dolphin Search
5.0 (2)

Private Charter Humpback Whale Watching & Dolphin Search

Our Exclusive Private Charter Sanity Vessel holds as many as 32 passengers.   Humpback Whale Watching and Dolphin Search minimum 2 hours with additional hourly rate...

2 to 8 hours • Free Cancellation
2 to 8 hours • Free Cancellation
2 to 8 hours • Free Cancellation
5.0 (2)
from
$1,993
Exceptional Maui Whale Watch
5.0 (4)

Exceptional Maui Whale Watch

Spend more time with the whales, on our 2 1/2 hour whale watch, aboard Maui's ONLY air conditioned, luxury power catamaran. We are a family...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (4)
from
$148
Maui Pineapple Planting Experience
5.0 (3)

Maui Pineapple Planting Experience

Step into the heart of Hawai‘i’s pineapple heritage with the Pineapple Planting Experience—a hands-on, educational tour designed for those who want to dig deeper. Suit...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$152
Maui: Lahaina Cacao Farm Tour and Feast
5.0 (3)

Maui: Lahaina Cacao Farm Tour and Feast

Come Explore Maui’s Ku’ia Estate Cacao Farm! Your journey begins at the Ku’ia Estates Chocolate Factory in Lahaina, the largest chocolate factory in the state...

3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
5.0 (3)
from
$236

Frequently Asked Questions

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

Recent activity reviews
Maui Gold Pineapple Super Yummy
New York City
Maui Pineapple Planting Experience
JuliaJules829, Sep 2026
Maui Gold Pineapple Super Yummy
***I took the Maui Pineapple Tour: The Planting Experience in September 2026, and it was fantastic! Our guide, Rudy, was excellent. I loved learning about the history of the Maui Gold plantation and tasting fresh pineapple straight from the field. ***A few essential tips: Wear dark-colored tops, long socks, and non-slip rubber-soled shoes—it gets very rainy, windy, and slippery out there, so you will get dirty! Bringing a towel and a wide-brimmed farmer hat is also a must.
Read more
Have them drive so you can enjoy the ride!
New York City
Half Day Private Road to Hana Tour with Pickup
Jamie_B, Sep 2026
Have them drive so you can enjoy the ride!
This is a beautiful winding ride through the jungle. It is best to let someone local who knows the road do the driving so you can just enjoy the views of the flora, fauna and lovely waterfalls. Our driver Nick knew the best spots and was knowledgeable about all the places we were seeing. We would definitely do it again!
Read more
Excellent!
New York City
Historic Walking Tour in Kihei Maui with Local Guide
domfreire, Aug 2026
Excellent!
A fascinating and genuinely unique walking tour of Kīhei. Our guide is doing an impressive job of collecting and piecing together the area’s history, bringing it to life through stories and some wonderful cameo appearances along the way.It offers an authentic local perspective you simply wouldn’t get from a conventional tour. Highly recommended.
Read more
Uniquely authentic
New York City
Historic Walking Tour in Kihei Maui with Local Guide
domfreire, Aug 2026
Uniquely authentic
We had a fantastic walking tour of Kīhei with Keith de Devy. What makes Keith’s tour so special is the way he is collecting and piecing together the history of Kīhei, bringing together local stories, historical details and some wonderfully unexpected cameo appearances along the way.It doesn’t feel like a standard tourist tour at all. Keith gives you a unique, authentic perspective on Kīhei, its people and how the area has evolved. He’s clearly genuinely curious about the place himself, which makes the whole experience engaging, personal and great fun.A really cool way to see a side of Kīhei you could easily walk straight past without ever knowing it was there. Highly recommended!
Read more
Fun, fabulous and great meal in the treehouse
New York City
Maui: Lahaina Cacao Farm Tour and Feast
bogeymom, Aug 2026
Fun, fabulous and great meal in the treehouse
Fabulous, fun and educational….the chocolate was divine!!! Gabriel, our guide, was the best!
Read more
Don’t pass on a great tour!
New York City
Maui: Lahaina Cacao Farm Tour and Feast
T36KTjonathanm, Jul 2026
Don’t pass on a great tour!
Our visit was easily one of the highlights of our trip to Maui! My wife and I had an incredible lunch in the Treehouse as part of an amazing tour and the entire experience exceeded our expectations.Our guide, Sean, was outstanding. He was incredibly knowledgeable, friendly, and passionate about what he does. We learned so much about chocolate farming, production, and processing—things we had never even considered before. Sean answered all of our questions and made the tour both informative and engaging.The chocolate tasting was phenomenal. Every sample was delicious, and it was clear how much care goes into every step of the process. We were also really impressed by the farm’s commitment to sustainability and giving back to the local community. It’s refreshing to see a business so dedicated to making a positive impact while producing such exceptional chocolate.If you’re visiting Maui, don’t miss this experience. The Treehouse lunch, the tour, and the chocolate are all fantastic—and if you have the chance, ask for Sean. He made an already amazing experience even better!
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
Half day Road to Hana
New York City
Half Day Private Road to Hana Tour with Pickup
Marie_P, Jul 2026
Half day Road to Hana
It was a great experience, but what made it exceptional was a tour guide David Wright! He was knowledgeable, friendly, funny and an all around cool guide! Definitely worth the money spent!
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
Best Hana tour guide
New York City
Halfway to Hana Adventure
sedab610, May 2026
Best Hana tour guide
We did the Half way to Hana tour and our guide Davalynn was fantastic! She was so knowledgeable, joyful and provided helpful tips to make the drive on the winding road easy to handle. We had amazing stops and so many extra stops with beautiful insights from a true local. Highly recommend
Read more
Our guide, Fedor, was...
New York City
Full Day Private Maui Waterfall, Beach & Hana Tour
Jay_C, Mar 2026
Our guide, Fedor, was...
Our guide, Fedor, was fantastic. We had a great day on the Road to Hana and enjoyed every stop. It's easy to get lost in the beauty of the surroundings of Maui when you have a comfortable driver to take you along the way. We'd highly recommend this tour to all.
Read more
Highly Recommended Whale Watch
New York City
Exceptional Maui Whale Watch
M5717ORai, Mar 2026
Highly Recommended Whale Watch
We are Maui residents and had friends visiting. Booked the Pride of Maui Elua and it was fantastic. Captain Justin and crew were professional, knowledgeable and treated everyone with Aloha : ) It's a new boat which was super clean, a small capacity of 49 so lots of room. A large real bathroom, (not a tiny smelly "head") super clean as well. Option to be on the upper deck or down in the cabin which had comfy couch arrangements and open windows as well as A.C. On our whale watch tour there was an open bar, but I enjoyed a Perrier with fresh ginger. I also preordered a veg/gluten free lunch which was a nice salad wrap. All in all a great experience and I'll recommend them to any of our friends and family that come to Maui.
Read more
Private Whale Watch Tout
New York City
Private Charter Humpback Whale Watching & Dolphin Search
Tom_L, Mar 2026
Private Whale Watch Tout
Great private tour! Diver Dan knew where to find whales & we saw plenty. Some very close, some in distance. Saw all types of behaviors - rolling, fin slaps, tail slaps, full breech. Just a great trip!
Read more
Maui wowie
New York City
Exceptional Maui Whale Watch
247ErinB, Mar 2026
Maui wowie
Very knowledgeable, great whale watching experience, Boat was fantastic, lots of room on the bottom or top, meal was as fabulous. Would do it again in a heartbeat
Read more
Rudy was an exceptional...
New York City
Maui Pineapple Planting Experience
2hy8bqh85w, Feb 2026
Rudy was an exceptional...
Rudy was an exceptional guide! The tour was well-paced and super informative. The information was interesting, and the property was beautiful. This was one of our favorite experiences in Maui!
Read more
Nice day tour
New York City
West Maui Self-Guided Audio Tour
N2980USjonw, Feb 2026
Nice day tour
This tour really surprised us. It was a nice day tour around the side of the island that the tours can't take you. Whale watching spots, blowhole, history locations, local eats, and of course shopping are pointed out. The second part of the drive is a bit tricky because of the one lane blind turns on the side of the slopes, but you are warned by the narrator before about turning back. The GPS keeps track of you and alerts of things to check out. Definitely worth the few bucks and an afternoon.
Read more
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