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    Maui Custom Charter

    5.0 (13 reviews)
    Closed 8:00 am - 8:00 pm

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    Enjoying apps on the sunset sail
    Camille D.

    Did the private sunset sail for our honeymoon. Lydia and Taylor were so nice and friendly! The sail was perfect and the appetizers (sushi, lillikoi and other fruits and veggies with a dip) were delicious - not just your average chips. It was also BYOB. Would recommend this to anyone looking to celebrate a special occasion or looking to enjoy a beautiful view!

    Living Large and in style on Shadowfax. We love Captain Mike!
    Jen T.

    Shadowfax, Captain Mike, Tina, Malcom and crew are the best ! This sailboat is the perfect size and with just 6 pax allowed, you will never be overcrowded (like many of the Maui boats I have been on). Tina is an excellent chef and most of her tasty delights are home grown on Maui. I have seen it all on Shadowfax and been out multiple times - Whale tail slapping, pods of dolphins, Lanai, Molokini, Molokai, West Side, the Pali, South Side, snorkeling with turtles. I take all my friends out on Shadowfax since I live here and every single one has said sailing with Mike and Tina is the highlight of their trip. When you live on Maui and find the best of anything you share ! So here I share one of Maui's best activities to do on the water. If you do nothing else on Maui, SAIL ON SHADOWFAX !!! If you live here, take your family and friends out very chance you get ! Aloha ~

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    2 years ago

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    1 year ago

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    11 years ago

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    7 years ago

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    11 years ago

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    7 years ago

    Had a great time. If you're looking for an intimate sailing experience I highly recommend Captain Lydia and Shadowfax.

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    10 years ago

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    11 years ago

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    Review Highlights - Maui Custom Charter

    The sail was perfect and the appetizers (sushi, lillikoi and other fruits and veggies with a dip) were delicious - not just your average chips.

    Mentioned in 5 reviews

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    Sea Maui - Memorable sunsets

    Sea Maui

    (1.2k reviews)

    Sea Maui's cocktail sunset cruise was easily one of the highlights of our trip. Nick, Luke and…read moreJames were absolute rock stars. And when they say open bar... they mean it. Beers, cocktails, spirits, pretty much whatever you wanted and the crew constantly walked around asking if anyone needed another drink. The heavy appetizers were also way better than I expected for "boat food", chicken katsu, Chinese chicken salad, pasta salad and kalua pork sliders, everything was really good. (No pictures cause I mopped it lol) The cruise itself was around 1.5 to 2 hours and our ride was incredibly smooth, although obviously that'll depend on the weather. They also offer a kamaʻāina discount if you call to book, which brought it to around $100 per person for us. Between the views, legit open bar, surprisingly good food and an awesome crew, I thought it was absolutely worth it. Would do this again in a heartbeat.

    We've sailed with Sea Maui 8 or 9 times on their Sunset Dinner, Sunset Cocktail and Whale watching…read morecruises. For us, we prefer the Sunset Cocktail cruise as it's the perfect amount of food and drinks. This last trip, we took the whole family for the express snorkel trip. It's a shorter trip, which worked perfectly for the younger kids and didn't tie up a big amount of island time. Captain Nick and his crew was all about making sure all had a great time while keeping safety at the top of mind. They guaranteed we'd see turtles... we did! Immediately. I accused them of being remote controlled because they were there right on cue! I'm not a big snorkel guy, but I had a blast. We'll keep returning to Sea Maui. Greatest crew on Maui !!

    Trilogy Excursions - Professional pictures taken

    Trilogy Excursions

    (2.4k reviews)

    Captain Michael and crew who led our "Discover Lanai" day were awesome! Super attentive, the food…read morewas abundant, the boat was very clean, and I felt safe out snorkeling even with a pretty big swell shift from the Hurricane. The details: Our tour started by meeting at tree at the Sheraton, which sounds awkward but for us was super convenient and it was fun boarding the sailboat from the beach but you will get a little wet! Captain Michael walks you though the day and then you are off for about ~90 minutes to Lanai. During that time you are served (not a buffet) two meals. The cinnamon rolls were great and the breakfast croissants are now something I make at home. There was also a photographer on board so we took advantage and took some family photos (you buy at the end and I found them a whole lot cheaper and less stress than an actual family shoot). Once you get to the Island you can take a golf cart or take a short walk to the beach where they have all the gear you need. After the safety briefing you have about 2 hours to snorkel with the crew serving as lifeguards in the water. It is VERY easy to lose where you are when you've got your head underwater. I appreciated how attentive the crew was to where the four of us were at since there were a few times we needed some gentle guidance out of a harms way (shoreline rocks). The photographer also captures your snorkel sesh. After snorkeling, you're treated to another full meal of noodles and chicken. Followed by anything you might need for a little seasickness to prep for the journey back . My 12 yo son was pretty full at this point and had befriended the captain who let him help get the boat ready for the return trip. That was very cool! The ride home was a bit bumpy (Hurricane Lowell was coming) but Captain Michael did a great job avoiding anything major and even found a pod of dolphins. We also enjoyed the mai tais! Great experience! We will book more tours in the future. I would have booked another snorkeling or sunset tour during this trip but the water quality really deteriorated with the upcoming storm.

    The crew on our Trilogy sunset dinner cruise--Kayden, Kevin, Michelle, and Captain Kukii--did an…read moreamazing job making the evening unforgettable. The level of service exceeded our expectations from beginning to end. Everyone was friendly, attentive, and made us feel incredibly well taken care of throughout the cruise. The four-course meal was stellar and much better than we expected from food served on a boat. Everything was fresh, beautifully prepared, and delicious. Between the incredible crew, exceptional service, wonderful food, beautiful ocean views, and Maui sunset, this was the perfect way to end our time in Maui. We couldn't have asked for a better final evening on the island.

    Makai Adventures - Baby breeching

    Makai Adventures

    (380 reviews)

    An Absolute Must-Do in Maui! March 6, 2026…read more Our morning trip with Makai Adventures was easily the highlight of our vacation! If you are looking for an intimate, high-quality whale watching experience, look no further. The Boat The vessel is fantastic. It's an inflatable-style boat, but don't let that fool you--it was incredibly stable on the water. It seats about 20 people, so it feels personalized rather than crowded. Most of the seats are shaded, which was a huge plus for staying comfortable in the sun while we scanned the horizon. The Crew A massive shout-out to our captain and naturalist Levi & Travis! They were the perfect duo: Safety-First: We felt totally secure and well-cared for the entire time. Informative & Funny: We learned so much about whale behavior, and their humor kept the energy high and the vibes great. Genuine Kindness: You can tell they truly love what they do. The Whales The wildlife did not disappoint! Since we went out in the morning, the water was beautiful, and we saw so many whales. We spent the entire trip watching them breach and splash around. It was a non-stop show of tail flukes and massive splashes. Thank you, Makai Adventures, for such an awesome and unforgettable adventure. We will definitely be back!

    We booked last minute, but are so glad we decided to do it! The crew (Levi and Allison) were…read morefantastic - very knowledgeable, made it really fun and light with jokes, and were kind in letting us move around to see an up close encounter. We have recommended them to others and will book with them again if we come back during whale watching season.

    Maui Custom Charter - boatcharters - Updated September 2026

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