If you’re looking for a tropical Hawaii that’s more low-key than Honolulu but not quite as sleepy as the North Shore, head to the east side, or windward side, of the island. Here you will find lush jungles and an excellent string of beaches surrounding the town of Kailua.
The lifestyle here feels more like a beach town than a city, but it also has enough going on to entertain you in the evening. This is our rundown of what to do when you’re spending the day in Kailua.
2 beautiful Beaches
Oahu is blessed with white sandy beaches, and no visit to Kailua is complete without a visit to one of the nearby beaches. Two favorites are Kailua Beach and Lanikai Beach.
Kailua Beach is 2.5 miles long, perfect for walks any time of day, but especially in the early morning (the sun rises offshore) and during the evening twilight. The beach is easily accessible and has great people watching but can get crowded in front of the main beach park area, where kayaks, boats, wind surfers, kite surfers, and stand-up paddlers launch and head out towards the offshore islands (see below).
If you’re seeking something more relaxed, the crowd thins out as you head north along the beach. Considering entering at the Kalama or Oneawa beach parks if you want more room to breathe.
Lanikai Beach is just south of Kailua Beach, although you cannot get there along the coast by foot. Drive into Lanikai neighborhood, park on the street (please be respectful of local residents), and enter at one of the many public beach access walkways.
You’ll get a great view of the offshore Mokulua islands from Lanikai, referred to locally as “The Mokes,” and the water at Lanikai is usually very calm, creating a serene and safe environment for swimming and snorkeling.
Activities / Adventures
There are many local ways of life in Kailua besides going to the beach, and they all take place outside. The following is a small list of things to do while in town:
- Kailua Beach Adventures offers kayaking and stand-up paddleboards for rent, including lessons and tours to the offshore islands.
- The Lanikai Pillbox is a popular sunrise hike, with views over the ocean and the Mokes, and more advanced hikers should head to Olomana for a steep climb that rewards with views of Kailua, Kaneohe, and Waimanalo.
- For mellow waves and longboard surfing, head to Castles Break at the far north end of Kailua Beach.
- After working hours, hang out around the canal at Kailua Beach Park to watch the outrigger canoe teams head out for an evening practice. Known as “paddling,” it is one of the most revered and ancient sports in all of Hawaii, with competitions and clubs on every island.
In the following video shot on Christmas day 2017 by Gemini Connect you can see an abridged version of the Lanikai Pillbox hike:
Get a taste of the local life (eating, drinking and farmers markets)
Eating and drinking like a local is one of our favorite things to do while on holiday, and this is extremely easy while in Kailua.
Farmers Markets in Kailua
There are three farmers markets in Kailua but you have to be visiting on Thursday or Sunday to see them:
- The People’s Open Market every Thursday morning at Kailua District Park;
- The Hawaii Farm Bureau Market every Thursday evening at the Kailua Town Center parking garage; and
- The Lōkahi Kailua Market every Sunday on Uluniu Street.
These markets are a great way to see a dose of local life, to buy local products, and to try delicious foods from local vendors.
Places to eat in Kailua
Kailua may be a small town, but it does have a lot to offer in the way of tasty local fare:
- Buzz’s is the only beach-side restaurant, just across from Kailua Beach adjacent to the canal. At night it’s a pricy (and delicious) steakhouse – we love it during happy hour, when you can sit out on the deck for a drink and a range of reasonably-priced appetizers.
- For a proper seafood dinner, head to Nico’s on the north edge of town, including poke nachos, clams, swordfish, and fresh local catch.
- Other great eats are the Kalua pork at Kono’s, the ramen at Rai Rai Ramen, the sushi and Japanese at Tokoname, and the sandwiches at Kalapawai Market.
Finally, Lanikai Juice is a good place for if you’re just looking for a refreshing smoothie or acai bowl snack, and if you’re planning on grilling out on the beach you should pick up marinated meats at Hibachi.
Kailua Bars and Cafes (great places to grab a drink)
After a long day outside, there are plenty of local places to grab a drink:
- If it’s beer you crave, check out Lanikai Brewing’s Tap & Barrel or the beloved beer bar Grace in Growlers, a nonprofit establishment that donates its proceeds to charity.
- Three Peaks, once simply a beer bar, has now expanded to brew its own beer, too, under the name Olomana Brewing.
- Maui Brewing has a tap room in Kailua, though if you’re looking to support local businesses, our previously mentioned options would be a better choice.
Otherwise, the aforementioned patio at Buzz’s is a great place for a mai tai (heralded as the best and strongest in town, mind you). And, believe it or not, the Windward Bar at Whole Foods is a popular hangout for locals.
Kailua doesn’t have many upscale nightlife experiences, but it does have a small, jazzy speakeasy called Gaslamp if you’re looking for a reason to spruce up a bit.
Putting it all together: a sample 1-day itinerary for Kailua:
You should now have more than enough ideas for things to do and places to see to spend not one but three full days in Kailua. We propose the following 1-day itinerary for you if you don’t want to make the hard choices (those of removing things from your itinerary) yourself.
Start out early with a coffee-in-hand, sunrise stroll on Lanikai or Kailua Beach, then hit Lanikai Juice for a healthy breakfast (smoothie or acai bowl). Head to Kailua Beach Adventures and hop on a kayak tour out to the offshore islands, then grab sandwiches from Kalapawai Market (Kailua Beach location) and eat them on the beach, relaxing for the rest of the afternoon.
Go to the deck at Buzz’s for happy hour during the sunset hour for mai tais and appetizers, and explore the town later that night for dinner and a local beer.
Other 1-day itineraries for Oahu:
We have made other “1 day in …” itineraries for Oahu which are very useful to start planning your trip: