• Kayaking

    Kayak Kailua Bay on the beautiful island of Oahu, Hawaii. Kayaking in Kailua is truly an amazing experience. We provide kayak rentals, kayak tours, and kayak delivery. Kayak paddle, safety vest, are included. Call us at 808-261-7873 for more information. Group discounts available. Reserve kayaks today.

    Reserve a Kayak

  • Kiteboarding

    Kiteboarding in Hawaii is an awesome way to experience Aloha. Warm sun and crystal waters offer a great combination to beginners and experts. Kailua beach has sandy beaches and is a safe launch for learning. It also offers off shore waves to kite surf on. Book a lesson now or rent some new gear today.

    Reserve Kiteboarding Lesson

  • Stand Up Paddle

    Stand Up Paddle boarding has exploded in popularity in Kailua and across Hawaii. It’s a great way to tour Kailua or Laniki Beaches. Paddle Kailua Bay, even catch some waves. SUP lessons and rentals are available. We’ll deliver the boards or you pick up from our shop. Rent a SUP board today.

    Reserve Stand Up Paddle Gear

  • Surfing

    Surfing and Hawaii has been synonymous for decades. We have more surf breaks around Kailua & Oahu than you’ll find anywhere. We offer surfing lessons in Oahu by boat. This ensure a safe environment and good waves. If you are advanced surfer, ask about tow in surfing. Take surfing lessons now.

    Reserve Surfing Lesson

Windward Watersports – The Best Kayak Rentals, Tours & Lessons in Kailua, Hawaii. Enjoy Vacation.

Windward WaterSports on TV!

Check out Windward WaterSports’ Jeff  Tobias teach Alison Haislip from G4 how to kiteboard.

The crew head out to an offshore sandbar on WWS’ 35′ boat “Arleene“.  The winds were light but they managed to faceplant Allison a few times before she called it quits.  If we can get Alison this far in only 20 mins, just imagine how fast you could learn!  With our radio helmet coaching system we guarantee to get you up and going faster than any other school.  Check it out.

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Windward Watersports is your one stop shop for water sports on Oahu’s windward side.  We rent kayaks, stand up paddle boards, snorking equipment, surf boards and more. We also offer guided and self guided tours by kayak or stand up paddle board.

We offer extended rental programs- So if you are staying on the island for 1 week or 4 we will drop off and pick up kayaks, snorkel gear, surfboards or any of our other rentals we offer right at your front door.
Kailua is a special place.  We do our best to show you all that it has to offer while educating and preserving its fragile ecosystem.  A portion of your rental will go to protecting the beaches and off-shore islands of Kailua so the next generations of visitors can enjoy this special place.

Kailua is a beautiful beach town nestled below the Koolau mountains.  Voted most beautiful beach in America.  Kailua is a true  watersports paradise.  Windward Watersports has everything you need to get out there and have a good time.  Lessons, rentals and tours are all here.  Come on out and get wet!

Windward Watersports home to Kailua Kiteboarding School

KKS is Oahu’s premiere kitesurfing school. Insured & safe.  KKS’s owner Jeff Tobias was the first instructor to teach the sport here in Kailua over 10 years ago! Over that time he has developed methods that will get you on the water safer and faster than anyone else. If you want to learn to kitesurf come to the only school on Oahu ran by a professional kiteboarder.  Certified, insured and permitted.