Shadowfax Sailing Review
4.9Overall Score
Reader Rating: (7 Votes)

Private Sailboat Charters in Paradise

I have always, always wanted to learn how to sail a boat. Personally, having never been seasick and generally opting for activities on the ocean rather than in it, sailing seems like the perfect equalizer between me and the big blue Pacific.

And you know what? It totally is.

But since I am far from captain’ing anything but a car ride to the nearest beach, I decided to leave the hard work up to Captain Mike, owner and all-around boss man for Shadowfax, a private 44′ sailing yacht on Maui.

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The Boat

While I can’t say I’ve ever met a boat I didn’t like, the Shadowfax certainly went above and beyond my expectations. Once on board, I was pleased to find a cozy galley (that’s the kitchen, for you non boat-word using folks – don’t worry, I had to Google it), storage area, sitting area and table highlighted by beautiful teak wood.

The sailboat is obviously well-maintained with just the right amount of wear to let you know it’s logged some ocean hours.

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My favorite part of the Shadowfax is definitely ‘the princess seat,’ a raised two-seater area at the stern, perfect for feeling fancy and wonderful and having slightly more fun than everyone else. But honestly, any seat is a good seat.

For guests who choose to charter an overnight sailing excursion, there’s even a private berth (that’s boat-word for bed) for such occasions. While we didn’t have time for an overnight trip this time, I would absolutely love to experience a full evening on a sailboat in Hawaii. If that doesn’t sound amazing, I don’t know what does.

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Shadowfax comes equipped with everything you need for a day on the water – a surprisingly clean bathroom, cooler stocked full of beverages (of the adult and non-adult variety), kitchen prep area, ample seating, snorkel gear, and views you just can’t appreciate from larger boats.


The Tour

We arrived at the conveniently-located Maalaea Harbor around 9:15am for our 9:30am private snorkel sail, thankfully a much less painful start-time than most other boat tours, most of which require a 7am or earlier check-in time.

Captain Mike and Malcolm quickly welcomed us aboard, kindly grabbing our shoes, bags and gear before ushering us down below to relax, grab a seat and sign our waivers. We were given a quick overview of the various areas of the sailboat, as well as instructions about how to properly use the bathroom.

After chatting with Captain Mike and Malcolm and munching on fresh yogurt, fruit and granola, it was departure time! The wind was howling the day of our tour, which made for a much more exciting ride, I must say. We began by sailing along the coast a little further south towards Sugar Beach and Kihei Town, before turning back and heading towards our snorkel spot for the day, a secluded area along the Pali Highway and West Maui Mountains where we could spread out to snorkel with no one else around. Amazing!

shadowfax sailboat charters The Shadowfax, as sailboats tend to do, go with the wind, which means heavy leaning every now and then. At 40 degrees, you’ll feel like you may fall over at any second, but Captain Mike was quick to remind us that the boat had previously hit 95 degrees and yet still remained right-side up. And honestly, the leaning was really, really, ridiculously fun. Howl on, wind!

Malcolm guided us to some cool snorkeling areas while Captain Mike prepared some pupus aboard the boat, including delicious pretzel sandwiches, a veggie platter, chips, dip, orange slices and more. I relaxed with a frosty cold beer (or two) in the sunshine, and soaked in the views as much as possible.

After going on tours with more than 5 boat companies since moving to Maui, this was by far the most relaxing and personalized experience I’ve had. It was wonderful to enjoy a day with only friends and family members, and the laid-back approach was the perfect way to spend an Aloha Friday in paradise. 


The Service

Captain Mike and Malcolm were absolute perfection on the water.

It’s clear that Mike values safety and knows his stuff when it comes to sailing – with over 30 years of experience and the fact that he sailed the Shadowfax to Hawaii from California, it’s really no surprise. We were offered every single convenience you can think of during the tour, from sunblock to snorkel gear to fresh ginger for seasickness, not to mention the opportunity to talk story with two very interesting, charismatic and friendly gentlemen.

I would highly recommend this tour for the service alone, not to mention all the other perks.


Shadowfax Tour Options

maui sailing chartersA variety of tour options are available – we can’t wait to try whale watching or an overnight tour next time!

4 Hour Snorkel Sail

9am to 1pm – $159 per person (4 to 6 passengers)

2.5 Hour Sunset Sail

5pm to 7:30pm – $99 per person (4 to 6 passengers)

Private Charter

2 hour Sailing Charter – $650 (1 to 6 passengers), +$325/hour for additional time

4 Hour Snorkel Sail

$1,300 (1 to 6 passengers), +$325/hour for additional time

Interisland/Live Aboard Charters

$1,400 per day (1 to 4 passengers) – 2 day, 1 night minimum

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For more information or to book a tour, please visit Shadowfax or call (808) 572-2345. Big mahalo to Captain Mike and Malcolm for a wonderful experience and sailboat adventure!


2 Responses

  1. Avatar

    I wanted to check if it was possible to make a trip aboard for
    snorkeling, approximately 2 days. we are a couple and 1 year old.
    we do not have problem to distribute the boat with other tourists.
    the travel date would be September of this year


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