Maui Sailing Trips

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Maui Activities

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23 Results
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  • Four Winds Molokini Snorkeling Tour from Maalaea Harbor

    Four Winds Molokini Snorkeling Tour from Maalaea Harbor

    784

    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...
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     5 hours  Free Cancellation
    from
    $202.59
    Details
    from
    $202.59
  • Molokini Snorkel and Performance Sail: Mā’alaea Harbor

    Molokini Snorkel and Performance Sail: Mā’alaea Harbor

    207

    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,...
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     5 hours  Free Cancellation  Instant Confirmation
    from
    $200
    Details
    from
    $200
  • Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

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

    152

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $159
    Details
    from
    $159
  • Midday Whale Watch: Mā’alaea Harbor
    Likely to Sell Out

    Midday Whale Watch: Mā’alaea Harbor

    99

    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,...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $100.22
    Details
    from
    $100.22
  • Hawaiian Canoe Sailing Experience in Maui

    Hawaiian Canoe Sailing Experience in Maui

    56

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $179
    Details
    from
    $179
  • Half-Day Deluxe Molokini Snorkel Excursion in Maui

    Half-Day Deluxe Molokini Snorkel Excursion in Maui

    95

    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...
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     5 hours  Free Cancellation  Instant Confirmation
    from
    $309
    Details
    from
    $309
  • Day's End Cocktail Sunset Sail
    Likely to Sell Out

    Day's End Cocktail Sunset Sail

    60

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $159
    Details
    from
    $159
  • Turtles & Tacos Luxury Catamaran Snorkel

    Turtles & Tacos Luxury Catamaran Snorkel

    87

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $199
    Details
    from
    $199
  • Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

    Sunset Sailing on a Floating Tiki Bar Charming Hawaiian Catamaran

    81

    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....
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $119
    Details
    from
    $119
  • Luxury Catamaran Whale Watch

    Luxury Catamaran Whale Watch

    43

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $159
    Details
    from
    $159
  • Snorkel Sail Adventure off Ka'anapali Beach, Maui
    Likely to Sell Out

    Snorkel Sail Adventure off Ka'anapali Beach, Maui

    36

    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,...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    $183.08
    Details
    from
    $183.08
  • Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
    Likely to Sell Out

    Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

    42

    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...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $289
    Details
    from
    $289
  • 2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
    Likely to Sell Out

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

    16

    Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $279.95
    Details
    from
    $279.95
  • Lāna'i Coast Snorkel and Sail
    Likely to Sell Out

    Lāna'i Coast Snorkel and Sail

    2

    Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the...
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     5 hours  Free Cancellation  Instant Confirmation
    from
    $216.22
    Details
    from
    $216.22
  • Midmorning Whale Watch from Lahaina Harbor
    Likely to Sell Out

    Midmorning Whale Watch from Lahaina Harbor

    2

    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,...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $100.22
    Details
    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:

View all kid-friendly Activities →

Q: Which Maui Sailing Trips have Instant Confirmation?

A: Maui Sailing Trips with Instant Confirmation include:

View all Activities with Instant Confirmation →

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:

View all tour styles in Maui →

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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.

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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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