Sailing Cruises

Get ready for real sailing, small group settings and cruising Maui's crystal clear waters aboard one of our elite sailing vessels! Whether you want to enjoy a beautiful sunset, snorkeling or just looking for the thrill of sailing Maui's trade winds, we are sure you will find the perfect Maui sailing cruise!

Reviews

"OMG, It was amazing. The Boat staff was so much fun and the food was so tasty. I will make sure this is a part of our trip every year., "

Robert VilleneuveDecember 21 2014
reviewed Deluxe Dinner Sail - Kaanapali Beach
Sort by: Select View:   
  •  
  •  
  •  
$56.95 PWF Lahaina Luxury Sunset Sail
 

PWF Lahaina Luxury Sunset Sail

Sail into Maui's sunset aboard the Ocean Spirit luxury catamaran and enjoy delicious food, drinks and music!

Duration Location Family Sail Adult Family Sail Child
2 hours PWF Store, 612 Front St, Lahaina Our Price $56.95
Regular Price $69.00
Our Price $49.00
Regular Price $49.00
  •  
  •  
  •  
$99.95 PWF Honolua Bay Snorkel Adventure
 

PWF Honolua Bay Snorkel Adventure

Join the crew of the Ocean Spirit, Maui's newest luxury catamaran on a fun cruise to beautiful Honolua Bay

Duration Location Adult (Reg $125) Add On Child (Reg $75)
5 hours Our Price $99.95
Regular Price $125.00
Our Price $75.00
Regular Price $75.00
  •  
  •  
  •  
$57.95 Maui Sunset Champagne & Chocolate Sail

Maui Sunset Champagne & Chocolate Sail

Sail the Maui sunset in style, enjoy champagne and chocolate, aboard the Scotch Mist sailing yacht.

Duration Location Adult Private Charter
2 hours Lahaina Harbor, Lahaina, HI 96761 Our Price $57.95
Regular Price $69.00
Our Price $1249.95
Regular Price $1500.00
  •  
  •  
  •  
$154.95 Alii Nui Royal Feast Dinner Cruise
 

Alii Nui Royal Feast Dinner Cruise

Experience one of Maui's most luxurious catamaran as you sail towards the sunset

Duration Location Adult Adult
2.5 hours Maalaea Harbor, Maui HI Our Price $154.95
Regular Price $170.00
Our Price $154.95
Regular Price $170.00
  •  
  •  
  •  
$76.45 Deluxe Dinner Sail - Kaanapali Beach
 

Deluxe Dinner Sail - Kaanapali Beach

Dine aboard a sleek sailing catamaran while enjoying Maui's most beautiful sunset views.

Duration Location Adult Junior
2.5 hours whalers village, kaanapali maui hi Our Price $76.45
Regular Price $85.50
Our Price $71.15
Regular Price $75.20