Captain Porter and the entire North Shore Sailing Adventures team was fantastic! My family of four (with two tween boys) did a snorkeling adventure in June 2025. From booking the reservation, to the instructions on when/where to meet up, to the recommendation on getting to Hale'iwa early in the morning to rent snorkel gear, it was a very smooth process. Captain Porter and his deckhand were laid back, informative, and fun to be around. There wasn't a focus on time and it was a very casual, relaxing experience. They gave us clear instructions aboard the boat to keep us safe. We anchored in Waimea Bay and got to swim with dolphins! Captain Porter's wife even made us sandwiches for lunch! Love that they keep it private to one family. Really helps make it special and exclusive. This was the highlight of our trip to O'ahu! Highly recommend! It's worth the price. read more

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Simply put our favorite thing to do on Oahu. Captain Porter and his crew are always the best.

First time sailing and I'm glad we did it with such an amazing crew, Captain Porter and Chad! We did the sunset cruise and I was just amazed by the beautiful landscape, deep blue waters, and the double rainbow we saw! At one point we spotted a large pool floaty in the middle of the ocean and the crew skillfully grabbed it so it wouldn't harm any wildlife. Overall just a really thoughtful, kind and knowledgeable team who we got to know as if we were long time friends. read more

North Shore Sailing Adventures - Sunset - Sailing Near Me - Haleiwa, Hawaii

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If you're looking for a sailing adventure that is not only fun and educational, but also SUPER personalized, this is the way to go. From the moment my wife and I stepped on the KEET, it felt like I had known Capt. Will and Mateo for years. They took time to get to know everyone on the trip and also gave us a lot of their own background (where they're from, how they got into sailing). We set out around 9am and were told all about the boat and the owner, which was super interesting. They told us about each type of bird that flew over, and every fish that we saw (mostly flying fish!). We were even lucky enough to see a mother and child whale duo, which I understand is rare this late in the year. We sailed for about 1.5 hours before turning around and cruising a little closer to shore. While cruising back, Will and Mateo told us about each beach/bay/cove and where the best surfing/swimming/snorkeling was. Mateo was even kind enough to recommend several hikes for my wife and I! Tragically we had only booked the three hour tour. I would have loved to stay out all day on the Keet. Upon returning to the harbor we were even fortunate enough to meet the owner, Capt. Porter, who was as nice as the day is long. **If you are ANYWHERE on the island of Oahu, please take some time to head to the North Shore and hang out with this crew.** read more

North Shore Sailing Adventures - Waimea Bay - Sailing Near Me - Haleiwa, Hawaii

Porter was referred to us by the person at whose place we are staying. What a great recommendation! Porter and Chad were amazing. We definitely saw whales and they knew exactly how and where to spot them. The boat was immaculate and the ride was great. We saile the waves beautifully and the weather cooperated as well which was a major bonus. We would definitely sail with them again, and they were also just so pleasant too. Thank you Bernie. HIGHLY RECOMMENDED! read more

Me and my family decided to do a last min whale watching excursion as we read it is a great experience for those visiting Hawaii. Since we were visiting North shore for just the day, I was disappointed to know that all bookings happen in advance and it's best to book excursions ahead of time. I still decided to try my luck and landed up contacting North Shore Sailing Adventures and left a vm fully expecting to not receive a positive response. But to my surprise I received a call from a very pleasant lady Annastacia stating that we could sail the same afternoon as they had an opening. The entire booking process was easy with clear instructions on how to get to the pier. As we arrived at the pier at 3 pm, little did we know that this private sail would be the highlight of our trip. The kids were beyond happy to set sail and the entire team at NSSA was warm n welcoming. Captain Porter was very knowledgeable about whales and he patiently taught our kids on how to look out for whales, made them hear whale sounds and answered every question they had about whales. We spotted many whales on our 3+ hour sail and the icing on the cake was the amazing whale sightings we saw towards sunset.. Captain Porter n his crew spotted them and we were at the right place at the right time.. it almost felt like the whales had put on a show just for us, with them jumping out of water several times and doing flips. The whales truly seemed to have enjoyed our attention and the kids were beyond thrilled with everything they experienced. I HIGHLY recommed sailing with NSSA as Captain Porter and his crew ensure you have a great time. It surely was non-commercial and felt like a more personal experience for us that our entire family will never forget. "Because when you stop to look around, life is pretty amazing!" Mahalo North Shore Sailing Adventures - until we meet again read more

North Shore Sailing Adventures - Sailing Near Me - Haleiwa, Hawaii

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Had a great morning out sailing with the North Shore crew. They were extremely knowledgeable, attentive and patient with the group. We were lucky enough to have seen several groups of whales - including some newborn calves. Highly recommend these guys as a way to spend a morning or afternoon on the North Shore. read more

North Shore Sailing Adventures - Sailing Near Me - Haleiwa, Hawaii

We just had the most magical morning sailing with Captain Porter and Will, and sweet Millie. If you are looking for true Aloha, then this is your boat and crew. They took such good care of us, the boat is meticulous and safe, and the views were amazing. We were even blessed to sail with spooner dolphins swimming all around us. It was truly a magical morning. Thank you again North Shore Sailing Adventures...you guys are the best!! read more

North Shore Sailing Adventures - Captain Porter and Miko with the spinner dolphins. - Sailing Near Me - Haleiwa, Hawaii

Sailing on the North Shore with Capt Porter aboard Keet is an absolute must! The sailing is as comfortable as it gets! Capt Porter is knowledgeable & passionate about the ocean & all the sea life & wants to make it the best experience for you. We sailed up to Waimea, went for a swim and within 10 minutes were surrounded by hundreds of spinner dolphins. One of the best dolphin experiences I've ever had (having grown up on the North Shore). We will be back! read more

North Shore Sailing Adventures - My husband and sister-in-law, enjoying the downwind sail. Kaena Point in the background. - Sailing Near Me - Haleiwa, Hawaii

My fiancé, friend and I had such an awesome time whale watching! Porter and the crew were great company for our 3-hour trip. It was really amazing to see 4 or 5 whales at close range, and to hear them "talking" to each other through the hydrophone. We had the boat all to ourselves. Truly felt like we were out on the water with great friends. I can't say enough good things about North Shore Sailing Adventures! If you're looking to go whale watching or snorkeling on the North Shore, go with these guys. read more

North Shore Sailing Adventures - Back in the harbor after our whale watching adventure - Sailing Near Me - Haleiwa, Hawaii

This sailing experience made our vacation! The captain is highly experienced and engaged us in stories of his adventures sailing around the world. We were so lucky to see turtles and even watch dolphins swim with our boat. Even though I've never sailed before, I got to learn so much about the intricacies of a trimaran. We really feel that we got a much more personalized tour than we would have had with the larger operations that host large tourism groups. If you are looking for a more local and authentic experience, I highly recommend this tour operator. read more

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Man! what is there to say...it was amazing and I cant wait to see them the next time I am on Oahu for some more sailing (maybe a beer or two?). Imagine you have a good friend (they professional....but not uptight) who has a sailboat and they are like "Hey, when you come out, swing by and we'll go out on my boat (and they have a nice boat and know how to sail). Naturally you would be pretty stoked on that and would definitely call them after you landed. That is the feeling you get on their boat, on the water and around them. No BS, hustle and bustle touristy type stuff. No fake Aloha. Capitan Porter and his crew are very personable, knowledgeable and just plain fun to be around. YOU CAN NOT GO WRONG booking a charter with them. Hope you get to experience it andenjoy it as much as we did! read more

This sunset sail was one of the most magical experiences of my life. It was just me, Captain Porter, and his first mate Chad. The weather was gorgeous with a tiny bit of rain, which meant that the rainbow over the shore lasted for a solid three hours (occasionally becoming a double rainbow). On the way out, we saw several schools of flying fish, and then came the dolphins. They surrounded us for about half an hour, sometimes popping out of the water and spinning in the air. There was a mother and tiny little baby! Captain Porter and Chad were fantastic, helpfully pointing things out, friendly, and warm. The captain even lent me his jacket when it cooled off. I would do this again in a heartbeat, and I probably will be back for whale-watching season in the spring. Don't leave Oahu without taking this sail! read more

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We were lucky enough to meet someone having lunch at The Sunrise Shack and he recommended this tour. Thank God we listened to him, we got in touch with Mili and Anastasia! Excellent service. but the best was today when we went to the Trimaran with Captain Porter and Willie. spectacular anecdotes told by Cpt Porter, spectacular sailing the North Shore. GREAT EXPERIENCE. read more

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We had such a blast with you guys! Your boat tour was our favorite part of the trip. I loved that it was just my family. The kindness of capt. Porter and first mate Will was amazing. Loved that they were there, they added so much to that special time with my family. Can't wait to sail with you guys again! read more

Totally pleased and would highly recommend the sunset sail. We were celebrating my in laws 50th anniversary. Captain Porter and Chad were very friendly and informative. read more

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Excellent Sailing on a beautiful Sail Boat! Captain Porter and Will were gracious and professional! We sailed for six hours, saw and swam with dolphins, snorkeled with fish and Sea turtles. We came home with beautiful memories, with our three children. Our kids cannot wait to go back and do the same sailing adventure with Captain Porter! read more

Porter, Ashley, Millie, Allison and the team are outstanding!!!!! We had the opportunity to go out at 7:30AM today and saw 500 dolphins. We jumped in the ocean and swam with dolphins above and below us. An unforgettable experience. read more

So it's a given, this is the best sailing charter across the universe, but I think my life changed once I met Captain Porter. You guys, he seriously has THE CHILLEST VIBES you will ever encounter. From the moment we met him, I was like, "do people like this really exist?" He is SO cool! I literally had no other way of describing him other than having the best energy I've ever been around. He's so humble, laid back, generous, welcoming, hospitable, and knowledgable that you'll feel like you're just sailing with your oldest and dearest friend. And HIS STORIES. And none of that gets left ashore when you set sail. We were celebrating our friends' engagement and Porter (and his awesome right hand man Will, hayyy Will!) made this an experience I will never forget. Do yourself a favor and sail with this company. You won't regret it I PROMISE lol. You'll all be smitten. I was, just ask my boyfriend! A MUST whether you live here or are on vacation, honestly just so you can meet and hang out with Porter haha read more

North Shore Sailing Adventures - Setting sail on Captain Porter's catamaran!! - Sailing Near Me - Haleiwa, Hawaii

This was the most amazing experience of my trip! Captain Porter and Captan Will are so good with people and took us seeing whales, turtles, and sharks! Not to mention, Captain Porter is a marine biologist and shares so many interesting facts about the whales. We dropped an hydrophone into the ocean and we could eve listen to whales! Really emotional, worth every penny. If you're considering taking a tour, you should absolutely do it. read more

North Shore Sailing Adventures - So close! - Sailing Near Me - Haleiwa, Hawaii

This company/experience had it all. From Anastasia to Captain Porter and Will, these guys made our North Shore experience unforgettable. We did it all- sailed, saw dolphins, paddle boarded, and even some snorkeling. North shore Sailing Adventures went above and beyond, even providing snacks and drinks. First class all the way. Could not recommend them more. read more

North Shore Sailing Adventures - Sailing Near Me - Haleiwa, Hawaii

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Since we are Oahu residence and live the ocean, We cruise often on different boats. Our crew on the KEET, Will and Chad we two of the best we've had. Knowledgeable, friendly and attentive. Great cruise. Great day on the ocean. We will become regulars. read more

Captain Porter and Will went above and beyond to make this experience the best possible. I can not recommend North Shore Sailing Adventures more. Porter is an experienced sailor and a marine biologist that further adds to the experience. Worth every penny and we will be back read more