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Join Holo-Holo Charter’ on their Napali Sunset Sailing Tour aboard Leila, a 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 Kauaʻi sunset cruise.

Adult Ages 13+
Child Ages 5-12
  • Beautiful Kauaʻi Sunset
  •  50-Foot, Kauai-Built Sailing Catamaran
  • Seasonal Whale Watching

Napali Sunset Dinner Sail

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

You’ll be taking Leila—their 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.

They only hoist the sails if weather permits, wind is needed to fill the sails! They will 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 you will be are covering over 60 nautical miles, so they will be motoring most of the trip, but when conditions permit, they will sail for up to thirty (30) minutes or more.

Once situated, they will cast the lines, and take a right out of Port Allen Harbor, making the 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, you’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 they’ve turned around and are pointing south is usually when they are heading downwind, which makes this the best time to get their sail in! Upwind sailing can be a bit bumpy but downwind is dreamy, so they’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 Kauaʻi dinner cruise bell rings, it’s time to enjoy a locally-made meal—they’ve got pupus (appetizers) to start, followed by a delicious Hawaiʻian-inspired dinner to fill you up. In the beverage department, they 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, you’ll share a sparkling wine toast to celebrate the day, because you got to enjoy another beautiful day in paradise!

By the time you 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 2:00 p.m. at the Port Allen location (time varies by season).
  • For safety, no pregnant women or children under 5 are allowed on this tour.
  • Tax not included