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  • Sunset + Sail

Napali Sunset Dinner Sail - 4.5hr

Adult Ages 13+
Child Ages 5-12

Napali Coast Sunset & Sailing Tour

If you’re game for an exciting, visually stunning, and delicious afternoon adventure on Kauai’s iconic Napali Coast, come aboard our spacious catamaran, and let’s sail off into the sunset! The Napali Sunset Sail is a full-on four-and-a-half-hour Napali Coast cruising and sailing excursion that combines world-class sightseeing, high-quality food & beverage, ocean wildlife viewing, outstanding hospitality, and plenty of afternoon glow and sunset vibes.

We’ll be traveling on Leila, a 50-foot-long, 28-foot-wide motorized sailing catamaran. Leila sits low to the water, providing more stability, safety, and comfort than many other top-heavy tour boats. She’s gorgeous and capable and the island’s only commercial sailing vessel that was proudly built right here on Kauai. There’s plenty of room to stretch out and relax on Leila, both inside the cabin and on deck, and there are two bathrooms for everyone’s convenience.

We’re heading into the heart of Kauai’s renowned Napali Coast, which is often recognized as the most beautiful coastline in all of Hawaii, and even all of America. Must see to believe! As the oldest of the Hawaiian Islands, Kauai has some of the state’s most dramatic geological features, many of which comprise the sacred Napali Coast. The cliffs, the valleys, the “Cathedrals”, the beaches, waterfalls, sea caves, Honopu Arch… it’s music to the eyes!

You’ll stay well-fed and hydrated on this tour. We offer a creative selection of cold beverages, including juices, sodas, domestic and Hawaii craft beers, hard seltzers, red and white wine, sparkling wine, and our signature Koloa Rum Mai Tai. We begin our food service with a variety of meats & cheeses, crackers, and fresh veggies with ranch & hummus. For the main course, we serve pineapple, garden greens with lemon/herb vinaigrette, somen noodle salad, hapa rice, teriyaki chicken, and roasted veggies with tofu. Our satisfying meals are prepared fresh everyday by our local caterers, Rose & Bros., using whole ingredients, right down to the sauces. Our service ware and linens are reusable, and Holo Holo Charters is the only Kauai tour boat company to be certified an Ocean Friendly Restaurant by the Surfrider Foundation.

We’re out in nature, and we’re appreciating Kauai’s astounding beauty. We’re eating, we’re sipping, learning about the island’s history, legends, and culture. We’re also watching for ocean wildlife! Common species observed on Kauai boat tours include Hawaiian spinner dolphins, flying fish, green sea turtles, pelagic sea birds, and seasonally (December- April), massive North Pacific Humpback Whales that have migrated 3,000+ miles from their summer feeding grounds in Alaska to their “winter home” in our warm Hawaiian waters, where they mate and calve.

At some point during the tour, depending on the day’s wind and wave direction, we’ll hoist the main sail, unfurl the jib, kill the motors, and let Leila do what she was built to do—sail along by the power of the wind. If you’ve never been on a boat under sail, it’s worth experiencing! Sailing is peaceful and powerful and ancient—the feeling is in our bones. Please know that while Kauai has reliable trade wind patterns and that we’re able to sail comfortably most days, there are also days we cannot. We’d much rather keep our guests comfortable and having a splendid time, rather than force sailing in unfavorable conditions. Leila allows us to be flexible.

We’ll serve our Kauai Coffee Coconut Caramel Crunch Brownies for dessert and at sunset, offer a sparkling wine toast—we’re fancy like that! After the sun sinks into the ocean and under the horizon, we’ll return safely back to the dock in Port Allen before it’s completely dark.

Bring layers on this tour, and on every tour! Kauai’s weather conditions are notoriously variable; lots of rain, lots of rainbows. Pro tip– no matter what you’re doing and where you’re going on Kauai, it’s always a good idea to bring a jacket.

This Napali Sunset Sail tour is a smart choice for travelers that want to experience the amazing Napali Coast, but aren’t necessarily interested in swimming and snorkeling, which most day tours include. It’s a fantastic option for those that want to experience sailing on the ocean, and it’s also ideal for photographers.

If you have any questions at all about the Napali Sunset Sail or any of our Kauai or Niihau boat tours, please don’t hesitate to call our reservations desk at 808-335-0815. We’re happy to help you select the most appropriate Kauai boat tour for you and your group.


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 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!  

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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.