See Waikiki from a private sailboat

Aloha! You are in Honolulu, looking for the perfect sunset cruise. There are so many options, from big boats to catamarans to charter sailboats. We research everything and can recommend you see Waikiki from a private sailboat from Captain Castaway.

As a reminder, we don’t get compensated for these Journeys with Stephen, so we can objectively analyze the available excursions while staying true to our “upscale on a budget” philosophy.

When to go – morning or sunset?

If you search for cruise tours from Honolulu you will find a myriad of options, and one of the first decisions is what time of day to go. There are morning cruises that sometimes offer swimming or snorkeling, as well as viewing Hawaiian marine life. The ocean can be calm in the early morning, and whale watching, during the season, can be fun.

Sunset cruises are a photographer’s delight, from golden views of Honolulu to seeing the city lights after dark and brief fireworks on Fridays. And of course, there is the classic Hawaiian sunset from the vantage point of the ocean. Having experienced extraordinary whale watching on Maui and dolphins galore off Dana Point, we opt for sunset.

What about a big boat?

Want to do something really touristy? There are boats that offer dinner, drinks, and a show for packages that can exceed $200 a person. With as many as four decks and hundreds of people, this might attract that couple from North Dakota on their first trip off the mainland. Not for us.

Catamarans could be fun

Boats that leave wading distance from Waikiki Beach look interesting and reasonably priced. And there are many choices. The well-reviewed Kepoikai II is 42 feet long, but that means they can cram 50 people on board. Worse, the sail is only one hour, so the experience is mostly over before you can really enjoy it. Na Hoku III costs more, but at least the cruise is 90 minutes. Sponsored by Pacifico and Modelo, you can imagine what interests the 50 people who squeeze onto this catamaran. Holokai is another popular choice; they tout their famous “Holokai Hooch” cocktail as part of the $80pp price.

The list goes on with what are generally known as “booze cruises.” One we research departs just 15 minutes before sunset, so it seems the experience on these catamarans is more about partying than the sail and the views.

The private charter experience

Frustrated by the big boats and crowded small ones, we research chartering our own vessel. Captain Bruce offers a nice power boat, but the starting price for a sunset cruise is more than $1,000. To be fair, that’s not bad if you have a really large party. There are just three of us. Mana Cruises lists a sunset cruise at $800 – per hour, 2-hour minimum. Ouch. Eternal Tides wants us to send them a form for a quote, sign a waiver, pay a retainer, and so on. Others, such as Oahu Ocean Adventures, look promising, though they might book three more people to join us – which could be troublesome.

The “Goldilocks” answer

In all, we explore online literally dozens of options. Too big, too crowded, too boozy, too quick, too expensive. What happened to “just right?”

We are staying at Ilikai Marina condos, with a view below us of the extensive Ala Wai boat harbor. I begin to focus on the many offerings right there and discover Captain Castaway’s Waikiki Sailing Adventures. It begins to tick the right boxes:

• A reasonable fixed price for up to six people, but can be booked with just the three of us.
• A sunset cruise that is scheduled for 45 minutes before sunset and lasts two hours.
• Nothing but 5-star reviews, especially for Captain David, who also owns the 34-foot sailboat.
• A true sailing experience, though Running Silent also has a friendly electric motor if needed.

We book it online for Thanksgiving afternoon/evening.

Our time with Captain David

The excursion is much more than “just right.” Captain David is a 20-year veteran of Hawaiian Islands sailing and ocean work. He operates shark cage tours on the North Shore in between these gigs. Best of all, he brings a certain Zen that makes everyone comfortable. Since I did a fair amount of sailing out of Newport Beach, California in a previous life, we share numerous stories. For some reason, all of my stories are about sailing adventures that scared me, from my wild certification sail to enormous swells to my silent whale encounter.

We sail out towards the setting sun. Looking back, Honolulu presents us with a perfect rainbow, as if to say, “try to top this!” With the mainsail out and then the jib, we sail at a brisk pace along the shoreline (a mile out) past Diamond Head. By then, the sun has set, and the scene gradually shifts from a golden Waikiki to spectacular evening city lights on the return voyage.

We are offered the chance along the way to take the helm, and why not? As Captain David says, it’s like riding a bike and will come back to you. I’m not entirely sure, but it is fun to feel the thrill of sailing again, even for a short while. We move around the boat, with some of us happily perched on the bow for much of the trip. After two hours, Captain David asks if we want to keep going. I feel a little guilty that we have spent that much time already, and tell him we are probably ready to return to the dock.

Yes, it takes a lot of research, but it pays off in the end with the perfect sunset cruise and a unique opportunity to see Waikiki from a private sailboat. (Check out my YouTube video highlights above).

I have sailed on a former America’s Cup boat from Lahaina to Lanai. I have sailed from Newport Beach to Catalina Island. I have maneuvered the Bahamas and even done the Caribbean as a passenger on a sailing yacht. Now this Hawaiian experience adds another wonderful memory. Mahalo!

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