Kauai Sailing Catamarans allows you to experience the majestic Na Pali coast.  On the custom built catamaran “Lucky Lady”. Sailing along you will pass by majestic seacliffs, waterfalls, sea caves, pristine beaches and remote wilderness coastline. The experienced captains tell tales of Hawaiian history & legends. Enjoy snorkeling and waterside fun or just relax on the spacious main deck or the panoramic observation deck.  Encounter spinner and bottle nose dolphins, Hawaiian green sea turtles and in season (December-April) magnificent humpback whales.
For true trade wind sailing on Kauai join the crew of Holoholo Charters aboard “Leila”, a beautiful 48′ sailing catamaran. When the winds permit, they sail while you are enjoying a continental breakfast on the way to the Na Pali Coast. Along the way the crew will be entertaining you with stories of the Hawaiians who once lived in this beautiful area. Considered to be “The Jewel of Kauai” with 3,000 foot cliffs, green valleys, hidden beaches, secluded waterfalls and breathtaking beauty, the Na Pali coast is a sight to be enjoyed from sea level.
Lucky lady snorkel sail
Sail along the Na Pali coast
kauai snorkeling
Sail along the Na Pali coast

CCruise Ship Iconruise Ship Passengers

Lucky Lady Na Pali Snorkel and the Leila Na Pali Snorkel Sail Morning Snorkel Tour do not work for cruise ship passengers due to the early morning check in time and the length of the tour.


The Leila Na Pali Snorkel Sail Sunset Motor Tour is available for cruise ship passengers who are on one of the NCL ships that overnight in Nawiliwili. You can do the sunset tour on day one; You will need a rental car since the check-in location is about 40 minutes from the cruise ship dock.


Activity Tips

Kevin Ditamore – Owner / Manager

You MUST SEE the Na Pali coast … it is unarguably the MOST beautiful stretch of coastline in the world. Rugged, isolated, rocky spires pointing toward the heavens like a thousand cathedrals but carved by wind and rain … waterfalls that disappear into sea caves … it looks like miles of scenery created specifically for a fantasy movie set.

Helicopter tours give a unique aerial perspective and we highly recommend them, but the time spent above the coast is brief. Boat tours offer a different (and much longer) view.

These sailing catamarans are a great choice for people who want to see this beauty, but aren’t up for the more adventurous rafting tours. We do love the rafts because of their ability to go in and out of sea caves when the ocean swells permit (typically from May to October). These catamarans have masts, so they are too tall to enter any of the caves. But they DO offer creature comforts and amenities you won’t find on the smaller rafts.