Kailua – A Piece of Paradise on the Windward Shore

Published
Categorized as Oahu Vacation Information

Scenic Beaches Border Revitalized Kailua Town

Kailua is a peaceful town on Oahu’s windward coast with upscale residential areas and scenic beaches bordering Kailua Bay.

In one sense, Kailua is your typical suburb, a thriving small community with many local businesses and community organizations. Kailua is a bedroom community of Honolulu, and many Kailua residents commute the 12 miles southwest to Honolulu each day for work, driving over the Nu‘uanu Pali in the majestic Ko‘olau Mountains.

What really makes Kailua different from your average suburb, however, is that it is also an ocean community and many resident’s lives revolve around their daily trips to the sea. This connection to the ocean is what makes the area a popular vacation destination.

If you decide to stay in Kailua during your Oahu vacation, please check out our Kailua vacation rentals.

Kailua Beach One of Hawaii’s Finest Beaches

Kailua Beach is a beautiful crescent of white sand about two miles long with a gently sloping ocean floor. Designated as the “Best Beach in America” by coastal expert Dr. Stephen Leatherman, Kailua Beach is a great place for a nice long stroll along the scenic shoreline.

Windsurfers, kitesurfers, and sailors all enjoy the ideal conditions of Kailua Bay with its steady tradewinds blowing from the northeast. Stand up paddling and kayaking are also very popular.  Outrigger canoe clubs train in the bay, and several large regattas are held here each year.

Many ocean enthusiasts like to paddle or swim out to visit the offshore islands – Flat Island and the Mokulua Islands – which are seabird sanctuaries.  This ocean adventure is only for people who are experienced and know what they are doing.  The islands can appear much closer than they actually are, and the ocean can be dangerous with currents and unpredictable swells even when it appears calm.

Also in the Kailua region is 830-acre Kawai Nui Marsh, the largest area of wetlands in the Hawaiian Islands. The dike along Kawai Nui Marsh is a relaxing and enjoyable hike.

Shopping – My Passion

After a morning at the beach I enjoy strolling around the revitalized Kailua Town where there are shopping opportunities galore. I have to confess I am an avid shopper, and so I love all of the boutiques, galleries, and antique stores in Kailua – and Macys of course!

The small and easy-to-access Kailua business district is a great place to find just about anything you need. One of my favorite places in Kailua is the Nohea Gallery which supports local artists and craftspeople.

When it comes to Bakeries I am partial to the Nene Goose Bakery on Keolu Drive, and also Agnes Portuguese Bake Shop on Hoolai Street.

In the boutique category you will often find me at Olive Boutique on Kihapai Street or at Muumuu Heaven on Kailua Road.

If you want to see some exquisite furniture check out Red Bamboo which is also on Kailua Road.

When you need a break from all that shopping get some refreshments at Lanikai Juice Company where the fruit is always fresh and healthy.

More fresh food can be found at the local Farmer’s Markets. I recommend the one held in Kailua District Park from 9 to 10 a.m. (be on time). Farmers offer locally grown vegetables, fruit, flowers and even fresh fish.

Kailua Dining and Night Life

Kailua has several nice places offering entertainment on weekends. I really enjoy Jarons restaurant which has live music Thursday through Saturday.

Restaurants of all types are found in Kailua and include a diverse array of cultural cuisines including Japanese, Moroccan, Italian, Thai, and more.  I tend to gravitate toward the great Steakhouses and Seafood restaurants which never fail to satisfy me, but you will have to make up your own mind.

Surrounding Kailua’s business district are mostly modest single family homes in very pleasant residential areas.  I usually stay in this area as the neighborhoods are so nice and there are affordable and yet very comfortable luxury vacation rentals available, and I just love the close access to the beach as well as town.

History of Kailua

In ancient times, Kailua was home to ali‘i (royalty) and chiefs, and several heiau (sacred places of worship) were located in this region.

In the 1930s, Kailua was a small, sleepy town with a population of about 3,000.  This changed during World War II when the Army’s Fort Hase and the Navy base now known as Marine Corps Base Hawaii expanded on lands purchased from Kaneohe Ranch.

Kaneohe Ranch closed in the 1940s and donated large amounts of land to the community for schools, churches, and a hospital. In the late 1950s a four lane highway was built that tunneled through the Ko‘olau Mountains, making it much easier to commute to Honolulu.

By 1960 the population of Kailua had grown to more than 24,000, and has more than doubled since that time. Castle Hospital (now Castle Medical Center) opened in 1963.

Today Kailua is still a small town though it is still the largest town on O‘ahu’s windward side.  With some of the most nicest beaches on the island, it is now wonder that scenes from Lost, Magnum P.I., and Hawaii Five-O were filmed here.

With beautiful beaches, great shopping and dining, and wonderful places to stay, some people come to Kailua and never leave.

Additional Resources:

Kailua Chamber of Commerce