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A Perfect Day in Kailua

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Kailua is the kind of town you expect from Hawaii – full of long, sandy beaches, aqua blue waters, hillside hikes, and nary a high rise building in sight. Just 20 minutes along a scenic mountain drive from Waikiki, is well worth a day trip, if not a home base for your Oahu vacation.

Start your day in Kailua the way the locals do – with a big plate of delicious macadamia nut pancakes at Boots n Kimo’s. A local staple, the tiny yet charming restaurant has just moved to a larger space down the street, so hopefully the wait for a table will be reduced. This place is always bustling, and you’ll discover why when you devour your stack of pancakes drizzled in their signature mac nut butter sauce.

After breakfast, you will be ready to work off those calories the most scenic and fun way possible – with a kayak trip out to the Mokes. “The Mokes” are the local lingo for the Mokulua Islands (“twin” islands) that are about a quarter mile off the coast of one of Oahu’s most famed beach, Lanikai.

Head over to Kailua Sailboards & Kayaks (it’s also not a bad idea to call ahead and make a reservation) to rent a kayak. They offer doubles and singles, and will set you up in the canal to head out. A challenging paddle, yet still doable for beginners, it will take you about an hour (depending on winds) to get out to the Mokes.

Along the way you will be amongst outrigger canoes, surfers, kite boarders, sea turtles, and coral reef. Once you get to the island and disembark, you will be richly rewarded with panoramic views of Lanikai Beach and the hills beyond, as well as the impressive Ko`olau mountain range, Waimanalo Beach, and Kaneohe.

If you planned ahead, you can enjoy a restful picnic on the island’s sandy stretch before heading back. There is not much room to wander on the Mokes due to their steep and rocky terrain, but the more adventurous visitors tend to trek around to the back and jump off some of the rocky cliffs. Unless you are a very strong swimmer and have a local guide to take you, this is not recommended. The waves and current out at the Mokes can be very dangerous, and are best enjoyed from a boat.

After paddling back in to Kailua Beach and returning your kayaks, head over to the famous Kalapawai Market, a charming plantation style deli and market adjacent to the beach. Open since 1932, Kalapawai has an unbeatable location, great sandwiches, and assorted sundries you might need for the beach. Choose a sandwich and drink, and then head to the beach a few hundred yards away to sprawl out for a well-deserved nap or relaxing float in the water.

Ready for some more adventure? You’ve already gotten a great view of Oahu during the kayak trip, how about a fantastic view of the Mokes? A quick yet steep hike up the Lanikai Pillbox trail will reward you with 360 degree views, the highlight of which will be an aerial view of Lanikai beach and the reefs leading out to the Mokes, surrounded by the brightest blue-green water you have ever seen. There is little shade on this hike, so it’s best to go in the late afternoon, when the sun lights up the Mokes and is less intense than at mid-day.

A long day out in the sun and you will most likely be looking forward to a big, hearty dinner and a few cocktails. Dinner and drinks can be found at Lucy’s Bar and Grill, a casual yet still “nice” restaurant with an amazing ahi tower appetizer and outdoor patio seating.

If you aren’t completely exhausted after dinner and want to hit up the nightlife, you may be a bit disappointed that Kailua is decidedly sleepier than Waikiki and Honolulu. There are however a few bars, mostly of the “dive” variety. Try Boardriders if you want some live music and a local surfer vibe (go early to avoid the cover), Creekside for a unique Hawaii biker scene, Bob’s for a pool hall atmosphere, and Kailua Palace if you aren’t intimidated by its “locals only” reputation.

What & Where:
Boots & Kimo’s
(151 Hekili St., Kailua; 808-263-7929)
Kailua Sailboards & Kayaks (130 Kailua Rd, Kailua; 808-262-2555)
Kalapawai Market
(306 South Kalaheo Ave, Kailua; 808-262-4359)
Lucy’s Bar & Grill (33 Aulike St, Kailua; 808-230-8188)
Boardriders Bar (201 Hamakua Dr # A, Kailua; 808-261-4600)
Creekside Bar (153 Hamakua Dr, Kailua; 808-262-6466)
Bob’s Sports Bar (170 Hamakua Dr, Kailua; 808-263-7669)
Kailua Palace (115 Oneawa St, Kailua; 808-261-7879)

Lanikai Pillbox Hike Directions & Info:
Kaelepulu Drive – across from Mid-Pacific Country Club
The trailhead is on the left side of the street, just before the turn-around entrance for the Blue Stone condo complex. You have to walk up what appears to be a driveway, and the dirt trail begins alongside a fence. Although I have done it frequently in just flip-flops, you should watch your footing going up, and use the provided guide ropes when needed, as it can be slippery.

For more information about Oahu check out these great books on Amazon Oahu Revealed: The Ultimate Guide to Honolulu, Waikiki & Beyond, Frommer’s Honolulu & Oahu Day by Day by Frommer’s, and Driving and Discovering Hawaii: Oahu, Honolulu, and Waikiki

Ready to visit Oahu? Check out these great Airfare and Hotel deals to Oahu icon

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About the Author

Katie King
Katie A. King is a freelance writer/producer and aspiring screenwriter living in Silver Lake. She has worked in both film and television production, and has published creative writing and photographs in various print publications. She can be reached at Katieking78@gmail.com.

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  • Anonymous

    Great article – definitely makes me wish I were there!