Winning on Water

maui sailboat charters

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.

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Shadowfax, for example, a 44′ foot private charter sailing yacht, is most assuredly one of those ways. No offense, apartment pool. But… you know.


Winning on Water


best maui boat toursIf 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 9am and were warmly welcomed aboard the Shadowfax by Captain Mike, who’s been sailing for the last 30 years in scenic areas like Miami, the Bahamas, California, and now Maui. Not only is he lifeguard-certified, PADI Scuba Certified, and CPR certified, but he’s also a really radical guy, and clearly knows sailing like the back of his hand. And the front of his hand, too. Basically, you can trust in Captain Mike.

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Malcolm, the first mate, was extremely helpful in getting us aboard the boat, showing us the ropes (literally and figuratively), and even prepared us a delicious breakfast bowl of papaya, granola and yogurt. Yum!

What’s even more fascinating is the fact that Malcolm taught himself how to swim at Big Beach at the age of 37, and is now clearly a seasoned sailor. If you know anything about Big Beach, that’s an impressive (and perhaps slightly insane) feat.


The Shadowfax


One of the best things about the Shadowfax 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 Shadowfax.

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The sailboat itself has it all – bathroom, kitchen area, cooler, plenty of seating, snorkel gear, you name it. If you can’t find something you need or want aboard the Shadowfax, you may, in fact, be extremely high maintenance. True story.

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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.


Available Tours


While we decided to partake in the 4 hour private sail and snorkeling tour ($159 per person for 4 to 6 passengers), Captain Mike offers just about every kind of private sailing tour you’d want, including sunset sailing, whale watching during winter months, and even interisland and live-aboard charters, where no more than 4 guests can spend the night on the Shadowfax!

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Cocktails were included with our tour, and the spread of yummy pupus was just what we needed on a hot Maui day. The service from Captain Mike and Malcolm went above and beyond, and I really appreciate their laid-back yet professional demeanor.

From everything that I’ve experienced aboard the Shadowfax, 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 Shadowfax or call (808) 874-1110. Mahalo for reading!

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