Hawaii Sailing Trips

Upon booking, I noticed a disclaimer that said:“Parents/Guardians, please note: while we are an all-ages experience, guests are advised that we are a bar with what can be a party atmosphere. We are not responsible for the actions or expressions of other guests on board.”As a parent traveling with four kids, I was a little concerned at first. However, I decided to go ahead with the booking because of the cost, free drinks snorkeling activities offered, and I’m so glad I did.Our excursion was very relaxed. There were no rowdy guests or inappropriate behavior, and the crew didn’t encourage any kind of party atmosphere. If you’re worried like I was, I’d say it’s simply a general disclaimer rather than a reflection of what you’ll necessarily experience.One thing I was especially glad about was not booking one of the large catamaran cruises with the inflatable water slides and trampoline. Before the trip, I had seriously considered it because it looked like a lot of fun. But while we were out on the ocean, I actually saw one of those boats, and it looked absolutely packed—there had to be close to a hundred people on board.In that moment, I knew I had made the right decision. The smaller catamaran we chose was much more peaceful, with fewer people, plenty of room to relax, and a laid-back atmosphere. Instead of feeling crowded or rushed, we were able to truly enjoy the beautiful Hawaiian scenery, the ocean breeze, and the experience itself. For me, that’s exactly what a vacation should be—relaxing, not hectic—and I’m so thankful we chose the quieter option.My kids all said this was one of their favorite activities of our trip! The snorkeling equipment was clean and sanitized, and the crew did an excellent job making sure everyone felt safe and comfortable. They even gave a thorough demonstration for beginners, which made the experience much less intimidating.We were lucky enough to see sea turtles, big fish, and coral reefs while snorkeling. But surprisingly, my kids’ favorite part wasn’t even the snorkeling—it was relaxing on the catamaran’s netting while the waves splashed up underneath them. They said it felt like an ocean water park ride and couldn’t stop laughing the entire time.This excursion created some of our favorite family memories from Hawaii, and I would absolutely recommend it to other families.

Very good experience with Erik, Zac, and Isaiah. They made the trip so much fun and were very informative about the ocean and safety of all the gear. We saw turtles, dolphins, and fish. The drinks were amazing and the view was even better!

Excellent experience! Nice boat, good snacks & drinks. Listening to the whales was awesome. Adding music by Josh made it to relaxing and leveled up!

I had a lot of fun with Ray he told me how to foil in one lesson I even took a kite boarding lesson after one of the best days of my life.

Josh is awesome to work with. His equipment is great and well taken care of. He matches the equipment to your needs and has many options. He is a long time Kailua local and knows the spots and conditions. Foiling was fun and he made it easy. Two way radio helmet meant no need to return to him for coaching just spend all your minutes having fun with Coaching as you to. Josh is safety focused and a very patient teacher. Highly recommend.

We really enjoyed the whole trip sailing Waikiki with South Shore Sail. From the moment we walked up to the greeters they made us feel very special and welcome. The whole crew was very professional and friendly. One and half hours was just right to get a little outing on the water and the free drinks was a plus! I will reccomend this sailing company to everyone! The cost is very reasonable and was so much FUN!

Great crew! Great cruise and very friendly! Drinks flowed nicely! I highly recommend this trip for everyone.

Justin, Johnny and Johnny were awesome guides. We happened to have the boat to ourselves (me and my 3 kids) which was coincidental but amazing. We all had a fantastic experience - Johnny took us out far into the canyon to spot some cool fish. We saw one sea turtle from the boat, but not lucky enough to see any while snorkeling. Despite that, it was a great time out on a really beautiful catamaran, with friendly and fun guides/captains!

I got up and riding on my first lesson and then progressed and improved during the next two lessons that I had. Great fun and the two instructors I've had were very helpful and made the experience great. I will be having additional lessons. Highly recommended.

Took a wingfoil lesson... Josh was great! Patient, informative and encouraging through the whole lesson. Definitely much harder to learn then it looks but had a great lesson and will definitely try it again soon! Highly recommend taking a lesson with Josh!