5 Things You Have to Do in Kailua, Oahu

5 Things You Have to Do in Kailua, Oahu

By land and sea, the windward town calls to active clients By: Marty Wentzel
<p>Island Snow has two shave ice locations in Kailua. // © 2016 Creative Commons user <a href="https://www.flickr.com/photos/45688285@N00/"...

Island Snow has two shave ice locations in Kailua. // © 2016 Creative Commons user _e.t.

Feature image (above): A hike up Kaiwa Ridge Trail leads to stunning windward Oahu views. // © 2016 Vance Martin

Related Content

Discover five unique Hawaii festivals with aloha spirit.

When it’s time to unwind, President Barack Obama and his family have chosen Kailua, Oahu, as their preferred retreat. Located on the island’s scenic windward side, Kailua represents a mellow escape from the fast pace of Honolulu.

Even though Kailua is a thriving community with boutiques and restaurants, it’s still a beach town at heart. Known for its strikingly turquoise waters and soft white sands, it’s a beautiful getaway for travelers staying in bustling Waikiki (about a 40-minute drive).

Kailua Beach Park serves as a focal point for visitors and locals alike, but there’s much more to do than just swim and sunbathe. Here are five fun pastimes awaiting clients in Kailua, a little slice of paradise.

Kailua is relatively flat. That makes it easy to explore by bike, especially on weekdays when traffic is lighter. Clients can rent a two-wheeler from the Bike Shop and get to know the area while pedaling along its many miles of bicycle paths. Kailua is even easier to tour on an electric bike. Pedego Kailua’s two- and four-hour guided e-bike excursions include a catered lunch.


The Kaiwa Ridge Trail leads to spectacular views of the windward side. Measuring 1 mile each way, the path is a steep and rocky climb, but the summit rewards hikers with fine photo ops. It’s nicknamed Pillbox Trail for the WWII military bunkers along the route. Look for the trailhead across from Mid-Pacific Country Club. Be sure to observe the “no parking” signs in the neighborhood.

Kailua Bay has reliably calm waters, making it ideal for kayaking. Clients can paddle and play during guided tours to remote beaches and hidden tide pools. Some outings take folks to the offshore Mokulua Islands, home of nesting seabirds. Most tours provide a picnic lunch and time for snorkeling. For independent travelers, kayak rentals are also available.


Segway Tours
Visitors glide effortlessly along sidewalks and bike paths while standing on these unique two-wheel, self-balancing electric vehicles. Tours include a bay and beach itinerary with panoramic views and tide pool explorations. Another option focuses on the rich history, culture and nature of the area. Segway also offers private tours geared to the skill levels and interests of the participants.


Shave Ice
When Obama and his family vacation in Kailua, the president always stops at Island Snow, serving Hawaii’s exotic version of the snow cone. Obama’s go-to flavor combination of lemon-lime, cherry and passion-guava syrups is now dubbed the Snow-bama. With two locations, Island Snow provides a sweet spot to regroup before setting out for more adventures in Kailua.