Updated - Sail Maui - Maui: Alihilani Sunset Sail - Maalaea Harbor

Updated - Sail Maui - Maui: Alihilani Sunset Sail - Maalaea Harbor

Embark on an extraordinary sunset sail with us aboard our vessel ‘Alihilani. The name ‘Alihilani captures the place where the horizon meets the sea, a vision we are excited to share with you.

  • Duration: 120 Minutes (approx.)
From USD $94.00
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Sail Maui - Maui: Lanai Beach Picnic Sail - Lahaina Harbor

Sail Maui - Maui: Lanai Beach Picnic Sail - Lahaina Harbor

The adventure begins in Lahaina Harbor where we set out across the Au’ au’ channel to Lana’i. A continental breakfast featuring some of Hawaii’s tastiest tropical fruit is served as you enjoy the panoramic view of the islands of Maui...

  • Duration: 420 Minutes (approx.)
From USD $199.00
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Updated - Sail Maui - Maui: Lanai Coast Snorkel and Sail - Lahaina Harbor

Updated - Sail Maui - Maui: Lanai Coast Snorkel and Sail - Lahaina Harbor

Join us aboard ‘Alihilani for an adventure along the incredible coast of Lana’i. This trip explores the pristine reefs along Lana’i’s south shores. Stunning sea cliffs, uncrowded snorkeling sites, and expansive island views make this trip

  • Duration: 270 Minutes (approx.)
From USD $179.00
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Updated - Sail Maui - Maui: Molokini Snorkeling Tour and Performance Sail - Maalaea Harbor

Updated - Sail Maui - Maui: Molokini Snorkeling Tour and Performance Sail - Maalaea Harbor

Molokini is 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 tropical fish.

  • Duration: 300 Minutes (approx.)
From USD $184.00
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Sail Maui - Maui: Pali Coast Snorkeling Tour & Performance Sail - Maalaea Harbor

Sail Maui - Maui: Pali Coast Snorkeling Tour & Performance Sail - Maalaea Harbor

The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline which, particularly at Coral Gardens, boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Feel the wind in your hair and

  • Duration: 180 Minutes (approx.)
From USD $74.00
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Sail Maui - Maui: Paragon Performance Sunset Sail - Lahaina Harbor

Sail Maui - Maui: Paragon Performance Sunset Sail - Lahaina Harbor

A perfect Maui experience is not complete without witnessing the beauty of a sunset out on the ocean. Join us for our Paragon Performance Sunset Sail and watch the sun dip below the horizon as we glide along the picturesque West Maui coast.

  • Duration: 120 Minutes (approx.)
From USD $94.00
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Sail Maui - Maui: Private Charter Sail - Lahaina Harbor

Sail Maui - Maui: Private Charter Sail - Lahaina Harbor

Sail Maui is the perfect choice for your event! You and your guests will thoroughly enjoy sailing along the tropical coastline aboard one of the fastest, most sought-after boats on Maui. Charter our whole fleet to accommodate large groups..

  • Duration: 120 Minutes (approx.)
From USD $999.00
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Updated - Sail Maui - Maui: Afternoon Sail with the Whales - Maalaea Harbor

Updated - Sail Maui - Maui: Afternoon Sail with the Whales - Maalaea Harbor

We generally spot humpbacks on all of our trips during the winter, but this season we’re offering an exciting new opportunity to sail with the whales. We’ll embark from Māʻalaea Harbor and set sail in the afternoon trade winds.

  • Duration: 90 Minutes (approx.)
From USD $84.00
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Sail Maui - West Maui Snorkeling Tour & Performance Sail – Lahaina Harbor

Sail Maui - West Maui Snorkeling Tour & Performance Sail – Lahaina Harbor

Nobody knows the waters of Maui better than our crew. Let us be your hosts as we explore and snorkel the incredible West Maui coast on Paragon. What’s our destination? Some of our favorites are...

  • Duration: 270 Minutes (approx.)
From USD $169.00
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Updated - Sail Maui - Maui: Private Charter Sail - Maalaea Harbor

Updated - Sail Maui - Maui: Private Charter Sail - Maalaea Harbor

Sail Maui is the perfect choice for your event! You and your guests will thoroughly enjoy sailing along the tropical coastline aboard one of the fastest, most sought-after boats on Maui. Charter our whole fleet to accommodate large groups..

  • Duration: 120 Minutes (approx.)
From USD $1,199.00
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Sail Maui - Maui: Sail with the Whales – Lahaina Harbor

Sail Maui - Maui: Sail with the Whales – 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, the ‘Au ‘au channel off the coast of Maui boasts the greatest number.

  • Duration: 150 Minutes (approx.)
From USD $89.00
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Updated - Sail Maui - Maui: Early Bird Sail with the Whales – Lahaina Harbor

Updated - Sail Maui - Maui: Early Bird Sail with the Whales – Lahaina Harbor

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.

  • Duration: 150 Minutes (approx.)
From USD $99.00
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Sail Maui - Maui: Twilight Whale Watch - Maalaea Harbor

Sail Maui - Maui: Twilight Whale Watch - Maalaea Harbor

We generally spot humpbacks on all of our trips during the winter, but this season we’re offering an exciting new opportunity to sail with the whales. We’ll embark from Māʻalaea Harbor and set sail in the afternoon trade winds.

  • Duration: 120 Minutes (approx.)
From USD $89.00
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Sail Maui - Maui: Wahine Wednesday Sail-A-Bration – Lahaina Harbor

Sail Maui - Maui: Wahine Wednesday Sail-A-Bration – Lahaina Harbor

Calling all Ladies.. it’s time to Sail-a-brate YOU! Ahoy, Ladies! Get ready to set sail and soak up the good vibes with us on our Wahine Wednesdays Ladies-Only sailing charter!

  • Duration: 120 Minutes (approx.)
From USD $104.00
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Updated - Sail Maui - Maui: Midday Sail with the Whales - Maalaea Harbor

Updated - Sail Maui - Maui: Midday Sail with the Whales - Maalaea Harbor

Set sail on a unique adventure aboard Paragon, our 47’ performance sailing catamaran, as we explore Maui’s whale-watching paradise. Experience the elegance of pure sailing, basking in the serene sounds of the ocean...

  • Duration: 90 Minutes (approx.)
From USD $84.00
Book Now
Updated - Sail Maui - Maui: Morning Sail with the Whales – Maalaea Harbor

Updated - Sail Maui - Maui: Morning Sail with the Whales – Maalaea Harbor

Set sail on a unique adventure aboard Paragon, our 47’ performance sailing catamaran, as we explore Maui’s whale-watching paradise. Experience the elegance of pure sailing, basking in the serene sounds of the ocean...

  • Duration: 90 Minutes (approx.)
From USD $84.00
Book Now
Updated - Sail Maui - Maui: Early Sail with the Whales – Maalaea Harbor

Updated - Sail Maui - Maui: Early Sail with the Whales – Maalaea Harbor

Join us aboard our vessel Paragon, a 47’ performance sailing catamaran, for a captivating sail with the majestic humpback whales. Our sailing journey is designed to be in harmony with nature, allowing you to relax to the...

  • Duration: 90 Minutes (approx.)
From USD $84.00
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Updated - Sail Maui - West Maui Snorkel & Sail - Maalaea Harbor

Updated - Sail Maui - West Maui Snorkel & Sail - Maalaea Harbor

Sail with us on an unforgettable West Maui Snorkeling & Sailing adventure. This charter offers a unique opportunity to sail either along the idyllic West Maui coastline or across the channel to the enchanting Lāna’i coastline.

  • Duration: 315 Minutes (approx.)
From USD $184.00
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Updated - Sail Maui - Maui: Morning Pali Coast Snorkel & Sail - Maalaea Harbor

Updated - Sail Maui - Maui: Morning Pali Coast Snorkel & Sail - Maalaea Harbor

Set sail on a unique adventure aboard Paragon, our 47’ performance sailing catamaran, as we explore Maui’s whale-watching paradise. Experience the elegance of pure sailing, basking in the serene sounds of the ocean...

  • Duration: 240 Minutes (approx.)
From USD $119.00
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Updated - Sail Maui - Maui: Afternoon Pali Coast Snorkel & Sail - Maalaea Harbor

Updated - Sail Maui - Maui: Afternoon Pali Coast Snorkel & Sail - Maalaea Harbor

Join us for a breathtaking afternoon sail along Maui’s stunning coastline, a journey accessible mainly by boat. This exclusive charter presents a unique opportunity to witness some of Hawaii’s most gorgeous coral reefs.

  • Duration: 240 Minutes (approx.)
From USD $109.00
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Updated - Sail Maui - Maui: Midday Performance Sail – Maalaea Harbor

Updated - Sail Maui - Maui: Midday Performance Sail – Maalaea Harbor

Set sail on a journey unlike any other with our premier sailing charter, dedicated to those who hold a true appreciation for the art of sailing. Join us aboard Hawaii’s premier sailing catamaran Paragon.

  • Duration: 120 Minutes (approx.)
From USD $84.00
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