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Maui Cruises, Sailing & Water Tours

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Maui Activities

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Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise

Come enjoy Prime Rib, Baby Back Ribs, Kiawe Smoked Chicken Leg and Thigh combo, Fresh Island Fish, or Penne Pasta with Thai Basil Marinara. A …More

4.6 (651)

Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise

Come enjoy Prime Rib, Baby Back Ribs, Kiawe Smoked Chicken Leg and Thigh combo, Fresh Island Fish, or Penne Pasta with Thai Basil Marinara. A...

2 hours • Free Cancellation
4.6 (651)
from
$150
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 …More

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
4.7 (503)
from
$189
Lanai Eco-Raft Snorkel & Dolphin Watch Small Group Tour from Maui

The only Semi-Private Snorkel Raft Tours on Maui, making it the closest you can get to a private charter experience. With 3 certified lifeguards onboard …More

Likely to Sell Out
Likely to Sell Out
4.9 (269)

Lanai Eco-Raft Snorkel & Dolphin Watch Small Group Tour from Maui

The only Semi-Private Snorkel Raft Tours on Maui, making it the closest you can get to a private charter experience. With 3 certified lifeguards onboard...

5 hours • Free Cancellation
4.9 (269)
from
$97
FULL SHADE VIP Premiere Whale Watch-Raft Kaanapali Beach

Guaranteed to spot the majestic whales and hear them sing or your money back! Experience the awe-inspiring beauty of West Maui’s coastal waters on your …More

Likely to Sell Out
Likely to Sell Out
4.9 (102)

FULL SHADE VIP Premiere Whale Watch-Raft Kaanapali Beach

Guaranteed to spot the majestic whales and hear them sing or your money back! Experience the awe-inspiring beauty of West Maui’s coastal waters on your...

2 hours • Free Cancellation
4.9 (102)
from
$129
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 …More

5.0 (632)

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
5.0 (632)
from
$318
Maui Eco-Raft: 2 Hour Dolphin Watch Sightsee Tour (Semi-Private)

Small group whale watching onboard our small group, smooth ride raft vessel. Native Hawaiian owned and voted Cool Hawaiis Traveler's Choice, Hawaii Ocean Rafting has …More

Likely to Sell Out
Likely to Sell Out
5.0 (110)

Maui Eco-Raft: 2 Hour Dolphin Watch Sightsee Tour (Semi-Private)

Small group whale watching onboard our small group, smooth ride raft vessel. Native Hawaiian owned and voted Cool Hawaiis Traveler's Choice, Hawaii Ocean Rafting has...

2 hours • Free Cancellation
5.0 (110)
from
$97
Ultimate 4 Hour Lanai Snorkel and Dolphin Encounter

Our small group snorkeling tours are locally owned and operated, making you feel like a part of our Maui ohana! Since 1982 we have offered …More

4.9 (945)

Ultimate 4 Hour Lanai Snorkel and Dolphin Encounter

Our small group snorkeling tours are locally owned and operated, making you feel like a part of our Maui ohana! Since 1982 we have offered...

4 hours • Free Cancellation
4.9 (945)
from
$149
2-Hour Molokini Guaranteed Snorkel Trip from Maui

Trip Highlights - 15 minute boat ride to Molokini - Snorkel the crystal clear waters of Molokini crater, Maui's 1st Snorkeling destination - Small group …More

4.9 (932)

2-Hour Molokini Guaranteed Snorkel Trip from Maui

Trip Highlights - 15 minute boat ride to Molokini - Snorkel the crystal clear waters of Molokini crater, Maui's 1st Snorkeling destination - Small group...

2 hours • Free Cancellation
4.9 (932)
from
$119
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in …More

4.8 (830)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in...

5 hours • Free Cancellation
4.8 (830)
from
$213
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 …More

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
4.6 (78)
from
$50
Clear Kayak Tour with Pontoons and Optional Snorkeling-Unlimited

Paddle out on a guided tour over majestic coral heads in search of Maui's vast array of sea life. The bottom of the clear kayak …More

4.9 (229)

Clear Kayak Tour with Pontoons and Optional Snorkeling-Unlimited

Paddle out on a guided tour over majestic coral heads in search of Maui's vast array of sea life. The bottom of the clear kayak...

3 hours • Free Cancellation
4.9 (229)
from
$134
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 …More

4.6 (220)

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
4.6 (220)
from
$181
Maui Sunset Dinner Cruise - A Hawaiian Hula Experience

For a one-of-a-kind Maui Sunset Cruise and cocktail dinner party aboard Pride of Maui, the most spacious and stable catamaran on Maui. Freshly prepared and …More

4.6 (740)

Maui Sunset Dinner Cruise - A Hawaiian Hula Experience

For a one-of-a-kind Maui Sunset Cruise and cocktail dinner party aboard Pride of Maui, the most spacious and stable catamaran on Maui. Freshly prepared and...

2 hours • Free Cancellation
4.6 (740)
from
$168
From Kihei: Molokini Snorkel & Whale Watch Tour

This activity is unique because it combines two of Maui’s best ocean experiences into one trip: Molokini Crater snorkeling and bonus whale watching. Guests get …More

4.9 (201)

From Kihei: Molokini Snorkel & Whale Watch Tour

This activity is unique because it combines two of Maui’s best ocean experiences into one trip: Molokini Crater snorkeling and bonus whale watching. Guests get...

2 hours 30 minutes • Free Cancellation
4.9 (201)
from
$161
'Alihilani Lahaina Sunset Sail

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for …More

Likely to Sell Out
Likely to Sell Out
5.0 (195)

'Alihilani Lahaina Sunset Sail

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for...

2 hours 30 minutes • Free Cancellation
5.0 (195)
from
$117
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted …More

4.9 (96)

Happy Hour Sunset Sail on Maui's Luxury Catamaran

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted...

2 hours • Free Cancellation
4.9 (96)
from
$181

Frequently Asked Questions

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

Recent activity reviews
Great time even with a bit of wind!
New York City
2-Hour Molokini Guaranteed Snorkel Trip from Maui
D4619PNalyssaa, Sep 2026
Great time even with a bit of wind!
We had a great time! We were worried about the wind, but once we got in the water the waves weren’t that big of a deal. The guides were also great!
Read more
A nice Sunset Cruise in Maui
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Ken_S, Sep 2026
A nice Sunset Cruise in Maui
Wanted to do a Sunset dinner cruise and the itinerary and meal seemed like a good choice. The crew was great, hard working and very attentive. The meal (we chose the Prime Rib) was good and cooked as requested. We saw beautiful sunsets but weren’t able to see the Molokini Crater due to the weather.
Read more
Awesome Dinner cruise
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Kelly_Q, Sep 2026
Awesome Dinner cruise
Great food, great music, great staff! The boat was very clean and stable during rough seas due to high winds
Read more
Great Time!!!
New York City
2-Hour Molokini Guaranteed Snorkel Trip from Maui
R2687KXashleyh, Sep 2026
Great Time!!!
Crew was great with communication, explaining some of the history and great personalities. Highly recommended. 2 hours was plenty of time out there.
Read more
Excellent boat ride
New York City
Lanai Eco-Raft Snorkel & Dolphin Watch Small Group Tour from Maui
F5434AOdavidd, Sep 2026
Excellent boat ride
Thanks captain Jack and B for a great time. Dolphins all over the place and lot's of info about islands. Love the humor that captain Jack uses in almost every story! Highly recommended
Read more
Top notch
New York City
Maui: Molokini and Turtles Luxury Yacht Snorkel
Sloane_P, Sep 2026
Top notch
Despite booking on an extremely windy morning, Captain Justin and his excellent crew Emily, Kirstie, and Anna ensured every member of our party was welcome, safe, and card for. They accommodated our very strict vegan diet with grace and provided abundant food. The boat is extremely comfortable and steady, even in high winds. Justin is a gifted communicator and kept us up to date at all times. Most importantly, I observed the crew interacting personally with every member of every party in different ways, giving every person what they individually needed-encouragement, friendliness, instruction, a listening ear, or just a smile. They truly thought of everything. This was truly a top notch experience.
Read more
I Recommend!!!!
New York City
Maui Eco-Raft: 2 Hour Dolphin Watch Sightsee Tour (Semi-Private)
Noah_V, Sep 2026
I Recommend!!!!
Amazing work and huge insight on everything we experienced, both members were very helpful and knowledgeable with everything that we saw and they even offered drinks and chips, 10/10 amazing experience, HIGHLY RECOMMEND 09/22/26
Read more
Worth it
New York City
Ultimate 4 Hour Lanai Snorkel and Dolphin Encounter
MellissaPierce, Sep 2026
Worth it
We really enjoyed our guides Lexie and Jill. They are fun but serious about safety. The boat ride on a choppy day was so very smooth. They took us to a great location with lots of fish and coral. We didn't see any dolphins or turtles but not for lack of trying. Conditions weren't ideal. Breakfast was good and drinks were cold. It's a small boat and wasn't full so we had plenty of space. The 4 hour tour was worth the cost even though we only got to snorkel at 1 location due to low visibility.
Read more
So worth the cost , crew...
New York City
Happy Hour Sunset Sail on Maui’s Luxury Catamaran
Brenda_R, Sep 2026
So worth the cost , crew...
So worth the cost , crew were friendly, helpful very attentive to everyone & Captain Jordan knew her stuff! Captain kept us in the best water since the wind was very strong, I felt very comfortable the whole ride. Highly recommend!
Read more
Highly recommend Mauri: Molokini & Turtles Luxury Yacht Snorkel
New York City
Maui: Molokini and Turtles Luxury Yacht Snorkel
Debra_H, Sep 2026
Highly recommend Mauri: Molokini & Turtles Luxury Yacht Snorkel
Appreciated option of wet suit top as Molokini water colder, as well as hot shower & clean toilets after superb Molokini snorkeling. Food delicious & plentiful. Captain gave detailed instructions, & he & crew were very safety conscious.
Read more
Sunset fun
New York City
‘Alihilani Lahaina Sunset Sail
Ramiro_F, Sep 2026
Sunset fun
Great crew, Great cruise. Recommend highly. Made great friends and crew made sure everyone was taken care off.
Read more
Experience that lives up to the hype + plused by the crew
New York City
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Jason_H, Sep 2026
Experience that lives up to the hype + plused by the crew
Great for families with small kids. Not overbooked, great boat and accommodations, multiple ways for young kids to engage in the experience - life vests, floating vessels, placards to pinpoint wildlife, etc. crew was very engaging, personable, and caters to our family needs. Even let the kids "drive" the boat. Couldn't recommend more.
Read more
Lovely Maui Experience
New York City
‘Alihilani Lahaina Sunset Sail
laurazD7578IN, Sep 2026
Lovely Maui Experience
Jess Jen and Brayden were wonderful hosts. The food and drinks were great. It was a relaxing and fun evening.
Read more
It was very nice. Food...
New York City
Maui Sunset Dinner Cruise – A Hawaiian Hula Experience
Ana_A, Sep 2026
It was very nice. Food...
It was very nice. Food was good, crew was friendly, music as great. Overall, recommend booking this sunset cruise.
Read more
Chill Vibes
New York City
Maui Sunset Dinner Cruise – A Hawaiian Hula Experience
Joel_M, Sep 2026
Chill Vibes
Great vibe, great crew, and would highly recommend. From start to finish it was great and the food was good too.
Read more
Dolphins are beautiful!
New York City
Maui Eco-Raft: 2 Hour Dolphin Watch Sightsee Tour (Semi-Private)
Dave_S, Sep 2026
Dolphins are beautiful!
Meeting point is not at the dock so you will walk a short distance to the boat. This is because of the fire destruction that happened.
Read more
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