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Shadowfax – One of Maui’s True Sailing Excursions

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If you’re looking for a true sailing experience on Maui, reserving a trip with Sail Maui Nui’s Shadowfax is an experience you won’t want to miss out on.

For a full review of the trip, scroll down.

In the meantime, here are a few things you may want to keep in mind for the trip:

Contact Info

300 Ohukai Rd. B227
Kihei, HI 96753

[email protected]

Phone: 808 874 1110

You can text Cpt. Mike on the boat anytime at (808) 870-1741.

E-mail at [email protected].


Shadowfax is one of the best sailing experiences Maui has to offer

Restaurant Name: Shadowfax

Restaurant Description: True sailing out of Maui's Maalaea Harbor


  • Service
  • Sailing
  • Comfort
  • Cleanliness
  • Safety
  • Food
  • Amenities
  • Cost


Going on the water is generally a great way to spend the day. Especially if you're not from an area that has great access to the ocean. So when you go out on the water, you want the real thing; a true experience. As far as sailing experiences go, you would be hardpressed to be find a better sailing company. If you're looking for the best sailing, and I mean the true sailing experience, Sail Maui's performance sailing catamarans, Paragon and Paragon II, and Sail Maui Nui's Shadowfax are going to be your best bet.

There is one really good way to tell if you're going to get true sailing. Engine size. If the boat has a small engine, the captain and crew typically don't try to depend on it too much. If you want to find the boats that really sail, look for the sailboats with the smallest engines.

This section includes all contact with captain, crew, owner and employees. And it is all top par.

Maalaea has a handful of boats that advertise themselves as sailing boats, however not all of them sail as much as they can. This is understandable, as Maalaea is one of the windiest harbors in the world, but when you book a sailing boat to go sailing, you want to sail. If this is you, Shadowfax is one of the best boats you can go out with (Sail Maui's Paragon and Paragon II take our Top Spot.) This monohull goes out with one captain and one crew and, depending on the wind, will give you one of the best sailing experiences on the island. It's not uncommon to get the boat heeling over to 30 degrees and it's definitely an exciting ride. If you're looking to sail, you can't go wrong with Shadowfax.

Shadowfax takes out a maximum of six passengers, which is nothing compared to some of the boats we saw leaving the harbor. There are some boats out of Maalaea that are Coast Guard certified to carry 149 passengers and while that may be impressive in the sheer size of those boats, they certainly don't scream comfort.

The six-passenger maximum for Shadowfax makes for a wonderfully comfortable trip out on the water. You don't have to worry about being treated like cattle or packed into a seat where you can barely move. Another great thing about the low passenger count is that you can really get to know the captain and crew and it feels like you are on your friend's boat. It also allows for really great customer service.

Taking care of a boat definitely isn't easy. B.O.A.T. just stands for Busting Out Another Thousand. It can be expensive and it definitely is time consuming. And from the looks of it, they must have a round-the-clock crew maintaining Shadowfax. The teak wood trimmings were all perfectly maintained and seemed freshly stained, the lifelines around the perimeter all seemed in good condition and

Safety's always a big thing when doing any sort of adventurous activity. You hear the horror stories about people's trips in Mexico and you don't particularly want to end up an anecdote. You want to have fun, but you also want to live to tell the tale.

When we boarded Shadowfax and everyone got situated, Captain Orien gave us the safety briefing. He assured us that while sailing can be dangerous, they only take it to the comfort level of the passengers and that it is always, he assured us, safe.

I have to admit that upon hearing this, my hopes were slightly crushed because I was looking for an exciting trip, but I understand that as a business, they have to make the trip comfortable for everyone aboard. But I wasn't disappointed.

It certainly seemed like a windy day. The captain and crew set Shadowfax up for a triple reef, which pretty much means they tapered the sail down to about half it's potential size at full sail so that they could maintain their control in the windy conditions.

Crew Malcolm offered us food which was stored in the cabin, we weren't hungry and we didn't anticipate getting hungry on a sailing day like this day.

Shadowfax was not particularly outfitted with luxurious amenities; however, it was completely set up for sailing, as a sailboat of this kind is expected to be. Going out on this kind of trip, Shadowfax had everything you could expect a sailboat like this to have. If you're looking for a luxurious cruise, you would be better suited looking into Ali'i Nui out of Maalaea Harbor or Hula Girl (or her sister ship which is only taken out for privately booked charters, Shangri-la) off of Kaanapali beach.

Crew Malcolm did offer us scented hand towels post-trip to freshen up, which was a nice touch.

For a single person, the cost for the trip runs $129 unless you find a deal somewhere. This trip is worth every penny. The charters usually go out for about two hours (unless you book out a private charter on Shadowfax) so it comes down to around $60 an hour for one person. Now, after saying that, you're not going to find many things on Maui that are 1) much less expensive and 2) an experience that rival your trip on Shadowfax. The ticket buys you one of six potentials seats on Shadowfax and regardless of how many people reserve a seat on Shadowfax, you are pretty much getting a privately chartered sailboat.

You can book different trips which will change the standard price (private charters start at $375 per hour with a two hour minimum.) If you're interested, contact the owner and sometimes Captain Mike. His contact info can be found here.

Totally worth it.

Sailing on Shadowfax is without a doubt a favorite water excursion of ours and something we would definitely recommend. Customer service, comfort, and last but not least sailing all leave nothing to be desired and, while the cost of the trip is a little more expensive than some of the ticket prices other boat companies may offer, the trade off is a higher quality trip and a much better experience. You probably don't want to be packed on a big boat like a sardine with 148 other people. This trip is exciting, fun, safe and just about as true to sailing as sailing can get.

Shadowfax ranks among our top water excursions that we'd recommend to experience while on Maui!



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