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 →

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 (102)

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 (102)

from
$169

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing …More

5.0 (46)

Lahaina Maui | Romantic Luxury Sunset Sail | Motors Off Sailing

Experience a romantic Maui evening aboard Paragon, Sail Maui's flagship 47-foot performance sailing catamaran. Settle in together and experience the peace and serenity of sailing...

2 hours Free Cancellation

5.0 (46)

from
$127

Maui: 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 …More

5.0 (89)

Maui: 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

5.0 (89)

from
$195

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full 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 …More

5.0 (95)

Lahaina Maui Romantic Lanai Snorkel Sail | Meals & Full 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

5.0 (95)

from
$243

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 …More

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

4.9 (59)

from
$179

Molokini Crater Snorkeling Trip 2-Hour 10:30am Start

Join us on our late-morning Molokini Crater snorkeling tour, complete with complimentary snacks, tropical juices, bottled water, and premium snorkeling gear. Expect a lively, splash-filled …More

4.9 (132)

Molokini Crater Snorkeling Trip 2-Hour 10:30am Start

Join us on our late-morning Molokini Crater snorkeling tour, complete with complimentary snacks, tropical juices, bottled water, and premium snorkeling gear. Expect a lively, splash-filled...

2 hours 30 minutes Free Cancellation

4.9 (132)

from
$154

The Best Maui 3 Hour Molokini and Turtle Town Snorkel

Not recommended for pregnant travelers. Turtlely Cool!… Departing Molokini, we’ll make one more stop and snorkel with sea turtles in a shorline destination (locations will …More

5.0 (169)

The Best Maui 3 Hour Molokini and Turtle Town Snorkel

Not recommended for pregnant travelers. Turtlely Cool!… Departing Molokini, we’ll make one more stop and snorkel with sea turtles in a shorline destination (locations will...

3 hours Free Cancellation

5.0 (169)

from
$216

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and …More

4.8 (176)

Turtles & Tacos Luxury Catamaran Snorkel

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and...

3 hours Free Cancellation

4.8 (176)

from
$169

Maui's Best Whale Watch and Super Raft Adventure

Our High-Speed Explorer Super Raft offers an "up-close encounter" with the majestic Humpback Whale, that larger vessels do not. With our deep V-Hull, you get …More

5.0 (2)

Maui's Best Whale Watch and Super Raft Adventure

Our High-Speed Explorer Super Raft offers an "up-close encounter" with the majestic Humpback Whale, that larger vessels do not. With our deep V-Hull, you get...

2 hours Free Cancellation

5.0 (2)

from
$132

Maui: Coast of Ka'anapali Beach Sunset Dinner Sail aboard Gemini

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 …More

4.7 (236)

Maui: Coast of Ka'anapali Beach Sunset Dinner Sail aboard Gemini

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

4.7 (236)

from
$168

Guaranteed whale sightings. Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a …More

5.0 (129)

Maui: 2 Hour Prime Time Whale Watching

Guaranteed whale sightings. Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a...

2 hours Free Cancellation

5.0 (129)

from
$120

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and …More

5.0 (40)

Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and...

5 hours Free Cancellation

5.0 (40)

from
$214

Maui: 2 hour Lahaina Sunrise Whale Watch

Guaranteed whale sightings. Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a …More

5.0 (75)

Maui: 2 hour Lahaina Sunrise Whale Watch

Guaranteed whale sightings. Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a...

2 hours Free Cancellation

5.0 (75)

from
$106

Four Winds Maui Afternoon Snorkel Tour to Coral Gardens

Our afternoon Maui snorkel tour on the Four Winds goes to Coral Gardens (or Molokini Crater; location is weather dependent). This tour is a lighter …More

4.8 (35)

Four Winds Maui Afternoon Snorkel Tour to Coral Gardens

Our afternoon Maui snorkel tour on the Four Winds goes to Coral Gardens (or Molokini Crater; location is weather dependent). This tour is a lighter...

3 hours 30 minutes Free Cancellation

4.8 (35)

from
$143

Unlimited Guided Snorkeling Tour for Beginners Plus

Prefer not to feel like cattle? Gabriel’s Ohana is a small family owned and operated company. We provide a quality of customer service unmatched. Our …More

4.9 (42)

Unlimited Guided Snorkeling Tour for Beginners Plus

Prefer not to feel like cattle? Gabriel’s Ohana is a small family owned and operated company. We provide a quality of customer service unmatched. Our...

1 to 3 hours Free Cancellation

4.9 (42)

from
$85

Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a comfortable cruise with …More

4.9 (46)

Maui Mid Day Magic Whale Watch

Experience the small-group feel and incredible close encounters on either of our small group vessels. Customize your boat ride by selecting a comfortable cruise with...

2 hours Free Cancellation

4.9 (46)

from
$106

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?