Cool Hawaii
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Groups About Contact
Start your search
Change your search
Place or activity
Select Dates

Maui Cruises, Sailing & Water Tours

132 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
97
57
22
Duration Clear
3
106
37
0
1
Price Clear
$0 $500+
Rating Clear
110
130
132
Specials Clear
131
42
1
15
0
Features Clear
1
99
106
8
85
3
Accessibility Clear
6
40
87
Families Clear
94
26
45

Maui Activities

Attractions

Guides

Calendar

Maui Mid Day Magic Whale Watch

Guaranteed whale sightings! Our boat is newly remodeled for passenger comfort. This boat is a photographers dream, and boasts 360-degree views with plenty of elbow …More

4.9 (46)

Maui Mid Day Magic Whale Watch

Guaranteed whale sightings! Our boat is newly remodeled for passenger comfort. This boat is a photographers dream, and boasts 360-degree views with plenty of elbow...

2 hours • Free Cancellation
4.9 (46)
from
$80
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take …More

Likely to Sell Out
Likely to Sell Out
3.5 (4)

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take...

2 hours • Free Cancellation
3.5 (4)
from
$60
West Maui Snorkeling Experience by Boat from Ka'anapali

Join us for a 4.5 hour snorkeling tour! Swim with turtles, see beautiful reef fish, and look for dolphins! All equipment is provided, along with …More

5.0 (938)

West Maui Snorkeling Experience by Boat from Ka'anapali

Join us for a 4.5 hour snorkeling tour! Swim with turtles, see beautiful reef fish, and look for dolphins! All equipment is provided, along with...

5 hours • Free Cancellation
5.0 (938)
from
$193
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 …More

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
Molokini Crater + South Maui Coast Adventure from Kihei, Maui

Speed through the water from Maui to the Molokini Crater for a small-group snorkeling adventure where the underwater visibility often exceeds 180 feet (55 meters)! …More

5.0 (1,612)

Molokini Crater + South Maui Coast Adventure from Kihei, Maui

Speed through the water from Maui to the Molokini Crater for a small-group snorkeling adventure where the underwater visibility often exceeds 180 feet (55 meters)!...

5 hours • Free Cancellation
5.0 (1,612)
from
$233
From Ma'alaea Harbor: Sunset Whale Watch Tour Aboard the Malolo

Enjoy this 2-hour guided adventure in a high-speed catamaran to watch the whales in their natural habitat. Depending on the whales’ behavior during your whale …More

4.2 (68)

From Ma'alaea Harbor: Sunset Whale Watch Tour Aboard the Malolo

Enjoy this 2-hour guided adventure in a high-speed catamaran to watch the whales in their natural habitat. Depending on the whales’ behavior during your whale...

2 hours 30 minutes • Free Cancellation
4.2 (68)
from
$50
Maui: Whale Watching Cruise with Open Bar from Ka'anapali Beach

The BEST possible way to experience the majestic Pacific Humpback Whales up close and personal. The waters off shore of Ka'anapali Maui are host to …More

4.8 (844)

Maui: Whale Watching Cruise with Open Bar from Ka'anapali Beach

The BEST possible way to experience the majestic Pacific Humpback Whales up close and personal. The waters off shore of Ka'anapali Maui are host to...

2 hours • Free Cancellation
4.8 (844)
from
$103
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

Sip on cocktails and take in the world-famous Maui sunset as our attentive crew serves you a delicious three-course meal table-side. Come aboard the Quicksilver …More

4.4 (793)

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

Sip on cocktails and take in the world-famous Maui sunset as our attentive crew serves you a delicious three-course meal table-side. Come aboard the Quicksilver...

2 hours • Free Cancellation
4.4 (793)
from
$140
Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing …More

Likely to Sell Out
Likely to Sell Out
4.8 (211)

Maui Sunset Sail

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

2 hours • Free Cancellation
4.8 (211)
from
$138
Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, …More

Likely to Sell Out
Likely to Sell Out
4.9 (103)

Midday Whale Watch: Mā’alaea Harbor

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii,...

2 hours • Free Cancellation
4.9 (103)
from
$100
HIGH QUALITY Whale Watch Adventure Aboard Luxury Super Raft

Simply the best whale watch in Maui! Hop aboard Maui's newest and only custom built Super Raft for an exciting up close whale watch adventure. …More

Likely to Sell Out
Likely to Sell Out
5.0 (149)

HIGH QUALITY Whale Watch Adventure Aboard Luxury Super Raft

Simply the best whale watch in Maui! Hop aboard Maui's newest and only custom built Super Raft for an exciting up close whale watch adventure....

1 hour 45 minutes • Free Cancellation
5.0 (149)
from
$95
Whale Watching Experience

The Magic Merman is the only raft-style boat that departs from Ka'anapali Beach. Exploring with us is the best way to get as close to …More

Likely to Sell Out
Likely to Sell Out
5.0 (154)

Whale Watching Experience

The Magic Merman is the only raft-style boat that departs from Ka'anapali Beach. Exploring with us is the best way to get as close to...

2 hours • Free Cancellation
5.0 (154)
from
$102
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, …More

4.9 (218)

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

5 hours • Free Cancellation
4.9 (218)
from
$200
Maui: Turtle Reef Kayak Tour of Makena

This fun and educational Maui kayaking tour starts at Makena Landing and paddles around the bay area. The calm, clear ocean is perfect for various …More

4.8 (328)

Maui: Turtle Reef Kayak Tour of Makena

This fun and educational Maui kayaking tour starts at Makena Landing and paddles around the bay area. The calm, clear ocean is perfect for various...

2 hours 45 minutes • Free Cancellation
4.8 (328)
from
$121
5 Hour Molokini Snorkel & Turtle Tour in Maui

Maui Snorkel Charters has been perfecting the Maui Snorkeling experience since 2010. If there is any question you'd like to ask, don't hesitate to call …More

5.0 (212)

5 Hour Molokini Snorkel & Turtle Tour in Maui

Maui Snorkel Charters has been perfecting the Maui Snorkeling experience since 2010. If there is any question you'd like to ask, don't hesitate to call...

5 hours • Free Cancellation
5.0 (212)
from
$219
The Best 2.5 Hour Molokini Snorkel Tour & Whale Watch

You are able to Snorkel in better areas than the "big boats" Most customers love the hydrophone we stick in the water to listen to …More

Likely to Sell Out
Likely to Sell Out
5.0 (62)

The Best 2.5 Hour Molokini Snorkel Tour & Whale Watch

You are able to Snorkel in better areas than the "big boats" Most customers love the hydrophone we stick in the water to listen to...

2 hours 30 minutes • Free Cancellation
5.0 (62)
from
$175

Frequently Asked Questions

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

Recent activity reviews
Everything was awesome. 4...
New York City
Molokini Crater + South Maui Coast Adventure from Kihei, Maui
James_H, Sep 2026
Everything was awesome. 4...
Everything was awesome. 4 different snorkeling sites. Sea turtles. Bonus dolphin sighting. Breakfast and lunch provided!
Read more
This was a great tour....
New York City
Molokini Crater + South Maui Coast Adventure from Kihei, Maui
Angelica_V, Sep 2026
This was a great tour....
This was a great tour. There were 4 snorkeling stops and we were never rushed at any of them. Our captain, Kaika, was extremely informative giving us information about each area we stopped at and the surrounding Maui area. Molokini is the highlight of course, clear blue waters and going to the back wall was a bonus! The light breakfast and lunch was perfect! Highly recommend this tour!!
Read more
Awesome Maui Morning!
New York City
5 Hour Molokini Snorkel & Turtle Tour in Maui
Hurley_R, Sep 2026
Awesome Maui Morning!
What a great day! The crew did a fantastic job! Communication prior to arrival was outstanding! Jen and Sophia were very kind, knowledgeable & accommodating. Couldn’t recommend this crew & company any more! ⭐️⭐️⭐️⭐️⭐️
Read more
Turtles!
New York City
West Maui Snorkeling Experience by Boat from Ka’anapali
LoveTravel728272, Sep 2026
Turtles!
Great snorkeling trip! We saw dolphins, turtles and oodles of exotic fish. Captain Makiya and guide Shasta were top notch, attending t our comfort and making our experience perfect! Shasta swam with us pointing out wildlife and educating us. Best snorkeling trip we've taken!
Read more
First timers !! Thanks Mike and Jess
New York City
West Maui Snorkeling Experience by Boat from Ka’anapali
Adventurer302145, Sep 2026
First timers !! Thanks Mike and Jess
We were a family of 5 snorkeling for the first time. In our group I couldn’t swim and was terrified to even get close to the water. Everything felt so overwhelming but kudos to Jess who made me feel so comfortable and confident enough to try it. It was a beautiful experience to say the least. Both Mike and Jess cared for everyone’s comfort and constantly checked on us. They served delicious food and drinks! Thank you for a lovely time :))
Read more
A must do !
New York City
5 Hour Molokini Snorkel & Turtle Tour in Maui
Lauren_D, Sep 2026
A must do !
HIGHLY RECOMMEND!! Captain Doug and Eleni were amazing, very informative and created a feeling of being with family. We were able to stop at multiple locations and they kept us away from other tour groups. If you’re in Maui definitely have to book this tour.
Read more
Best kayak trip ever!
New York City
Maui: Turtle Reef Kayak Tour of Makena
ricknW8105MY, Sep 2026
Best kayak trip ever!
This was an amazing trip! Tyler was our guide and took us to some great spots along the coast. We saw several turtles and learned about Hawaiian history from Tyler. I would highly recommend South Pacific Kayak s and Outfitters for your kayak trip!!!
Read more
Maui Sunset Sail from Lahaina
New York City
Maui Sunset Sail
F6516QAlarryf, Sep 2026
Maui Sunset Sail from Lahaina
Friendly crew. Sunset and rainbows were awesome. We've been on PacWhale sailings before and will go again. The cause is wonderful and the price is fair. We saw a wonderful sunset and multiple rainbows above Maui.
Read more
So many turtles you don’t know where to look
New York City
Maui: Turtle Reef Kayak Tour of Makena
Cincy45209, Aug 2026
So many turtles you don’t know where to look
Absolutely a fantastic kayaking and snorkeling experience for the whole family. Our girls , 10 and 11 along with my husband and I made sure that this tour was on our list of things to do based on our experience 3 years ago. Our guide Miah who was the dad of our previous guide made the morning fun and we had a great time all around. There were so many turtles at one point, I didn’t know where to look. Such a great morning to spend on the ocean with a great company. We had the option to purchase a great package of photos from our trip and they are the highlight of the week. Looking forward to when we return. Book this trip - you won’t be disappointed.
Read more
Very pleasurable experience.
New York City
Maui Sunset Sail
dalejQ363DG, Jul 2026
Very pleasurable experience.
Friendly staff, great ride, supporting a good cause!
Read more
Best Molokini Tour!!
New York City
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
Paul_K, Jul 2026
Best Molokini Tour!!
Amazing excursion! Crew with advanced skills and heartfelt hospitality, catering to your needs from boarding to departure. Beautiful must book with this tour/sailing yacht and you will be very pleased. Thank you Josiah and crew for your Perfection! Sincerely, Paul and Alondra
Read more
Fantastic Molokini Experience
New York City
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
paulkX810HZ, Jul 2026
Fantastic Molokini Experience
Molokini creator/dome is a must do in Maui and this company does it with heart and precision. The trip was priceless and the crew was delightful. They provided everything you like from the minute you step on, to the minute you step off. Lovely birthday outing for my daughter with a memory of a lifetime. Thanks Josiah and crew! It was a blast!!!! Paul & Alo
Read more
What a fun and relaxing...
New York City
From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Italo_T, Jul 2026
What a fun and relaxing...
What a fun and relaxing dinner. The crew and atmosphere were amazing. The live music and food made this a perfect evening
Read more
Arrive early so you can...
New York City
Maui Catamaran Sunset Cocktail Cruise from Ma’alaea Harbor
Daniel_A, Jul 2026
Arrive early so you can...
Arrive early so you can get good seats up front. The kids had a great time, good pictures, fun experience.Very friendly crew and solid beverage options.
Read more
Amazing trip to Lanai
New York City
Lanai Snorkeling Half Day with Sea Scooter
chrismT2866EP, Jul 2026
Amazing trip to Lanai
Dan and Danny were awesome captains. They helped get our senior travelers on the boat with no issues and were very accommodating. Our kids (both under 13) had a great time swimming and snorkeling off the coast of Lanai. Marissa was an amazing host on the boat. The food was perfect for everyone to snack on. the views and trip were amazing from beginning to end.
Read more
such a great excursion
New York City
Lanai Snorkeling Half Day with Sea Scooter
Rosalind_H, Jun 2026
such a great excursion
Captain Dave and Marisa were excellent tour guides. Dave called and moved our booking out two more days because the water was not clear on the day of our booking. we had such great weather and the water was clear. Smooth ride with a little hawaii history. This was our first time using scooters to snorkel and if you can add this to your excursion, do it!!!! it just makes it easy. my teenagers loved them. Dave and Marisa provided drinks, sodas, waters and fruits and pastries. didn’t see hoards of fish. but saw a ton of different coral and porpoises. they were quite a few brightly colored fish. highly recommend. would definitely do a tour again with them!
Read more
Maui Activities
Attractions
Guides
Calendar
View more
View more