Wonderful sailing company. Small company that delivers incredible personalized service. We did a 3 hour private sunset cruise with Captain Bailey and crew member Phil and it was spectacular. Have not edited my videos yet but the number of whale sightings was insane. We saw multiple breaches and tail splashes as we followed a mama, baby and escort (from an appropriate distance for many, many minutes. Both Bailey and Phil were incredibly knowledgable about sailing, whale watching, the island and life in general. Our close friends booked this cruise and invited us and we look forward to our next outing. read more

Kainani Sails Maui Sailing Charters - On the boat with just before Sunset with the island of Lanai behind us. - Sailing Near Me

We elected to charter a trip with Kainani Sails Makai on March 21 - snorkeling, whale watching and sunset. Best decision of our Maui trip. Hands down. 10/10 If you are trying to decide between going on a large power catamaran or book Kainani - I will save you time, stress and mental energy. Book Kainani now. It is worth it. I'm the trip planner in our family (read cover-to-cover Maui Revealed and several other guide books on the island). Sailing - it was a relaxing day with nice wind and calm waters. Snorkeling - We saw so many fish (trumpet, convict, ember parrotfish, humuhumunukunukuapu'a) and even honu (sea turtle). It was a special day that I'll always remember. Captain - Ely = smooth and steady. Clear directions and focus on safety protocols. We felt safe the entire afternoon on board .. especially for one member who first time on a sail boat and snorkeling in open ocean water. Crew - Phil = perfect personality for a relaxing day on the water. Snorkeling guide extra ordinaire. Catering - We really enjoyed the poke tuna bowls, macadamia nut cookies, fruit on board. Water and beverages as well. What I didn't expect but enjoyed - We thoroughly enjoyed the journey to and from the sailboat. It felt special - in contrast, a power catamaran was down the shore with 75+ people boarding. Will I book again? Absolutely. (For those reading this far, unrelated Maui travel trip tip: the Hawaiian muffin at Maui Bread Company in Kihei and the pies from Leoda's in olowalu are worth the stop as well!) read more

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Our private charter was one of the highlight of our Maui trip. It's so private and personal. There's something about having a crew that caters to your need and interests and take it at your pace instead of rushing with a crowd. Boat was clean and well taken care of. We booked a private snorkeling sail and saw bunch of turtles. We also had dolphins riding the bow! Poke lunch was catered from Down the Hatch from shore. Def worth it. 10/10 recommend. read more

Kainani Sails Maui Sailing Charters - Sailing Near Me

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Given the choice between cost and quality, I will choose quality every time. Even though I wanted to give my family the experience of a Maui sunset on the water, I did not want to do it with 75-100 other people on a catamaran- especially during COVID! When I found that Kainani' offered a private sunset sail, I jumped at the opportunity. And the crew did not disappoint! Kaeo and Phil were perfect. They were patient and accommodating for my mom (who had a bit of a hard time getting into the tender and then onto the sailboat). They were engaging, knowledgeable, funny, ... all the personal characteristics we wanted them to be to make those 3 hours special and memorable. A Hawaiian vacation is a lifetime experience. Spend the money on the Kainani Sail experience. Don't shortchange yourself on one of those $100 cruises. I highly recommend Kainani Sailing charters. read more

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What an incredible experience! We're so glad we did a private trip and the crew were absolutely perfect. They took us to an amazing snorkel spot where we saw more sea life than we've ever seen here and took amazing care of us. Thank you Noah, Andrea, and Micah!! read more

TLDR; book with these guys and don't think about it any more!!! One of the best vacation experiences we've had - not only on Maui but really anywhere. Our 5 hour private sail charter was easy to book, super reasonably priced and service was out of this world. From the shop to book and order lunch, to Keao our amazing and friendly captain - there is nothing that could be improved. Beutiful boat, delicious snacks for breakfast and totally amazing lunches - everything was awesome. We stopped to snorkel and saw tons of fish and even a few turtles! We came across some dolphins who sailed with us for a bit. The boat was comfy and amazing - I literally can't say enough good things about Kainani Sails. read more

5 stars, highly recommend. We sailed the island for a bit and then snorkeled. Everyone enjoyed it. Great boat, great crew, fantastic experience! read more

Amazing private boat tour worth every penny! Eli and Amanda were the best! They were so hospitable and very knowledgeable! 10/10 can't recommend enough! We will definitely be coming back! read more

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Ely and Phil were incredible. This was my daughters' first sailing trip and they LOVED it. Both were afraid of snorkeling due to sharks but Phil jumped in with them and showed them all the fish and the turtles. No fear after about 30 seconds. He was so patient and his knowledge of the reef and fish is amazing. I appreciate his expertise. In all the snorkeling trips I've been on, this was the first to have someone know the environment and share it. Made it top notch. We started the day with rain, winds and a rainbow. We saw spinner dolphins on our way out. We saw five turtles. On our way back we saw more spinner dolphins under our boat. How lucky were we!!! I definitely recommend this tour company. It was a highlight!!! read more

We had an amazing charter on the Beneteau 45 for a sunset sail. The captains Austin and Kirsten were incredible. The boat is awesome. And of course there are not many more beautiful places to sail. read more

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This was an amazing sailing trip for our family of four. The crew were so nice and were expert guides, giving us information about the island, the animals, and history. My kids had so many questions about fish, and they were always enthusiastic and informative. I thought they would get annoyed with all the questions, but they were never anything but enthusiastic and encouraging. We snorkled and saw fish and turtles; we saw whales and whale calves; we read books on the front deck. It was a perfect day. Also, the morning banana bread was amaaaazing. We would definitely do this charter again. read more

Kainani Sails was extraordinary! Our captain Lilly and Joy were professional, knowledgeable, greats hosts and made us feel at home on the boat from beginning to end! Excellent sail, service, lunch, whale watching and snorkeling. We saw whales and enjoyed best snorkeling spots. Beautiful deli style lunch with all the fixings. Perfect for groups 6 and under. Really quite a treat ! We will be back - thank you KS for your hospitality. read more

We had an absolute blast on our sailing charter. Kersten and Austen made our trip as incredible as ever. They were so attentive and helpful with everything. We had the time of our lives, thanks to the amazing crew. The boat was perfect for our small group, it was clean and well cared for. We also were served a delicious lunch prepared especially for our group. I'd recommend this boat and especially the crew. We'd do it all over again in a heart beat!! Our trip was simply magical. read more

I couldn't have asked for a better experience with Kainani. It was certainly the highlight of our experience on Maui and I look forward to booking another charter in the future. Buying the additional hour is a must as you won't want to return to the beach after this amazing sail. read more

We had a fantastic sail to Honoloa Bay today. Everything about the day was perfect thanks to Sergio and Keao. Both were very professional, polite, accommodating, skilled and fun. Sergio was our private guide at Honoloa Bay telling us about the marine life. We saw turtles, a large variety of fish, a reef shark and spinner dolphins. The lunch was very fresh and included sandwich makings, veggies and fruit. It was a perfect day and thanks so much for helping us make some family memories before we drop our son at college in a few weeks. Thanks for a great time!! read more

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If you're going to charter a boat, I highly recommend Kailani Sails. Special thanks to Captain Lilly and Amanda for being great hosts and snorkel guides. We had such a great time and couldn't have asked for a better crew. The sail boat was beautiful and loved that tuna salad. We will be back! read more

Kainani Sails Maui Sailing Charters - Family fun on the sun! - Sailing Near Me

​​​Kainani Sails ​Makai Adventures is the best! We were in Maui for ten nights and the 1/2 day snorkel trip we spent with Keao and Eli was the highlight of the trip. The boat is small (perfect for 2 couples) but, beautiful and they have all the snorkel gear and everything you'll need for a perfect day on the water. We were picked up right on time and sailed up to Honolua Bay to the outer reef to snorkel. Eli got everyone set up and snorkeled with us, showing us the very best spots and explaining everything about all the fish and underwater life. We've snorkeled all over Maui but, to get out to this area you really need a boat and someone who knows where everything is. Eli is a snorkel master and we saw turtles and more - bigger - beautiful fish than we've ever seen by far. Just sailing around was amazing and we sailed with pods of playful dolphins on the way home, jumping across the front of the boat. We ever saw a baby dolphin! Keao allowed my friend Martin to pilot the boat for awhile (he grew up sailing) and he had such a blast. I'm pretty sure the four of us will remember this trip forever. We're already making plans to go back! read more

We had the BEST time on our private sunset sail. The captain, Nick and co captain Joy are awesome. Could not have had a better time. Next time we come back to Maui we will for sure call on Kainani Sails again! Highly recommend them. read more

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Perfect for kids! We had a great experience with Captain Ely and Phil. We were a little nervous about how little our kids are (4 and 7) and the fact that they are not strong swimmers. Didn't matter. Ely and Phil made the experience super memorable for all of us. The weather was looking questionable and they took us to a great spot where we found some sun and some great snorkeling. Lunch and service was top notch. They had all the equipment and snacks a young family could need. Can't wait to do it again. Thanks Kainani! read more

Went sailing with my husband as part of our honeymoon in Hawaii, and had the most amazing time! Just when we were getting disillusioned by strip malls and blended drinks in plastic coconuts, the incredible Captain Keao showed us ancient ruins, took us swimming with turtles, and caught us fresh fish, which he made into sashimi for us! Oh yeah, and he cut down real coconuts for us. If you really want to experience Hawaii, grab some Dramamine and step away from the cookie-cutter resort for a few days to sail on the Kainani ("beautiful ocean"). You will not be disappointed. read more

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What an awesome experience!! We went out on the 43' Beneteau with Iwa and Keao yesterday in Maui for 5 hours. We were celebrating my husband and my 5 year wedding anniversary and we invited my cousin and her husband along to join us. We took off from Lahaina Harbor around 1 pm and had the most amazing day on the boat. Iwa and Keao found the most perfect snorkeling spot where we spotted some beautiful turtles. I opted to float around in the ocean instead of snorkeling and they had plenty of gear to accommodate whatever we wanted to do. Both Iwa and Keao were amazing - they refilled our beverages and brought us snacks as we relaxed and watched the sunset. This is most definitely a tradition we will have to repeat every year when we are out here!! read more

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So much fun! This was a great way to supplement a vacation on Maui. We went for a half day excursion with Kainani Sails and it was one of the best things we chose to do on Maui. Everything you could want: sailing, snorkeling, whale-watching, and getting out into the ocean. We saw turtles, heard the whales from our snorkeling location, and made some unforgettable memories. The crew is awesome, knowledgeable, and accommodating. They were perceptive of the things we wanted and we had a blast with them. We highly recommend booking this sailboat! read more

WOW!!!! I'm not a Yelper.....but Captain Steve and Austin are the best. So knowledgeable, so fun, so safe. There cannot be a better experience in the water in Maui!! Well, maybe one..... but this is absolutely the next best. These folks take customer service to the very highest level possible. We've been coming to Maui since 1975....been on so many whale outings we can't count em.....but this is by far THE BEST!!! read more

We had a terrific sail around Maui. Personal pick up from the beach north of Black Rock and a short dingy ride to the boat. We had one of the best snorkel trips and saw seven turtles and a reef shark. Captain Nate and shipmate Amanda were personable and knowledgeable which made the three hour sail one of the best boat trips we have been on. I highly recommend booking with Kainani. read more

Went on a trip with my family a month ago and could not recommend this charter more! Both me and my sister in law are pregnant and the crew was so intensive and kind making sure we were comfortable the whole time! It was a rough day out on the water so my sister did get sick but they were on top of things and never made anyone feel bad. Lunch was a simple packed sandwich that was perfect for this kind of activity! Drinks were flowing for those who were not pregnant on the way home... Everyone seemed to enjoy themselves! read more

We had a fantastic trip!!! Iwa (pronounced Eva) helped us arrange a charter that fit our schedule. The Captain, Keao (pronounced K-ow!) was great! He found us the best snorkeling in the islands (even after a storm). We saw tons of whales and sailed with a pod of dolphins. Everyone caught fish and we snorkeled with sea turtles. Keao was also great with kids, playing cards with them around the clock. I've chartered in Hawaii before and this is the best outfit there is. They said that it was like having family on board (the good kind) and the feeling was mutual. I cannot say enough good things about Iwa and Keao. You will not be disappointed if you charter with Kainani Sails. read more

One of our most memorable activities in Maui. Everything about the sail boat ride was perfect. The gorgeous views and the kind crew aboard made for a perfect day. Nick and Amanda had snacks ready for us after a snorkel tour before we sailed til the sun went down. The day couldn't have been better and we highly recommend Makai tours to anyone visiting the area. read more

Kainani Sails Maui Sailing Charters - Sailing Near Me

We had an incredible experience sailing with Lily and Amanda this morning! I'm visiting my retired parents on Maui with my partner and brother. We were able to see more whale breaches than we could count on the first part of our trip. The display the whales put on was truly breathtaking and Amanda shared a lot of her knowledge about the pod dynamics with us. They then brought us to a great snorkeling spot where we got close to a bunch of sea turtles, a wide variety of fishes, and a white tip shark! The captain, Lily, was very accommodating and flexible in terms of what we wanted to see and do while we were on the boat. They set out a light lunch of sandwiches and crudités for us after snorkeling that was delicious! We were well taken care of and the safety features of the boat were explained to us clearly as soon as we were aboard. I'd definitely recommend this company and this particular team to a close friend! read more

Went sailing with my wife, 6 month old baby and 3 year old. At first we were a little unsure about the safety of the kids but after leaving the harbor we quickly felt very comfortable. The kids had a great time! We saw several whales, dolphins, and turtles. The boat was well maintained and the tour was very professional and accommodating. We had an amazing time and the food was incredible! Thank you Kainani Sails for the memorable trip! read more

This was an incredible day on Maui. Our excursion began with a quick ride from the shore to the sail boat in a dinghy. All of our belongings were safely packed away in a tub and carried for us. Once aboard the same boat fresh fruit, beverages were offered. The captain set up chairs for us to enjoy the hour long scenic ride to the bay. Throughout the trip the music was tailored to our likes. Once we arrived in the bay the snorkel equipment came out-in great condition, not over used or difficult to adjust. We snorkeled for. Little over an hour with the captain, all the while he was scoping out the reef for interesting sea creatures. He held a sea urchin so we could see up close. He discovered the turtle napping spot where we saw four turtles. Another 3 turtles were discovered swimming about. Once we boarded the boat lunch was served. A delicious sandwich bar. No paper serving pieces either...this was first class. About halfway back to shore the sails were up and Mother Nature took over. It was the most relaxing and wonderful excursion. Can't wait to sail Kainani Sailing again. read more

Kainani Sails Maui Sailing Charters - Sailing Near Me

Fabulous 5-hour morning snorkeling and whale watching sail with superb hosts Gina and Keao! Both have a wealth of knowledge about Hawaiian ocean wonders. Gina knows her marine biology and her passion about it came through to satiate our curiosity about everything we were seeing (and we saw a lot!) Keao was a confident, but relaxed (in a chill way), captain who made appropriate adjustments to our sail to let us get the most out of a day on which certain sights were off limits due to excessive wind. They took us to great spots to snorkel and then to see whales (as someone who has gone on other disappointing whale watches, this was thrilling). Totally cool and worth the cost. Do it. read more

Exceeded my expectations! For sure I will do this again. I shopped around and finally took my chance with Kainani Sail and was not disappointed. Keao & Iwa were great hosts and took good care of us. Well worth the money and will highly recommend this trip to any who wants a fun day on the water without the crowds of people! read more

Just spent 3 nights aboard the Kainani and we had a blast! Keao is an expert sailor and an all-around great host. The boat is efficiently organized (and compact). Keao enabled us to make the most of our marine adventure--turtles, dolphins, manta rays and even whales! The hardest part was finding a place to leave the car while we were gone. Iwa also provided excellent information and customer service during the booking and planning processes. I highly recommend Kainani Sails! read more

I have been sailing with Iwa and Keao a couple of times, and each time seems to be better than the last! We have caught fish, seen tons of whales and dolphins, and have been snorkeling at the best spots around Maui and Lanai. They are very safe and knowledgeable about sailing and marine life, and are also super fun to be around. Whether you choose to do a multi-day excursion or just a shorter day trip, Kainani Sails is the best option for your vacation. read more

We just returned from a fabulous week in Maui and our afternoon sail on Kainani was one of the highlights of our trip (which included six days of pampering at The Westin Resort). Since we are experienced sailors, we wanted to focus on sailing rather than whale watching, but saw plenty of whales in the process. The winds were high and the seas a bit choppy but that only added to the excitement and overall experience. Captain Keao and crew Ewa were very professional yet friendly and fun to be with and we exchanged stories throughout the afternoon of many sailing experiences. We look forward to booking a cruising week on Kainani in the near future! read more

Awesome day of sailing, snorkeling, and whale watching Keao and Taryn were wonderful. Full of knowledge and knew how and when to share it! The best sailing charter I've been on, would highly recommend. read more

Had an incredible time on a three-hour sunset sail! Nick and Joy were so attentive! Genuinely nice people who wanted to make sure we were having a good time! Lovely fruit and cheese platter. Joy took some awesome pictures of the family. We could not be more pleased with our incredible evening! read more

We have been to Maui several times and were really looking forward to the adventure trip on Kainani Sails, because we could snorkel and kayak some places that are hard to get to if you are not on a boat. We arrived (8pm) a day early and the hosts were nice enough to let us come aboard and stay the night , even though we were supposed to board the next day. We were a little shocked upon arrival that the hosts weren't seasoned sailors and were new to the travel industry. Off to our six night sailing adventure, which included meals. We headed to Molokai the first day and the whale watching was spectacular as well as crossing the channel. Staying in the harbor on Molokai was the calmest night sleep we had. The next day we visited the small town of Molakai and then headed toward Lanai, we fished off the back of the boat and caught an Ahi Tuna. Eating it right away was a first! We sailed everywhere and nice meals were made for us. My husband had to leave after the second night of the trip to return home for business. So at $400 a night my husband felt I would be treated with the same respect and service that we had had and that my vacation would be a positive and memorable one, even if he couldn't be there with me. He asked to be dropped off at Manele Bay on Lanai (we were on the backside) so he could take the ferry back to Maui. The hosts immediately set sail to get him back to Mala Wharf on Maui, even making sure we made dinner early before he had to catch his taxi. After he left, let's just say things changed. The next morning priorities were changed. Instead of sailing, errands needed to be done like going to the post office and with parts breaking on the boat, they would not leave until parts were ordered, approx. 3-4 hours. Once underway they sailed for 1-2 hours and then we never sailed again for the remaining 3 days. Activities also changed. I didn't expect them to do everything with me, but some things I needed them for. At the first mention of fishing while my husband was still on board, the host immediately took him fishing on the Zodiac; when I asked to go fishing on the Zodiac to fish, he said he was reading. I am easy going... so I just jumped off the boat and went snorkeling, but these were places I have been to numerous times on Maui while staying on land. I also asked to be taken ashore (which I don't think was too much to ask) and was told I could swim. I suggested several other things and not much was accommodated. The hosts were busy napping, catching up on their reading or making phone calls to their entire family. It costs a lot to travel to Maui and to stay there, so you want to make every moment count, and this might be lost on the hosts. I never felt comfortable with their sailing experience in the Maui channel from day one. The first day when we were headed to one spot on Molokai, the weather changed and so we went into the harbor, which worked out great. When I was by myself I was offered three options to go to, I picked Molokai.... then five minutes later the weather was too rough, so I choose Honolua Bay. Sailing friends of the hosts went to Molokai and called to say how beautiful it was. I felt they were unprepared and unfamiliar with the anchorings and where was safe to go. After a rocky night in Honolua Bay, we decided to go down to Black Rock (both on Maui) where we experienced another rocky night. I understand that weather changes and that safety is a top priority, but their constant unsureness and guessing was not comforting. I still don't understood why we couldn't dock in Lahaina Harbor and even asked if we should go to Ma' a lea Harbor because to me they seemed secluded and safe. (They likened themselves to pirates and not having the proper permits.) After my husband left I felt like a burden to the hosts and what they wanted to do, what they wanted to feed me (everyday lunch was a turkey sandwich and the female host said she wasn't a good cook and one night was hot pasta noodles with broccoli, tomatoes and salad dressing- not what I was expecting paying $400/night). I couldn't complain, because I was on their boat. There seemed to be something else going on, almost infighting, not the professional service I am used to getting while traveling and there was no escape. I talked it over with my husband and decided to come home a day early. I told the hosts first thing in the morning that I needed to leave the boat that evening as I had an 11pm flight and that I wanted to snorkel and go to town in Lahaina. I was assured none of this was a problem. After lunch weather changed and I was told I was getting off the boat and not coming back. I was given a few options, one of which was a hotel room that they couldn't deliver, so my vacation ended with me being dropped off on shore in Lahaina 8 hours before I wanted to depart with all our luggage - for a night we had paid for! and then made excuses that they had a poor night sleep! read more

Not enough words to describe the great time that we had on our sail with Iwa & Keao. Took my family of five, and had an outstanding experience. From the first contact to setup our reservation to the beach drop off at the conclusion of the sail, I could not have been happier or asked for more. I was looking for a quiet, private sunset sail to enjoy with my family and to make memories and we did just that. My kids had a blast - including my 5-yr old, who despite being petrified at first on the way to the boat, became quite adventurous by the end of our sail. A lot of that can be attributed to Iwa, who went out of her way to really make my kids comfortable and enjoy their trip. As for Keao, we couldn't have asked for a better captain. My 10-yr old spent nearly all his time learning to sail with Keao and absolutely loved it. As for the rest of us, we soaked it up - being on a private sail boat, not a 40-60 person catamaran, and had a great time. I expected, and got, a private sail, but the crew and personal experience far exceeded my expectation. I would highly recommend Kainani Sails and Keao & Iwa to anyone looking for a truly remarkable and memorable sailing experience! read more

This is one of the most amazing things I've ever done. I wandered the sea with Captain Kaeo, a Coast Guard certified gourmet chef with years of sea travel behind him. He makes it look easy, and he's charming.The stories he tells are hilarious and his manners are good enough that my very southern mama was impressed. I'd give you boat details, but I just know she had two baths, three bedrooms, was decorated with very good quality and care and that she is BEAUTIFUL. I was standing at the bow while a super pod (50+) of dolphins swam below me, including one just born baby that jumped out of the ocean right next to the boat. I went to two islands, both of which you cannot get to by any means other than boat. My kids and my disabled mother had no problem living on board or getting around, and Kaeo was so sweet and caring for my mom. He really was a gentleman. I could write a book about all the things we did and loved about this trip, but what I really want you to take from this Yelp! is that you should do this. It is the most amazing thing I've ever done, it brought my family closer and it really was a "no worries" trip. read more