Winning on Water


It doesn’t take much to enjoy yourself in the water on Maui. A $4 floatie from the ABC Store, some SPF, and game on!

But some ways are better than others.

Sailing off the coast of Maui on a private catamaran or yacht with Maui Custom Charters is most assuredly one of those ways. No offense, apartment pool. But… you know.


Winning on Water

If ever asked whether or not you’re interested in joining a snorkeling tour aboard a private sailboat on Maui, the answer is “hell yes.”

Our group arrived at Maalaea Harbor a little after 9 am and were warmly welcomed aboard the S/V Nova, a 42′ sailing yacht (they also have a 47′ sailing catamaran called Artemis), by Captain Anna, who’s been on the water for the last 15 years in scenic areas like French Polynesia, Florida, the Marshall Islands, Puget Sound, and of course where she is from Maui. Not only is she lifeguard-certified, PADI Scuba Certified and CPR certified, but she’s also a really radical woman and clearly knows sailing like the back of her hand. And the front of her hand, too. Basically, you can trust in Captain Anna.

Maui boat

Captain Makana, the first mate, was extremely helpful in getting us aboard the boat, showing us the ropes (literally and figuratively), and even preparing delicious breakfast snacks. Yum!

What’s extra fun is the fact that Makana was born and raised in Hana and is now nearly related to Captain Anna as their siblings are to be married. He used to be a professional surfer and has traveled the world competing in surfing.  Makana captains a private charter fishing boat in Alaska during the summers and sails around Maui in the winters.


The S/V Nova

One of the best things about the S/V Nova is that it maxes out at 6 guests, the perfect option for groups of friends and family members who would rather enjoy a more private, custom experience for only slightly more money than the average big boat tour. In my opinion, this is one of the best deals on Maui, and one that is highlighted by the fantastically sideways ride (see: sailboat on extremely windy Maui day) aboard the S/V Nova.

Maui Hawaii boats

The sailboat itself has it all – 2 bathrooms, a kitchen area, an icebox, plenty of seating, snorkel gear, you name it. If you can’t find something you need or want aboard the S/V Nova, you may, in fact, be extremely high maintenance. True story.


During our tour, we were served breakfast and lunch, beverages, and taken for a beautiful sail along the coast of South Maui before heading back to sail along the West Maui Mountains, ending at an area near Olowalu for scenic snorkeling (gear included). We particularly enjoyed snorkeling in an area that was completely empty except for us – yet another thing you won’t find on larger snorkel boat cruises.


The S/V Artemis

The newest member to the team is the S/V Artemis. Sailing off the coast of Maui aboard the S/V Artemis is an unparalleled adventure that encapsulates the essence of Hawaiian maritime beauty. Designed by world-renowned Robertson & Caine, S/V Artemis is a 47′ Leopard sailing catamaran boasting a sleek design and well-crafted sails. She gracefully cuts through the crystalline waters of the Pacific, offering a unique perspective of Maui’s stunning landscapes. As the Artemis glides over the gentle swells, passengers are treated to panoramic views of the island’s lush greenery, golden beaches, and the iconic silhouette of Haleakalā in the distance. The warm trade winds carry the scent of saltwater and tropical blooms, creating an atmosphere of tranquility that envelops sailors on this nautical journey.

Maui Honeymoon Activities Private Sailing

The S/V Artemis is not merely a vessel; it’s a floating haven that beckons enthusiasts and explorers alike. The crew, seasoned sailors with a deep connection to the sea, expertly navigate the waves, ensuring a safe and enjoyable voyage. Onboard, guests can relish in the serenity of the open ocean and feel the mist of the water on the vast trampoline found on the bow of the vessel or relax in a princess chair and take in the views of the Valley Isle. Whether basking in the glow of a vibrant Hawaiian sunset or marveling at the marine life that graces the waters, sailing on the S/V Artemis off Maui is an immersive and unforgettable encounter with the maritime wonders of the Aloha State.


Available Tours

While we decided to partake in the 4-hour private sail and snorkeling tour ($2200 for up to 6 passengers), Captain Anna offers just about every kind of private sailing tour you’d want, including sunset sailing, whale watching during winter months, and even inter-island charters, where you get to cross the open water and see other islands from the water (weather dependent).

sailing tours in Maui

The crew served up delicious cocktails (it is BYOB, make sure to give the boat a call for specialty mixers), and the spread of yummy pupus was just what we needed on a hot Maui day. The service from Captain Anna and Captain Makana went above and beyond, and I really appreciate their laid-back yet professional demeanor.

From everything that I’ve experienced with Maui Custom Charters, this is what it means to be winning on water. I recommend you give it a try for yourself.


To read more about tour options or book a private charter, please visit Maui Custom Charters or call (808) 874-1110. Mahalo for reading!

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