Going on a sunset cruise in the winter can be less-than-great as the water can get choppy and the weather can turn rough, but it also means that sunsets are earlier and that you’ll get a chance to see whales.

We were lucky on our sunset cruise: the water and weather were incredibly calm, making for an amazing sunset tour.

diamond head from shore 2


Once we checked in, we strolled over to where the Holokai was landing from its previous sail.

Unlike previous cruises I’ve been on, the Holokai is a beach-boarding vessel, which means it slides right up onto shore and lowers a staircase to board.

You’ll be getting your feet when you try to embark, but that’s not a big deal since it’s a barefoot cruise anyway—all footwear must be removed before boarding and then stored in one of the various cubbyholes around the boat during the sail.

The boat pulls up far enough on the beach that the water doesn’t go much further past your ankles, so you don’t have to worry if you were wearing long pants like I was. I just rolled them up to the top of my shins before boarding and didn’t get so much as a splash above my feet.

There were about 30 people on board, and there was enough room for all of us to comfortably sit on the bench seating at the beginning of the cruise. Of course, after we had set off we could all move around the boat, standing by the rails or sitting on the netting.


As we departed from shore, the captain and crew member(/bartender) had a short briefing on safety and emergency procedure.

Though normally pretty boring, these two made the talk much more engaging by adding humor and personality, setting the mood for the sail by starting us off with smiles.

The briefing ended with an introduction to the open bar, in which they also told us about their famous Holokai Hooch, a mix of POG and rum that was very delicious and, in my experience, very, very treacherous—but hey, we were on a boat!


If you weren’t yet aware, I enjoy going on boats. Something about being away from shore—especially busy Waikiki—is just so relaxing, and the cool breeze, calm waves, and beautiful sunsets don’t hurt.


As we sailed out and back I could see the coral beneath us clearly (though couldn’t manage to snap a good picture). The Waikiki area must be a great snorkeling place if you’re able to sail further out from the beach.

It’s no surprise that Holokai’s afternoon snorkel was our best selling tour of 2017. It’s probably a great time.


The sunset sail wasn’t completely free of marine life, however: a pair of whales made their appearance during our cruise!

They didn’t stop for pictures, sadly, but they popped up multiple times as we were sailing along, and the captain hit the brakes when we were nearby so we could watch them.

In general, whales aren’t as sociable as dolphins are (spending half their lives in Alaska makes them cold), so we didn’t see much of the humpbacks besides a few mist spouts and dives.

It was a welcome surprise in any case, however, as whale watching isn’t an advertised benefit of the Holokai sunset sail.

Know that if you’re going to be in the waters of Hawaii between the months of December and April, you might spot some visiting humpbacks whales.

Also know that just because you’re here and looking for whales, doesn’t mean you’ll find any—as we learned on the Star of Honolulu.


After the sun had gone down and the whales had waggled their tails at us for what seemed to be the last time, we turned the catamaran round and sailed back towards the beach.


We were going pretty fast, which made it hard to take a panorama shot with my phone… didn’t stop me from trying, though!

The breeze was a bit chilly for me in just an aloha shirt, so you might want to bring light cover up if you’re worried about that.

As for myself, I just grabbed another can of beer to deal with the cold.


Holokai’s sunset sail was a really fun time, even if we hadn’t been visited by whales.

The friendly crew of the Holokai, beautiful view of Waikiki, and (of course) generous open bar make for an excellent way to unwind at the end of the day, and where better to do it?

If you want to experience this relaxing cruise for yourself, book it on HawaiiActivities. You can also check out other cruise options on the Holokai, as well as see a list of all our sunset cocktail cruises.