Leila Na Pali Sunset Dinner Sail

40 Reviews |
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Badge of Excellence |
Kauai, USA

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4 hours 30 minutes (Approx.)
Mobile Ticket

Keeping you safe during COVID-19
What you can expect during your visit
Gear/equipment sanitized between use
Guides required to regularly wash hands
Hand sanitizer available to travelers and staff
Regular temperature checks for staff
Regularly sanitized high-traffic areas


Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Ginger Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will share legends and stories of this sacred and historical coast as we bask in the glory of her 4000’ cliffs, emerald valleys, sparkling waterfalls, secluded beaches, and majestic wildlife including Hawaiian spinner dolphins and humpback whales (seasonally, December- April). We’ll stop the boat to serve you a nourishing and delicious meal in the most stunning and romantic setting Kauai has to offer. Sailing across the ocean by the power of the wind will ignite your senses and make you feel alive! We’ll raise a toast as the sun falls below the horizon and the afterglow casts warm hues upon the island. Treat your loved ones to the very best on this adventurous-yet-relaxing golden-hour excursion where photo opportunities abound, and treasured memories are made.


  • Close encounter with wildlife
  • Romantic experience, perfect for couples
  • Once-in-a-Lifetime Experience
  • Travel by boat and see the sights from the water
  • Dinner included
  • Free drinks included



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What To Bring

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Average 4.75 out of 5 stars based on 40 verified reviews from Cool Destinations and TripAdvisor

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Leila Na Pali Sunset Dinner Sail
Leila_B, Jan 2022 Verified
So happy we added this tour to our Kauai vacation. Unlike other tours, this boat only holds about 35 people and seems more personable. Captain Kelly and crew were amazing hosts. The food and drinks were delicious, and we were well taken care of. Captain Kelly is an expert sailor and knows how to maneuver the boat so that everyone gets an equal shot at the amazing views, no matter which side of the boat you are on. This is a catamaran, so you may get wet if you sit or stand in certain areas, but there is also plenty of space to stay warm and dry. All in all, would do it again in a heartbeat. Highly recommend!
Leila Na Pali Sunset Dinner Sail
48robynr, Jan 2022 Verified
Simply wonderful day out on the water. The trip was fantastic. Kaylin and Jay, the crew, did an awesome job and Captain Dave’s driving and commentary was great as well. Would highly recommend this activity!!
Leila Na Pali Sunset Dinner Sail
Geoffrey K, Jan 2022 Verified
The following was written by my wife Janette.On Saturday, December 11, 2021 we booked our first cruise to the Na Pali coast with Holo Holo Charters. There were approximately 50 passengers on board, plus the Captain and two crew. We were fortunate weather-wise; the calmness of the water was like a summer day on Kauai, which was very unusual for December. For safety reasons, we were asked to board barefoot. Our shoes were collected and stowed in a rolling cart, which remained at the dock. We felt we could comfortably entrust our safety to the Captain, who has been running these cruises since the 60’s. He was very specific about preparing the passengers for a bouncy ride and lots of water spray, especially near the bow. Still, quite a number of passengers decided to brave the bow seats and were soon soaked, but seemed to really enjoy themselves. The towering beauty of the emerald cliffs of Na Pali is difficult to describe. It was an extra nice treat to see it all on a summer-like day. Captain J was very knowledgeable about the entire area. Because of the calm waters, he gave us a bonus on the way back. He was able to steer the boat partway into one of the caves, which was truly awesome! The hard-working crew of two were very busy during the entire trip, serving beverages and snacks, plus a tasty dinner on the ride back. We don’t drink so we can’t speak to the quality of the liquor on board. What impressed us the most on this trip was the congenial atmosphere among all the passengers. As annual travelers to Hawaii Nei since 1975 we have taken many whale watch cruises on Maui in December. On every cruise, there were always some passengers who seemed unfamiliar with boats and therefore not comfortable with the experience. This cruise was different; everyone seemed to genuinely enjoy themselves. Maybe the shoeless thing is what did it, by putting everyone on an equal footing! We highly recommend seeing the Na Pali coast with Holo Holo Charters. They are the best!
Leila Na Pali Sunset Dinner Sail
651haleyk, Dec 2021 Verified
This was one of our favorite outings on our honeymoon. We really enjoyed the captain and crew! Incredible views and saw lots of whales! Make sure you bring a raincoat, you can get very wet.
Leila Na Pali Sunset Dinner Sail
Mike_S, Dec 2021 Verified
Even with winter conditions, the cree made the trip very pleasant. The views were amazing! We recommend this to everyone!
Leila Na Pali Sunset Dinner Sail
Joseph_M, Dec 2021 Verified
Had a great time with knowledgeable staff, really fun time would recommend to anyone who wants to see NaPali coast
Leila Na Pali Sunset Dinner Sail
ashleybW8927RJ, Dec 2021 Verified
The views from this sail are absolutely breathtaking. The cocktails and dinner were delicious. Definitely bring your bathing suit though, you will get wet. The only downside (if you choose to see it this way) is that there are a lot of people packed onto the boat - so many that you may not be able to sit in the less wet part of the boat. So be prepared, bring extra gear for all types of weather, and get ready for an amazing experience.
Leila Na Pali Sunset Dinner Sail
Christopher_T, Dec 2021 Verified
Crew from beginning to finish done a phenomenal job. Could not have asked for a better experience. The captain not only was very skilled with the boat but he was very skilled with handling every wave he done an incredible job with the vessel
Leila Na Pali Sunset Dinner Sail
Tammy_P, Dec 2021 Verified
My husband and I were here on Kauai on our first visit to Hawaii and we decided to take the sunset dinner sail. I’ll be honest I envisioned a leisurely sail with dinner and cocktails! But that is not what was delivered. However, the views were spectacular and the food was delicious! And although I was exhausted after and slept for 12 hours and I’m sore all over today! I would do it again in a heartbeat! So much fun! A great adventure! I can’t wait to bring my son and daughter next year!
Leila Na Pali Sunset Dinner Sail
Sarah_T, Dec 2021 Verified
The crew , Kelsey (I hope that is right) Brian , and Mark were amazing. They couldn’t have been nicer and they made our experience so much fun. It was very rough waters at times but that was to be expected. We had all the drinks we could want and we saw the amazing coast line. We even got to see a whale breach. The food was traditional Hawaiian and it was awesome. We had a great time.

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Product code: C-2064P10

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