The windward side is typically just that, windy, a weather condition that can adversely affect surfing conditions unless the winds are blowing offshore. Unfortunately, the windward side usually sees onshore winds, leaving little in the way of consistent, good quality waves for surfing. On the other hand, sports like sailboarding and kitesurfing that flourish in the windy conditions are popular in this region, centered around Kailua where most of the outfitters are located.
The outer reefs of Maunalua Bay hold a wealth of surf spots for expert surfers who are comfortable with very long paddles to the breaking waves and surfing over shallow and sharp coral reefs. Because the waves break so far offshore mixed with a lack of shoreline access, it’s nearly impossible for the visiting surfer to distinguish between the different breaks and know which break is surfable and which waves are breaking over dry reef.
There are some options, however, for those who would like to learn to surf, or charter a boat to surf in Maunalua Bay. Hawaiian Surf Adventure (7192 Kalanianaole Hwy., 808/396-2324, 9am-5pm Mon.-Sat.) accesses a secluded wave in Maunalua Bay by boat, which is a gentle surf break perfect for beginner surfers. There are no crowds to contend with, just you and the instructor. Group lessons are $89; private lessons are $149. Hawaiian Surf Adventure also offers stand-up paddle lessons and tours of Maunalua Bay starting at $99 as well as outrigger canoe tours. Island Watersports Hawaii (377 Keahole St., 808/224-0076, 7am-7pm daily) also taps into the uncrowded waves of Maunalua Bay with two-hour group surf lessons for $99 and 1.5-hour private lessons starting at $125. If you’d rather stand-up paddle the bay, two-hour group lessons are $99 and 1.5-hour private lessons start at $125.
To the east of Koko Head is the infamous Sandy Beach, known for its powerful shorebreak. As a favorite of local bodyboarders and bodysurfers, the water’s edge fills with heads bobbing up and down, waiting to drop into a heaving barrel, right onto the sand. If this sounds dangerous, that’s because it is. Every year people are seriously injured at Sandy Beach, with everything from broken limbs to broken necks, even death. The waves can get big, especially in the summer months. If you’re not a strong swimmer or comfortable in the surf zone, take solace in the fact that it’s quite amusing to watch people get slammed from the safety of the beach. Check with lifeguards for current conditions. There are also two surfing breaks over a sharp and shallow coral reef, Full Point and Half Point, at the north end of the beach.
All along Kailua beaches, from Lanikai to Kalama Beach Park, the ocean conditions are usually just right for stand-up paddling. With a soft, sandy bottom, little to no shorebreak, and generally calm water, the area around Kalama Beach Park is perfect for distance paddling up and down the coast. If you paddle out from Kailua Beach, there is Flat Island to explore. And if you’re paddling from Lanikai Beach, there is a bit more rock and reef off the beach, so you can explore the near-shore waters or paddle out to the Mokulua Islands. During the winter months, there are two surf breaks that reveal themselves on either side of Moku Nui, the larger of the two islands. Keep in mind that if the surf is big enough for waves to be breaking on the outer reefs, the ocean currents will be much stronger. Stand-up paddle surfing should only be attempted by expert stand-up paddlers.
Stand-up paddling can become more of a chore than a pleasurable experience in extremely windy conditions. When the wind does pick up and the ocean surface becomes choppy and bumpy, sailboarders and kitesurfers take to the water in Kailua instead.
You can rent stand-up paddle boards at Kailua Sailboards & Kayaks (130 Kailua Rd., Ste. 101B, 808/262-2555 or 888/457-5737, 8:30am-5pm daily) for $49 half day and $59 full day, with multiday prices and free carts to walk the board to the beach. They rent beginner and advanced sailboard setups starting at $59 half day and $69 full day, and offer a Windsurf Tour for $99. They have kiteboards and gear for sale, but pre-ordering your gear is recommended. The retail outlet is within walking distance of Kailua Beach Park.
Windward Watersports (33 Hoolai St., 808/261-7873, 9am-5pm daily) is a complete water sports shop selling new and used boards and gear for many activities. They rent stand-up paddle boards starting at $49 half day and $59 full day, with two-hour lessons for $99. They rent kiteboards starting at $30. Actual rental of the kite is contingent upon your skill level, or beginners can take a one-hour course with a certified instructor. Located in Kailua town, they’ll help you put racks and watercraft on your vehicle for the short drive to the beach.
Hawaiian WaterSports (167 Hamakua Dr., 808/262-5483, 9am-5pm daily) also located in Kailua, rents stand-up paddle boards starting at $69 for a full day with multiday rentals. They have a wide range of boards 7-14 feet and boards for all skill levels, and you can exchange your board at any time during your rental period. Sailboard rentals start at $59 half day, $69 full day, and they also offer two-hour lessons—group lessons start at $99, private for $179. Kiteboards are also available for rent starting at $29 per day. Different lessons are offered depending on your skill level. Private lessons start at $179 for 1.5 hours of instruction.