The first rays of pink and orange sun flicker across the gentle morning waves as a paddle boarder launches into the water. My toes sink into the soft sand as I walk along the shoreline. I leisurely continue down the beach, watching for the changes in color as the sun moves upward over the Mokulua Islands, located a few miles off shore. While I’ve watched countless sunrises from Kailua’s Lanikai Beach, there’s something about Kailua’s humble island charm that keeps drawing me back.
This town on the east side of Oahu is the laid-back traveler’s dream. I’ve spent every summer in this unobtrusive town since I was a child. Over the years, it has started to attract a bit more visitors, especially after former President Obama started vacationing in Kailua during his presidency. If I could have a vacation home anywhere, it would be along the beach in Kailua. With miles of pristine shoreline, great local eats, and nearby hiking, it’s truly a postcard-worthy destination.
Here are some of my favorite things to do in Kailua.
Watch the Sunrise
Watching the sun rise on Lanikai Beach is the most beautiful scene I’ve witnessed in all my travels. The changing morning colors overhead, along with the picturesque Mokulua Islands and the sound of gentle waves is dream-like. Check the weather for the exact time the sun is expected to rise and arrive at the beach 30 minutes beforehand. Bring a beach towel to sit and relax, or take a walk down the shore.
Breakfast from Agnes Bakery
After such an early morning, you’ll need some breakfast and coffee. My favorite is Agnes Bakery located in Kailua town. This no-fuss Portuguese bakery sells delicious fresh and hot malasadas (essentially a Portuguese doughnut) and a selection of other pastries and breads. If you’re staying in a hotel or house with a lanai (patio, in Hawaiian) this is the perfect breakfast to pick up and enjoy outdoors.
Hike to the Pillboxes
Also known as the Kaiwa Ridge Trail, this hike is one the easiest and most rewarding trails on Oahu. Rated as easy to intermediate, the short walking trail has a moderately steep grade, which takes hikers to two bunkers formerly used by the military. Today, they’re used as spots to watch the sunrise or take a rest mid-hike. From the top, you’ll be rewarded with an incredible view of the Mokulua Islands, Lanikai Beach, and Kaneohe Bay in the distance.
The trailhead is located on an unnamed street, but there is a sign with the words “Pillbox Hiking Trail” that will point you in the right direction. You have to pass through some brush and go up an initial steep incline to reach the actual trailhead. If you’re not a seasoned hiker, this hike is a great option. I’ve seen people do it wearing flip flops (known in Hawaii as rubber slippers) and many locals bring their dogs along.
Shopping in Kailua Town
While seemingly touristy, these specialty shops carry local items and handmade goods that are loved by both tourists and locals. My favorite is a store called Global Village. The store sells clothing, local artwork and decor, jewelry, and a variety of knick-knacks that are island-inspired. I rarely leave without making a purchase. Another go-to is Island Snow, a shaved ice shop that also has a large selection of surf/skate clothing and their own line of t-shirts, hoodies, and hats.
What to Wear
No one in Hawaii ever dresses too fancy. I always pack outfits that are easy to throw on and still look presentable. I love wearing simple outfits of denim cut-offs with tees or tanks from local shops. I also pack a bunch of casual dresses to use as beach cover-ups and pair with sandals for dinner.
Leis and flowers are iconic symbols of Hawaii so I always love the opportunity to wear a lei or haku (pictured above). They’re the best accessories!
