One of my favorites from the trip was the sunset sail.
Even though I had wet pants, like the whole time.
We went with Kai Kanani, though there are a ton of options for both this and the snorkeling that we did the following day with the same company. I’d recommend this company hands-down… the crew was great and it wasn’t a miniature carnival cruise, as some of the other boats we saw appeared to be. We were quite pleased to learn that we had chosen wisely and were not on one of the boats that looked like floating frat houses.
What they have to say about themselves:
Come sail away
Take a moment to get away from it all. Toast to your sweetheart, family or friends or take a moment alone to enjoy the raw beauty of Hawaii as you witness another stunningly picturesque Maui sunset from the best possible vantage point (360* ocean views). Our trip includes freshly prepared pupus (Hawaiian for appetizers) served with a smile by our hospitable crew, a premium open bar, and bubbling champagne. The perfect end to another perfect day in paradise!
They tell you that you should wear shorts (the is definitely not a pants excursion), because you board from the shoreline… so there’s a possibility that you’ll get wet. I probably should have stayed in my swimshorts, because I was wet to the waist upon boarding. The short kids just can’t avoid it.
We were the first to arrive, big surprise to everyone I’m sure… and soon learned that though the boat has a capacity of over 80, there would only be 16 on this trip. Not bad…
We were a little nervous at first about the other travelers – it’s a sunset boat ride… romantic, right? Folks kept to themselves at first, but shortly after we set out, it was clear that we were in friendly waters. At one point, a very drunk newlywed (she and her new husband had been married just 3 days earlier on the beach) leaned over to Megan and told her that I was a catch.
The crew (Val, Liz and Carey, if memory serves) were great – really friendly, hospitable, and full of knowledge about the islands.
They had a full bar (from which one of the other passengers was quickly cut off… having arrived drunk), beer on tap (both local – Long Board, which was tasty – and the standard Bud Light), and plenty of snacks. The music selection was well programmed with music I’d forgotten I knew all the words to – a little Jack Johnson, Van Morrison, Mazzy Star. Good stuff.
The boat is beautiful and big with two restrooms that were surprisingly not horrifying (I’m not a big fan of boat toilets – usually not so clean, and pretty stuffy.) The front of the boat has two netted areas to sit (or recline) in that have you right over the water.
Getting off the boat was an equally wet experience as boarding, and by then I’d dried, but by that point I couldn’t have cared less. That’s the sign of a good evening – when the little inconveniences float away.
It’s not a cheap trip (but then, nothing on Maui is cheap), but we enjoyed it, and would certainly recommend it to other folks as a laid-back, relaxing way to spend an evening off of Maui. 
