Kailua Town

Located about 40 minutes from Waikiki is Kailua, a laid-back, beach town with mom-and-pop shops, art galleries, and quaint cafes — all five-minutes from award-winning Kailua Beach. 

Perhaps the most famous town on Oahu’s windward side, Kailua is far removed from the bustle of Honolulu. As you drive through the neighborhood you’ll see million-dollar homes (the price to live in paradise), people riding bikes to and from the beach, and local businesses like surf stores and artisan coffee shops. 

Archeologists believe that Hawaiians have lived in Kailua for at least 1,500 years. However, the neighborhood’s modern development didn’t begin until freeways were constructed across the Ko’olau Mountain Range, which connected Kailua to Honolulu. 

Fun Fact! Kailua is a favorite vacation spot for former president Barack Obama. The 44th President of the United States was born and raised on Oahu — so we’d consider him an expert on the island. He loves Kailua so much, he’s vacationed there every Christmas since he took office! 

About Kailua Beach Park

Kailua Beach | Daniel Ramirez from Honolulu, USA, CC BY 2.0, via Wikimedia Commons

Now, for one of Kailua’s main draws — the beach. This beach is so good, it was actually named 2019’s “Best Beach in America” by Dr. Beach. 

Kailua Beach is a three-mile stretch of shore with soft, white sand and turquoise waters. The waves are gentle, which make this spot great for kayaking, paddling and stand-up paddleboarding. You might even see people windsurfing! If you’re interested in trying out a water sport yourself, you can rent gear in Kailua Town. If not, spend some time relaxing in the sand while embracing the beauty of this beach. 

Where to Eat in Kailua 

There are so many great places to grab a bite in Kailua. Here are some of our favorites: 

• Boots and Kimos 
• Mokes 
• Cinnamon’s 
• ChadLou’s 
• Nalu Health Bar 
• Morning Brew 
• Lanikai Juice 
• Konos 
• Over Easy 
• Goen 
• Maui Brew Co. 
• Kalapawai Market 

Tips for Your Trip

1. Parking at Kailua Beach Park fills up on the weekends. You might have to drive around or wait for a spot. Try to arrive early to find one! 
2. There are public restrooms, showers to rinse off in, volleyball courts and picnic tables at Kailua Beach Park. There are also lifeguards on duty. 
3. If you’re on Shaka Guide’s East Oahu Shoreline Drive, Kailua is a great place to stop for lunch! 

SHAKA GUIDE'S OAHU TOURS: Grand Circle Island Tour, East Oahu Shoreline Drive, Honolulu's Backyard Rainforest Tour, Legendary North Shore Loop, Heart of Waikiki Walking Tour, Historic Downtown Honolulu Walking Tour