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Top 10 Best Maui Sailing Trips

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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 743 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 $191.78
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Maui
  • Superb743 reviews4.7

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

    Free Cancellation
    Start From $191.78
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 189 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 $133.05
 
Sunset Sail from Ma'alaea Harbor Likely to Sell Out

Sunset Sail from Ma'alaea Harbor

  • Maui
  • Superb189 reviews4.6

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

    Free Cancellation
    Start From $133.05
 
 

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

(4.6 of 125 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 $139.00
 
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
  • Superb125 reviews4.6

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

    Free Cancellation
    Start From $139.00
 
 

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

(4.7 of 39 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
  • Superb39 reviews4.7

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

    Free Cancellation
    Start From $119.00
 
 

Luxury Catamaran Royal Sunset Dinner Sail

(4.9 of 12 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 Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail

  • Maui
  • Superb12 reviews4.9

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

    Free Cancellation
    Start From $289.00
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 7 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 $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Maui
  • Superb7 reviews4.9

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

    Free Cancellation
    Start From $172.85
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.8 of 57 reviews)

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More

Free Cancellation
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Maui
  • Superb57 reviews4.8

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....

    Free Cancellation
    Start From $289.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel Sail

(4.8 of 57 reviews)

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More

Free Cancellation
Start From $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel Sail Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel Sail

  • Maui
  • Superb57 reviews4.8

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....

    Free Cancellation
    Start From $169.00
 
 

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

(4.9 of 156 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 from Ma'alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

  • Maui
  • Superb156 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
 
 

'Alihilani Sunset Sail from Ma'alaea Harbor

(5 of 66 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 from Ma'alaea Harbor Likely to Sell Out

'Alihilani Sunset Sail from Ma'alaea Harbor

  • Maui
  • Superb66 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
 
 

Day's End Cocktail Sunset Sail

(4.5 of 10 reviews)

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More

Free Cancellation
Start From $169.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Maui
  • Exellent10 reviews4.5

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....

    Free Cancellation
    Start From $169.00
 
 

Luxury Catamaran Whale Watch

(5 of 11 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Nui provides max... More

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

Luxury Catamaran Whale Watch

  • Maui
  • Superb11 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Start From $159.00
 
 

Midday Sail with the Whales Ma'alaea

(4.9 of 99 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
 
Midday Sail with the Whales Ma'alaea Likely to Sell Out

Midday Sail with the Whales Ma'alaea

  • Maui
  • Superb99 reviews4.9

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

    Free Cancellation
    Start From $91.89
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.8 of 53 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
  • Superb53 reviews4.8

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

    Free Cancellation
    Start From $179.00
 
 

Morning Snorkel Sail from Lahaina Harbor

(4.4 of 36 reviews)

The Scotch Mist is a fun and fast sailing yacht, built in 1982 for racing by famed builder Bill Lee in Santa Cruz, California. In fact, she is the fastest production line sailboat of her size in the world, having won “first in c... More

Free Cancellation
Start From $143.60
 
Morning Snorkel Sail from Lahaina Harbor Likely to Sell Out

Morning Snorkel Sail from Lahaina Harbor

  • Maui
  • Exellent36 reviews4.4

The Scotch Mist is a fun and fast sailing yacht, built in 1982 for racing by famed builder Bill Lee ....

    Free Cancellation
    Start From $143.60
 
 

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

(4.8 of 6 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 $284.09
 
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
  • Superb6 reviews4.8

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

    Free Cancellation
    Start From $284.09
 
 

4-Hour Koa Kai Molokini Adventure Snorkel

(5 of 10 reviews)

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More

Free Cancellation
Start From $169.00
 
4-Hour Koa Kai Molokini Adventure Snorkel Likely to Sell Out

4-Hour Koa Kai Molokini Adventure Snorkel

  • Maui
  • Superb10 reviews5

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....

    Free Cancellation
    Start From $169.00
 
 

1.5-Hour Koa Kai Adventure Whale Watch

(5 of 1 review)

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More

Free Cancellation
Start From $109.00
 
1.5-Hour Koa Kai Adventure Whale Watch Likely to Sell Out

1.5-Hour Koa Kai Adventure Whale Watch

  • Maui
  • Superb1 review5

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....

    Free Cancellation
    Start From $109.00
 
 

Morning Sail With the Whales Ma'alaea

(5 of 8 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 Sail With the Whales Ma'alaea Likely to Sell Out

Morning Sail With the Whales Ma'alaea

  • Maui
  • Superb8 reviews5

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

    Free Cancellation
    Start From $91.89
 
 

Afternoon Sail With the Whales from Ma'alaea Harbor

(5 of 8 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
 
Afternoon Sail With the Whales from Ma'alaea Harbor Likely to Sell Out

Afternoon Sail With the Whales from Ma'alaea Harbor

  • Maui
  • Superb8 reviews5

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

    Free Cancellation
    Start From $91.89
 
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