Stand-Up Paddleboarding (SUP) is one of the most relaxing and scenic ways to experience Kailua Bay. Cruise over vibrant coral reefs, drift alongside sea turtles, and take in the lush mountain views — all at your own pace.
Our top-quality paddleboards are stable, beginner-friendly, and ready for adventure. Whether you’re up for a solo paddle or want to explore with friends, SUP is a must-do activity for your Oʻahu stay.
Glide across the calm, clear waters of Kailua with premium SUP rentals from Windward Watersports. Whether you’re new to stand-up paddleboarding or looking to explore the Windward Coast on your own terms, our high-quality boards and expert advice will get you on the water with confidence.
Stand-up paddleboarding (SUP) is one of the best ways to experience the natural beauty of Kailua. Paddle through tranquil ocean lagoons, explore hidden coves, and even make your way to offshore islands like Popoiʻa (Flat Island) or the Mokulua Islands.
Calm waters perfect for beginners
Incredible views of the Koʻolau Mountains
Sea turtle and reef fish sightings
Access to protected offshore islands
Our staff will guide you with safety tips, route suggestions, and local insights so you can make the most of your paddle session.
Every SUP rental comes with:
Stable stand-up paddleboard (various sizes)
Adjustable paddle
Safety leash
Life jacket (PFD)
Local area map and expert tips
Optional roof pads and straps for transport
We maintain our boards regularly to ensure a smooth and safe experience for all paddlers.
Choose from a variety of SUP rental options to suit your schedule:
Hourly SUP Rentals – Perfect for quick sessions or first-timers
Half-Day Rentals – Great for paddling to Flat Island or just cruising the bay
Full-Day Rentals – Spend the day exploring Kailua’s coast at your own pace
Multi-Day Rentals – Ideal for vacationers wanting gear on hand
Need to take your board to another beach? Just ask—we’ll help you load it safely.
No experience? No problem. We’ll show you the basics: how to launch, stand, balance, and paddle. Want extra guidance? Ask us about private SUP lessons for all ages.
SUP is easy to learn and fun for all ages. Our boards are stable and beginner-friendly, making this a perfect family or group activity. We also offer tandem boards for paddling with younger kids or furry friends.
Located near Kailua Beach, one of Hawaii’s best SUP spots
High-quality boards for beginners and advanced paddlers
Friendly, knowledgeable staff with local expertise
Safety-focused setup and instruction
Affordable rates and flexible rental times
Thousands have discovered the magic of SUP in Kailua—come see why!
Don’t miss your chance to explore the Windward Coast by paddleboard. Book your SUP rental online or give us a call to reserve your gear today. Windward Watersports is your launch point for adventure on Oahu’s east side.
Is stand-up paddleboarding hard to learn?
SUP is easy to learn with just a few quick tips. Most people are up and paddling within minutes.
Can I paddle to the Mokulua Islands?
Yes! The Mokes are a popular destination. We’ll provide a route map and safety briefing.
What should I bring?
Swimsuit, reef-safe sunscreen, water, and a towel. We’ll provide the rest
