I cant say enough positive things about my experience with Tradewinds Charters for a New Year's Eve Party. I worked closely with Ken through the whole process, which was months in advance, and he was always patient and helpful. The actual evening was perfect. They were prepared for my party of 49, and nothing was missed. The actual event was so perfect, from the polite and helpful crew, to the set up of the vessle. I wouldn't have changed a thing. Really a 5 star experience and much tanks to Kena nd Tradewinds. read more

What a wonder sail with a wonderful captain. Excellent excellent excellent! Thank you

Capt. Ken, Just wanted to send my Mahalo for the awesome sail yesterday..!!! Capt. Paul made us welcome and did a great job hosting our gang. We ended up with 11 aboard and, even with that crowd, Paul gave us a great sail. His timing was great, with the right mix of sailing, swimming time, pupu's and a quiet end of the day sunset sail as the sun dropped below the Waianae range. While most aboard were returning kamaina, it had been a long time since they'd been home sailing these beautiful waters. And a great time was had by all...!!! A VERY big Mahalo to Paul and your whole team for making it memorable ... Trust that we will "spread the word" to any who are asking "what should I do..." when visiting our islands. Mahalo Nui Loa, Ken & Cat S/V Manu Kai Alameda, Ca read more

I booked "My Sunshine" for a 3-hour charter for 5 guests. We were celebrating a friend's 25th birthday, and she reaallly wanted to go on a boat with her close friends. The entire booking process was great, and Ken was very kind when I spoke to him the day prior to our departure. However, I had a couple of real issues with the ride. On the day of, we showed up to the boat & met captain Nate. It started out smoothly & he was very kind. As we drove away from the harbor, he informed us that he would be taking pictures during the ride to send them to us afterward (which we never got, btw). We felt a little weird about this considering we brought a camera for that purpose & each had our own phones, & Nate wanted to take them on his own phone. However, we didn't verbally object & went with it. As the ride continued, we started to feel uncomfortable as Nate repeatedly encouraged us to "drink more", grabbing & waving the alcohol we brought in the air. None of us were really up for it, as we were just enjoying the ride & the view. When we didn't ecstatically say "yeah, okay!", he said "well why'd you bring it if you weren't going to drink it?!" As an all-girl group of 20-somethings, the dynamic was strange & we were pretty standoffish at this point. A little later, one of my friends was walking alongside the boat & the railing next to her snapped & she almost flew overboard. Her heart sank & after taking a moment to gather herself, we tried to fix it. (Nate was down in the cabin this entire time). We then realized that none of the others were fastened with the same equipment, and this was one of a kind. I called him from the cabin & asked him to help us. He consoled us by saying "oh don't worry about that, it was already broken" - and proceeded to leave it open for the entirety of this trip. Luckily, we arrived at the spot where we were able to swim. We spent about 30 minutes in the water when he informed us we had 30 minutes left to swim. 10 minutes later, he rushed us out to insist that we follow their company's other boat so we could see dolphins. We didn't care much, as our entire group is local to the island (which he knew) & we were more interested in the time we spent together, in the water specifically. When we approached the dolphins, he said "Look, they came to help captain Nate get a big tip!" This comment angered us all, as it was the 4th time he mentioned his tip, and because he rushed us out of the water to ensure he gets a larger tip.... Look, I understand that the clientele is typically visitors & tourists, but we were not & were super clear on that from the beginning. Overall we had a decent time, but it was not worth the money I spent considering the awkwardness my friends & I felt the entire time. Not to mention the boat was dirty, and there were things all over as if someone lives there currently. The fridge/amenities didn't work aside from the bathroom. We also never signed any sort of release for our photos to be taken, and not receiving them at the end of the trip makes this all the more WEIRD. P.S. The only reason I gave 2 stars is because I do believe this is likely a great company, and I really trust all the reviews I read. I don't want to knock the entire company for one captain, and I see that he isn't mentioned much in the other reviews. read more

Booked another charter with Tradewind, and had the best time. Captain Nathan was amazing, and took a bunch of great photos of our group. So happy with Tradewinds' services, will definitely be back again. read more

I have personally been on a 1/2 dozen charters at least and given Ken 100's of referrals and everyone was really happy! Thanks Ken!

My cousin and I booked the 8 hour reef fishing trip with Captain Ken after researching a few different fishing charters and sites. Ken was very friendly over the phone, and even mentioned having us snorkel and whale watch since we were taking the boat out for the whole day. The idea of doing all this in one trip with our families sounded amazing. We contacted Ken the day before and he said his colleagues, Chris and Duke, would be our guides. When we arrived we found free parking at the park near the dock. The boat was quaint but nice. 40' sounds big until you see it. Chris greeted us and was nice and helpful with getting our gear on board. Duke was late, but so were we, so we didn't grovel over it. Duke smelled like he'd been at sea for about a month with no shower and one of his toes looked like all the flesh had been stripped from it. Thankfully he bandaged up the toe, unfortunately the smell lasted throughout the trip. Duke was not as personable initially and my cousin actually had to ask him if he was feeling ok. He was sweating perfusly and said he was fine, he just had a long night. After that he was much nicer and helpful. Our trip started out with a slow long ride from the dock to our fishing spot on the east side of Diamond Head. On the way out we found, chased and ran along a couple of pods of dolphins, which made for some great videos and pictures. Then we saw some whales at a distance for which we chased around for awhile. After all the dolphin and whale chasing was done we slowly got back on course to our fishing spot. When we arrived we checked our watches and found that we had already blown over half our day's trip chasing sea life. Though we got some great pictures this was not the intent of our trip. As we approached our spot Chris made a comment about not being in that area much, so Duke assisted him with locating a spot he said was well known for good fishing. We finally parked 4 1/2 hours into our trip and Duke brought up the fishing poles. I looked at them and thought this has to be a joke. They were standard open reel poles with a half ounce weight and a hook with a small piece of squid on it. Not what I had in mind but I figured these guys knew what they were doing. So we cast out and sat around for about 20 minutes without a single bite. Duke kept saying the swells were causing poor visibility for the fish so they weren't biting. Having an onboard fish finder would've been handy. My cousin mentioned snorkeling since we weren't catching fish. Again, Duke and Chris both said the swells were making visibility bad. They said we shouldn't snorkel either because we wouldn't see anything through the murky water. They then had us reel our poles back in and said they would go to another spot near Waikiki. We pursued what ended up being another 2 hour boat ride back to where we started. They had us stop and fish near the mouth of the boat dock where we started just so they wouldn't have to trek all the way back. We only had about one hour left when we were told to throw our poles back in the water. It was about 30 minutes into the fishing that I caught some 6 inch baby fish that ended up being our only catch for the day. 4 pm came around and without hesitation they were headed for the dock. My cousin and I were very upset about the fishing and snorkeling part of this trip. We essentially slow boated around the ocean for 6 hours and fished in crappy fishing spots for 2 hours. Everyone on the boat was disappointed or nauseated. The kids had to play on their iPads just to pass the time of boredom. We brought the issue up to Duke as we were signing the final paperwork to pay. Duke got defensive and kept saying we could've cut the trip short 4 hours into it. We didnt know that and we were under the impression the whole time that there was more promising areas to fish. We agreed to just talk to Ken and go our separate ways. My cousin talked to Ken the next day and not only got my wife and daughter added for free, but he cut $400 off the price. He made it as fair as he could have which is why I gave it 2 rather than 1 star. In closing, this company should not be selling fishing trips without a fishing boat, proper equipment, and a fish finder. They should also have a back up plan in case the weather or the water is unfavorable. To be honest, we still don't understand the "swells" they were describing. It was a beautiful sunny day with little to no wind and the water was slightly cloudy but still visible enough to see a dolphin 20 feet down in the water from the front of the boat. We feel like the slow boat drive was to waste time, the return to the fishing dock was for a quick return to the dock, the fishing was horrible, and they were overpriced. They need to stick to sight seeing, whale watching, snorkeling, and memorial tours. I would not recommend them for fishing, but I would for all the others events. read more

Wonderful boat and tour guide, had a blast time went by fast, got to swim with a sea turtle, wish the reef was nicer in the area we went but other than that it was great! read more

We were booked for a cruise on October 23, 2021 and decided to cancel 45 days prior to scheduled cruise date after our airline canceled our flight from San Francisco to Tahiti due to Covid; we discovered that all of French Polynesia was under lockdown/curfew due to Covid. At the time of our cancelation, 45 days prior to our cruise date, Tradewinds was included in the lockdown, no sailing allowed. We asked them for a guarantee that the cruise would sail by Oct 23rd before we rebooked very expensive flights, which they were not able to provide. We had paid Tradewinds $3100 for our all inclusive fee, which they said they would not refund because we were canceling after the 90 day contract rule. We BEGGED them for our money back and even found another couple to replace us on the cruise should it actually be allowed to sail, which it did. The other couple took our place and paid them the $3100 as well, so they actually got double payment!! Tradewinds still refused to issue us a refund. We called our credit card company and they said that because we were aware of Tradewinds 90 day cancel policy, we were out of contract, even though 45 days prior to our cruise date, they were not sailing (and never informed anyone in our group) and not sure they would be allowed to sail by our cruise date. Tradewinds has kept our money and required the couple we found to replace us on the cruise to pay as well. I was confident that Tradewinds was an ethical company until this happened; just like so many other companies, they are more concerned with profit than doing the right thing. We have now spent $3100 and received absolutely nothing but misery in return. What a disappointment they are. Buyers beware, this company does not negotiate special circumstances and cares only about profit. read more

I've have hosted several birthday parties and special events with Tradewind Charters and it's always a great time for all. Watching the Waikiki Skyline from the ocean or seeing the fireworks from Hilton Hawaiian village makes the perfect backdrop to the event. I highly recommend Captain Ken to plan your next party. read more

We had a most memorable time and cannot wait to sail again, 3 adults 3 teenagers and a 10 year old all sailed and swam with the turtles off beautiful Waikiki! Crew was friendly and made us all feel safe. 3 hours of bliss, like something you see in a movie, treat yourself to a wonderful time!!! read more

I've been to Haunama Bay, but this was more exciting for me. I got to swim with turtles! The anchor wasn't dropped until the best spot was found & there were fun noodles so you didn't have to tire while seeing the sea life. For those of you that get seasick, they even provide an all natural remedy! My ideal snorkel experience. read more

Our family has just booked our 6th sailing trip with Tradewind Charters. Every trip has been wonderful. We have taken our family and our friends on these fun filled excursions. The 40 ft. sail boat and captain take us out for 3 hours of the most fun and beautiful views of the Honolulu/Waikiki coast line that can be viewed. The ocean is so many shades of blue and green. The captain is friendly and knowledgeable. We bring a picnic type lunch and our drinks and sit back and relax and watch the view. We stop for snorkeling at the "Turtle Cleaning Station" where we swim with the sea turtles. This is a wonderful and fun way to spend the day. We HIGHLY RECOMMEND Tradewind Charters to anyone, whether you have been to Oahu before or are a first time visitor. read more

Yesterday we sailed on the "Love Boat" with Capt. "Crash" and Duke for a wedding cruise. Crash is just a nick name. He is a professional sailor. He served as our Captain and our wedding official. He did a lovely job and is very personable. The "Love Boat" is a 40 year old vessel. No problems there, as it is a totally seaworthy craft. However, the boat needs some TLC. The cuddy cabin is a complete mess and is dirty. The exterior teak is heavily weathered and in desperate need of refinishing. I am surprised that someone taking people out for a memorable day does not take the time to clean and prepare the boat so that it presents itself as best as its condition permits. John H read more

Aloha Capt Ken, So good to be back in the Islands enjoying another delightful cruise with you. Full moon, country tunes, delicious grub & awesome company! Mahalo, Linda & Jim read more

What an amazing experience!!! I proposed on a private sunrise cruise with Captain Bobby and his wife Darla. They knew all about the surprise proposal and helped take photos and play our song. The weather was not cooperating but we have a funny story about our engagement. Plus since the winds were so strong and they felt bad they took us out again 2 days later at sunset to make up for it...no charge!!!! Highly recommend these guys for an intimate cruise. read more

Amazing experience! Captain Paul was knowledgeable and made the trip so much fun.

Rather than having a rehearsal dinner for our wedding in Hawaii, we decided to have a catamaran cruise for all our guest to get to know each other before the Big Day. Tradewind Charters offered us a 2 hour cruise around Waikiki Bay inclusive of beer, wine, and cocktails for approximately $50/person. They ran out of white wine, which was a bit disappointing, but the rest of the bartending was good. I believe the catamaran holds up to 50 persons, but I would not recommend having more than 40 persons (the amount we had). There was a captain and bartender on the catamaran to service all our needs, an ipod/stereo connection to bring your own music, and a table/bar to bring your own catered snacks or sandwiches. The catamaran cruise was promised to be on the flat waters of Waikiki Bay, but there must have either been a big swell that day or we ventured a bit further out than planned as there was some heavy rocking of the boat. This resulted in several of our guest getting seasick and the boat having to return to the dock a half hour early to allow those passengers to get back to dry land. All-in-all, I would recommend Tradewind Charters subject to your party size and their ability to tolerate the motion of the ocean. Again, the boat was in good condition and the captain/first-mate were very kind and accommodating. read more

We planned a sunset dinner cruise for bachelorette party with Tradewind Charter. Our host and river was Paul. Paul was absolutely fabulous, kind, and our entire group had a blast. The sunset views were great and our group of 12 really enjoyed it. The booking experience with Tradewind was seamless. Both Cheryl and Ken were helpful. Would definitely recommend! read more

We had a great time being taken out by Paul. Did a bit of fishing and scattered our parents ashes. We were made to feel very comfortable and welcome. Only wish the weather had been nicer so we could have done some snorkelling as well. The certificates for the scattering of the ashes were a beautiful touch. Will definitely use their services again next time we travel to Hawaii. read more

It was awesome, they were very flexible to accommodate our group. We were instructed about the boat, the harbor and things about Oahu and given a first rate excursion. Paul was our captain and things were arranged with Ken. This outing was one our best adventures in Hawaii and would highly recommend Ken and his team. Great job and if we get back to Oahu this will be the first thing we book. Thanks again. David from Calgary Alberta. read more

Our captain, Bobbie, and his wife, took us out for our cruise. They were very pleasant and told us lots of information about the surrounding area. The boat accommodated all us (11) very easily and we were allowed to sit out on the bow so we could enjoy the view more. We were going to snorkel, but the water was rough and wouldn't allow it, which was disappointing but of course not their fault. Free water and beverages were supplied. We would very much recommend them. read more

HORRIBLE. Charged my credit card $495, didn't even go on cruise. Did not advise he would ever charge card. Emailed twice, and no response. BE CAREFUL, DO NOT GIVE "CAPTAIN KEN" YOUR CREDIT CARD NUMBER. I've had to open a case with my credit card to get my money back!!!! Use one of the many honest operators in Waikiki, there are many. read more

It was a fabulous day and a fabulous sailing experience! Thanks Chris for making this a wonderful experience!

We bought a coupon through Living Social for the group Charter online a month in advance. We were all prepared for the charter and had no other plans for the day. An hour and a half before our scheduled appointment I received a call from Tradewind explaining that the Captain called in saying he couldn't make it. I thought this to be a lie considering It was scheduled for 1:00 pm and they had already done a charter for that morning and why would they wait an hour and a half before our scheduled appointment? They ruined our entire day and all they offered us was a rescheduling, which we could not do because we were leaving Hawaii the next day, or a refund. I do not recommend you make an appointment through this company for the same thing might happen to your family! THANKS FOR A RUINED DAY TRADEWIND! That trip only cost my family and my friends family thousands of dollars just for that entire day to be ruined by your company! read more

My family has used Tradewind Charters for spreading the ashes of my Mother and Father. Everything about how they handled the entire expereince was very professional and sensitive to our feelings. All the relatives who participated in the events had only very positive things to say about Captain Ken and the way he treated all of them. We would highly recommend this company for any of the services they offer to all of our friends. read more

We did the evening fireworks boat trip and had a nice time. The food was average, but the boat ride and fireworks were very romantic and a nice touch on our honeymoon. We enjoyed it! read more

My family and I have used Tradewind Charters everytime we come to Oahu. It's a definite must do. The private 3 hour sailing and snorkeling is the most perfect, relaxing and exciting experience. You have your very own private captain, who is very personable and friendly. You aren't in large groups of tourists, as you have your very own private sailboat and experienced captain. I would definitely recommend this experience to anyone I know. read more

We should have known we were being ripped off when there was bad weather and we had to find another venue. The bride arrived in a limo to a car park. That's where he planned on holding the ceremony. We were charged around $10,000 for a few plates of sushi and then he said we couldn't take the flowers because they were for his wife. We had junkies in the park and it was devastating for the bride. Don't do it!!! read more

We have used Tradewind Charters and the Love Boat at least a dozen times and we love it. Captain Ralph and Captain Paul and First Mate Duke are amazing. They know the area and the sea life and keep you educated during the entire trip. Every time we sail with the Love Boat is like the first time. We always have a new and exciting experience. We highly recommend Tradewind Charters and the Love Boat to anyone who wants a wonderful sailing experience looking at the coast of Waikiki and Diamond Head. Tim and Maureen Wright read more

Captain Chris, not to be confused with Captain Ken, took us on a memorable snorkeling excursion. He led us straight to the hot spots where there were loads of turtles and schools of fish and he kept conversation lite and fun. Overall VERY fun excursion and we highly recommend Captain Chris. read more

Capt Ken was unwilling to make any concessions on our wedding reception charter despite many problems, concerns and mishaps. We checked out his boat several days ahead of our booked 3 hour sunset dinner cruise for 23. We immediately grew concerned when we realized there was not nearly enough seating out of the weather for our party - though the boat was advertised for up to 40. There is no where to set down a plate of food or drink - so it's all in your lap. Despite very stormy windy conditions (The AZ Memorial cruise had been cancelling daily) Capt Ken would not allow any kind of a refund when we discussed cancelling a few days ahead. We warned our party not to wear high heels, or risk turning ankles on the matting - despite pictures of decked out people on his website. He was totally unresponsive to our worries so we swallowed hard and decided to try, but thought about cutting it short even if there were no refund. When a horrendous traffic jam on Ala Moana made everyone late - including his caterers - he offered no reduction for our shortened cruise time. It turned out to be only moderately rough conditions - but my mother threw up and others just got extremely quesy and ate little. The Capt realized a bit late that we hadn't yet served the wedding cake (sans flowers) and he began whacking and hacking with the knife and throwing it on the plates, to get that chore out of the way before we hit the dock. Once back at the dock, Capt Ken tied up the bride with paperwork and signing stuff ( a refund for the missing cake flowers that we'd paid extra for, etc) as well-wishers tried to say goodbye and leave. When the Maid of Honor started transporting left over food, the Capt protested that his crew normally gets that. We had paid for a minimum 25, though our seasick party was less, and he wanted the food!! A vehicle parked at the boat basin was broken into and robbed while we sailed. "Too bad". Despite his nice crew, I would suggest finding another charter company and NOT doing business with this individual. read more