Maui Sailing Trips

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
from
$202.59

Sunset Sail from Ma'alaea Harbor in Maui
Likely to Sell Out
Likely to Sell Out

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing...

 2 hours  Free Cancellation
from
$137.82

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve,...

 5 hours  Free Cancellation  Instant Confirmation
from
$200

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  Instant Confirmation
from
$199

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale...

 3 hours  Free Cancellation  Instant Confirmation
from
$159

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  Instant Confirmation
from
$179

Half-Day Deluxe Molokini Snorkel Excursion in Maui

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  Instant Confirmation
from
$309

Midday Whale Watch: Mā’alaea 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  Instant Confirmation
from
$100.22

Day's End Cocktail Sunset Sail
Likely to Sell Out
Likely to Sell Out

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s...

 2 hours  Free Cancellation  Instant Confirmation
from
$159

Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall....

 2 hours  Free Cancellation  Instant Confirmation
from
$119

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  Instant Confirmation
from
$119

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Likely to Sell Out
Likely to Sell Out

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  Instant Confirmation
from
$289

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Likely to Sell Out
Likely to Sell Out

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea,...

 2 hours  Free Cancellation  Instant Confirmation
from
$279.95

Snorkel Sail Adventure off Ka'anapali Beach, Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky,...

 4 hours  Free Cancellation  Instant Confirmation
from
$192.17

Morning Whale Watch: 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  Instant Confirmation
from
$100.22

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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Maui Sailing Trips?

A: According to verified reviews on Cool Hawaii and TripAdvisor, the best Maui Sailing Trips are:

Q: What are the best kid-friendly options for Maui Sailing Trips Activities?

A: According to verified reviews on Cool Hawaii and TripAdvisor, the best kid-friendly Maui Sailing Trips are:

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Q: Which Maui Sailing Trips have Instant Confirmation?

A: Maui Sailing Trips with Instant Confirmation include:

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Q: Which Maui Sailing Trips have Free Cancellation?

A: Maui Sailing Trips 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

Q: Got any more Maui trip ideas?

A: We sure do. Check out our curated lists of hand-picked Maui Activities.

View all Maui Trip Ideas

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

A: Based on our sales data over the past year, the most popular styles of tours and activities in Maui are:

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Cool Hawaii wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

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.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
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  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.