Maui Sailing

Molokini Snorkel & Performance Sail

Molokini is one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of tropical fish. Sail Maui combines the elements of performance sailing in the trade winds with snorkeling in the protected, crystal clear water at Molokini crater for a truly outstanding experience.

Discover Molokini aboard Paragon II, where your trip includes a continental breakfast on the leisurely sail across Ma’alaea Bay. Take in the stunning landscape that makes Maui special, and during whale season (December – May), spot the humpback whales as they swim nearby. While at Molokini, swim, snorkel, and rinse off with our fresh water shower. After snorkeling, we’ll invite you to indulge in a freshly prepared lunch and refresh with a variety of beverages, including wine and local beer.

Aboard Paragon II you will experience the thrill of a lifetime! Our Molokini snorkeling trip boasts the best sailing of all our trips. Maui’s afternoon trade winds can really get the boat going, so join Paragon’s friendly crew at the helm and try your hand at sailing the high seas!

Adventure Sunset Sail

There’s nothing quite like a Maui sunset, with Molokini silhouetted on the horizon and the presence of friends and loved ones and the best crew on Maui taking care of your every need.

Kai Kanani’s Adventure Sunset Sail is a two hour sail featuring live music, a stellar menu from Wailea’s own The Market-Maui and an open bar full of local spirits such as Ocean Vodka and Kula Rum, as well as wine from Ulupalakua’s MauiWine. At sunset, we pour the award-winning Lokelani Sparkling Rosé for a sunset toast.

As the only catamaran in South Maui, we sail alone with the ocean our canvas and the wind as the brush. Our captain and crew are there to serve you and your friends and make the tour as comfortable as possible. Sit back and enjoy the best evening of your Maui vacation.

Private Sunset Charter

Join us for your own Private Sunset sail. Perfect for celebrating birthdays, anniversaries, proposals, bachelorette parties, quality family time, and more!

Take your loved one and friends sailing on your own boat with the help of a few crew. If desired, we offer a hands-on learning experience for those who wish to learn about sailing! Unlike many other companies that motor the majority of the time, we pride ourselves on sailing as much as possible.

Want to spend a little extra time on the water? Add an extra hour on to your sail.

For 7-12 guests we offer the opportunity to charter the fleet for a buddy boat sail. We depart at the same time and set sail side-by-side for a once in a lifetime sunset adventure.

Monohull Private Custom Charter ~ Nova

S/V Nova is a unique experience in that it offers pleasant, personal, private sailing adventures for up to six passengers. We have done weddings, proposals, birthdays, ash scatterings, and private dinners.

Monohull Private Afternoon Snorkel & Sail

Come join us on our afternoon snorkel sail. We begin by sailing around beautiful Maalaea bay which offers offshore steady winds and calm water.
We then sail over to West Maui’s breathtaking Pali cliffs or to a satellite reef off the shoreline of north Kihei for our own private snorkeling spot.

Tucked beneath the cliffs are large coral outcroppings that make for beautiful underwater topography and snorkeling. We have a variety of sites along this coast which are some of Maui’s premier snorkel sites including coral gardens. Only accessible by boat, you and your family can get away from large crowds and enjoy the peaceful serenity of a more private and tranquil spot.

Full Day Snorkel & Sail

Come join us on our full day sailing adventure. We begin by sharing several different options for the day's adventure and make sure everything is catered to your desires, the weather conditions, and current wildlife sightings. We then spend the day sailing around beautiful Maalaea bay and beyond. We can visit several different snorkel spots including West Maui’s breathtaking Pali cliffs, satellite reefs off the shoreline of north Kihei, or even a sunken pier off of Lahaina.

Enjoy hands-on sailing instruction, or sit back, relax, and sip a cocktail while your experienced captain and crew take care of everything for you. If you want to try your luck at fishing, we will set a few trolling lures behind the boat and keep our fingers crossed that a hungry fish decides to take a bite.

Our full-day sail is the preferred charter during whale season where you never have to choose between spending more time sailing, snorkeling, or whale watching. And during the summer, we get to enjoy our windier season and really experience all that Ma'alaea has to offer.

For 7-12 guests we offer the opportunity to charter the fleet for a buddy boat sail. We depart at the same time and set sail side-by-side for a once in a lifetime sunset adventure.