Review for Windward Water Sports 33 Hoolai St, Kailua, HI 96734 Owner/Instructor: Jeff Tobias On August 31, I contacted Windward Water Sports, owned and operated by Jeff Tobias, regarding a kayak rental. Since it was a Sunday and most other rental businesses were closed, we reluctantly went with this company -- a decision I sincerely regret. From the outset, the experience was chaotic and unprofessional. Calling ahead yielded little useful information; staff were unclear, unresponsive, and seemingly uninterested in helping. We were forced to book online due to the lack of timely or reliable communication. Upon arrival, we were issued kayaks and life vests that were in poor, unsafe condition. The life jackets were tattered, worn out, and looked completely unmaintained -- a major safety red flag. It's clear that this business does not prioritize safety or equipment standards. There was no proper safety briefing, and we received no warnings about the unfavorable weather or ocean conditions. The water that day was rough, choppy, and unsafe -- especially for first-time kayakers. No one at Windward Water Sports made any attempt to reschedule us or even disclose these conditions. A responsible and ethical business would have recognized the risk and acted accordingly.The parking at the launch site was disorganized and overcrowded, costing us nearly an hour of our already limited rental window. What should have been a 20-minute paddle to the snorkeling area took over 90 minutes due to the dangerous wave activity. Once we arrived, visibility in the water was zero -- snorkeling was completely out of the question. To make matters worse, on the return trip, one person in our group capsized and could not reboard their kayak without assistance -- a terrifying experience that further reflects the lack of proper safety measures, briefing, or equipment quality. After this ordeal, I requested a partial refund, understanding that we used the kayaks briefly. I was met with a flat denial. The justification? "Business has been bad." That is not a valid excuse. It is completely unacceptable to prioritize your financial struggles over the safety, experience, and basic rights of your customers. At this point, given the unsafe conditions, defective equipment, and the lack of disclosure or professionalism, I am demanding a full refund. That is the only reasonable and ethical course of action. Jeff Tobias needs to do the right thing and issue a full refund immediately. This wasn't just a poor experience -- it was negligent, unsafe, and unethical. I will be filing complaints with relevant consumer protection agencies and posting this review across all major platforms to warn others. Avoid Windward Water Sports. Your safety and your money are worth more. read more

Friendly staff and good equipment! We wanted to rent on Sunday to go to Kaneohe. Unfortunately, most places are closed on Sunday, but not Windward! We called day of to confirm we are able to go to the sand bar on a Sunday. He had a few kayaks left and suggested we reserve it ASAP. We showed up at 10:15 to get our 2 tandem kayaks. Jeff and another employee helped us load it onto the top of our Nissan Altima, taught us how to load it, and told us where to park to get to the sand bar. We were off within 15 minutes. The kayaks are a lot heavier than I expected. They mounted them with ease but it was much harder for us to do on our own. It isn't hard in terms of the order to do everything or how to do it, but it was hard just because it is heavy. Overall I'd rent from here again as long as you have strong people to carry the kayaks. The rental for Kaneohe sand bar must be a full day rental (we used about 4.5 hours but would have felt rushed to get it back in 4 hours). It includes an anchor as well. It was $75 per tandem kayak + tax for us. read more

The thing I like best was the detailed instructions he gave us on where to paddle, the best place to park (it was awesome) the best way to get up on the shore without capsizing and even how to explore the island and what was there. I felt super prepared and we had an amazing day. Not too bad to load and unload and walk to the beach. Because of where they explained to park it made it really easy to get straight out to the islands without having to deal with Kailua Park. Reasonable price. read more

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All equipment worked and usage of kayaks worked out great. Easy pickup and drop off. Staff was friendly and made our rental successful. Will use them again when needed. read more

We rent a tandem kayak and land on flat island and manana island. The stuff walk us through all the details, from where to park to trick of landing, help to load the boat. It was hospitable , patient and instructive, we enjoy the beatific day with Windward read more

Purchased the half-day single kayak rental for 2 through Groupon, and called to book my reservation. I arrived at 9am on 10/5/19 and the guy working was super cool and helpful. He suggested routes we can take, and explained conditions and rules for the islands. If you want to stop on the protected islands, they charge $3 a person. The half day rental is for 4 hours, which was plenty of time. He helped us load the car with the kayaks and strap them on. It's not as hard as it looks! I was able to put them back on with my boyfriend when we were done kayaking. We drove down to Kailua Beach and parking was easy to find (it was still early in the morning). From there, we walked the kayaks out to the ocean and made sure we had everything we needed. I brought a towel which I don't recommend because it was soaking wet after. Bring water, wear a hat, sunglasses and sunscreen. I wore a mini backpack that had my phone/wallet in a ziploc bag. We first went to the seabird sanctuary island, and docked there to walk around and chill. We saw many crabs there! After, we kayaked to Lanikai beach. We saw sea turtles out there which was awesome! We decided to skip on the Mokes since we were pretty tired at that point and wanted some time to swim in the ocean, which is exactly what we did before heading back! This is one of the most beautiful beaches on the island so I highly recommend kayaking there. Thank you Windward for the awesome experience! read more

Windward WaterSports - Between Lanikai and Kailua beach - Rafting/Kayaking Near Me - Kailua, Hawaii

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Owner very nice and accommodating, informative and kind. He helped us load and unload our vehicle for transport, since delivery is not an option per local rules. Kayak was easy for kids but paddle boarding on the ocean was tough for them (windy!!!) and we didn't make it to lanakai beach for snorkeling as planned. Consider all kayaks if your experience on ocean is limited. read more

I am a local, it's been 20 years since I've taken a kayak out and Jeff, the owner made it SO EASY! My visiting girlfriend from Salt Lake City Utah and I easily managed a two person kayak and with Jeff's expertise we were set to make it out to the Mokulua islands. We are two women over 45 and relatively fit so this could help you say "yes" to having a lot of fun! What I appreciated most... 1. I could pull up right in front and load up the kayak 2. Jeff explained ALL the finest details from setting up the kayak, paddle use, the best location to launch for the most direct trip to the island, where to park after dropping off out kayak... even inside the white lines in the road so we wouldn't get a ticket and all in an easy manner that was completely understandable. 3. It was shared with us how to get the boat onto the island and where NOT to go for both safety and ecological reasons. 4. Jeff and his colleague helped take the kayak off afterward and even offered to rinse off our car from the salt water that dripped from our kayak on the short ride back! WHOOP WHOOP! Finally, with all of that, the price was right. Actually, it was better than I could ever expected. Well worth the little we paid. Bonus... we saw a mama monk sea and her pup on the island, the Queen's Bath around on the East side and most of all had over the top and unexpected fun. Note: The kayak is not light so be prepared to manage it both down to the beach and then back onto your car after. But Jeff will tell you that anyway:) read more

Windward WaterSports - And we are off! - Rafting/Kayaking Near Me - Kailua, Hawaii

Jeff was great!! Gave us lots of tips around where to go what to avoid when kayaking. Where to stop and snorkel. Really easy to put on the car and drive right where we put the kayak in. So don't let that detour you from coming here. Thanks Jeff!! read more

Jeff was so great, he gave us advice on where to go and how to navigate the waters. I definitely recommend this shop for the price and experience. read more

These guys are fantastic, and honestly just awesome humans in general. Jeff and the crew were so helpful. From delivering the boards to our house in Kailua, to giving us insider tips on where to eat, drink, golf, and take the Stand Up paddle Boards out, these guys are truly top notch. The prices are probably the best on the island for full week rentals and the equipment was great. Being avid stand up paddle boarders, my husband and I were thrilled with the quality of the rental SUPS we were given. Jeff is a guy who genuinely cares about the happiness of his customers and it shows. Best customer service on the island. Mahalo boys, we had a blast read more

Windward WaterSports - Rafting/Kayaking Near Me - Kailua, Hawaii

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Amazing experience, the guys gave perfect instructions for how to minimize the schlep despite the need to drive a ways to the beach. Very helpful, well-curated kayak adventure! read more

Rented twice from Windward water sports and had the highest level of customer service with a touch of "hey! Let's have fun" attitude. We walked in the first time with kayaks just flying out the door...I thought oh no..we're too late. But nope we got ours and was out the door in seconds. Need less to say...we had an amazing adventure Next time we go back we are going to try SUP and then take a lesson in kiteboarding We love you guys!! Thanks for being so awesome to me and my family!! read more

Called 3 other kayak rental the day before and they were all booked up for next day kayak rentals. I had read another review that Windward Water sports only place that he rents from so I figure I give it a try , not sure if it was our luck but Windward still had a two person kayak .. so I booked it over the phone and was told it be ready to pick up by 9 am when they open . Come the day of to pick up, everything went smoothly, we had to sign a waiver and didn't take more than 10 mins to load the kayak onto our Honda Civic rental car. Quick and efficient customer service. read more

The owner is a super nice dude and treated me very well. I used a paddle board and it was in great shape. The beach you take off from is beautiful and there are far less people than Waikiki. Definitely recommend. read more

Windward WaterSports - This is where I took off from, made it to the island out there, it wasn't too hard and it was really nice. - Rafting/Kayaking Near Me - Kailua, Hawaii

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Grabbed a Groupon to rent some single kayaks and was happy they offered to give us a double instead because the winds and current that day were pretty strong and the boat was so heavy! Service was super friendly and helpful. They told us where to park, which areas were off limits to paddle, supplied straps and supports to help secure the kayak and helped my friend to load it onto our car. Man...I didn't realize how heavy that boat was until they weren't around and I had to help unload, carry it to the water and rehoist it onto the car... So a note to people who are small and short like me: be sure to park as near to the beach as you can to drop the boats / gear off and then repark the car...and park near a curb for extra leverage to help rehoist the boat on the car... Or ask if they supply a wheeled dolly. I saw a couple rental places that supplied that and I think that'd be super helpful. Overall gear was in decent condition. The paddles were a little flimsy so it wasn't as energy efficient in paddling vs the waves and wind but it got the job done. Hope you have fun on the water!! read more

Great place to rent water gear! They hooked it up! You'll need a car in order to get from Windward WaterSports to the beach. The guy explained to us how to get in/out of the kayak properly, how to row, how the wind and currents were for the day, and how to get to the Moku Nui island, making sure to avoid the reef! We got a double kayak, and it comes with seats with backrest so you're resting comfortably as you paddle. They can rent you dry bag (highly recommended) and snorkel gear for $5 extra (you probably won't have enough time to snorkel though). read more

Windward WaterSports - Rafting/Kayaking Near Me - Kailua, Hawaii

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This review is specifically for Miles. He really saved the day for us when we thought there was no chance in us finding a kayak rental. He was super friendly, helpful and informative. If I ever need to rent another kayak and i'm in the area I know where i'll stop first. read more

Windward WaterSports - Rafting/Kayaking Near Me - Kailua, Hawaii

We had the best day on the water and at the beautiful Lanakai beaches! These men spent time explaining the fastest, safest way to get to the island which came in handy when we encountered wrapping waves from both sides! They helped load and unload kayaks and made sure we hit the right spots along the way so we could see turtles!! It was a day our family will remember forever! read more

3h lesson was meh. Trainer walked kite up the beach alright but didnt really be interested to help me get better.

These guys are a class act. They have been around on Kailua longer than anybody and really know what they are doing. They made my experience very low stress despite not kiting in almost a year and in need of some serious refreshing. The helmet mic actually worked, compared to several other places I have been where you lose contact with the instructor as soon as you get out in the water (suspect this with any bluetooth based devices). It does really help to get immediate feedback about what you are doing and tips to improve. I would call before booking anything online because lesson times are a little inaccurate on the website due to covid. Jeff called me right back after I booked a last minute lesson and set everything up perfectly for my ability level after asking me questions about my experience. Highly recommended. Amazing spot to kite read more

I called up to try to get out kiteboarding. I am not a beginner but not totally confident in my abilities either. For kite instructors I think it is hard, because you want to help your students but stuff can go wrong quickly if they over-estimate and over-describe their skills. Anyway, Jeff listened to where I was and helped me get out and have a great day. The wind was close to perfect, but stayed up wind, worked a bit on my transitions. It was my first time out in like 3 years but it all came back. I had Jeff, who owns the shop, and he was really nice and easy to work with. Just a great day. read more

Rented kayaks from them prior to coming to the island. Not sure what to expect when we pulled up and we were beyond impressed, not only do you get a great package with the rentals you get a run down on the trip to the island. They explained where to park, where to tour when on the island, what "red roof" to look for as a point of reference, perfect tour guide without actually being with us on the kayak. To top it off that washed our rental car of all the salt water when we returned the kayaks. read more

I suggest coming to Windward WaterSports for rentals rather than TwoGoods. The owner was very friendly and SUPER informative about where and how to kayak to the islands - answered all of our questions patiently. Half day kayak for tandem is about $55 which also includes the seats. He helped us get the kayak secured on our car as well. Overall GREAT service and not as crowded so got the attention we needed! read more

My first time renting here and the owners were absolutely AMAZING! Friendly, professional and very accommodating to all of our needs! Thank you guys for ALL the custom mermaid hats! I highly recommend a unicorn hat in your future! Stay lit! Thanks guys read more

Windward WaterSports - My bestie with her custom mermaid hat - Rafting/Kayaking Near Me - Kailua, Hawaii

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The staff here are super friendly and very informative - they gave us specific advice about routes, gear, weather, etc and helped us load everything onto our car to get started. We found them via a Livingsocial deal, and overall had a wonderful, seamless kayaking experience for a great price! read more

Amazing experience , professional and quick service Great information for my group of 12 Would definitely recommend these guys to anyone and will be doing this again read more

I bought 2 self guided tours for my nieces who were visiting this week. I called Windward Watersports 5 times to make a reservation and no one ever answered the phone. I left a message twice, with my name and number and still no call back. It looks like other have had similar communication experiences with this company. With 3 or 4 other businesses offering kayak rentals I would avoid these guys and stick with one that is more customer orientated. BTW, Groupon is great. I e-mailed them about the lack of communication and they refunded the purchase immediately. read more

This review is for 5 of us who purchased a Groupon and almost had our day ruined by a miserable experience. We excitedly arrived at Windward with Groupons for $30 Half-day Paddleboarding- comes with board, paddle, and life vest. I would like to say that we all thought the lady who checked us in was incredibly nice and friendly. She got all 5 of us checked-in and gave us information and genuinely wanted us to have fun. She gave us verbal directions to the meeting point at Kailua Beach where we'd find their employee dropping off our equipment. She also gave us a waterpoof business card in case we had any questions or needed help (waterpoof business cards: GENIUS!) She assured us the winds out at the beach were not bad today and we should be fine. She also informed us that their employee will give us a quick lesson and make sure we are ready to go. However things started to go south from then on. Apparently this business is still very new and learning to work out the kinks but the guy (about early 20s, blond, wearing board shorts that were about to fall off) who dropped off the equipment, his attitude was appalling. We got a little lost getting to the beach, but found him just finishing unloading our boards. We noticed there were no life vests (which were included in what we paid on the Groupon.....), he sheepishly said he forgot it. One of our friends was just learning to swim and was expecting a life vest! He didn't even OFFER to take the 5 min drive back to get it. He just dumped the boards and paddles at the top of the hill pretty FAR from the shore and brushed off my friend's worries and said, "Oh you'll be fine." Then we stood awkwardly waiting for him to tell us what to do. He realized that we were all new at this. We asked him to give us the basics, he looked distracted and showed us how to hold and carry the boards. Then he said, "Alright guys, I'm not really suppose to be here right now. But have fun!!" Then he left. WOW. The winds were strong and we had difficultly carrying our own boards, we ended up lugging the boards to the shore and figuring it all out on our own. While I understand that we did not pay for "lessons" but the least they could do was give each customer the basic instructions for their own SAFETY. The procedures in how the customers get their equipment could be improved, specify a meeting point or use signs, tell us your employee's name, have your employee act like he cares. I'm really sorry to say our paddle boarding experience with Windward WaterSports was dark mark on our otherwise awesome Hawaiian vacation. read more

Super easy to find and not overly expensive. I've written from here a couple of times and they've always had excellent service I've even showed up a little late for turn in and pick up and it wasn't a problem. I recommend!! read more

This review is for a group kiteboarding lesson. Instructor Kyle was very friendly and patient, an all-around nice guy to work with. Would recommend him. Have to knock off points because overall their "customer service" approach is laid-back to the point of being borderline unprofessional. They expect customers to call THEM to confirm whether lessons are go/no-go due to weather. Also, instructor was 30 minutes late arriving for the lesson with no phone call or apology. With just a little effort on their part, these folks could make the customer experience more positive and hassle-free. read more

These guys have treated us really well. Last year we rented two SUP boards for a full week, they took great care of us and everything worked out great - they even gave us some good suggestions on places to go and some advice on the weather (it is not like the mainland - more windy). So this year we are going back and reserved two boards for a week again. We leave tomorrow and unfortunately looks like the weather is going to be terrible for the whole week. We emailed them and they gave us a full refund, no questions asked - only two days before we were to arrive. They also said looks like a couple days might be OK, so if we want to come in for just the daily rentals we would be welcome to do that - weather permitting, we definitely will. They've treated us well and we support small business. read more

We rented 8 tandem kayaks last weekend and had a blast! The guys unloaded our kayaks right in front of our house and were super friendly and helpful. Most of our group had never kayaked before, so they gave us a 5 minute rundown on the best practices. We had an amazing trip and they were super easy to work with. Will definitely be calling them again when we return! read more

We have rented kayaks from here twice and will probably keep doing so. They guys at the store are so nice and super chill with the hours you need to return them. The first time we rented a kayak l, the owner was really helpful and took the time to inform us on the weather that day and how to best navigate to the Mokes. The second time we rented we weren't going to be able to return the kayak before they closed at 5, and they said it was no problem just returning it early the next morning go no additional charge! The prices are really reasonable, quality of the items are good, and the staff is knowledgeable. What else could we ask for? read more

We had Groupons for the 4 hour self guided eco tour. We called to arrange our day & time, took care of paying the tax with a cc, so they told us don't come to the office - we'll meet you at the beach at 9am. We get there @ 9 & all the other companies are there, but not ours. The others are helpful & call Windward to tell them we're waiting. They show up about 9:45am & we're understandably a bit hesitant & worried. We tell them we don't need lessons, we've kayaked before. We just need the dry bag & bottle of water included in the Groupon deal. Uh oh, no water & when I say I really want it cuz I counted on it & didn't bring my own, the owner literally ran down to the store to buy two bottles & was really gracious about it. He also explained his main guy no-showed him which was why he was late. We were assured we would get 4 hours even though we started an hour late, and we did. We had a great time kayaking to two islands and I was thrilled to see a turtle swimming below my boat. read more

Friendly and professional. My family and I live here in Honolulu and had not participated in the stand-up paddleboard craze yet. I called this business and reserved 3 boards to be ready for us within the hour. They gave us a resident (kama`aina) discount of 15% off. We paid at the store, then drove over to Kailua Bay to grab our boards and head into the water. After a little while paddling around, we realized that one of the boards was defective and, therefore, more difficult to maneuver. After our day, we went back to the store to tell the owner/manager about the defective board. He refunded our money immediately for the broken board. No questions asked. Very nice. We had fun pretending to be tourists for the day and this place made it possible. read more

My husband and I stopped in to see if they had any SUP's for sale. The girl behind the cash register says are you guys professionals? We said no but it will be a family board and want something good. She said ,"we only have 1 and it is $1050, but you would be better off going to Costco and getting one there! That's what I have and it works great!" Come on! We don't have to be a professional to get service in helping us find a board. But sending us to Costco cause you have a cheap foam board one is not my idea of good customer service. I really liked the board that they had for sale but decide against purchasing something here due to there own staff not having faith in there products! read more

Recently I stopped by windward water sports ran by Jeff and David, because I was interested in renting some kayaks while some friends were in town. When I had got there I saw that he taught kite boarding lessons as well. At first I was a bit nervous about doing a lesson, but he had explained to me that he had been doing this for 20 years and that he was a professional kite boarder for 10 years which to me shows how experienced he is. I signed up for his zero to hero package which is a 3 day lesson, and within no time had me up on the board comfortably. I asked him about purchasing some equipment and he was able to really educate me on which kite to buy for a beginner like me that would be the most cost effective. If you are ever interested in doing kite boarding, kayaking or just renting a bike go check Jeff and David on 33 hoolai street in Kailua. read more

Windward WaterSports - Owner Jeff doing cleaning up around the shop making sure the community looks good!!! - Rafting/Kayaking Near Me - Kailua, Hawaii

I am born and raised in Kailua and have everything I need in terms of watersports equipment so I have had minimal dealings with any of the watersport places in Kailua but I had to write a review for this company since it was my first experience with them. I had to get a small tear in my kite repaired and I was going to take it to Naish but left on a trip so my wife decided to surprise me by getting it repaired while I was gone. She decided to bring it here instead which has proven to be a HUGE mistake. They told her that it would be done in no later then 1 week. She called back a week later and was told that it would be done the next day. Sure enough, she got a call that it was ready to come pick up but she wasn't able to go in because of work. We both went by 2 days after they called to pick up the kite but it wasn't there. The guy working had no idea where it was and didn't even know when it would be available. We told them we had received a call that it was there but he had no idea who or why anyone called since it wasn't at the shop. He said that they would call that day or the next to let us know when we could get it. 5 days later and still no call so my wife calls them to ask where the kite is. They tell her they don't know and will call her when they find it. She decides to just go to the shop and what do you know....its sitting in the back. Completely unprofessional business and I am going to tell every single person I know on this island never to go here or recommend anyone to go here. DO NOT EVER get your kite repaired by these kooks and for that matter, anyone visiting Kailua, go rent your kayaks or water equipment from Twogood or some other place. There are more then enough of these watersport places in Kailua already so it would be nice to see the bad ones go out of business. read more

The most invigorating experience! Got put on to Windward Water Sports by Paradise Bay (@ Kaneohe) and LOVED EVERY MINUTE! Registration was easy, the team at HQ made us feel at home! Never kayaked 'for real' before, so I was a little reserved about the experience before we got in the water but our guide Kepa was really knowledgeable, natural and 'cool'. He was sensibly FUN and that kind've approach really helped us feel comfortable (Ocean kayaking is a big deal!). We were slightly late getting out, but that wasn't due to the team @ WWS, a couple had arrived late etc, this probably did make us 'strapped for time' but our group didn't seem to mind (if that were me, I'd hope my group would be patient too!) as well as having a 'cool group', Kepa didn't at all rush or make us feel restricted during the tour. On this trip we choppered over Oahu, swam with dolphins, horsebacked Kualoa but THIS by far has been the best experience of all. A long day - kayaking, climbing around the bird sanctuary, snorkelling @ Lanikai but well worth it, we're definitely coming back! Thanks Kepa and everyone @ Windward Water Sports! You guys are THE ULTIMATE! read more