Beachfront Kailua, a small town with a local vibe located on the windward side of the Big Island, is having a moment. While we don’t like to blow the cover on a serene, authentic getaway spot that truly embodies the aloha spirit, we also don’t want you to miss out on the wonders of Kailua. Less than a half an hour drive from Honolulu International Airport, Kailua is a beloved getaway of beach bums and high rollers alike. President Obama has vacationed in Kailua with his family several times, so you know it must be up to snuff. Check out our itinerary of can’t miss activities and destinations in this calm, authentic alternative to nearby Waikiki. Travelers looking less for a tourist trap and more for, well, paradise should hop a flight to Honolulu and cruise on over to Kailua.

Kailua Beach Park


Steady trade winds make Kailua Beach a premier windsurfing destination. In fact, Kailua is the hometown of legendary windsurfing champion Robbie Naish, who brought international attention to the sport for the first time in the 1970s. Kailua Beach is also a frequent winner of best beach competitions, and it’s easy to see why with its white sandy shore and miles of turquoise water. If you’re looking for something more active than just sunbathing, check out kayak rentals and kiteboard lessons.

The Mokes


Mokus Kailua (Mokulua Islands) are a set of small islands sitting off the coast of Kailua, frequently referred to as “the Mokes.” Because Kailua is a protected bay with a far outer reef, the gentle waters out to the Mokes make it a great place to kayak and paddleboard. While the beach at Moko Nui can get a bit crowded, hit the trail to the backside for peace, quiet, and an awesome rugged cove where adventurous types can jump into the water below.

Lanikai Beach

Lanikai means “heavenly beach” in Hawaiian, and we’d say that’s a pretty accurate description, Protected by Kailua Bay, Lanikai Beach has gentler waves, making it a great spot for snorkeling and swimming. There’s also plenty of picnic tables and shady spots here, making this a great family destination for a perfect beach day.

Farmers Markets


Oahu has no shortage of farmers markets chock full of local produce, and Kailua boasts some of the island’s best. Located behind the Kailua fire station on S Kainalu Drive, the Thursday morning farmers market has a huge selection of locally grown fruits and veggies and a small town vibe. The market is only open 9-10 am Thursday mornings, so be sure to go early to get the best produce and fresh cut flowers. Thursday evenings in Kailua feature a second farmers market, this one located in the the parking garage near Longs and Pier 1 Imports. While this one is less picturesque, it’s sheltered from rain, and is a popular local hangout. The evening market runs from 5:00-7:30 pm and you can get great affordable plate lunch specials here, too.

Lanikai Pillboxes Trail

A favorite amongst locals and tourists, the Lanikai Pillbox hike is an easy, hour long hike that affords amazing panoramic views of Lanikai Beach. The trail is named for the two military bunkers—or pillboxes—along the way. If you’re an early riser, this is an amazing spot to catch the sunrise.

Kalapawai Market


In business since 1932, the Kalapawai Market is Kailua’s go-to spot for coffee, sandwiches, and anything you may have forgotten on the way to the beach.

Lanikai Brewing Company


For more local flavor, check out Lanikai Brewing Company. Swing by their weekend tasting hours and sample the appropriately named Pillbox Porter or the Imperial IPA. These are great souvenirs to take home and remember all the places you’ve been in Kailua!
Photos:Markus Jobstl; Haikus; PhotoBobil; MarlonBu; William Bigelis; Maddie W; Robert Linsdell; Lanikai Brewing Company