Captain Castaway's Waikiki Sailing Adventures — Attraction in Honolulu

I booked the private sunset & fireworks cruise months in advance as an anniversary surprise for my husband, and it turned out to be the absolute highlight of our trip. First of all, Captain David's boat is in pristine condition and runs so smoothly. As someone who's used to loud boat motors, I was shocked at how gracefully she cut through the water in total silence. Second, and most importantly, Captain David himself is one of those rare people you come across that just radiates good energy. If meditative yoga classes were a person, they would be Captain David. He's so kind in a humble way, extremely knowledgeable, and takes the time to explain all about his boat, how and why he chooses his routes for each trip, and points out interesting things all around. He thoughtfully answered every question I asked and gave detailed explanations about the sailing race that happened to be going on around us. He invited us to move to the very front of the boat just in time to have an unobstructed view of the golden sunset dripping into the water on the horizon.

In case you were wondering what to wear, I would advise against a sundress if you want to make your way around the boat. I learned that the hard way, in gusty wind. :D

All in all, my husband was impressed, I was impressed, and I plan to recommend Captain Castaways to anyone I meet who's planning a trip to Honolulu.

Pro tip-the parking lot gets very backed up on Friday night after the fireworks show. I suggest staying at one of the hotels within walking distance of the harbor or getting dropped off/ picked up...

We just returned to our hotel following our most awesome excursion with Captain David on his sunset cruise. It was a wonderfully relaxing evening with a picturesque sunset and bright moonlight dancing on the water afterwards. Stays out later than other sunset cruises, so you can see the stars, appreciate Diamondhead after dark, and the city skyline all lit up. Never expected to find a private tour (just two of us) that we’d enjoy and appreciate as much as this. Not at all surprising to see that there have only been five star reviews. If you’re here searching for reasons to take this trip, you probably now realize that there is no rationale for not doing so. Everything other reviewers have conveyed is very...

⛵️ My family and I got to go sailing with Captain David and it was amazing!!! Highly recommend if you are looking for a private sunset sail experience on Oahu. I’m a local on the island and this is an experience I would recommend to all my friends and family. Truly special and the Captain is also local with great knowledge of the water. The dock is near Waikiki with plenty of parking available. Usually the tours I’ve been on are crowded and full of tourists, however; this one is local and private with a great vibe and an awesome Captain. We did the sunset sail and the water was calm and we caught a beautiful sunset. Definitely will be...