The Best Sailboat Rentals in Hawaii

Sailing Charter on 52' Classic Hawaiian Luxury Catamaran in Honolulu, Hawaii

INCREDIBLE BOATING EXPERIENCE!! We even got to sail alongside dolphins. Would advise if you are considering adding food, to bring your own rather than due catering due to portion sizes being small for the price. Otherwise, would recommend Richie's team wholeheartedly.

ONE OF A KIND, exhilarating trimaran sailing and swimming experience in Waikiki

Kiah and Natalie provided exceeded all expectations on our sunset cruise. We went with her suggestion to maximize the daylight, and had plenty of time to enjoy one of the best sunsets. Kiah constantly asked if there was anything we needed, if we were comfortable, and engaged in all types of conversations! Thank you for your time and care to making our sunset cruise the highlight of our vacation!

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

I booked a private ride to do a photoshoot and Tony was super helpful with suggestions and what we needed. Everything went really seamless and I’m so grateful! Would definitely book again!

The best value Sunset Cruise off Waikiki! Beneteau 43ft.

We went sailing with Captain Tom and deckhand Raul. They were fantastic! We saw the sunset, a nearly full moon over Diamond Head, and just had the most wonderful time. So much more enjoyable than a group catamaran trip. We'll be doing this again. Thank you!!

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

Captain Tony went out of his way to help me with my proposal to my girlfriend. He called me a day before and he was happy to help with planning. We sailed out far enough where diamond head was in the backdrop of the proposal. While I was surprising my girlfriend he was taking photos and videos! Overall it was a great experience and highly recommend. We will certainly be touring with him again. Thank you!

Private sailing on 45 foot Luxury yacht, day sailing, sunset sail, snorkeling

Rented Tony’s Sail boat for my sister’s 30th! We had such a great time. He was very attentive with my group and shared his life experiences with us. Pretty cool life he as! Ask him. Will rent again if we come back!