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    Sail Winona

    5.0 (4 reviews)
    Open • 6:00 am - 9:00 pm

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    Trilogy Excursions - Professional pictures taken

    Trilogy Excursions

    4.9(2.4k reviews)
    12.4 mi

    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.

    Photos
    Trilogy Excursions - Captain Michael

    Captain Michael

    Trilogy Excursions - Justin BEING A FREAKING BOSS

    Justin BEING A FREAKING BOSS

    Trilogy Excursions - MY EPIC WIFE VIBING DURING SUNRISE!!!

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    MY EPIC WIFE VIBING DURING SUNRISE!!!

    Sea Maui - Memorable sunsets

    Sea Maui

    4.9(1.2k reviews)
    14.9 mi

    Sunset dinner cruise highly recommend. Value for cost very reasonable and the staff are awesome!read more

    I'd add that right into the social part--it makes it clear the crowd was fun without making it…read moresound like a booze-cruise-only vibe. We had the BEST time on the Sea Maui Sunset Cocktail Cruise! From the very beginning, the experience was wonderful. We called to book and spoke with Sunshine, who was exactly that -- an absolute ray of sunshine! She was so sweet, incredibly helpful, communicated everything clearly, and genuinely made us even more excited for the experience. When it was time to board, it was immediately clear that the crew knew exactly what they were doing. We visited during "hurricane" season, so the swells were definitely LARGE -- but that didn't stop us from having the time of our lives! Great music, amazing staff, fun fellow cruisers, drinks flowing, delicious food, and the most incredible Maui sunset. The vibes were absolutely immaculate from start to finish. Somewhere along the way, I also became the unofficial, official iPhone-ographer of the boat and ended up taking photos for sooo many people! One of my favorite things about the cruise was the crowd -- it was truly all ages, and ALL ages were awesome and an absolute pleasure to party with. We met so many genuinely nice people, including a group we clicked with so well that we decided to keep the night going afterward and ended up hanging out and doing karaoke together! That probably says everything you need to know about the fun, friendly, social atmosphere Sea Maui creates. We had such a great experience that I'm already excited to hopefully book a private charter with Sea Maui for our wedding welcome party next year! 10/10 experience. Highly recommend. Thank you, Sunshine and the entire Sea Maui crew for such a memorable evening! And enjoy the pics! Sea Maui, hit me up and I'll send you the rest -- I have HUNDREDS. :

    Photos
    Sea Maui - Mai tai time

    Mai tai time

    Sea Maui - Sunset cruise

    Sunset cruise

    Sea Maui - Whale tail

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    Whale tail

    Sail Maui- Maalaea - Maui Sunset Sail

    Sail Maui- Maalaea

    4.8(326 reviews)
    0.1 mi

    My friend and I booked a snorkeling excursion here and a fantastic group of professionals made us…read morefeel safe, special and secure before during and after the snorkeling. Breakfast croissants and cinnamon rolls with fruit were served in the morning and lunch was served after we snorkeled. Visibility was good on the morning we went although I felt the ocean was a little crowded with people not only from our group but also from other tour boats. Overall, the trip was pleasurable, as the crew was top notch, knowledgeable, and always looked out for us. Special shoutout and thanks to Joe and Ollie! They had a bar as well, so I sipped cold white wine on our way back to shore, staring at the vast ocean waves!

    Brandon, Braxton, Matt, Megan and Nate: this was our family's BEST Excursion!! Even if we could…read moreleave 100 Stars, it wouldn't be enough!! The crew were experts in getting us all organized, on board safely and out to our Snorkeling Area!! They were super professional, fun, friendly and knowledgeable! Breakfast, Lunch, Beverages and Ginger Chews were all included and we even got to see dolphins on our way back to Mā'alaea Bay. Now, we're planning to visit Maui every year at this time and a huge reason is that we can't wait to get back out snorkeling with these awesome folks on Sail Maui Mā'alaea Bay. A+++++++++ Thank you again, Brandon, Braxton, Matt, Megan and Nate!!Mahalo!

    Photos
    Sail Maui- Maalaea - Look at this great photo Brandon took of my daughter and me !

    Look at this great photo Brandon took of my daughter and me !

    Sail Maui- Maalaea - Brandon explains things to my son

    Brandon explains things to my son

    Sail Maui- Maalaea - Paragon

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    Paragon

    Pride of Maui - The Pride of Maui returning from Molokini

    Pride of Maui

    4.3(850 reviews)
    0.1 mi
    43 years in business
    Locally owned & operated

    My husband and I had a wonderful time! This was (I think)…read moreour third sunset cruise with Pride of Maui, and it was fantastic. Incredible crew, lovely boat, delicious food, and fabulous entertainment. Our cruise was last Thursday (9/3/26), and as the hurricane was beginning to make things very windy around the islands, we couldn't go too far out to sea, so our crew made sure we still had a great spot to view the sunset, all while sticking close to the coast to keep us safe. Would definitley recommend to anyone!

    While on our Babymoon, I booked a reservation for my husband and I to go snorkeling on the Pride of…read moreMaui. I chose this particular tour because it was a smaller group size and I did not want to feel crowded or overwhelmed on a boat with strangers. It was the perfect amount of people, and my husband and I ended up chatting with most of the other passengers, having lots in common. Our captain was Caiden, who was extremely kind, informative, and entertaining. We also had crewmates Sienna, Diego, and Jim looking out for us and making sure that we were comfortable and had all of our wants and needs met. I felt completely safe and comfortable the entire trip and I appreciated having a certified lifeguard on boat with us. The snorkeling experience was phenomenal and being pregnant, it made me feel so calm and relaxed. I appreciated learning the history of the two various locations we snorkeled at and the opportunity to see a sea turtle. The ship itself was pristine, and the restrooms were some of the cleanest I have ever experienced on a boat. The breakfast and lunch that they served us was tasty, and the macadamia nut cookies at the end were the perfect sweet treat. I appreciated that they were able to offer me mocktails since I cannot drink at this time, and those were tasty as well. This experience was worth every penny and I would definitely come back and do it again.

    Photos
    Pride of Maui - Starboard side of the Pride of Maui

    Starboard side of the Pride of Maui

    Pride of Maui - Guests jumping into the water to snorkel

    Guests jumping into the water to snorkel

    Pride of Maui - Guest enjoys Maui SNUBA diving, one of the most incredible ocean activities

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    Guest enjoys Maui SNUBA diving, one of the most incredible ocean activities

    Hawaii Nautical - Maalaea - Whale breaching, these visitors are seen March-December.

    Hawaii Nautical - Maalaea

    4.5(8 reviews)
    0.0 mi

    I booked a snorkeling tour for one person in March 2026. Both my booking confirmation through…read moreGetYourGuide and the confirmation from Hawaii Nautical clearly reflected that the reservation was for one guest. The evening before my tour, I called to confirm everything. During that call, the representative noticed what appeared to be a duplicate reservation and assured me she would cancel the duplicate booking. She also recommended that I contact GetYourGuide to verify I would not be double charged. GetYourGuide confirmed that my reservation had always been for only one person and that I had only been charged once. Despite this, approximately two hours before my scheduled departure, I received a call informing me that my tour was being canceled because there were not enough passengers. I even offered to purchase a second seat so the tour could proceed, but that offer was declined. What is most frustrating is not simply that the tour was canceled, but that this issue could have been communicated much earlier. If the company knew they were unlikely to meet their minimum passenger requirement, there was no reason to wait until two hours before departure. By that point, I had already arranged transportation, incurred cancellation fees on my ride, and lost the opportunity to book another snorkeling excursion during my vacation. Yes, I was refunded, but a refund is the bare minimum when a company cancels a service for reasons entirely within its control. The last-minute cancellation created unnecessary inconvenience and wasted valuable vacation time. If you're booking with Hawaii Nautical, especially as a solo traveler, be aware that your reservation may be canceled at the last minute if they don't have enough passengers. I would have appreciated more transparency and significantly more notice.

    Spencer and Sam made our engagement absolutely unforgettable. What I didn't realize at the time was…read morethat they had been secretly coordinating with my now fiancé to create such a magical, perfectly planned experience. Every detail felt so thoughtful and special. They not only guided us to the most beautiful spots, but also took amazing photos and made sure we fully enjoyed every moment. Their energy, professionalism, and genuine excitement for us made the whole experience even better. If you're in Maui, I cannot recommend booking with them enough. And if you can request a captain; definitely ask for Spencer and Sam. They're the best.

    Photos
    Hawaii Nautical - Maalaea - Off we go ! Good tunes and a sunny day

    Off we go ! Good tunes and a sunny day

    Hawaii Nautical - Maalaea - Snorkeling near turtles

    Snorkeling near turtles

    Hawaii Nautical - Maalaea

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    Maui Magic Snorkel - BRAND -NEW Maui Magic

    Maui Magic Snorkel

    4.8(270 reviews)
    0.1 mi

    1. I had previously went snorkeling on the big island company and had a very poor experience. I was…read moreterrified of open water but the staff on Maui magic were very flotation device friendly. They were more concerned about my overall experience, not shaming me for my fear but rather making sure I enjoyed myself by being as accommodating as possible. And it wasn't just one person, it was all of them. Making this an extremely special and cathartic experience. 2. The food. Ok, I mean the eggs, muffins and croissants were awesome but can we talk about the tacos!!! Bro! The pork tacos were incredible. The mahi mahi tacos were also very good. The pineapple salsa was a must have! And this was all before I had 2 mai Tais... so this isn't my taste buds under the influence. 3. The charter itself was wonderful. The boat was comfortable, there was plenty of space. We went to 2 different spots and were given plenty of time to explore. The music was on point, a little Fleetwood Mac, Green Day, etc. it was eclectic alt chill. Legit they could make their own Spotify playlist, 4. It's not the cheapest, or the most expensive. But I don't know how it gets better than this and I think it was 100% worth the money. So a huge thank you to the crew of Maui magic. Maybe saying it was a magical experience seems kind of cheesy but go head and call me a big ole cheese ball, because I'm here for it!

    Amazing snorkel trip with the family. The captain and crew were great. Really accommodating and…read moremade sure everyone had a safe, good time. Started off with a light breakfast and saw some dolphins on the way for our first stop in Molokini. Lunch was far better than expected which I had the grilled fish tacos and was probably better than I've had at one of the restaurants we've eaten at in Wailea. The slide was fun and grandson had a blast. Saw some turtles on the way back as the captain stopped so we could all check out. Only thing I thought probably shouldn't do is charge $10 for a wet suit top. It's not the amount but if they fell they need to charge, raise adult price up $5 bucks to cover since seems would be better to include as part of the total cost. I would highly recommend since we have done snorkel trips on other boats and this is was by far the best.

    Photos
    Maui Magic Snorkel
    Maui Magic Snorkel
    Maui Magic Snorkel

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    Sail Winona - boattours - Updated October 2026

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