Maui Cruises, Sailing & Water Tours

Q: I need a ride! Which Maui Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Maui Cruises, Sailing & Water Tours include Hotel Pickup: Private Road to Hana Waterfalls, Black Sand & Hidden Gems View all Activities with Hotel Pickup →

Q: Got any more Maui trip ideas?

We sure do. Check out our curated lists of hand-picked Maui Activities. Top 10 Maui 2026 Senior-friendly tours Maui The best tours and activities for culture lovers in Maui Top Day Trips from Maui Things to do in Maui this summer View all Maui Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Maui?

Based on our sales data over the past year, the most popular styles of tours and activities in Maui are: Maui Outdoor Activities Maui Nature & Wildlife Maui Luxury & Special Occasions Maui Luxury Tours Maui Cruises, Sailing & Water Tours View all tour styles in Maui →

This is the newest attraction tour in Maui, Hawaii. Our water bikes are rare around the world and we are the only water bike tours …More

5.0 (406)

Water Bike Tour in South Maui

This is the newest attraction tour in Maui, Hawaii. Our water bikes are rare around the world and we are the only water bike tours...

1 hour 45 minutes Free Cancellation

5.0 (406)

from
$131

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 (674)

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 (674)

from
$150

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical …More

5.0 (135)

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical...

5 hours Free Cancellation

5.0 (135)

from
$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 …More

4.9 (274)

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 (274)

from
$97

Maui: 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

4.9 (103)

Maui: 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 (103)

from
$129

Maui: VIP (12 Guests ONLY) Ultimate Whale Watch

Our Exclusive VIP whale watching tours are 2 hours long with a maximum of 12 guests. Our small groups make every seat a front row …More

4.9 (225)

Maui: VIP (12 Guests ONLY) Ultimate Whale Watch

Our Exclusive VIP whale watching tours are 2 hours long with a maximum of 12 guests. Our small groups make every seat a front row...

2 hours Free Cancellation

4.9 (225)

from
$125

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

5.0 (112)

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 (112)

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 (951)

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 (951)

from
$175

Maui: Whale Watch Cruise Aboard the Malolo From Ma'alaea Harbor

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)

Maui: Whale Watch Cruise Aboard the Malolo From Ma'alaea Harbor

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
$60

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

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 …More

4.7 (90)

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

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

4.7 (90)

from
$148

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 (836)

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 (836)

from
$213

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 (952)

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 (952)

from
$99

Maui: Molokini Snorkel & Whale Watch Tour From Kihei

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)

Maui: Molokini Snorkel & Whale Watch Tour From Kihei

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

Maui: 2-Hour Whale Watch from Lahaina Harbor

*Hawaii Ocean Project has been one of Lahaina's favorite whale watches for over a million visitors for over 30 years!* - Stay dry and move …More

4.9 (230)

Maui: 2-Hour Whale Watch from Lahaina Harbor

*Hawaii Ocean Project has been one of Lahaina's favorite whale watches for over a million visitors for over 30 years!* - Stay dry and move...

2 hours Free Cancellation

4.9 (230)

from
$70

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 (744)

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 (744)

from
$168

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

5.0 (226)

Lahaina Maui Sunset Sail on 'Alihilani

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 (226)

from
$127

Frequently Asked Questions

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

What are the best options for Maui Cruises, Sailing & Water Tours?

What are the best kid-friendly options for Maui Cruises, Sailing & Water Tours Activities?

According to verified reviews on Cool Hawaii and TripAdvisor, the best kid-friendly Maui Cruises, Sailing & Water Tours are:

View all kid-friendly Activities →

Which Maui Cruises, Sailing & Water Tours have Instant Confirmation?

Maui Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Activities with Instant Confirmation →

Which Maui Cruises, Sailing & Water Tours have Free Cancellation?

Maui Cruises, Sailing & Water Tours with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include:

View all Activities with Free Cancellation →

I need a ride! Which Maui Cruises, Sailing & Water Tours have Hotel Pickup?

Got any more Maui trip ideas?

What are the most popular styles of Tours and Activities in Maui?