Growing up in Kailua, the Windward side of the island of Oahu always brings fond memories of the beautiful, lush greenery of the Ko’olau mountain range down to the blue Pacific Ocean beaches. I spent my entire childhood in the city of Kailua and there is nowhere else in the world that I can imagine calling home.
Here are a few places that you shouldn’t miss when visiting the small town of Kailua. There are several bed and breakfast places in the city of Kailua, but no hotels; you would need to go to the other side of the island and the majority of hotels are in Waikiki, roughly a half hour drive through the mountains.
Places to stay: Bed and Breakfast and Vacation Homes in Kailua
Sharon’s Kailua Serenity — Bed and Breakfast
127 Kakahiaka Street, Kailua, HI 96734 – (808) 262-5621
Prices are comparable to a hotel room in Waikiki, if not better as you are in the midst of local residents, outside of the busy tourist area. They are located four blocks from Kailua Beach, where you will find canoe paddlers practicing their strokes in beautiful canoes, windsurfers are a safe distance in the foreground for you to enjoy while playing near the shore with individuals and families.
Kalapawai Market — Shop and Eat
306 South Kalaheo Avenue, Kailua, HI 96734
Hours of Operation: Daily 6 a.m. to 9 p.m., The deli is open daily 7 a.m. to 8 p.m.
This is a well known establishment since 1932, when my Aunt and Uncle Richard and Elsie Wong ran the store. It was also my first job as a cashier when I was a junior at Kailua High School. Since my family retired some years ago, Kalapawai Market has been modified with a deli in the back where my Aunt and Uncle lived and raised my cousins. The side warehouse looking building used to house a workshop that my cousin Randy would shape surfboards. The exterior remains familiar with the same color scheme with spruced up pain and lettering but still is a local favorite beach store on your way to a picnic at the beach.
Mount Olomana — Hiking
Besides the beaches of Kailua, if you’re interested in observing and hiking the beautiful mountains that you drive through and pass on your way to and from Kailua, you’ll want to look into some of the hiking trails that locals and visitors have enjoyed for many years.
The Hawaiian Trail and Mountain Club rate this hike for Intermediate level hikers and the third peak for advanced hikers only.
Always be aware of your environment and never go off of the trails. Each year the Honolulu City and County Fire and Rescue are called out to look for lost hikers. Earlier this year a classmate of mine, although experienced and hiking with a group of friends, had gone beyond the normal hiking peak; slipped and fell to his death. I say this to warn you that no matter what your experience, there are many hiking trails that are safe to journey on for healthy individuals, but you must heed the warnings. If you are a less experienced hiker, I would highly suggest a great hike on the other side of the island at Diamond Head Crater.
Favorite Place to Eat in Kailua, Oahu
Unfortunately many of the little hole-in-the-wall eateries we used to visit regularly in Kailua are no longer around; like Andy’s Drive In, Craig’s Bakery and the little Okazuya lunch box place that was only open a few hours in the morning and after school near the intersection of Kailua Road and Oneawa Street. However, there is one gleam of light and that is Maui Tacos in Kailua. Originally started on the island of Maui, their twist on the tastes of the islands into their Mexican style could give the Tex-Mex a run with the name, Mexican Surf Grill.
Kailua 539 Kailua Road, Kailua HI 96734, Ph: (808) 261-4155
This is a quaint little eatery that you can order take-out or eat in their small shop or at the tables outside. Great for lunch of dinner, there’s free parking, casual food similar to a quick stop to eat but you’ll want to savor the flavors of every bite. My favorite is the Signature Maui Tacos made with marinated grilled fish and the Maui Taco Salads, again with fish. They have vegetarian, combo specials and traditional Mexican style also. Their salsa bar is awesome, I especially love the Mango Salsa.
Other Articles of Interest
Travel guide to the North Shore of Oahu
Family travel guide to Hawaii National Monuments
Five places I would see before leaving Oahu
Best places to visit on a Honolulu vacation
Hawaii cuisine — Favorite local foods and eateries in Honolulu, Hawaii