Build sailing skills with instruction tailored to your experience
4 hrs
Up to 4 people
Water, sparkling water, juice
Set sail for hands-on instruction tailored to your experience, whether you are new to sailing or building on existing skills. Bring your own alcohol or extra food to store in the onboard cooler.
Rebook or receive a full refund with at least 72 hours' notice. Full refund if the operator cancels due to weather. No-shows are charged the full price.
Product ID: V5FTNV
Gratuity is welcomed for the crew. A 15–25% gratuity is typical for private boat charters.
Lahaina Harbor, Maui
Ali and Keahi are the heart of this operation, a couple whose genuine love of sailing and deep connection to Maui comes through in every review. Guests consistently rave about how personable and knowledgeable they are, turning what could be a standard boat tour into something that feels personal and memorable. Wildlife sightings, particularly whales, come up constantly, though reviewers are refreshingly honest that nature does its own thing out there. The private charter format is a real differentiator here. Families with young kids, couples celebrating milestones, first-time sailors, repeat visitors over multiple years, the common thread is that people feel genuinely cared for rather than herded through a tourist experience. Ali's habit of sharing local dining and activity recommendations has even earned its own shoutout in more than one review. Across the board, these are some of the most enthusiastic reviews you'll see for any Maui activity. The consistent five-star rating over a large number of reviews is hard to argue with. If you're on the fence, the flexibility and communication Ali and Keahi brought during a stretch of stormy weather says a lot about how they operate when things get complicated.
Highly recommend taking a sail with the sweetest couple in Maui! The sailing experience was exactly what we hoped, a day at sea with the breeze in our hair. We snorkeled in a remote location, with no other boats. The best experience we could hope for, simply amazing! 🤩
Holly Wilkes
July 25, 2026
Highly recommend taking a sail with the sweetest couple in Maui! The sailing experience was exactly what we hoped, a day at sea with the breeze in our hair. We snorkeled in a remote location, with no other boats. The best experience we could hope for, simply amazing! 🤩
Holly Wilkes
July 25, 2026
Private snorkel gear and instruction, plus a sail along Maui’s coastline
A tailored private sail with Maui coastal views and onboard refreshments
Sail offshore Maui as the sun sets on a private yacht
Learn the basics and dive a Kaanapali coral reef—no experience needed
Dive Kaanapali in a private group with your own instructor
Dive Lahaina’s underwater sites with sharks, turtles, and a wreck