Maui Cruises, Sailing & Water Tours

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Maui Activities

Attractions

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Afternoon Whale Watching Tour in Maui with Dinner
5.0 (3)

Afternoon Whale Watching Tour in Maui with Dinner

Witness the majesty of humpback whales in their natural habitat during this Afternoon Whale Watching Tour in Maui. From December 15 to April 15, enjoy...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3)
from
$167
Maui Luxury Boston Whaler Private Charter for up to 6 Passengers
Likely to Sell Out
Likely to Sell Out
5.0 (2)

Maui Luxury Boston Whaler Private Charter for up to 6 Passengers

Welcome to your very own private Maui adventure! Ali’i Nani, roughly translated to “Beautiful Royalty,” evokes elegance, prestige, and the ultimate in luxury. Whether you’re...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (2)
from
$3,795
Private Stand Up Paddling Lesson in Makena
5.0 (2)

Private Stand Up Paddling Lesson in Makena

Makena Bay is one of the most popular launching points for so many water activities as it offers such a great experience. Calm waters over...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (2)
from
$183
Maui Dolphins & Turtles - Makai Adventures
5.0 (2)

Maui Dolphins & Turtles - Makai Adventures

Take a ride on our brand new boat, MAKAI, along the West Maui coast. Enjoy beautiful views while looking for dolphins and a quick stop...

2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
2 hours 30 minutes • Free Cancellation
5.0 (2)
from
$135
Private Charter Full Day around Lanai 3 Snorkel Stops 7 Hrs
5.0 (2)

Private Charter Full Day around Lanai 3 Snorkel Stops 7 Hrs

Visit the coast-line of Lanai on a full day 7-hour small group trip and go on a dolphin discovery adventure. You will be transported on...

7 hours • Free Cancellation
7 hours • Free Cancellation
7 hours • Free Cancellation
5.0 (2)
from
$6,500
Private Charter Humpback Whale Watching & Dolphin Search
5.0 (2)

Private Charter Humpback Whale Watching & Dolphin Search

Our Exclusive Private Charter Sanity Vessel holds as many as 32 passengers.   Humpback Whale Watching and Dolphin Search minimum 2 hours with additional hourly rate...

2 to 8 hours • Free Cancellation
2 to 8 hours • Free Cancellation
2 to 8 hours • Free Cancellation
5.0 (2)
from
$1,993
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
Maui Intimate Luxury Powerboat Private Charter
Likely to Sell Out
Likely to Sell Out
5.0 (1)

Maui Intimate Luxury Powerboat Private Charter

Step aboard 'Amore', your private charter and discover Maui’s coastline in comfort and style. Designed for versatility, this premium vessel offers an expansive bow with...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$1,616
Whale Watching and Reef Snorkeling Kayak Adventure in West Maui
5.0 (1)

Whale Watching and Reef Snorkeling Kayak Adventure in West Maui

Our company mission is to educate and share the wonders of Maui Nui’s vibrant marine life. Our pedal kayak adventures commence from Olowalu Beach, a...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$200
Private Charter Sanity Vessel Tour Off Kaanapali Beach to Lanai
5.0 (1)

Private Charter Sanity Vessel Tour Off Kaanapali Beach to Lanai

Unique Private Charter departing from Kaanapali Beach. This Eco Educational Fantasy Tour on Sanity Vessel holds 16 passengers. which is 1/2 capacity due to Covid-19...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$2,875
Two Site Snorkel Adventure featuring the Molokini Crater K2
5.0 (1)

Two Site Snorkel Adventure featuring the Molokini Crater K2

Experience the vibrant underwater world at Molokini Crater, a renowned marine preserve just a short boat ride from Kihei. With over 25 years of expertise,...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (1)
from
$176
Sound of the Ocean Whale Watch Sail
5.0 (1)

Sound of the Ocean Whale Watch Sail

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (1)
from
$164
Maui Whale Watching Tour Aboard the Quicksilver From Maalaea
4.7 (1,603)

Maui Whale Watching Tour Aboard the Quicksilver From Maalaea

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

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (1,603)
from
$50
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
4.4 (791)

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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.4 (791)
from
$140
Maui Sunset Dinner Cruise - A Hawaiian Hula Experience
4.6 (735)

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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (735)
from
$168
Maui Ma'alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
4.6 (644)

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
2 hours • Free Cancellation
2 hours • Free Cancellation
4.6 (644)
from
$150

Frequently Asked Questions

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

Recent activity reviews
Windy but wonderful
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Raymond_S, Sep 2026
Windy but wonderful
The food was great. We all had different things and everyone had great things to say about their food. (Have the ribs) The servers were very attentive and the drinks were strong and yet tasty!
Read more
Sunset Cruise
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Janet_S, Sep 2026
Sunset Cruise
Staff was very friendly and always on the ready. Seeing the sunset while having my prime rib was great. Food and drinks were good.
Read more
pride of Maui Sinset Dinner Cruise
New York City
Maui Sunset Dinner Cruise – A Hawaiian Hula Experience
Amy_V, Aug 2026
pride of Maui Sinset Dinner Cruise
The experience was delightful and captured what we want to achieve. Yoder the beautiful sunset. The brief entertainment was satisfactory and the crew was professional with captain providing adequate safety information and expectations.
Read more
Beautiful cruise. Very...
New York City
Maui Sunset Dinner Cruise – A Hawaiian Hula Experience
Roshni_M, Aug 2026
Beautiful cruise. Very...
Beautiful cruise. Very friendly staff and good eats and drinks. A nice experience for friends or family
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
Amazing!!
New York City
Maui Whale Watching Tour Aboard the Quicksilver From Maalaea
Amanda_H, Jul 2026
Amazing!!
Most amazing experience ever! We went at the end of Janurary and the whales were super active. Our tour guide was amazing! I couldn't recommend this excursion more!
Read more
We saw multiple cow calf...
New York City
Maui Whale Watching Tour Aboard the Quicksilver From Maalaea
David_R, Jun 2026
We saw multiple cow calf...
We saw multiple cow calf pairs on our trip. A must do experience. Crew was excellent. Might be an issue if you are prone to motion sickness.
Read more
Don't miss a day on a boat!
New York City
Maui Intimate Luxury Powerboat Private Charter
KTMic, Jun 2026
Don't miss a day on a boat!
What a great day on the boat. Can’t say enough. We spent the day exploring several spots along the shoreline snorkeling and even jumping off Blackrock- what a thrill! The highlight was coming across a pod of spinner dolphins who surrounded the boat and put on quite a show for us. The boat was very well maintained. The crew was courteous and friendly. Certainly one of the best days of our trip. Bring your lunch to enjoy on the boat after one of the stops. Also be sure to ask if you have a credit to use at the general store. It provided a nice little snack after a long day in the sun. Gratuity was already included which was nice not to have to worry about that. Highly recommend Maui Nautical.
Read more
The best!
New York City
Maui Luxury Boston Whaler Private Charter for up to 6 Passengers
annabK7253FY, May 2026
The best!
We booked a private snorkeling afternoon for our family and had an amazing time!! Travis & Dustin are truly the best! Can’t recommend enough.
Read more
Nice boat and great sunset
New York City
From Ma’alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
L5558YTmelanies, May 2026
Nice boat and great sunset
Nice boat ride great food and photos taken of a lovely sunset.
Read more
Best Whale Watching Experience — Highly Recommend!
New York City
Afternoon Whale Watching Tour in Maui with Dinner
Traveler05511961837, Apr 2026
Best Whale Watching Experience — Highly Recommend!
We had an absolutely wonderful time on the afternoon whale watching trip with Gemini Charters! From start to finish, the experience exceeded our expectations.The wildlife viewing was incredible — we spotted plenty of whales and even got to see dolphins along the way. The dinner on board was delicious, and the Mai Tais were awesome.What really stood out was how easy and convenient the whole experience was. Boarding directly from the beach made for a seamless and fun departure that set the tone for the entire trip.Highly recommend Gemini Charters to anyone looking for a memorable time on the water — you won't be disappointed!
Read more
Level up!! 🐳
New York City
Sound of the Ocean Whale Watch Sail
GrandTour14896007913, Mar 2026
Level up!! 🐳
Excellent experience! Nice boat, good snacks & drinks. Listening to the whales was awesome. Adding music by Josh made it to relaxing and leveled up!
Read more
Private Whale Watch Tout
New York City
Private Charter Humpback Whale Watching & Dolphin Search
Tom_L, Mar 2026
Private Whale Watch Tout
Great private tour! Diver Dan knew where to find whales & we saw plenty. Some very close, some in distance. Saw all types of behaviors - rolling, fin slaps, tail slaps, full breech. Just a great trip!
Read more
Sun and moon cruising
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Yuri_I, Aug 2026
Sun and moon cruising
We were welcomed kindly, there were plenty of seats. The staff and food were great. Come with an appetite, the portions are generous as are the cocktails. The seas were calm, watched the sunset disappear over a mountain and had a full moon on our way back. The music, volume, picture staff added a good vibe. There’s plenty of parking. Overall a good experience, add it to your list of must do while in Maui.
Read more
Maui wowie
New York City
Maui Ma’alaea Sunset Prime Rib or Fresh Island Fish Dinner Cruise
Colin_F, Aug 2026
Maui wowie
Friendly crew good food good music.Left and returned on time.this was the windiest experience we gave had so we ended up eating inside.Captain did everything he could to get out of wind
Read more
Highly recommend
New York City
Maui Sunset Dinner Cruise – A Hawaiian Hula Experience
Mark_D, Aug 2026
Highly recommend
They do a great job adhering ti their schedule, make sure you do the same!The ribs were awesome, as was the cheese cake.
Read more
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Lowest Price Guarantee

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We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity starts.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
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If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Hawaii over a 12-month period.

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