Waikiki Sunset Sailing Tour: Experience Majestic Hawaiian Sunsets in a Small Group

Experience the majestic Hawaiian sunsets on our small group Waikiki Sunset Sailing Tour. Sail towards Diamond Head and enjoy the beauty of Oahu’s south shore as the sun dips below the horizon. Book now!

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Diamond Head State Monument - Watch a spectacular sunset over the Pacific Ocean, with Waikiki and Diamond Head as an iconic backdrop to a perfect evening on a sailboat with friends and family in small groups
  • Waikiki Beach - Waikiki shoreline Leave with a newfound appreciation for the people and marine life of Hawaii, and then gaze in awe as…
What's Included
  • Carbonated beverages included
Additional Information

Our vessel, The Universe, provides the ultimate means of observing Hawaii’s spectacular sunsets, renowned far and wide. Join us to bask in the orange glow of the setting sun as you create lifelong memories with your dear ones. Why settle for a congested catamaran or speed boat when you could enjoy a more personal voyage in our exclusive 6-people…

Location
Hawaii Yacht Club
Ala Moana Boulevard
Hawaii Yacht Club ALA WAI boat harbor slip 429 it’s about 100 feet before the yacht club just follow the google map to Hawaii yacht club
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(109 Ratings)
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Brent_d
Sep 5, 2025
Amazing sunset cruise!!!! - Our sunset cruise was perfect!! Communication before hand was great! Stunning views and perfect weather. The highlight of the cruise was getting to know capatain tony and hearing of his adventures and his knowledge of Hawaii. He did an amazing job of making our 4 year old feel comfortable and apart of everything!! Couldn’t have asked for a better experience!! Thank you Captain Tony!! Enjoy your time with your sister and nephew!!!
Review provided by Viator
V4125vlryana
Aug 30, 2025
Smaller, intimate sailing - incredible views! - We had a great experience with Captain Tony. He was incredibly friendly and knowledgeable about the area. The smaller, intimate sailing was just what we were looking for whilst on our honeymoon and we ended up sailing as the only passengers. The pictures don’t do the sunset justice, it was incredible to see from the boat. At the end, Tony provided multiple suggestions of how to best explore the island and places to visit, including a car rental and scenic route recommendation. This also includes his small group turtle snorkelling excursion which we have reviewed separately.
Review provided by Tripadvisor
H6678rjsusank
Aug 30, 2025
Fun on the Sunset Cruise - We had a wonderful time on the sunset cruise! Captain Tony was friendly, knowledgeable, and easy-going, which made the trip even more enjoyable. The scenery was breathtaking and the whole experience was very relaxing. We also loved learning about Hawaiian history from Captain Tony—he shared so much interesting information. Highly recommend this sunset cruise!!
Review provided by Tripadvisor
Michelle
Aug 29, 2025
Zen sailing watching the sunset! - Girls trip - The night before we left we booked this sunset sail. We were so glad we did. It was just the 3 of us as the other couple cancelled. Captain Tony was personable and very knowledgeable. We enjoyed sitting on the front of the sailboat as we headed towards Diamond Head. It was a gorgeous night. Other party boats were out and they were crowded and very noisy. If that’s your vibe this is not the sail for you. If you want a quiet, relaxing, zen sail then don’t hesitate to book this. It is well worth it. As we turned around and headed back we were able to watch the colorful sunset and moved to the back of the boat where Captain Tony talked about the landscape and Hawaii itself to us. This is a must if you love the ocean and watching sunsets.
Review provided by Tripadvisor
Beachoil
Aug 16, 2025
Great time - Tony knows the seas and the ropes as well. Had a wonderful time riding and talking. Gave us several recommendations for our remaining days on the island. The time went by to quickly. Thanks again Captain Tony.
Review provided by Tripadvisor
Garciajenc
Aug 6, 2025
Relaxing sunset sail - Captain Tony is a wonderfully knowledgeable guide, with a wealth of information about the Hawaiian islands. The sailing was smooth and relaxing
Review provided by Tripadvisor
Thedeanofme
Aug 3, 2025
10/10 - Been on the larger boats for a sunset cruise but this was much more intimate and peaceful. Captain Tony was absolutely amazing. Accommodating, helpful, responsive. Thank you, Tony!
Review provided by Tripadvisor
Dave
Jul 28, 2025
Perfect intimate sunset cruise - We were able to book this cruise on short notice and it ended up being a great decision. With a maximum of six passengers, we weren’t fighting for space or a seat or a view. This was in stark contrast to the numerous boats we saw underway that had dozens of people on them fighting to get the best view. I don’t know if he drinks dose of keys, but Captain Tony would certainly be in the running for one of the most interesting men in the world. In addition to a comprehensive knowledge of Hawaii, he had stories from his travels and adventures around the world to share with the boat. It was a great cruise and we book it again in a heartbeat.
Review provided by Tripadvisor
B9964ajmichaelr
Jul 24, 2025
- Excellent experience. Captain Tony was a great host and outstanding narrator. Highly recommended. Boat was clean and in great condition.
Review provided by Tripadvisor
Tl704
Jul 16, 2025
Fantastic sailing experience with personal touch - This was a fantastic sunset sail. Way more laid back and intimate than the crowded cruises we saw. There was a max of 6 people and the other group scheduled cancelled, but Capt Tony kept the reservation and took just us 2. The slip was pretty easy to find and the boat was well maintained and comfortable. The cruise was extremely enjoyable along the Waikiki waterfront. If you’re looking for a true sailing experience with a personal touch, I would highly recommend booking with Captain Tony.
Review provided by Tripadvisor
From $99
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).