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Top 10 Best Maui Sailing Trips

Found 22 Sailing Trips activities in Maui. Sort by Popularity.
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 74 reviews)

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 snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • Maui
  • Superb74 reviews4.8

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $199.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 51 reviews)

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 happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail

Day's End Cocktail Sunset Sail

  • Maui
  • Superb51 reviews4.7

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 31 reviews)

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, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Start From $183.08
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Maui
  • Superb31 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $183.08
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 806 reviews)

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 the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Maui
  • Superb806 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $202.59
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 39 reviews)

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 aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Maui
  • Superb39 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Luxury Catamaran Whale Watch

(5 of 40 reviews)

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 to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Maui
  • Superb40 reviews5

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Start From $159.00
 
 

'Alihilani Sunset Sail

(5 of 77 reviews)

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 a luxurious experience, allowing for incredible views of Maui and the inter islands while wa... More

Free Cancellation
Start From $112.90
 
'Alihilani Sunset Sail Likely to Sell Out

'Alihilani Sunset Sail

  • Maui
  • Superb77 reviews5

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Free Cancellation
    Start From $112.90
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.8 of 82 reviews)

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. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Free Cancellation
Start From $119.00
 
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor Likely to Sell Out

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

  • Maui
  • Superb82 reviews4.8

Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....

    Free Cancellation
    Start From $119.00
 
 

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

(4.7 of 158 reviews)

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 Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Free Cancellation
Start From $159.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

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

  • Maui
  • Superb158 reviews4.7

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Start From $159.00
 
 

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

(4.8 of 16 reviews)

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 innovative seating galore, to the beautifully designed convert... More

Free Cancellation
Start From $269.00
 
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

  • Maui
  • Superb16 reviews4.8

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....

    Free Cancellation
    Start From $269.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.9 of 208 reviews)

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, and is home to over 250 species of t... More

Free Cancellation
Start From $200.00
 
Molokini Snorkel and Performance Sail: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • Maui
  • Superb208 reviews4.9

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Free Cancellation
    Start From $200.00
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 91 reviews)

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 fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $309.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Maui
  • Superb91 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $309.00
 
 

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar

(3.5 of 2 reviews)

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 offers breathtaking views of the sunset complemented by deligh... More

Free Cancellation
Start From $136.42
 
2 Hours Holo Holo Sunset Cocktail Sail with Open Bar Likely to Sell Out

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar

  • Maui
  • Good2 reviews3.5

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

    Free Cancellation
    Start From $136.42
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 58 reviews)

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 Hawaiian history and culture. Cold water and snorkel gear are... More

Free Cancellation
Start From $179.00
 
Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • Maui
  • Superb58 reviews4.8

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Free Cancellation
    Start From $179.00
 
 

Lahaina Sailing and Snorkeling Adventure Tour

(4.8 of 58 reviews)

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 an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Start From $192.05
 
Lahaina Sailing and Snorkeling Adventure Tour Likely to Sell Out

Lahaina Sailing and Snorkeling Adventure Tour

  • Maui
  • Superb58 reviews4.8

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Start From $192.05
 
 

Sunset Sail from Ma'alaea Harbor in Maui

(4.6 of 214 reviews)

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 catamaran, Ocean Spirit. It’s the perfect way to ex... More

Free Cancellation
Start From $125.10
 
Sunset Sail from Ma'alaea Harbor in Maui Likely to Sell Out

Sunset Sail from Ma'alaea Harbor in Maui

  • Maui
  • Superb214 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $125.10
 
 

Morning Whale Watch: Lāhainā Harbor

(5 of 10 reviews)

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, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Start From $91.89
 
Morning Whale Watch: Lāhainā Harbor Likely to Sell Out

Morning Whale Watch: Lāhainā Harbor

  • Maui
  • Superb10 reviews5

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Start From $91.89
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 100 reviews)

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, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Start From $86.49
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • Maui
  • Superb100 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Start From $86.49
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(4.9 of 100 reviews)

PRIVATE CHARTER - 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, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach Likely to Sell Out

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • Maui
  • Superb100 reviews4.9

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
 

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

(5 of 1 review)

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More

Free Cancellation
Private Tour
Start From $159.00
 
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks Likely to Sell Out

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

  • Maui
  • Superb1 review5

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....

    Free Cancellation
    Private Tour
    Start From $159.00
 
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