This is my first kitesurfing lesson with Kyle and I was a little apprehensive due to safety issues with the sport. Kyle made me feel very SAFE in the water with the kite. He was very thorough and patient with me and our group. He is personable and I didn't feel threatened even when the waves were beating me a bit as I learn to fly the kite. I got hooked as soon as we tried BODY DRAGGING as I felt the kite's POWER! Must admit we had a rough start because of communication issues the day before when we had our lesson scheduled and could not find WINDWARD WATERSPORTS vehicle in Kailua beach. We drove from EWA beach to Kailua and I spent the morning looking for my instructor. This was worthwhile as I have confidence that Kyle was going to teach me how to become a worthy kiteboarder who can stay safe with the rest of the guys and gals who are more experienced. Going for my second lesson soon! 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

Super helpful staff and convenient location! We had the best day kayaking out to Chinaman's Hat and climbing to the top. I loved that they had 3-person kayaks, too. read more

Very flexible and great to work with! They called me the night before to explain the very poor weather conditions and helped me reschedule. So glad they did because I would not have known about the poor conditions for myself as I'm visiting. Highly recommend!! read more

Very simple and easy process. Rented a kayak from the for the day. The guy was very informative and knowledgeable on best places to park and how to get to where we wanted to go. Would recommend this place to anyone looking to kayak as the pricing was unbeatable. read more

My wife gave me a zero to hero kite surfing lesson package for Christmas and it was one of the best presents ever. I was fortunate to have Ben Corbett as my teacher and he is excellent. He is very personable. He is dedicated and will teach you to kite surf safely and ensure that you are ready to progress on your own upon completion. He goes above and beyond the call of duty to make sure you are satisfied with your experience. Have fun! read more

This is the best place to rent a kayak. Their kayaks are solid stuff, and will not sink. When you rent one they give you paddles, back supporters, loading equipment and life vests. They even can accommodate you if you're a small person and need a youth size life vest. The staff are really nice and helpful, and the guy helped me figure out where to park, where to launch the kayak, a good route to get to my destination, and he even filled me in on the how the water was that day (it was choppy). They don't just have kayaks, they have other stuff, too, like surfboards. This place is run by really good people, and I recommend it! read more

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

Jeff is a good instructor but his equipment is in bad shape. A third of the lesson was tied up with equipment malfunction fixes. Yet I was charged for a full three hours. Jeff promised to text me for next lesson but never did. Doesn't answer his phone and voicemail full. By the time I figured out Jeff was not happening, it was too late to arrange a lesson with another instructor. Pretty disappointing! read more

Once again a great time at this establishment. Just my second time. It calling for rentals was easy, kamaaina rate was a plus. Brought my cousins here who were on their honeymoon so we could kayak to the Mokes. We were 15mins late if our 4 hour rental due to missing our access point at the beach and they were super understanding. Guest service here is great, it's isn't crowded like Kailua Kayaks right by Kailua Beach. I will always make the extra 5 min drive to get Guest service like this! Thank you and keep up the good work! read more

4 parents 4 kids age 8-9 went kayaking & snorkeling in the sea to a rugged island, a beautiful white sandy beach & got to snorkel with a turtle! The conditions were perfect! The owner & guide friendly & well informed. read more

We called ahead to check on conditions, and they were honest with us about it being windy. After we decided we still wanted to go, they gave us a run through of how to assemble the seats of the kayak and how to paddle correctly. Then they strapped the kayaks on the car for us. I also want to note that from Waikiki it is about a 30-45 minute drive, but the views are amazing if you take route 61 so it is worth it. also, it wasn't 4 miles to the beach as someone else noted. The guy working there was awesome and very helpful. He showed us the best route to take to the parking lot to put our boats in the water, as well as the best path to take to the islands we wanted to go, and where the beat snorkeling spots were. I would go back again anytime I visit the island. read more

Called and they had the SUP delivered within the hour. Had a blast. Lanikai Beach and Kailua Bay are amazing. I'm in love with SUP now. Thank you so much for the great service, board, and experience. read more

Windward WaterSports - Thank you for delivering. Amazing service, board, delivery within the hour. Love Kailua Bay and SUP! - Rafting/Kayaking Near Me - Kailua, Hawaii

I'm on vacation in Oahu with my family and wanted to go kayaking. I did a yelp search and found this place. Wonderful experience. Jeff was thorough and concise not to mention sincerely nice. He gave detailed directions, recommendations, and ensured we had everything necessary to have a good time. He even hosed down our rental to get the sand and seawater residue off. Bonus points for recommending the acai bowl cart across the way- perfect snack after kayaking in warm weather. I highly suggest booking any rentals for water equipment through his business and will definitely recommend his business to others. read more

These guys were awesome! They didn't just take our money and send us off with a kayack. They gave us awesome instructions on the best spots to kayack to. They showed us how to load and unload and even the best place to park! They made our kayaking adventure flawless and for a great price! Great service!!! read more

Very friendly and helpful. The dude who helped us turned what could have been a bummer of a day into an awesome time! Highly recommended!

I purchased the chump to champ kite board lessons from Windward Watersports. I was skeptical at first if I would get the hang of the sport in that amount of time. I have zero boarding experience prior to these lessons. Jeff (the owner) took his time on the phone and at the shop answering all the questions I had and addressed my concerns. First day of lessons I met David at Kailua beach. He introduced himself and we went over some safety practices. David taught me how to setup and launch the kite. I flew the kite for a while and the whole time David was full of praise and we then went in the water. He taught me how to body drag and to power the kite. Honestly, I thought this was kind of weird, why am I dragging myself through the water with a powerful kite? Is this necessary? Lesson 3 proved why I had to endure all these steps that I didn't fully understand as to why I was doing them. That's David's version of wax on wax off. He is Mr Miyagi of kite boards. It all made sense and yes, I was riding downwind by the end of my lessons. I had such a great experience that I purchased a full kite package from Windward Watersports. The equipment I was training with was all new model kites and boards and David took his time to explain differences in the equipment on the market. After my lessons I went back to Kailua and came across David. He went out of his way to say hello. I definitely didn't feel like "just a customer". I was watching other kiters and was just trying to pick up on some techniques and talk about their equipment. I finally decided to purchase equipment. I decided I didn't want the hassle of buying used. I shopped around and ran into David and asked him for a kite package deal. He said of course and made me a complete deal that couldn't be beat with great equipment that will last me a long time and that I will learn into. Windward had all the gear in stock except for the board size I wanted. They ordered it and in the meantime, David took me out and showed me exactly how to care for and handle my new investment, he even loaned me his board so I could play a while with my new kite. I believe he did this out of love for the sport. My board took a while to show up but Jeff and David were very accommodating. They loaned me a board anytime I wanted to go out and kite. This type of customer service has me as a loyal customer for life. There is no reason for me to go anywhere else for any of my Watersports needs. I have a buddy who took kite lessons from "a guy" against my recommendation. His experience was nothing like mine. His instructor was distracted on the phone and he had multiple equipment problems. My friend will be taking lessons from Windward and David when he goes next time. I have to throw out a shout out to Ben. He also teaches for Windward. He has always been encouraging and helpful even though he wasn't ever officially a instructor of mine. He has even given some tips and instruction just again out of the love for the sport. My experience could not have been better! read more

Windward WaterSports - My first time up on the board. Thanks David. - Rafting/Kayaking Near Me - Kailua, Hawaii

I went into the store and spoke with someone asking about kiteboarding lessons. She took my information and said everyone was out giving lessons and someone would contact me. After not hearing back from them for 3 days, I went back to the store and spoke with Jeff, the owner. I told him my expectations and he suggested the "Chump to Champ" program. This was 9 lessons (broken into 3, 90 minute sessions) designed to make a someone a self sufficient kiteboarder. I had no illusions, I did not expect to win any competition or trophy at the end of this. I expected to be self sufficient, which is what is advertised. Jeff said he wanted to teach me personally but, he was leaving town. We scheduled something for after his return. Two days after Jeff and I spoke, I got a return call from the staff concerning my original visit. I thought this was odd since Jeff and I already set something up. The staff had no idea I had already paid for and scheduled lessons. The day before my lessons were to begin, I got a text from Jeff. He said he was tied up in the states. I said I understand, it happens. Not a problem. We rescheduled. The day before the rescheduled lesson I got another text from Jeff saying the same thing. Again, not a problem. Living on an island makes for difficult travel. Jeff gets back into town and the morning of the lesson, I get a text saying that he has a lot of administrative stuff to do for his business, can we push the lesson to the afternoon. This is still not a problem. I understand the difficulty of being a business owner. Early afternoon, Jeff texts me that John is going to do my lesson. He texts that he is a good instructor and he has been with Windward Water Sports for 4 years. I am still okay with this but, I'm thinking I took 10 days off work to learn how to do this and I spent a week waiting only to have someone else (who was available the entire time) giving me lessons. I met John and he and I began. I don't know if he was good or bad as an instructor. Truth is I had never done this before and no one in my shoes would be able to tell the difference. From day to day, I progressed at a normal pace but, I also regressed as well, which I'm sure is normal. At the end of the 3 days, I had only been on the board once and up for about 2 seconds. I was no where near self sufficient. Again, I didn't have any illusions of "winning the Gold". I live here and I just wanted to be able to do this on my own. Also, in John's defense, learning to fly the kite is probably the most important and overlooked aspect of kiteboarding and we did a lot of that. I actually feel confident that I can fly a kite. Jeff called me and I told him I was frustrated that I am no where near self sufficient. His solution was for me to buy more lessons. He said he would work with me. If I bought 1, he would give me 1 for free and he would instruct me himself. I reluctantly agreed and told him I would stop in the shop, pay for a lesson, and schedule something. He said okay. I stopped by the shop after work and they were closed (it was about an hour before their posted closing time). For the next 4 days, I called to try to set something up and he was never there. The staff was indifferent. They just said "Try back tomorrow." At no point did I get a call from them. I eventually gave up trying to make contact with Windward Water Sports and they didn't seem to notice or care. If you want to rent kayaks or paddle boards, they have lots of them and are more than happy to help. If you want kiteboarding lessons, go somewhere else. There are plenty of online, free, resources. Start there. read more

Came here to rent a kayak and the service was excellent. Jeff and David really know what they are talking about with the ocean. They also teach wind surfing and I was interested but ran out of time here on the island. Will go back and get lessons for kite boarding read more

My friends and I rented kayaks from here a could not have had a better experience! Kayaks came with everything you needed and they helped strap them to our cars. They also gave us some tips on paddling out to the mokes for those of us who had never done it. Great customer service!! I will definitely recommend Windward Watersports to my friends and visitors! Thank you for a great experience! read more

I purchased a groupon or living social coupon for 4 hours of SUP for two. At first it seems great--go to their website to make reservations online a month in advance (that's an important detail in just a minute), which is awesome for a smaller company to have set up. So I'm making plans for my stay-cation during a mainland girlfriend's vacation, and on this past Thursday, those plans included a morning at Hanauma Bay and an afternoon of SUP in Kailua, from 3 to 7pm. We knew we wouldn't have the boards out that long, but a couple hours of fun and using the sun starting to lower as our clock...all good. So we leave Hanauma at 1:45, start heading out that way. I get a phone call from Liz just after 2 pm that there was some glitch in the computer system that let me make reservations for that late--they close at 5. Now, we're on our way over there but now we're only getting half the time? No thanks, so we begrudgingly change the reservation to 1-5pm the next day, knowing that we'll have to skip the surfing rentals we were planning for after a morning snorkel sail, but such is life. The biggest problem I saw so far was that they don't look at reservations until literally an hour before the guests are supposed to arrive, even though they've had them for a month. Seriously? So the snorkel sail runs late (MaiTai Catamaran, highly recommended--ever see anything run longer than scheduled in Waikiki? They've usually got you back in 15 minutes early to start the next group) and traffic is a mess, so we don't get to Kailua until just after 2:00. Now we're sort of laughing that it was worthless, we rescheduled to get the time back and only end up with an extra 30 minutes or so. But we go in anyway, get directions to where we meet their truck at the beach, and head over. We get to Kailua Beach Park and take a little time getting our beach stuff together, putting on sunscreen, find the dirt road where we pick up the boards, etc. And the truck isn't there. So we wait, then call to ask WTF and Liz says he had to run back to the shop to unload the truck and will be there in a minute. Ok...so we keep waiting, at 3:00 I call again and Liz says basically "he's coming, he was there at 1pm and waited 45 minutes you weren't so get over it", and I go off. We reschedule because of their ineptitude, lose a bunch of our scheduled time because of the last minute switch, and she's gonna imply it's our fault we couldn't get there on time? Sorry that we made firm plans for lots to do on vacation that didn't accommodate a last minute change in the line up. Finally the driver arrives, and he's VERY friendly and helpful, and we finally get out on the water. We did our best to enjoy it but the lack of customer service--especially after a customer has been inconvenienced once--really soured the experience for my friend and I. TL;DR--Reservation system needs to be revised/checked more frequently. Small company needs to work on improving customer service to succeed with groupon quantities of customers. read more

Took some kites in for repairs and they promised me they would be ready the next day. I chose them over another shop merely because of turnaround time. Since I am on vacation I had limited time to get them fixed so I could use them while on my trip. Its been 4 days and I just called in for the third day in a row and they still haven't started. Im now picking them up to take to a different shop. read more

Reasonably priced, friendly staff, about a mile away from Kailua beach. Rented SUP boards here for half a day, came with everything we needed, including straps for the car and a permit for the islands, and had a blast. read more

We purchased a living social deal for our trip to Hawaii and had the most awesome time ever with windward watersports. The staff was really helpful in answering all of my type A questions from what to wear, to SPF recs, to a billion "will I get stung/bit/scratched/near death" questions. We went on the 4 hour kayak tour with an included lunch. Our guide was Kepa. We lucked out and got a private tour as the other couple was an hour late. He was so calm and reassuring I'm sure I would've flipped the kayak had he not been such a good coach. My fiancé and I were in a double, he was in a single, and I'm sure he could've smoked us if he wanted. He was pleasant the whole time and super informative about the ocean, coral, sealife, jellys, bugs, landscapes, etc. We also met the owner and his adorable daughter, also really nice people. I think the biggest bonus was that he didn't make us feel like total fishes out of the water or talk to us like kids. We were the first to the destination island and we walked around searching various tide pools and dodging black crabs, and by the time we got back to our boats another group arrived and that guide would have hands down driven me bananas. I cannot recommend them more highly. It was the highlight of our Oahu leg of the trip. read more

The guys there are awesome. Helped get the tandem kayak on our rental car with no rack. Worked great. Quick 7 minute drive to Kailua Beach. Had a great day on the water. Exactly what you want from renting a kayak. read more

I lived in Hawaii for about a year and as a college student used groupon alot to rent kayaks and standup paddleboards..i used several companies but windward watersports was one of the best! most affordable, able to take reservations at the last minute at times, friendly staff, etc. it helped make the best of my time in hawaii! def recommend them! read more

Rented three 2-person kayaks for our family for 1/2 day. The guys at Windward WaterSports were fantastic! They gave us lots of tips and helped us get the kayaks on and off our car. They were so friendly and helpful and even rinsed all the salt off our rental car when we were done. Reasonable prices too. I would highly recommend them. read more

These guys were great. Friendly and helpful. We rented two double and one single kayaks from them. They loaded them on our car and showed us where to go. We spent a little more then an hour on the water and kicked back on the beach midway. It was a great time for all of us. read more

I highly suggest renting from here! Staff is phenomenal...even rinsed our car off post trip. Friendly and knows the area. Gave us a quick lesson and showed us where was best to go. The kayaks were well taken care of and you have plenty of options for rentals...bikes, paddle boards, single and double kayaks, and any gear you need. Will definitely be back! read more

My BFF and I wanted to learn how to paddleboard, but didn't want to try to learn on our own. I'm glad we decided to get some instruction because it was well worth it! The two hours we spent with the instructor Cody was great! He took time to instruct us both, and knew how to explain different techniques to us in ways that we could understand. We started out in the canal to learn the basics and then he took us out in the ocean. We had a great time! Cody made our first experience on a SUP a memorable one. Jeff, back at the shop was also super helpful and friendly! Great customer service all around! read more

Awesome time kayaking to the Mokes! Rented 3 two-person kayaks for our group of 6. The guys at the shop were very helpful in informing us of where to park/depart from, how to get the kayaks tied to our cars, where to go on the Mokes island, how to get into and out of our kayaks.... Very friendly and easy to talk to & ask questions to. The kayaks seemed to be of normal quality. Will definitely do business with them again. read more

A bunch of friends and I rented a bunch of kayaks. We went out to the moles it was a blast! Jeff and the staff were a great help!

Windward Watersports is the best place to rent kayaks and stand-up paddle boards. They are the only ones who deliver your equipment right to you; we got our at Kailua Beach Park. The kayak are great, with back rests, too (only company that includes back rests). They have all the gear you might need. We got great lip protection and a case for my iPhone what keeps it dry and ready to use as a phone and a camera. If you want the easiest way to have a great day or half day at the beach, this is it!! read more

Awesome experience renting kayaks & SUPs from Windward Watersports. Super friendly staff & helpful too! Also the store has a great selection of Sun Bum products. Check these guys out! I'll definitely be back! read more

Took kiteboarding lessons and had a blast. I highly recommend kiting to anyone looking for a unique and challenging way to experience Hawaii. The instructor Ben was really fun, helpful, and knowledgable. read more

I absolutely love this place! It was the first time my family and I rented a SUP and a kayak so we were unsure of how to tie them onto the car, but David was so helpful and did it for us (also showed us how to do it). The customer service is absolutely amazing. I highly recommend this place! Also, kama'aina discounts are available. read more

Bike Rentals: 7 speed cruisers, 1 week rental $100, pick up & delivery. Outstanding customer service.

The snorkel gear is *the best* I've ever used. Everything fit perfectly for both my husband and I... and (best of all) no water ever crept into our masks/snorkels. We were able to see the beautiful sea life while completely relaxed due to our confidence in the equipment. Many thanks for such a wonderful experience! :) read more

I just rented a SUP for the week. I met Jeff the owner- he was very nice and helpful. He even put the SUP on my rental vehicle for me. I would rent from them again!!! read more

Purchased and kayaking and snorking trip. It was awesome the staff was awesome and our guide was friendly and let us take our time and we really enjoyed ourselves this place is a must. read more

Prices are reasonable, customer service was excellent and our experience with the kayak was amazing! They were really helpful with showing us the best route for kayaking to the Mok islands, as well as loading the kayak on and off our Jeep. They even washed our vehicle off before we left. I highly recommend this place for rentals! My husband and I will be back next time we need a kayak! read more