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Maalaea, HI

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Sail Maui- Maalaea

4.8 (326 reviews)
Closed • 7:00 am - 7:00 pm

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Sunset
Victoria A.

Great Sunset Cruise! Fun, safe, great service, good food and drinks, perfect evening! Honestly, don't know how it would be better! I am going to take my daughter next time and go again!

Sunset tonight !  Stunning

What a fantastic time my daughter and I had together taking the sunset sail on Monday ! Capt Brandon was fantastic ( and yes he looks like chris Pratt's doppelgänger). He gave great Hana recommendations and the entire crew was so much fun. Shout out to Matt with some killer picture taking skills , Tay with the drink recommendations and Jeremiah who docked us perfectly. I can't recommend them enough. The food was really good and drinks and food were included in the price. Go take this sunset cruise ! What are you waiting for ? 10 /10!!!

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!

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."

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.

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

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2 years ago

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

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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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Sea Maui - Memorable sunsets

Sea Maui

(1.2k reviews)

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. :

Four Winds Molokini Maui Snorkel Tour - Molokini Crater

Four Winds Molokini Maui Snorkel Tour

(804 reviews)

We had such a great time with Four Winds snorkeling at Molokini. The crew was top notch and made…read moreour trip awesome. We would definitely book with them again. This was a highlight or our trip. The glass bottom viewing area was a really cool experience as well.

Had an awesome experience on Four Winds snorkeling Molokini Crater. The staff was super down to…read moreearth and friendly. When you get on board they have a light breakfast with fruit, croissants and muffins that you can snack on, as well as fruit juice. The ride out, they explain some safety stuff and how the day is going to run. There are 2 floors to the boat with the upstairs being much more open. There were only about 30 people the day we went but I believe they have up to 100, so a more crowded day may have a different experience. Despite being in November, we ended up seeing several whales coming to the surface (apparently they are in abundance come January). They provide snorkel gear and fins, but you are more than welcome to bring your own (we borrow fins only as we brought our own masks). They provide a simple anti fog spray which worked great. They let us snorkel for about 2 hours in the surrounding area asking us to stay within 50 yards of the boat with a buddy. The staff answered all our questions about what fish we were seeing and recommendation for how to see the best fish. There is also a glass bottom that you can climb down a ladder in the boat to see the fish without going in the water. They served lunch while docked so you could eat while you took a break from snorkeling. It was fish tacos with a selection of fish, pork or being burger meat. They had a slaw and quinoa side and some chips. Nothing fancy but o found it delicious after working up an appetite snorkeling. They had cameras for rent (extremely expensive so I'd bring your own), a photographer that took picture you could purchase for a fee ($80 for all the pictures she took of us, again a little pricey), wet suit tops for rent ($10 each) and special snorkel masks if you are near sighted (I believe this had no additional charge). The boat was pretty new, clean and open which was nice. I would 100% go out with this company again.

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.

Sail Maui- Maalaea - boatcharters - Updated October 2026

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