Maui Cruises, Sailing & Water Tours

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Maui Activities

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Luxury Catamaran Whale Watch
4.9 (90)

Luxury Catamaran Whale Watch

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (90)
from
$119
Ultimate 3.5 hour Whale Watch & Snorkel
Likely to Sell Out
Likely to Sell Out
5.0 (89)

Ultimate 3.5 hour Whale Watch & Snorkel

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...

3 to 4 hours • Free Cancellation
3 to 4 hours • Free Cancellation
3 to 4 hours • Free Cancellation
5.0 (89)
from
$195
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
Kaanapali Beach Parasailing: Soar Above Maui’s Stunning Coastline
Likely to Sell Out
Likely to Sell Out
4.8 (78)

Kaanapali Beach Parasailing: Soar Above Maui’s Stunning Coastline

Experience stunning aerial views of Maui’s pristine coastline, lush landscapes, and turquoise waters from the comfort of your harness. Launch from the beautiful Kaanapali Beach,...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
4.8 (78)
from
$79
2 hour Lahaina Sunrise Whale Watch
5.0 (75)

2 hour Lahaina Sunrise 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
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (75)
from
$70
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
5.0 (74)

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (74)
from
$216
Maui South Shore Premier Kayak and Snorkel Tour from Makena Beach
4.9 (72)

Maui South Shore Premier Kayak and Snorkel Tour from Makena Beach

The Maui South Shore Kayak and Snorkel Tour combines an enjoyable lengthy paddle along the beautiful Makena coastline with a snorkeling adventure of a lifetime!...

3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
3 hours 30 minutes • Free Cancellation
4.9 (72)
from
$151
Kayak Whale Watch & Turtle Town Snorkel - Free Photos Included
5.0 (66)

Kayak Whale Watch & Turtle Town Snorkel - Free Photos Included

This is an intimate, owner-operated expedition led by a guide with over 10+ years of experience on Maui waters. Unlike the large harbor boats with...

4 hours • Free Cancellation
4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (66)
from
$150
Maui Whale Watching -PRIVATE- Air Tour: (2-5 People): SEE WHALES!
5.0 (63)

Maui Whale Watching -PRIVATE- Air Tour: (2-5 People): SEE WHALES!

Enjoy Maui’s #1 Ranked Outdoor Activity and ONLY *Private* Air Tour! As Seen on HGTV's 'Hawaii Life': Your Most Awesome Maui Day is just a...

1 hour • Free Cancellation
1 hour • Free Cancellation
1 hour • Free Cancellation
5.0 (63)
from
$420
The Best 2.5 Hour Molokini Snorkel Tour & Whale Watch
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
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (62)
from
$170
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Likely to Sell Out
Likely to Sell Out
4.8 (60)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (60)
from
$289
Deluxe Whale Watching Sail on Maui
Likely to Sell Out
Likely to Sell Out
4.8 (60)

Deluxe Whale Watching Sail on Maui

This special three-hour informative and fun whalewatch is led by a team of Pacific Whale Foundation’s certified Marine Naturalists and Marine Biologists, who explain and...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
4.8 (60)
from
$148
Hawaiian Canoe Sailing Experience in Maui
Likely to Sell Out
Likely to Sell Out
4.9 (59)

Hawaiian Canoe Sailing Experience in Maui

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (59)
from
$179
Honolua Snorkel Sail from Lahaina
5.0 (58)

Honolua Snorkel Sail from Lahaina

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way,...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
5.0 (58)
from
$181
The Best 4 hour inclusive Kanaio Sea Caves and La Perouse Snorkel
Likely to Sell Out
Likely to Sell Out
4.8 (57)

The Best 4 hour inclusive Kanaio Sea Caves and La Perouse Snorkel

We are the only company on Maui that has been going to the Kanaio Coast since 1985 and only we know all the secret places....

5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
5 hours 30 minutes • Free Cancellation
4.8 (57)
from
$170
2-Tank Dive Featuring the Molokini Crater
5.0 (51)

2-Tank Dive Featuring the Molokini Crater

Our world-class staff is friendly, knowledgeable, conscientious and excited to take clients diving. We take a maximum of twelve divers per cruise ensuring a more...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (51)
from
$239

Frequently Asked Questions

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

Recent activity reviews
Enjoyable experience
New York City
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Freedom599802, Sep 2026
Enjoyable experience
My husband and I enjoyed the experience. Just being on the boat was an amazing feeling! The crew was very nice and helpful making sure everyone was safe and feeling good. Food was great. I would recommend to sail with this company.
Read more
Super Fun
New York City
Kaanapali Beach Parasailing: Soar Above Maui’s Stunning Coastline
Adam_R, Sep 2026
Super Fun
The crew on the beach and on the boat were very friendly and helpful. The parasailing was fantastic.
Read more
Best Parasail Company in Lahaina
New York City
Kaanapali Beach Parasailing: Soar Above Maui’s Stunning Coastline
Mapuana_U, Aug 2026
Best Parasail Company in Lahaina
Everyone was amazing! I live in Wahikuli and always watched them go by and my partner came from Colorado and I finally had the opportunity to play tourist. It was so much fun, I can't wait to do it again.
Read more
This Lanai tour is the one to take !!!
New York City
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Y110BYmichaell, Aug 2026
This Lanai tour is the one to take !!!
Outstanding from start to finish. Sailing to Lanai was beautiful and fun. As we travelled around Lanai to our snorkeling spot, Captain Chase took us into a whole bunch of Spinner Dolphins. They raced around the bow of the catamaran and leaped out of the water in a spectacular show. Snorkeling was fun and food throughout the day was delicious……..yum ! So good ! Captain Chase, Ollie, and Bryce were always checking in on us making sure our glass or plate was full and asking if there was anything else we needed !! This tour supports Lahaina’s return to being an active port and the crew is very supportive and appreciative of being able to be a part of this return.
Read more
Unbeatable Value, Incredible Staff, and Masterful Problem Solvers!
New York City
2-Tank Dive Featuring the Molokini Crater
Wander26842857894, Aug 2026
Unbeatable Value, Incredible Staff, and Masterful Problem Solvers!
I cannot recommend Pro Divers at Maui enough! I just completed my PADI Open Water Certification with them, and the entire experience was absolutely outstanding. My instructor, Benja, and the rest of the staff were incredibly helpful, kind, patient, understanding, and fun. They made learning to dive highly enjoyable and completely stress-free. On top of great instruction, their pricing is highly reasonable and easily the most competitive on the island. What impressed me was how they handled unexpected logistics. During my course, Tropical Storm Fausto hit Maui, which forced cancellations of my scheduled shore and confined water dives. Instead of letting the course be ruined, Michel stepped in and found brilliant solutions to minimize the storm's impact. Michel coordinated with an external divemaster to utilize a resort swimming pool for our confined water drills and arranged to replace my shore dives with boat dives at Molokini Crater, which was significantly protected from the storm's effects. Getting to do most of my certification training around the stunning Molokini Crater was a dream come true! Whether you are looking to get PADI certified, are already licensed, want to try a beginner discovery dive, or just want to join a trip for snorkeling, look no further than Pro Divers. They are the absolutely amazing!
Read more
Great yacht and captain
New York City
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Gleb_K, Aug 2026
Great yacht and captain
Was great! Yacht was clean and comfortable. Captain was super friendly and nice. Weather and view as usual - great.
Read more
Excellent Snorkeling tour
New York City
The Best 4 hour inclusive Kanaio Sea Caves and La Perouse Snorkel
familytc, Aug 2026
Excellent Snorkeling tour
This tour was so much fun and we thoroughly enjoyed it. Our captain Angela was amazing and really funny, her helper Laurel was very nice and helpful. Highly recommend.
Read more
The only Molokini tour you need!
New York City
2-Tank Dive Featuring the Molokini Crater
R9886FKalexandret, Jul 2026
The only Molokini tour you need!
This tour was fantastic from start to finish. The crew was amazing, caring, understanding, and they kept the atmosphere light with a great sense of humor!The dive conditions were incredible. We had perfect visibility and the highlight was spotting around 5 baby sharks, besides a white tip, an octopus, nudibranchs and quite a few eels. Between the tanks, the provided snacks and juice hit the spot perfectly.Everyone on board was very kind, patient and professional, making it a very special day in the water. I had a wonderful time and highly recommend this specific trip to anyone looking to dive Molokini.
Read more
Very best sunset dinner cruise!
New York City
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Jaye_S, Jul 2026
Very best sunset dinner cruise!
Amazing food, service and most importantly the views were stunning.I would highly recommend this tour!
Read more
Unique and great tour
New York City
The Best 4 hour inclusive Kanaio Sea Caves and La Perouse Snorkel
sophiecI4463FI, Jul 2026
Unique and great tour
Excellent tour with captain Scott and Angela. We loved the discovery of the Kanai Coast and caves. Lots of knowledge shared by the team! And snorkeling spots (with nobody else but our boat) were great with lots of fishes to see.
Read more
Sailing Canoe Experience
New York City
Hawaiian Canoe Sailing Experience in Maui
CorporatePilot62, Jun 2026
Sailing Canoe Experience
Really fun experience! I have been a sailor for many years and have been to Hawaii quite a few times, this was a Great time with Sage and his son Cru! Very personal experience as there were only two others on board. A little snorkeling stop was nice too. Sage told us some cool Hawaiian history that I wasn't aware of, made it even more interesting. Highly recommend low key fun thing to do.
Read more
So many whales!
New York City
2 hour Lahaina Sunrise Whale Watch
Catherine_K, Jun 2026
So many whales!
This was such a fun morning! It was raining and cold but the girls were still so positive and fun! You can tell they’re passionate about what they do and love it
Read more
Wonderful experience
New York City
Hawaiian Canoe Sailing Experience in Maui
Heidi_H, Jun 2026
Wonderful experience
Great experience, wonderful crew, lots of history! We enjoyed the canoe and sailing as well as some snorkeling.
Read more
Spectacular day
New York City
Honolua Snorkel Sail from Lahaina
annakJ2499KW, Jun 2026
Spectacular day
Excellent tour, great staff, great snorkeling. We had the best day!
Read more
Bucket list experience!
New York City
2 hour Lahaina Sunrise Whale Watch
V882SNhannahr, May 2026
Bucket list experience!
Absolutely transcendent experience. Donnegal the whale gave us an incredible show on the last trip out of the season! Captain and crew were very knowledgeable and fun. Cannot recommend enough.
Read more
Really nice excursion,...
New York City
Luxury Catamaran Whale Watch
James_C, Apr 2026
Really nice excursion,...
Really nice excursion, great boat (60 ft) and fantastic crew. The food was pretty good (pulled pork sliders with a vegan option). Drink options were basic but open bar. Over all, it was a great experience. Just make sure you pay attention to the humpback whale season so you catch them migrating.
Read more
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