1. Sail Maui- Maalaea

    1. Sail Maui- Maalaea

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    Maalaea, HI

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    Sail Maui- Maalaea

    4.8 (322 reviews)
    Closed 7:00 am - 7:00 pm

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    Every minute was a gift!
    Jenifer F.

    The day was overcast and a bit cold but the warmth and hospitality of the crew and their attention to our comfort and confidence while exploring Molokini and the Lapehu point areas made this my favorite snorkel boat trip to date. We would all join Brandon, Joe, and Jandein any day for this sailing adventure. We were blessed with personalized care and more whale sightings (can you say 3 breaches in 3 minutes?) than I could have dreamed or imagined. I appreciated their accommodation for my dietary needs (GF) and the time sailing on the way back was a treat. Mahalo plenty, Sail Maui. We will be back!

    Captain Brandon, McKenzie and Joe!

    Great staff! Extremely professional, fun and informative. Captain Brandon, Joe and McKenzie were so friendly and accommodating. Drinks, sandwiches, and fresh fruit. Bathroom on board is a bonus! Highly recommend them for whale watching, sunset cruise or snorkeling.

    Snorkeling Molokini
    Kelly F.

    My wife and I wanted to snorkel at Molokini on our vacation. But we weren't looking to go with any BIG corporate crews. We found Sail Maui and gave them a try. WOW!!! We are so glad we chose SM. It's a local family owned company with midsize cat boats. Captain Brandon and the crew were hospitable, knowledgeable, and attentive. The trip itself was amazing. We detoured on our way to Molokini to catch sight of some whales. And we weren't disappointed, we witnessed whales mating and a baby whale completely breach. Then when we arrive at the crater, Cap. Brandon chose the perfect spot. Fantastic clarity and at least 20 different types of colorful fish. On our way back (after a delicious sandwich lunch) we dropped the sails and made our way to turtle town. All this for a price less than "The Big Guys."

    Whale sighting
    N. R.

    This has been the highlight to our Maui trip so far. -We had a lot of great whale sightings. -We had a beautiful view of the sunset. -The crew was great -- very friendly and accommodating with making sure we had drinks and food (there was an open bar). -The trip started and ended on time. 100% would recommend. Thank you!

    Allison P.

    My husband and I came to Hawaii to celebrate our 10 year anniversary. This sail, snorkel excursion was hands down the best thing we did all trip! From the views, snorkeling, and crew, it was all amazing. Greg, Cass & Dan were so friendly, knowledgeable, and professional. I wish I had booked the full day option so we could see the other side of Molokini Crater and snorkel even longer. If we ever make it back to Maui, this will be the first excursion booked!

    Sunset sail
    Molly G.

    My husband and I did both the sunset cruise and the Molokini snorkel adventure. We thoroughly enjoyed both! The crew on both days was super kind, knowledgeable, and attentive. The drinks on the sunset cruise were well made and the food was great! They served kebabs, caprese skewers, a veggie platter, egg rolls, and maybe some other things that I have forgotten since. As for the snorkel excursion, that was my favorite. We got lucky and had a group of only 10 people when normally it's about 50. Again, an amazing and helpful crew. It was my first time snorkeling and the captain helped me out a lot and gave me tips. More great food for breakfast and lunch! I can't recommend them enough. It'll be a good time no matter what sail you sign up for.

    K L.

    Shout out to Captain Greg for a fabulous sunset cruise! My family and I had an absolute blast that evening (Sunday), we genuinely appreciate your entire crew's enthusiasm and Hawaiian hospitality during our tour! Highly recommend.

    A Happy Crew

    We joined Sail Maui once again on their new catamaran, Akialoa. Captain Brandon, crew Lily and Nianoa. The captain's smile in the attached photo says it all, a fun and great trip. Not sure who had more fun, the captain or his passengers. We were mugged by seven whales in a competition pod that couldn't leave our boat alone. In fact, we had to stay past our return time because the whales wouldn't leave! We have many great whale watches in our experiences, this tops them all. Great crew, sail, and company.

    Sunset view from our sunset sail
    Jess P.

    We had the best time with Dakota and crew they were so professional and kind it felt like family and home away from home!

    Roomy boat with plenty of space for a large party :)
    Mimi T.

    Can't beat a sunset sail with open bar and snacks! We traveled at end of February so it was whale watching season. We saw a pod of dolphins and a whale on our sunset sail and a double rainbow Such amazing service the sailing team was super friendly always asking if we wanted another drink. With Covid they packed the sliders and cookie into a little container so it was super easy to grab and they even had banana bread! Even though the sunset was a little overcast it was a great experience. Highly recommend not too expensive considering all that you get 85.00 per person. The Alalani is their newer boat and I think with 50% capacity they were taking 40 passengers. Free parking in a public lot in front street in Laihana. So this is a great pick if you are staying at the west end but even from the east side it's not too far of a drive I think 30-40 min. Please wear a mask on front street we did see some people get fined

    Molokini

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    Wonderful, fun, and attentive crew. Beautiful views. Fantastic experience. Will sail with them again.

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    Page 1 of 9

    Sail Maui- Maalaea Reviews in Other Languages

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    Review Highlights - Sail Maui- Maalaea

    Had a amazing time with our guides Ben and Greg, so cool and their passion for their jobs is contagious.

    Mentioned in 40 reviews

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    We have nothing but amazing things to say about our Discover Lanaii tour with the Trilogy team…read moretoday. Zach, Justin and the Captain were amazing at taking care of our group and making us feel safe, appreciated and welcome on our tour. From giving our young boys an amazing experience with attention and care, to ensuring our older boys and parents were well taken care of. There were so many laughs, smiles, and a great time had by all! I would highly recommend Trilogy, this was our third time touring with them, and we will definitely be back again! Thank you for creating so many amazing memories and experiences for our family!

    What an adventure! We couldn't be happier with our experience on Trilogy IV. Captain Zech, Kanani &…read moreKenzie were just fun to talk with and took phenomenal care of us. I would 100% recommend taking this trip while you are in Maui. It is an experience you will never forget. We started to trip with cinnamon rolls and they provided really great gluten free muffin for me. Then made sure to always provide GF food options for me throughout the day. Snorkeling was fun and accessible because they had prescription masks available, which is a must if you cannot/do not wear contacts and want actually see the ocean life. We had a plenty of time to float and observe the fish. Lunch was delish and they prepared some tasty gluten free noodles JUST for me. On the way back, one of our daughters helped hoist the sail and we were able to catch the wind of a bit. We also had the good fortune of observing a pod of Hawaiian spinner dolphins on the way to and back from Lana'i. Book this trip! It is SO worth it!!!

    Rent A Maui Boy

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    I was worried that I had to high of expectations for Henry but he lived up to the hype! Henry…read moreescorted through the Full Day of Road to Hana and helped create memories that will live forever. This trip was specifically for my son who is wheelchair bound and he made sure that everything we did revolved around my son having the time of this life. We learned lots about the area, laughed till we cried and felt like we met our new best friend on Maui. I really wanted to be present with my group so the fact that Henry captured photos and took videos of the day was the main reason I chose him. We received both within a couple days and have shared the video and photos to everyone in our lives. To say this was a magical, amazing experience doesn't sum it up enough but if you are reading this, don't hesitate, BOOK WITH HIM NOW!

    One of my coolest days on Maui was the famous ALL DAY "Road To Hana" drive. I booked a small group…read moretour led by Henry @rentamauiboy, and the reason I booked him was because he takes allllllll the photos. Traveling solo, it feels weird to take selfies everywhere or worse, asking someone to take your photo. The tour was me and 2 other couples: one couple were newlyweds and the other couple were on their very 1st trip together (as a couple). (Honestly where do you go after a trip to a Hawaii?!?) We could not have had a group that meshed BETTER than all of us. Our guide Henry clearly knew "the good spots" because we didn't stop anywhere that anyone else was... he made us climb down treacherous "root ladders" and walk through the coldest water up to our necks but his ideas were always SO worth it. And he captured the best pics! I highly recommend this EXACT excursion because you don't have to worry about any photos. He has it covered, and trust me, it's truly UNFORGETTABLE!!!

    Hike Maui

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    Just Do It! First rate service and tour of Road to Hana! We…read morewere picked up promptly at our resort and our Driver/ Tour guide Tom was personable, fun and extremely knowledgeable about the islands history and the people of Maui. Food and drink were provided which was better than expected and plenty of it, along with plenty of bathroom breaks. The van was comfortable and limited to 8 guests and we had a good group. We were so glad we didn't drive it ourselves because Tom showed us sooooooo many things we would have driven right by. If you're not sure about taking the tour or driving yourself...do yourself a favor and take the tour and enjoy the Road to Hana!!!

    In response to the owners lies - (Original reviews in…read morephotos. Yelp said I reached my character limit capacity. Added more photos for our proof). There was no one else on the tour except one couple, whom we had no issues with. The 7 people on the bus was my family of 5 and one couple. 1. There was a hiccup in your booking system, you allowed us to book a tour because you did not close your online reservation window. If you were sold out why did the website allow us to make a reservation? Hence the "hiccup". After we booked the tour, we did move a flight around so this person could make the tour that we had a confirmation email for. Very unprofessional to email the next morning saying you were sold out AFTER we made the booking. Yes we did book late but if you were sold out you shouldn't have allowed us to make the booking plain and simple. We called multiple times because we were asking about pick up arrangements and were told to keep calling back to see when/if the tour filled up, because only then would they be able to tell us what pick up rotation we would be in. I wanted to know what hotel would be the first pick up, etc. I didn't care that our two parties were not on the same bus, which was why I didn't mention it in the booking. 2. Since you claim to have the proof that he wasnt speeding, why dont you show it? It absolutely does corroborate with the Google maps picture. I did move the camera to get a video of how bumpy the bus was DUE TO HOW FAST THE DRIVER WAS SPEEDING! But I'll include another video straight ahead where you can see how fast he flies past the mountain. As for your lies, you need to come up with better ones. I asked for a Spanish translator due to the fact only ONE person in our party spoke Spanish. The fact that you guys said we were speaking Spanish all day is hilarious because NO ONE IN OUR PARTY SPEAKS SPANISH except my mother in law, who didn't speak the whole trip. Let's add more proof that you guys are racist - when the driver picked us up II asked about the Spanish ear piece translator before my mother in law was there. The driver said no, he said I speak a little Spanish so I will do my best to speak to help you guys out. 5 minutes later he came up to my husband and started speaking Spanish. My husband told the driver he speaks ENGLISH. Louie said oh you were quiet miguel so i figured you were the spanish speaker. we were asking about translation for my mother in law. I'll also add he made multiple claims about how Latinas were "so violent" and people had to watch out for us. let's add to the review that not only are you guys liars, you are racist liars. Your tour driver is a liar, we were all sleeping on the drive back due to how sick/tired we were. Your tour driver is clearly lying to cover his mistakes. 3. We didn't ask the tour driver for ONE illegal thing AT ALL. Due to the fact he was an arrested convict (which you can find proof of by googling it) he made illegal stops on his own! He even mentioned how the rangers loved him and when HE chose to make the illegal stop in front of the waterfalls, the ranger allowed it bc they told him make it quick. We appreciate the opportunity but never asked him for one illegal stop. 4. I never said we missed anything, I said I couldn't help but wonder if we missed something. Since you want to be so detailed, we actually DID miss Ohe'o Gulch / Seven Sacred Pools (D) Charles Lindbergh's Grave / Palapala Hoomau Church Kipahulu scenic ocean views, St. Joseph Church Kaupo Ranchlands / Haleakala backside views / Maui's Last Lava Flows (D) Maui's Upcountry / Kula (S) 6. The entire tour WAS my family. Let me also add one thing I forgot to the review someone in your company gave our tour guide my number and he texted me twice asking me for his tip which was EXTREMELY unprofessional. This is an extreme safety violation. He unprofessionally texted me "This ***** Just making sure I did venmo right.. If sent tip, I have not recieved..." at 7:27pm. And "If you could let me know.." at 7:56pm. For my safety, I should NEVER have received text asking about a TIP! Even if he was wondering about the tip because he wasn't used to electronics, you still should never text someones personal cell phone number. Since he did mention multiple times that he was a liability I was scared he was going to show up to our hotel since he knew my number, hotel location, etc. Where is the response to the bulk of my review??? Do you have an explanation for how we know all this information about him being fired from his last tour job? How the current owner was only allowing him to drive as a fill in driver as a favor? Why was he a liability? Bc he speeds and risks the lives of passengers? In one of my videos I do have him talking about the story of how his dad gave him money and guns to illegally transport. As I have over 500 videos from this tour, you guys are lucky I don't want to go through and find the hard proof I have. Where is your hard proof?

    Maui Stargazing

    Maui Stargazing

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    We had an amazing experience stargazing with Janet on Haleakalā! This was absolutely worth the…read moremoney and one of the highlights of our Maui trip. From start to finish, everything was well organized and comfortable. We traveled in a tall Mercedes Sprinter van, which made the drive much more enjoyable with less motion sickness than expected. The seats were comfortable and there was plenty of room to store personal items. Janet provided warm jackets and pants, which were greatly appreciated since temperatures at the summit can drop into the 60s and feel much cooler with the wind. She really thought of everything. We toured the summit area of Haleakalā, enjoyed snacks and dinner while watching a spectacular sunset, and then transitioned into an incredible night of stargazing. The telescope views were stunning--far more detailed than I expected. We were able to see so much, and the images through the telescope were truly unforgettable. Janet is exceptionally knowledgeable and did a fantastic job explaining astronomy, the night sky, and Hawaiian history and culture. She used a laser pointer to guide us through the constellations, making it easy to follow along and understand what we were seeing. No question seemed too small, and her enthusiasm was contagious. Most importantly, the entire experience was fun, respectful, relaxed, and full of good vibes. Janet clearly loves what she does, and it shows. If you're considering a Haleakalā stargazing tour, I highly recommend booking with Janet. It was an incredible experience that we'll remember for years to come. She provides you with a PowerPoint presentation at the end and pictures highlighting the stars! Above and beyond! You can't see the objects you will see without her high powered telescope! It was spectacular !!

    I want to start with the disclaimer that everyone is on their own journey in life, and because of…read morethat, experiences are personal and may be seen differently by others. I also want to apologize for revising this review twice; my first attempt was rushed and full of misspellings, and the second was a quick fix of those errors. However, after being home and having the time to relax and reflect, I realized there were details gnawing at my soul that I needed to share. While I could have justified the $250 price tag if the experience had met my expectations of what was included, I simply cannot justify it for the experience we actually had. I am left with a soured, bitter aftertaste in my heart for an experience that I wanted with my family. It is hard for me to give a five-star rating just because someone "tried"; I believe a top-tier rating must be earned through the experience one had, and Jan lacked in presentation, friendliness, and overall value. For our party of four, we paid $1,000, and in hindsight, we could have had a significantly better experience by using our own rental car and buying a high-quality telescope for half the cost. Don't get me wrong, the views were amazing, but Jan expected the National Park (which she did not create) to carry the entire value of the tour. There was no historical context shared about the land; she simply relied on the scenery to do the work. The lack of consideration for her guests was most apparent in how she rushed us. Both of my parents have medical limitations--my mother is a brain surgery survivor and my stepfather was recently diagnosed with Parkinson's. Both were medically cleared by their doctors for this visit, so while their conditions were not life-threatening, they naturally move at a slower pace, or what some would refer to as "Hawaii time." At the stop at the top of the mountain, Jan initially told us we would have an hour to look around, then suddenly changed it to 15 minutes. This was incredibly insensitive; 15 minutes is a rush for someone physically fit, let alone for people managing mobility issues. The actual stargazing was equally frustrating and felt hypocritical. Jan would complain if someone accidentally turned on a phone screen, claiming it affected her dilated pupils, yet she had no problem using a high-powered laser pointer against rocks instead of the sky, refracting the light directly into our eyes. Furthermore, none of us got long at the telescope because she insisted on refocusing it after every two people, all while a personal friend of hers joined for free and took up our paid telescope time. To put the lack of value in perspective, we recently paid $165 for a snorkeling tour on a catamaran that included a crew of five, two full meals, and equipment. Here, we had to bring our own snacks and water, and Jan even requested to use our personal National Park passes to get the group through the gate. Between the conspiracy theories playing loudly on the radio, her robotic and demanding attitude, and the underwhelming equipment, we felt massively overcharged. You can find better value elsewhere or by driving yourself at your own pace.

    Sail Maui- Maalaea - boatcharters - Updated July 2026

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