Windward WaterSports
Surfing & Windsurfing • Water Sports • Kayaking & Canoeing
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9:00 AM - 5:00 PM
Monday
9:00 AM - 5:00 PM
Tuesday
9:00 AM - 5:00 PM
Wednesday
9:00 AM - 5:00 PM
Thursday
9:00 AM - 5:00 PM
Friday
9:00 AM - 5:00 PM
Saturday
9:00 AM - 5:00 PM
Sunday
9:00 AM - 5:00 PM
About
Windward Watersports offers a full range of ocean activities, including: Kaying, snorkeling, surfing, standup paddleboarding, bike rentals and kiteboarding! Come in today or checkout our website for more information!
Kailua, Hawaii

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Windward WaterSports
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Travelers talk about
(2 reviews)
(2 reviews)
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions

4.5
61 reviews
Excellent
52
Very good
5
Average
1
Poor
0
Terrible
3

Jessica H
11 contributions
Feb 2020 • Couples
They were amazing, super nice and helpful!! We were originally booked for a day that turned out to have terrible weather (super windy and a big rain storm). They checked the weather for us and changed our reservation for the best weather day during our trip, and then gave us some ideas on what we could still do that day around there. When we went back to actually kayak, they were very helpful with giving us the best itinerary for our time, provided detailed directions for driving and where to park, where to kayak, and where to snorkel. They provide free roof racks for the kayaks, and help get them up and down which was very helpful. All in all, they were very pleasant to work with and we highly recommend them to anybody wanting to rent outdoor equipment in Kailua.
Written February 8, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Anna K
1 contribution
May 2021
I had a wonderful experience renting kayaks last weekend. The owner was wonderful. He was friendly, super helpful, and gave us directions and guidance on where to Kayak. I would totally rent again from them, the customer service was fantastic!!!
Written June 2, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Laura S
Arlington, VA5 contributions
May 2014 • Couples
We went kayaking and snorkeling with these guys and our guide, Cody, was awesome! We kayaked out to Shark's Cove and climbed on the rocks, which was so beautiful and exciting. Then we kayaked over to Lanikai Beach for lunch- one of the most breathtaking beaches I've ever seen! The snorkeling there wasn't so great, but that wasn't a highlight of the trip anyway. Good times!
Written May 19, 2014
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

November W
New York1 contribution
Jul 2014 • Solo
I had to pay upfront for 3hs of kiteboarding lessons (1h on 3 separate days). After the first day, subsequent lessons were cancelled repeatedly by instructor. In the end they never happened, even though I was available another 5 days! They promised me a refund, which I never received, even after a long email conversation with the owner, Jeff. He never came through, and basically stole $200 from me.
Written November 8, 2014
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

mike h
Chicago, IL1 contribution
Mar 2014 • Family
STAY AWAY !! I purchased 3 single kayak rentals on GROUPON. I made a reservation 2 days prior and was told the kayak's were available for the day of my reservation. I called the morning of the kayaking day asking for directions and was not told of any problem. I drove 45 minutes to get there with my family and when I arrived, I was told there were no single kayak's available. The receptionist told me that she has called me and left me a message, but this was a lie. She then told me I could have a triple kayak for the same money I had paid. When I asked to see the triple kayak, I was shown a 2+1 kayak which is really only suitable for 2 adults and not the 3 adults in our party. In addition, that kayak normally rents for much less than I had paid. I asked to speak to the owner, but he was not answering his phone. After about 30 minutes, I was told that there were no life jackets available so all the talk of taking a different kayak was a waste of time! I asked for a refund and was given a refund receipt, but later that night, the owner texted me to say that he could not directly provide a refund. I am still waiting on my refund. The owner also called me to apologize and offer a free rental, but if a paid and reserved kayak order is not fulfilled, can you imagine what they would do with a free one !!?? It seems to me that this outfit was able to rent kayaks at a higher rate than I had paid on Groupon and did so with no concern for me or my family. We wasted a day of our vacation which also happened to be the last day of our vacation. Despite making the reservation in advance, confirming twice in advance and paying in advance, they still gave away our kayaks and wasted our time getting there and back as well as more time trying to get us into an unsuitable kayak which in the end they didn't even have lifejackets for !! Even worse, we were provided with lies (left a message, gave a refund, etc). IMAGINE...they don't have enough lifejackets !!?? While I was in the store, there was another family there who had had the same experience as me and was there for fulfillment of their previous reservation !! There are other outfits in Kailua that rent kayaks. DON'T waste your vacation time and money with Windward watersports. Find another reputable outfit to do business with. The prices elsewhere are the same and you don't get the lies, aggravation, wasted time, false apologies and wasted vacation time!!
Written March 31, 2014
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Aloha Mike, Let me start off by apologizing again. There was no excuse for what happened. It came down to an accidental over booking. I promise you that it was nothing more than that. We would never give out pre reserved equipment to a higher paying customer. If that were the case you would see a lot more reviews about that here. This is actually the second time in five years that we had an over booking. We try our hardest to exceed our customers expectations. I am terribly sorry that this ruined your day. As for the refund- We never charged you so we could not process a refund. You bought your voucher from groupon and they dont pay us until your voucher is used. They are great about refunds though and will take care of you with a quick phone call. Our offer stands, if you and your family are ever back here your entire day will be free. Thanks,
Written April 24, 2014
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

TrailBlazer253592
1 contribution
We made a reservation for 4 single kayaks for 1/2 day for Sunday and were told to meet across the street from Buzz's(a well known bar and grill). Arrived an hour early and waited for 1/2 hour past our reservation time, talked to every kayak renter on every corner only to be told no one had any reservation and no company does groupon( which was a pre paid discount coupon for 1 kayak rental). What should of been a simple meet you here and go pre paid tour became a no show by company, and after several phone calls the following day to owner we got excuses like blaming us for not phoning them when we could not find them. Offered to have us return and use a credit, but we did not have another day available to return to the other side of the island, as well as rent another vehicle at 130.00 for the day! Bottom line here is we showed they didn't, no refund offered, cost us 300 dollars and 1/2 a day waisted! This company seemed to forget that the customer is always right and I think this review will cost them a lot more than simple refund would of.
...and yes, we were also told Sunday is their busiest day and the kayaks always get rented...that means they doubled their money that day!
Written March 14, 2011
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Im not sure what to say to this. Our location is extremely clear. We are at the same place every day. Coincidentally i looked back trough our reservations and could not see anything of you ever being a customer of ours. I think this might be a case of mistaken identity. Our company along with 3 others are at the same beach launch site everyday. If you were a customer of ours i dont see how you could have not seen us. We have never had that happen before. This post is clearly fake. Its a shame that someone can bash a company like this and its such a respected sight. Please remove your post. Its a flat out lie.
Written April 8, 2011
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Jenni G
Portland, OR2 contributions
Jul 2013 • Friends
Absolutely wonderful! Jeff was our guide and he was great. We aren't in the best of shape, so he was very patient and helpful. He was friendly and knowledgeable about the area. The kayaking was a bit of work but he didn't make us feel rushed. He took us to a little island and took us cliff jumping. It was awesome!!! He was very instructive on where to step and how to walk on the rocks and talked us through the jump so that it was safe. There was also a short break for a simple and tasty sack lunch and snorkeling. Overall it was a little over 4 hrs. I would highly recommend this activity and would totally do it again sometime!
Written July 1, 2013
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Real_Expectations
Montreal13 contributions
Aug 2011
Before arriving to Oahu, Hawaii I did my homework and searched all kite board schools, I stopped my choice on Windward watersports. I was right; I booked a semi-private introduction course, the first day it was cancelled due to lack of wind. I was surprised at first but once you try flying the kite you understand that 15 mph constant wind is a minimum, without 15 mph winds, it is like trying to fly a regular kite with no wind it does not work, well Kite board is pretty much the same.

The first semi-private was rebooked for the next day; the course was 3 hours it touched all the right aspects and we got as far as body drag in the sea. I took a private lesson the same day late afternoon with the owner Jeff Tobias. Wow! Google this guy, it is like taking a golf course with Tiger Woods! He reviewed what I had learnt in the morning and we started from there, along with his helmet with integrated communication, he was able to voice his instructions while I was in the water, which really accelerated my learning.

I am back home, I am hooked, I am looking at buying my own equipment, I want to get better and better and go back to Hawaii and Kite in Kailua!

I windsurfed for several years; I just could not believe how easy kite board was compared to windsurf.

Thanks Windward!
Written August 17, 2011
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

VL1966
Denver, CO7 contributions
Nov 2019
Highly recommend you rent from these guys! They are the absolute best! This was our second time renting from Windward Watersports. We wanted to rent a tandem kayak to paddle out to the twin islands Tuesday of Thanksgiving week. Unfortunately, it was too windy to go out there, so they let us pick up a kayak on Wednesday before closing, and knowing they’d be closed Thanksgiving, told us to bring it back Friday morning. My daughter and I had an amazing time paddling to the Mokes, and enjoyed our time on the small island-we even saw Lani the Monk Seal make her way from the ocean onto the beach to sun herself. Unfortunately, as I put the kayak in the water to head back to Lanikai, I encountered a rogue wave which pushed the kayak into me. At that moment I felt my ankle snap and immediately knew it was broken. Fortunately there were people on the small island who called 911 and the ocean rescue folks came out and were able to get us back on rescue boards on the back of jet-skis. Lol, that’s a whole other story, I think that was the highlight of my 20 year old daughter’s trip. As they put me in the ambulance someone asked me who we rented the kayak from and I told them Windward Water-sports. The gentleman told me he knew Jeff and would contact him to retrieve the abandoned kayak, still on the island. My husband talked to Jeff and the other guy (David maybe), and felt badly they had to take time away from their families on Thanksgiving to go retrieve an abandoned kayak from the twin islands, but thats what they did. (You can’t really leave an abandoned kayak there, otherwise people start calling 911 about potential missing kayakers). I was still in my life vest at the hospital and my hubby was able to return it the following day. Anyway, I’m sure that’s not how they wanted to spend their Thanksgiving, but that day I was especially thankful for everyone involved who helped me that’s day.
Written December 8, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Kate T
California44 contributions
May 2019 • Couples
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 🤙🏼
Written April 30, 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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Windward WaterSports (Kailua) - All You Need to Know BEFORE You Go