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Top 10 Best Maui Sailing Trips

Found 28 Sailing Trips activities in Maui. Sort by Popularity.
 

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(5 of 81 reviews)

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 on weather, tides, and ocean conditions. • Explore Lana... More

Free Cancellation
Start From $216.22
 
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

  • Maui
  • Superb81 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Free Cancellation
    Start From $216.22
 
 

'Alihilani Lahaina Sunset Sail

(4.9 of 199 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 from the... More

Free Cancellation
Start From $117.30
 
'Alihilani Lahaina Sunset Sail

'Alihilani Lahaina Sunset Sail

  • Maui
  • Superb199 reviews4.9

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

    Free Cancellation
    Start From $117.30
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 163 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
  • Superb163 reviews4.7

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
 
 

Akialoa Mā’alaea Sunset Sail

(4.9 of 37 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail

Akialoa Mā’alaea Sunset Sail

  • Maui
  • Superb37 reviews4.9

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Start From $108.11
 
 

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

(4.6 of 84 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 $141.98
 
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui

  • Maui
  • Superb84 reviews4.6

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

    Free Cancellation
    Start From $141.98
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 857 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 $213.41
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Maui
  • Superb857 reviews4.7

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

    Free Cancellation
    Start From $213.41
 
 

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

(4.9 of 134 reviews)

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More

Free Cancellation
Start From $163.20
 
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar

  • Maui
  • Superb134 reviews4.9

Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....

    Free Cancellation
    Start From $163.20
 
 

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

(4.9 of 37 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 $203.16
 
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali

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

  • Maui
  • Superb37 reviews4.9

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 $203.16
 
 

Paragon Lahaina Sunset Sail

(4.9 of 35 reviews)

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More

Free Cancellation
Start From $102.00
 
Paragon Lahaina Sunset Sail

Paragon Lahaina Sunset Sail

  • Maui
  • Superb35 reviews4.9

Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....

    Free Cancellation
    Start From $102.00
 
 

Happy Hour Sunset Sail on Maui's Luxury Catamaran

(4.7 of 98 reviews)

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 drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More

Free Cancellation
Start From $180.80
 
Happy Hour Sunset Sail on Maui's Luxury Catamaran

Happy Hour Sunset Sail on Maui's Luxury Catamaran

  • Maui
  • Superb98 reviews4.7

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

    Free Cancellation
    Start From $180.80
 
 

Snorkel Sail Adventure off Ka'anapali Beach in Maui

(5 of 49 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 $193.17
 
Snorkel Sail Adventure off Ka'anapali Beach in Maui

Snorkel Sail Adventure off Ka'anapali Beach in Maui

  • Maui
  • Superb49 reviews5

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

    Free Cancellation
    Start From $193.17
 
 

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

(4.9 of 134 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 $305.89
 
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion

  • Maui
  • Superb134 reviews4.9

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

    Free Cancellation
    Start From $305.89
 
 

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

(4.8 of 61 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 at Sea (Adults-Only)

Luxury Catamaran Royal Sunset Dinner at Sea (Adults-Only)

  • Maui
  • Superb61 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
 
 

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

(4.8 of 223 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 Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

  • Maui
  • Superb223 reviews4.8

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

    Free Cancellation
    Start From $200.00
 
 

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

(4.5 of 24 reviews)

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More

Free Cancellation
Start From $59.95
 
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor

  • Maui
  • Exellent24 reviews4.5

Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....

    Free Cancellation
    Start From $59.95
 
 

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

(4.9 of 89 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 $139.00
 
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

Maui Premier Whale Watching Cruise - Luxury Catamaran Experience

  • Maui
  • Superb89 reviews4.9

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

    Free Cancellation
    Start From $139.00
 
 

Honolua Snorkel Sail from Lahaina

(4.9 of 61 reviews)

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More

Free Cancellation
Start From $180.92
 
Honolua Snorkel Sail from Lahaina

Honolua Snorkel Sail from Lahaina

  • Maui
  • Superb61 reviews4.9

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....

    Free Cancellation
    Start From $180.92
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 104 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 $100.22
 
Midday Whale Watch: Mā’alaea Harbor

Midday Whale Watch: Mā’alaea Harbor

  • Maui
  • Superb104 reviews4.9

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

    Free Cancellation
    Start From $100.22
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 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

Hawaiian Canoe Sailing Experience in Maui

  • Maui
  • Superb63 reviews4.6

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

    Free Cancellation
    Start From $179.00
 
 

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

(4.9 of 20 reviews)

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, this intimate evening cruise offers stunning views of the coast... More

Free Cancellation
Start From $279.00
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

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

  • Maui
  • Superb20 reviews4.9

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Free Cancellation
    Start From $279.00
 
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