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  • Sunset + Sail

Napali Sunset Sail

Adult Ages 13+
Child Ages 5-12

Napali Coast Sunset Sailing Tour

Join us on our Napali Sunset Sailing Tour aboard Leila, our 50-foot, Kauai-built sailing catamaran, and experience the astounding beauty of Napali’s 3500-foot cliffs, cascading waterfalls, sea caves, secluded beaches, and abundant marine and wildlife. Sit back and enjoy a delicious Hawaiian-inspired meal and celebrate the setting of the sun with a sparkling wine toast to wind down an unforgettable Kauai sunset cruise.

Here at Holo Holo Charters, we’re passionate about sailing! Turning off the motors, setting the sails, and letting the power of the wind move us across the ocean, really puts us in touch with our humanity and satisfies our need to explore and adventure. Sharing this passion is our business, so please come aboard our Napali Sunset Sailing Tour and let us wine and dine you up the Napali Coast, and take you sailing into the sunset!

We’ll be taking Leila—our spacious and beautiful 50-foot, Kauai-built sailing catamaran. Leila was very specifically designed to efficiently sail Kauai’s coast and to look amazing while doing it! Her narrow hulls and low center of gravity make for a most comfortable ride. You’ll find plenty of room to spread out on Leila’s deck and her nets, and there are two restrooms on board for your convenience.

Since we are passionate about sailing, we only hoist the sails if weather permits, we need wind to fill the sails! We try to avoid motor-sailing as many others do, sails up and engines on, as the joy of sailing comes from the quiet you can only experience with motors off and the natural push of the wind. On this tour we are covering over 60 nautical miles, so we will be motoring most of the trip, but when conditions permit we will sail for up to thirty (30) minutes or more.

We’ll get situated, cast the lines, and take a right out of Port Allen Harbor, making our way up Kauai’s westside to the Napali Coast. Make sure to keep your eyes peeled for dolphins, whales (seasonal), and turtles that frequent the area.

After passing Polihale State Park, we’ll be in the heart of the world-famous Napali Coast. Napali is the gem of Hawaii, and the warm afternoon is an excellent time to take it all in. Your captain and crew will narrate the journey, telling you the fascinating history and colorful legends behind Napali’s beaches, valleys, reefs, caves, and arches. Glimmering waterfalls and the changing colors of the late afternoon sky provide the most romantic backdrop for this incredible and informative experience.

When we’ve turned around and we’re pointing south is usually when we’re heading downwind, which makes this the best time to get our sail in! Upwind sailing can be a bit bumpy but downwind is dreamy, so we’ll set the sails, kill the motors and let Leila do what she does best–gracefully travel along the Napali Coast by the power of the wind.

When the Kauai dinner cruise bell rings, it’s time to enjoy a locally-made meal—we’ve got pupus (appetizers) to start, followed by a delicious Hawaiian-inspired dinner to fill you up. In the beverage department, we can offer you water, soft drinks, juices, or– if you want to kick it up a notch– beer, wine, seltzers, or our Ginger Mai Tai’s made with award-winning, local, Koloa Rum. At sunset, we’ll share a sparkling wine toast to celebrate the day, because we got to enjoy another beautiful day in paradise!

By the time we get back to the dock and conclude the evening’s Napali sunset dinner sail, you should have not a worry in the world, but a big smile, a rosy glow, a warm heart, and memories that will last a lifetime.


Your Tour Includes

  • See the Napali Coast, amazing marine life, and more!
  • Stir-fry Dinner with Hawaiian influence
  • Mai tais, beer, wine, and soft drinks during cruise. Sunset champagne toast
  • The chance to see humpback whales (peak season Dec-Apr)

Tour Details

  • Check-in at 1:30 p.m. at our Port Allen location (time varies by season).
  • For safety, no pregnant women or children under 5 are allowed on this tour.
  • Tax not included

Note that tours often fill up 2-3 weeks in advance. Booking your tour early in your vacation window is a good idea in case the weather forces us to postpone your tour.

Kauai private boat tours



We pride ourselves on creating fun and memorable ocean adventures for our guests. Your safety is our top priority; therefore, all tour routes, destinations, and snorkeling activities are dependent on ocean and weather conditions. If you are joining us during our winter season November – March, tours can be more often impacted by weather. Conditions around Kauai can change quickly, so our expert captains are constantly analyzing and may wait until check-in time to determine the best route for the day. If that occurs you will have the opportunity to go on the altered tour, reschedule to another day (availability permitting), or cancel your tour at no charge if it is weather-related. If you have any questions or concerns, please call us at 808-335-0815 so we can help create the best experience for you and your family!  


Leila: Our Sleek Sailing Catamaran

Napali Sailing Catamaran Tour

With her sleek construction and design, Leila slips quickly and smoothly through the waters. The catamaran design allows for level sailing. With no more than 10 degrees of “heel,” you won’t be sailing sideways.

Although Leila’s two-hull design is based on a historical prototype, she truly is a modern, state-of-the-art vessel. The space-age epoxy/glass construction used to build Holo Holo was used in making Leila as well. This composite makes for a strong and safe structure. The mast and sail are of the best quality and modern design. – Learn more.


An experience of a lifetime. The Captain and his crew were knowledgeable and helpful. We were able to go under a waterfall and get breathtaking pictures of the coastline.