Kailua

Local Flavor · Windward

Kailua

Local Flavor · Windward

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Hawaii

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Highlights

Kailua vibes like a chill beach town with stunning shores, killer hikes, local eats, and a laid-back, friendly scene.  

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Last updated

Aug 1, 2025

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@nymag

"Then we checked into our VRBO at one of our favorite beaches, Kailua, which is on the southeastern part of the island. It’s a really popular area, particularly for tourists. It gives me retirement vibes. There’s a trail nearby called Lanikai Pillbox and two little islands you can look out to. A lot of people will kayak between Lanikai and Kailua beaches. It’s an ideal place to stay."

Steal My Vacation: Evelynn Escobar
View Postcard for Kailua
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Gail U.

Yelp
If you're heading there on the H3 you'll be going through the Tetsuo Harano tunnel. As kids we'd only have access via the Pali and it was a challenge who could hold their breath the entire distance through the mountain tunnel. You will need to turn on your lights then turn them off once out of the tunnel. The view of the mountains with lush vegetation and a chance sighting of a waterfall if it's been raining is always a thrill. Proceed through part of Kaneohe and follow the signs. Some folks like to go to Lanikai Beach or have shave ice where Barack Obama gives it a thumbs up. For us we just go for a joyride and end up at a delicious breakfast place as there are several on the Windward side of the Island. Hopefully you won't be in need of one but Castle Hospital is close by. Some people dream of living in Kailua but to purchase the real estate be prepared to dish out multi millions of dollars and more.
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Nadine C.

Yelp
Touristing on the Island of Oahu... Kailua is a trendy town on the Windward side of the island. Most visitors stay in Honolulu which is on the South Shore. Kailua is north of Honolulu and Waikiki... about a half hours drive away... The most direct route would be through the Pali Tunnels. Some Hawaii residents think that Kailua is a tourist town. There are many things here that would attract out-of-towners - such as Kailua Beach and its ocean activities such as Stand Up Paddie Boarding and Kayaking. (Lanikai Beach is also beautiful and secluded.) Shopping would be another positive aspect of Kailua since there are many cute boutiques, big stores like Target; and necessities such as the US Post office, Foodland, Safeway, and Times Supermarkets, and credit unions like Aloha Pacific. As a resident, I enjoy Kailua for its foodie adventures. Besides Pieology, Over Easy, Uproll, Mahaloha Burger, Mother Bakery, and Boots and Kimos, there are small businesses like Agnes' Portuguese Bakery with fresh, hot malasadas; Baci Bistro with fine Italian cuisine; and Wilson Store with yummy snacks and refreshing shave ice. The Beet Box has healthy, delicious vegetarian options while Kaohao County Store serves deli sandwiches using Boar's Head quality products. Don't forget to go to the Farmer's Market on Sunday mornings at Pali Lanes and Thursday evenings at Kailua Town! It's really fun to go to Kailua. Sometimes it reminds me of Pasadena, California - especially areas where there's metered street parking... lol! Kailua usually has sunny and warm weather with cooling trade winds. It's no wonder why President Obama enjoys vacationing in Kailua!
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Kuuipo D.

Yelp
Kailua is one of the BEST towns. It seems to have everything here. There are beaches, great eateries, grocery stores, organic food stores, a dog park, and a visiting president once in a while! Kalama Beach Park is wonderful! I usually visit in the morning, when it isn't too crowded. You meet a lot of people walking their dogs. People run the whole length between here and Lanikai. I just walk to take in the beauty of Kailua's beach! The food choices in Kailua are many! Local places such as Moke's and Chad-Lou's are fantastic! Boots & Kimo is a crowd fave. Stores such as Safeway, Longs, Whole Foods, and Target still gives us the convenience of being open late or 24/7. This place seems to have it all & I'm lucky enough to get to live here!