Maui Cruises, Sailing & Water Tours

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Maui Activities

Attractions

Guides

Calendar

Maui Sunset Dinner Cruise & Whale Watch
4.7 (503)

Maui Sunset Dinner Cruise & Whale Watch

Experience Maui's top-rated whale watch with the experts in conservation and Marine Naturalists departing from the historic Ma'alaea Harbor. Enjoy a premium dinner cruise with...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (503)
from
$189
Award-winning Dinner Cruise: Four Course Dining Experience
Likely to Sell Out
Likely to Sell Out
4.4 (379)

Award-winning Dinner Cruise: Four Course Dining Experience

For a uniquely Maui dining experience, join the sunset dinner cruise, where you'll enjoy exquisite dining while surrounded by spell-binding views of the Pacific and...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.4 (379)
from
$170
Lanai Snorkel and Dolphin Watch from Maui
4.6 (219)

Lanai Snorkel and Dolphin Watch from Maui

Snorkel off the island of Lana’i and watch dolphins in the wild all in one trip. You'll discover why Lana’i has been rated one of...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.6 (219)
from
$181
Maui: Coast of Ka'anapali Beach Sunset Dinner Sail
Likely to Sell Out
Likely to Sell Out
4.7 (218)

Maui: Coast of Ka'anapali Beach Sunset Dinner Sail

Embark on an unforgettable two-hour Sunset Sail, promising a serene and memorable experience. Relax as our crew sets sail for two hours of smooth and...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (218)
from
$168
Kayak and Snorkel: Maui West Shore
Likely to Sell Out
Likely to Sell Out
4.7 (101)

Kayak and Snorkel: Maui West Shore

Go kayak paddling and snorkeling in the pristine waters of Maui's beautiful West Shore. Small groups with personal care. This is a convenient Kayaking/snorkeling tour...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.7 (101)
from
$119
From Ma'alaea Harbor: Whale Watch Cruise Aboard the Malolo
4.6 (78)

From Ma'alaea Harbor: Whale Watch Cruise 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 watching...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (78)
from
$50
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Likely to Sell Out
Likely to Sell Out
4.6 (78)

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (78)
from
$142
Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour
4.7 (70)

Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour

Take an adventure and experience an important part of Hawaiian history on this 1-hour canoe tour in Maui. Paddle a traditional Hawaiian outrigger canoe while...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.7 (70)
from
$155
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
Maui Magic Adventure Snorkel: Molokini Crater and Turtle Stop
4.7 (42)

Maui Magic Adventure Snorkel: Molokini Crater and Turtle Stop

The unique design of the Maui Magic allows access to destinations that other boats are unable to reach. The Maui Magic explores more of the...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.7 (42)
from
$224
Whale Watch and Scenic Tour from Kayak
4.7 (17)

Whale Watch and Scenic Tour from Kayak

This kayak tour is the MOST unique & special way to see the whales, the gorgeous West Maui coastline & ocean wildlife. Get ready to...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.7 (17)
from
$150
3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei
4.7 (15)

3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei

Explore the vibrant underwater world on a 3-hour Turtle Town Tour in Kihei, where you can snorkel with the endangered Hawaiian Green Sea Turtles. Begin...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (15)
from
$139
Private Charter 12 Passenger X-Treme Vessel 3 Hours
Likely to Sell Out
Likely to Sell Out
4.7 (11)

Private Charter 12 Passenger X-Treme Vessel 3 Hours

Travel & Hospitality Award Winner, BBB A+ Rated, Winner of  and 2018 Certificate of Excellence Cool Hawaii Award....

3 days 4 hours • Free Cancellation
3 days 4 hours • Free Cancellation
3 days 4 hours • Free Cancellation
4.7 (11)
from
$2,300
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
From Ma'alaea Harbor: Sunset Whale Watch Tour Aboard the Malolo
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
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.2 (68)
from
$50
West Side Discovery Kayak & Snorkel Tour
3.8 (4)

West Side Discovery Kayak & Snorkel Tour

Soak up the beauty and colors of the Hawaiian landscape on a Maui snorkeling trip along the shoreline of Olowalu, one of Maui's biggest reef...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
3.8 (4)
from
$124

Frequently Asked Questions

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

Recent activity reviews
Superb sail
New York City
Lanai Snorkel and Dolphin Watch from Maui
cphoenix2016, Sep 2026
Superb sail
Crew and captain were extremely professional, and the catamaran was beautiful. While we couldn't go to Lanai due to weather conditions(pending hurricane), the captain took us to a safe location to snorkel. As an added bonus, we were "up close and personal" to MANY dolphins going to the sight and returning back. They swam directly under and beside the boat. Incredible!
Read more
Makena kayak and snorkel tour
New York City
Kayak and Snorkel: Maui West Shore
joelaI1580PE, Sep 2026
Makena kayak and snorkel tour
Excellent tour and guide with Tyler
Read more
Great experience
New York City
Award-winning Dinner Cruise: Four Course Dining Experience
G6203WFdalel, Sep 2026
Great experience
“This trip was absolutely fantastic. The food was amazing, and the crew did an outstanding job. The ride was incredibly smooth, and getting on and off the boat was easy—even for two people in their 60s. We truly had a wonderful experience.”
Read more
Great experience!
New York City
Maui: Coast of Ka’anapali Beach Sunset Dinner Sail
sharonlwrites, Sep 2026
Great experience!
Fantastic casual-dinner cruise! The staff were incredibly friendly and helpful. I’m a vegetarian so I wasn’t sure if there would be food I could eat, but the buffet provided plenty of options. The grilled chicken my family ate was reported as great. It was a misty evening which provided bits of rain, unbelievable sunset, and multiple rainbows. Note - you leave your shoes behind (true of all boats) and you will get wet getting on board (also true of boats).
Read more
Beautiful 1st wedding anniversary celebration
New York City
Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar
Eleanor_M, Aug 2026
Beautiful 1st wedding anniversary celebration
We were trying to find a perfect way to celebrate our 1st wedding anniversary and this went above and beyond
Read more
Owen, Anna, and Nick were...
New York City
Maui: Ka’anapali Luxury Sunset Cocktail Sail with Open Bar
Breanne_N, Aug 2026
Owen, Anna, and Nick were...
Owen, Anna, and Nick were the best! Such a fun trip and a great experience. 10/10! Thank you! We had a blast.
Read more
A beautiful experience...
New York City
Maui: Coast of Ka’anapali Beach Sunset Dinner Sail
Kendra_T, Aug 2026
A beautiful experience...
A beautiful experience all the way around! The crew was amazing, the dinner delicious, and the sailing experience provided spectacular views of the shoreline, ocean, and sunset! Highly recommend this activity—you won’t be disappointed!
Read more
Amazing
New York City
Award-winning Dinner Cruise: Four Course Dining Experience
607laceyv, Aug 2026
Amazing
Great staff, very friendly and welcoming. Big shout out to mckenna
Read more
Surfing lessons with dolphins!
New York City
Lanai Snorkel and Dolphin Watch from Maui
jefedh, Aug 2026
Surfing lessons with dolphins!
No time share presentation! LOL Great crew. The education obtained on the outing was outstanding. A great blend of adventure, education, fun and socializing!
Read more
5 star experience !!!!!
New York City
Maui Magic Adventure Snorkel: Molokini Crater and Turtle Stop
Susan_S, Aug 2026
5 star experience !!!!!
Fantastic !!! Not a large crowded experience. Crew were fantastic, very accommodating and kind. A definite top notch experience.
Read more
Friendly staff very...
New York City
Maui Magic Adventure Snorkel: Molokini Crater and Turtle Stop
Amy_D, Aug 2026
Friendly staff very...
Friendly staff very attentive, food was great ! Would highly recommend for families with younger children
Read more
Great guide
New York City
Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour
Mimi_G, Jul 2026
Great guide
Jesse was a fantastic guide, very knowledgeable about cultural and geographical history of the area, oceanography etc. Saw only one sea turtle but it was huge and beautiful, swam under our canoe and came up to surface to say hello!
Read more
Incredible experience with a master crew
New York City
3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei
alissas772, Jul 2026
Incredible experience with a master crew
We recently went out on a snorkel adventure with Maui Snorkel Charter, and it was truly an amazing time. We saw so many incredible fish species and were lucky enough to spot several turtles.A special thank you to Captain Jenn and our first mate, Sofia, who were both top-notch throughout the entire trip. They made the experience fun, educational, and safe. We had some pretty rough seas on the ride back, but Captain Jenn was a master of her craft as she handled the boat with ease and made everyone feel completely comfortable. We couldn’t have asked for a better crew. Highly recommend booking with them if you’re in Maui! #lostatlastgirls #Brad70th
Read more
Great Excursion!
New York City
Maui: Hawaiian Outrigger Canoe Cultural and Turtle Tour
Vida405, Jul 2026
Great Excursion!
This was a last minute excursion. Alex was a great outrigger skipper! We saw quite a few green sea turtles! He was very informative and we had a blast! We had our 12 year old that loved it!
Read more
First time Kayak and Snorkelers and it was AMAZING!
New York City
Kayak and Snorkel: Maui West Shore
Jordan U, Jun 2026
First time Kayak and Snorkelers and it was AMAZING!
Best experience for the family! We were all first time kayak and snorkelers and the experience was everything we wanted! Our tour guide, Tyler was super knowledgeable about some of the history behind the caves and coral we saw. He was patient and showed us everything we needed to be successful and he made sure our experience was special! I’d definitely recommend and would go again if we’re back this way!
Read more
Great snorkeling at Turtle Town and Red Hill
New York City
3 Hour Turtle Town Snorkel and Whale Watch Tour in Kihei
marklM1373QT, Jun 2026
Great snorkeling at Turtle Town and Red Hill
Had a great time (our second time out) with Captains Jen and Eleni. Not only did we have fun at Turtle Town (my wife’s favorite) but also Red Hill ( a location I have never been to.). The ride was smooth and pretty quick as they depart from Kīhei boat ramp. I’m hoping to squeeze in one more trip with them before we head home!
Read more
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