Oahu’s Lush Windward Side: Kailua Town and Lanikai

For a cool taste of the trade winds, head to Oahu’s lush Windward side. Windward Oahu is an easy drive over the Pali Highway (61) from downtown Honolulu to quaint Kailua Town.


Kailua Town

Kailua Town was once a sleepy beachside community that drew few outside visitors. Today it’s grown to a thriving community that attracts thousands of visitors every week. It’s also a popular place for people to settle down and raise a family. Unlike busy Waikiki, Kailua is very much a local retreat, although its residents welcome visitors.

Downtown Kailua is relatively compact with a number of unique restaurants and boutique shopping. While downtown, you’ll probably spot a dog or two. Kailua is one of the most dog-friendly spots on Oahu, and many local businesses sport a water bowl for furry companions. Bicycling is popular in downtown Kailua because it is so compact. Several shops will rent bikes for the day that allow you to explore all of downtown or take a short ride over to Kailua Beach.

Kailua Beach and nearby Lanikai Beach are often thought to be two of the most beautiful, and dog friendly, beaches on Oahu. They both look out at the Mokulua Islands (Mokulua means two islands), commonly known as The Mokes. Adventure seekers can rent a kayak or stand-up paddleboard to get a closer look. Both islands are bird sanctuaries, and the smaller islet, Moku Iki, on the right, is off-limits to visitors, as is the interior of the larger island on the left, Mokulua Nui. The beach at Mokulua Nui is open to all.

As with any beach or open-water excursion, if you spend time out on Kailua Bay, be sure to protect your skin, drink plenty of water, and pay close attention to ocean conditions. As our lifeguards say: “when in doubt, don’t go out.”

Photo by Shutterstock/Shane Myers Photography


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