Maui Cruises, Sailing & Water Tours

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Maui Activities

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Makena-Wailea Explorer Trip in Maui
4.6 (63)

Makena-Wailea Explorer Trip in Maui

This 4 hour South Maui kayak and snorkel eco-adventure is No Ka Oi! Enjoy the calm and clear waters of Turtle Town where you will...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
4.6 (63)
from
$115
Morning Whale Watching Tour in Maui with Continental Breakfast
5.0 (4)

Morning Whale Watching Tour in Maui with Continental Breakfast

From December 15 to April 15, enjoy a morning whale watching adventure in Maui, where you can witness majestic humpback whales in their natural habitat....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (4)
from
$115
Whalewatch Sail from Lahaina
4.8 (85)

Whalewatch Sail from Lahaina

Experience Maui's top-rated whalewatch with the experts on Maui's newest, eco-friendly sailing catamaran, that offers maximum space and comfort with optimum viewing. Each informative and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (85)
from
$112
WHALES GUARANTEED Maui Whale Watching Makai Adventures
4.9 (1,167)

WHALES GUARANTEED Maui Whale Watching Makai Adventures

Our boat is really what sets us apart from other companies- we have a fast, fun and comfortable boat where everyone gets a cushioned seat,...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,167)
from
$109
Akialoa Mā’alaea Sunset Sail
Likely to Sell Out
Likely to Sell Out
5.0 (32)

Akialoa Mā’alaea Sunset Sail

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (32)
from
$108
Maui: Whale Watching Cruise with Open Bar from Ka'anapali Beach
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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (844)
from
$103
Whale Watching Experience
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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (154)
from
$102
Paragon Lahaina Sunset Sail
Likely to Sell Out
Likely to Sell Out
5.0 (30)

Paragon Lahaina Sunset Sail

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (30)
from
$102
Midday Whale Watch: Mā’alaea Harbor
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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (103)
from
$100
Morning Whale Watch: Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
4.9 (29)

Morning Whale Watch: Lahaina 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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (29)
from
$100
Afternoon Sail With the Whales from Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Afternoon Sail With the Whales from Lahaina 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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (1)
from
$100
Midmorning Whale Watch from Lahaina Harbor
Likely to Sell Out
Likely to Sell Out
4.5 (2)

Midmorning Whale Watch from Lahaina 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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.5 (2)
from
$100
2 Hour Prime Time Maui Whale Watching
5.0 (129)

2 Hour Prime Time Maui Whale Watching

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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (129)
from
$100
Whale Watching from Ma'alaea Harbor
4.8 (573)

Whale Watching from Ma'alaea Harbor

Experience Maui's top-rated whale watch with the experts departing from Ma'alaea Harbor. These informative and fun two-hour whale watches are led by a team of...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (573)
from
$100
Guaranteed Whale-Watching Tour by Raft from Kihei, Maui
4.9 (690)

Guaranteed Whale-Watching Tour by Raft from Kihei, Maui

Enjoy a prime opportunity to see humpback whales as they migrate through Hawaiian waters from Alaska between December and May. Setting out from Kihei, cruise...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.9 (690)
from
$100
The Best 9 am 1.5 Hour Whale Watching Tour
Likely to Sell Out
Likely to Sell Out
4.8 (41)

The Best 9 am 1.5 Hour Whale Watching Tour

Most customers enjoy the hydrophone we put into the water to hear the whales sing the most. We answer any whale questions and will be...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
4.8 (41)
from
$97

Frequently Asked Questions

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

Recent activity reviews
Awesome
New York City
Akialoa Mā’alaea Sunset Sail
D_G, Sep 2026
Awesome
Our sailing trip was truly unforgettable. The breathtaking views made every moment special, and the exceptional customer service added a personal touch that enhanced our experience. The serene atmosphere allowed us to fully relax and enjoy the beauty of the surroundings. We would absolutely do it again and highly recommend it to anyone looking for a peaceful getaway on the water!
Read more
Great vibes,...
New York City
Akialoa Mā’alaea Sunset Sail
John_B, Sep 2026
Great vibes,...
Great vibes, drinks/snacks, and crew! Crew was very welcoming and responsive during the entire trip. Would definitely do again!
Read more
Great Sunset Cruise
New York City
Paragon Lahaina Sunset Sail
debetta2, Sep 2026
Great Sunset Cruise
The meeting spot was a parking lot, which was fine. The cruise was excellent. The crew made the cruise that much better, they were awesome and couldn't do enough to help everyone. The food was good and the drinks were great.
Read more
Getting Back to Lahaina
New York City
Paragon Lahaina Sunset Sail
turnbullstudios, Aug 2026
Getting Back to Lahaina
The trip was amazing and so fun to share with other locals. Thank you Maui Sail for giving back to the community and launching the boats out of Lahaina Harbor. It was an emotional trip. Mahalo Nui Loa.
Read more
Great time
New York City
WHALES GUARANTEED Maui Whale Watching Makai Adventures
Ed_B, Jul 2026
Great time
Seen a lot of whales. Guide and captain were great and very knowledgeable. Had a great time and would definitely suggest this whale watch.
Read more
Fantastic whale watching.
New York City
Morning Whale Watch: Lahaina Harbor
Kbecjeans, Jun 2026
Fantastic whale watching.
This review is late, but we still remember what a fantastic experience our morning whale watching tour was. We parked at the lot and were met and escorted to the harbor by the boat crew. We had two great guys, whose names I've forgotten. It was wonderful to be able to sail out of Lahaina Harbor which was one of the reasons we chose this tour. The sea was calm, the day beautiful. Right off the bat we had a mother and baby off the side and then their "escort" came right under the boat. There were other sightings, but those were the best. The education we were given was straightforward and interesting. I like that we had a small group. The highlight for me was when things had been a bit quiet and there were no other boats in the area they put a hydrophone down and the sound of the whales was magical, primordial and utterly memorable. I'd definitely recommend Sail Maui and would book them again if I ever get a chance.
Read more
Whale off the starboard bow
New York City
Morning Whale Watch: Lahaina Harbor
G9657BAbruceb, May 2026
Whale off the starboard bow
Excursion was excellent. The boat captain and her assistant were very knowledgeable and informative. They were able to answer all questions regarding the whales.
Read more
Whale watching
New York City
Maui: Whale Watching Cruise with Open Bar from Ka’anapali Beach
Elisabeth_S, May 2026
Whale watching
You will get wet boarding and exiting the boat. Don’t sit on the netting unless you want to get wet, and don’t bring anything on board that cannot get wet.
Read more
Family Whale Watch
New York City
WHALES GUARANTEED Maui Whale Watching Makai Adventures
635tjk, May 2026
Family Whale Watch
We were a little nervous that we wouldn't see much since it was the last week of whale watches being offered, but were pleasantly surprised to see a large competition group in addition to a couple other one offs. Over a dozen whales all together. Captains were friendly and knowledgeable, boat was comfortable for everyone in our group, ages 16-77. Highly recommend the experience.
Read more
Fun
New York City
Whale Watching from Ma’alaea Harbor
Flyer44276580545, May 2026
Fun
Great time. End if the season so we didn’t see any whales, but still fun.
Read more
Book it already!
New York City
Whale Watching from Ma’alaea Harbor
natoshas2026, Apr 2026
Book it already!
AMAZING!!! From the staff, to the boat, to the fantastic whales (we saw dolphins too), to the photographer, my family and I had the best experience. The staff are all marine biologists, so super smart, funny, and knowledgeable. We got to listen to the whales sing to one another and we couldn't have been more pleased with our whale experience!
Read more
Gemini Charters - Book this boat tour in Maui
New York City
Morning Whale Watching Tour in Maui with Continental Breakfast
Voyage745908, Apr 2026
Gemini Charters - Book this boat tour in Maui
Gemini Charters is fantastic! We enjoyed the crew - Captain Brad, Kate & Drew. Kate as our whale naturalists was ready to share whale facts for all of us. Drew was ready to make sure we all had a great experience. Captain Brad was constantly on the lookout for whales - we were pleasantly surprised that we had many sightings even though it was the end of the "official" season. The continental breakfast was delicious and we enjoyed ourselves so much we went back for another tour the next day for a different experience.
Read more
Whale of a tail
New York City
2 Hour Prime Time Maui Whale Watching
Pam B, Apr 2026
Whale of a tail
Emma and Shannon were fantastic! They were so knowledgeable and fun! We enjoyed watching a dozen whales interacting! Amazing!
Read more
AMAZING!🤩
New York City
2 Hour Prime Time Maui Whale Watching
C541VEangelal, Apr 2026
AMAZING!🤩
AMAZING!🤩 Emma and Cass were amazing and very knowledgeable!!! We learned alot about whales! We will be back and would due it all over again 1000000 times! Thank you for an amazing day! I have a new passion 😜
Read more
Family fun
New York City
The Best 9 am 1.5 Hour Whale Watching Tour
720tressaa, Apr 2026
Family fun
Super fun and we saw a whale and baby! A lot of good facts for the kiddos as well
Read more
Whale Watching - Heres the Scoop
New York City
Midday Whale Watch: Mā’alaea Harbor
Karen_L, Apr 2026
Whale Watching - Heres the Scoop
Beautiful catamaran, skilled crew, onboard bathroom, and plenty of shade available. Bring a light jacket just in case. Great drinks/snacks/sandwiches. Whales actually swam under the boat as we were watching them. Overall, a spectacular highlight of our day on the island!
Read more
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