Weekends Kailua: Eat, Hike, Bike and Kayak Your Way Through Oahu’s Charming East Side Town

ASN Weekends is our travel series dedicated to giving you exact 48-hour itineraries for how to maximize an adventure travel destination. We’ve done all the planning for you, all you have to do is book your trip!

Hawaii’s most populous island, Oahu, is most commonly associated with bustling Waikiki, historic Pearl Harbor, and the surf mecca known as the North Shore, home of the Vans Triple Crown of Surfing held each winter.

But nestled on Oahu’s eastern or “windward” coast, just 30 minutes from Honolulu International Airport, lies the lesser known, quaint town of Kailua.

Can’t beat views like this.

With its pristine waters, charming downtown area, and lack of high-rise hotels (or any hotels for that matter, but more on that later), Kailua is an ideal destination for those looking to experience a more relaxed side of Oahu … without feeling too isolated.

Yes, there is a Whole Foods, a Target, and even a Core Power Yoga in town for those hard-to-resist mainland urges, but there are also plenty of peaceful tree-lined streets, locally owned businesses, and secluded beach spots to make you forget about your 9-5 and embrace Aloha for a weekend.

And the best part? We’ve planned the weekend for you. From where to stay, to where to rent boards or get the best poke this side of the island, we’ve got you covered. All you need to do is start setting up those fare alerts!

Getting There
Flights: With multiple nonstop flights each day from many major US cities to Honolulu International Airport, and the announcements that United will expand its offerings to Hawaii and Southwest plans to enter the market in 2018, flights are abundant.

Wheels: while you can make use of public transportation and ride-sharing services, having a rental car will save you time and make your life a lot easier. There are six rental car companies located right at the airport and four others located off-site. Or try Turo, an Airbnb for cars where you can rent a ride from a local. From the airport it’s an easy, 30 minute drive over the mountains on either H-3 or the Pali Highway (61) to downtown Kailua.

Where to Stay
There are no hotels in Kailua, which is one of the things that makes this town so special, so Airbnb is the way to go. From a luxurious oceanfront Lanikai compound that can accommodate up to 10, to a secluded beach bungalow for two, or a glamping cabin with an outdoor bathroom, there are plenty of options at every price point. Our advice: Book early, read previous reviews carefully, and take note of proximity to the beach and parking availability as street parking can be tough in some neighborhoods.

Book your Airbnb early. Places fill up fast, especially during the busier summer months.

And now for the fun part …

What to Do
Assuming you arrived on a Friday and passed out early from the jet lag, take advantage of that time change by getting an early jump start on your day Saturday morning.

The view is worth waking up before the sun. Climbing to the Lanikai Pillboxes before sunrise.

6:30-8 a.m.: Catch your first sunrise by hiking to the top of the Lanikai Pillbox or Ka’iwa Ridge Trail. From the trailhead to the second pillbox takes 20-30 minutes and within the first 5 minutes you’re rewarded with breathtaking views of the windward coastline, the Ko’olau mountain range, and Nā Mokulua, the twin islands located off the coast of Lanikai commonly known as “The Mokes.”

The trailhead is located across from the Mid-Pacific Country Club entrance on Kaelepulu Drive, but you’ll need to find parking on either Aalapapa Drive or a side street off of it. Note that sunrise can be as early as 5:53 a.m. in the summer and as late as 7:10 a.m. in the winter. Begin hiking at least 30 minutes prior. Water and running or hiking shoes are essential.

The outdoor seating at Over Easy.

8:30-9:30 a.m.: Head back to Kailua town for breakfast at Over Easy, a cozy little café tucked off of Kuulei Road that puts out some of the best food this side of the island. Highlights include the Custard French Toast, Kalua Pig Hash, and Potato N’ Eggs. Add a Lilikoi Mimosa and a side of Fried Rice because you’re on vacation and you deserve it. Snag seats at the counter to watch the bustling kitchen in action.

9:30-10 a.m.: Even though you’re stuffed from breakfast, pop into Foodland, Hawaii’s largest locally owned grocery store, to pick up some drinks and snacks for the day ahead. The fresh poke is delicious, as are the maui onion potato chips, smoked ahi dip, and assortment of locally grown produce.

Paddling to the Mokes takes about half an hour each way.

10:30-2:30 p.m.: Rent kayaks for the afternoon from Kailua Beach Adventures. You can launch the boats from nearby Kailua Beach Park and paddle to Popoia or “Flat Island,” stop over at the picturesque white-sand Lanikai Beach for a snorkel session, then if you’re feeling ambitious, continue paddling the .75 miles out to The Mokes and enjoy your snacks from the small strip of beach accessible on the larger island.

A double kayak rental costs $67.15 for 4 hours if reserved online in advance. Snorkel equipment ($15), coolers ($5), and dry bags ($5) are also available. Kailua Beach Adventures also offers guided tours, as well as single and high-performance kayaks for more advanced kayakers.

3-4:30 p.m.: After returning your kayaks, swing into the historic Buzz’s Original Steakhouse, open since 1962, for drinks and pupus (appetizers) on the lanai (porch). Buzz’s exudes an old Hawaiian tiki charm and is the perfect spot to enjoy views of Kailua Beach. Favorites include the BFRD (Big F*ing Rum Drink), the Calamari Steak appetizer, House Made Mozzarella, Spring Rolls, and Ahi Sashimi.

5-6:30 p.m.: Either head back to your airbnb to unwind from the day’s activities or take a stroll along the 2.5 mile long crescent-shaped Kailua Beach. As you walk north away from Kailua Beach Park, the beach becomes less crowded and in some spots, you’ll catch a glimpse of the sun setting over the Ko’olau mountains.

7-8:30 p.m.: Grab dinner at fun, local favorite Uahi Island Grill. The breezy, relaxed patio is the place to sit and if you order one thing, we recommend the Red Curry Fish. (So does Guy Fieri who featured it on his show in 2014.) The Kale and Kalua Pork, Orange Duck Confit, and Sweet Potato Haupia Pie dessert are also winners.

9 p.m.: Turn in for the night after a packed day, OR for the night owls, sip hand-crafted cocktails while listening to a live saxophonist play jazz at Gaslamp, Kailua’s new and only speakeasy. It’s tucked inside the back of Kailua Town Pub and Grill and reservations are recommended.


ChadLou’s Coffee Shop

7:30 a.m.: Get your morning caffeine fix with a pour over or latte from the friendly baristas at Chadlou’s Coffee Roasters. They offer an assortment of freshly made breakfast options from Belgian waffles to Frittatas but our favorite indulgence is the chocolate chip banana bread.

Fresh produce from the Kailua Farmer’s Market.

8:30-9:30 a.m.: Mozy over to the Sunday Kailua Farmers Market at Kailua Elementary School. Listen to live music, get a green smoothie or freshly cut coconut to balance out the balls of fried dough you just consumed, and pick up some tropical fruits and more local treats such as baked goods, jams, salsa, salts, and the most delicious kiawe-smoked marlin dip from the friendly folks at the Forage Hawaii stand.

10 a.m.: Ditch your car for the day and rent a beach cruiser from The Bike Shop. Bikes are $15 for half day or $20 for full day. Kailua’s flat roads are perfect for cruising around town or to the beach, and it’s a great way to enjoy the neighborhoods.

Riding easy.

10 a.m.-12:30 p.m.: Spend a few hours exploring Kailua Town, checking out the funky boutiques and shops, and pick up some souvenirs while you’re out. A few of our favorites are Bikini Bird, a bikini mecca with cute beachwear and accessories, Aloha Beach Club, Hawaiian-made menswear and home goods with an all-natural shave ice counter located inside the shop, and Kimo’s Surf Hut, new, used, and vintage collectible surfboards.

Beachy goods at Olive Boutique.

12:30-1:30 p.m.: Refuel by grabbing lunch on Hekili Street in between shopping excursions. For killer slow-roasted kalua pork bombers (burritos) and sandwiches made with Aloha, pop into Kono’s. On the lighter side, Nalu Health Bar’s deep-purple açai bowls are arguably the best you’ll find outside of Brazil, as they source the açai directly from the Amazonian country. Their smoothies, fresh wraps and salads are also tasty (and healthy) options.

2-4 p.m.: Rent a foam board ($20 half day) back at Kailua Beach Adventures and check out Kalama Beach Park. This beach spot attracts fewer tourists than the southern side of the beach, and offers a fun sandy-bottom beach break that’s perfect for riding a foam board or bodysurfing. If the parking lot is full, street parking off N. Kalaheo side streets is an option.

So serene.

4:30-6 p.m.: Enjoy some frosty post-beach beers at Tap and Barrel, the Lanikai Brewing Tasting Room featuring island inspired brews such as the Route 70 Saison, sweetened with organic Ohia Lehua Hawaiian honey, or the Pillbox Porter, infused with Tahitian and Hawaiian vanilla.

6:30-8 p.m.: Pizza is always a good choice for dinner, and with its authentic Neapolitan pizza oven, sleek interior decorated with local artwork, and creative menu, Prima is the best Kailua has to offer. We have yet to find a pizza there that we don’t like but the Proscuitto Rucola, Funghi, and Spicy Meatball are fan favorites. Get the Grilled Casear Salad and cheesy Garlic Bread to start and enjoy some funky tunes while you nosh your wood-fired pies.

8:30 p.m.: Call it a night! You came, you saw, and you conquered Kailua like a pro.

Honorable mention: Kalapawai Cafe and Deli.

Some of our other favorite Kailua spots:
The Hibachi – best poke in Kailua, located in a beer and wine shop
Kalapawai Market – historic convenience store offering beach gear, made-to-order sandwiches, and local coffee and pastries
Maunawili Falls Trail – an alternative day activity feature a 3-mile hike to a waterfall with a swimming hole where locals cliff jump. Be prepared to get wet and muddy!
Creekside Lounge – every town has a favorite dive bar, and this is ours
Lanikai Juice – tropical smoothies, juices, and deliciousness
The Food Company – half local-style plate-lunch café, half fine-dining BYOB restaurant. What more could you ask for?

Photos: Jess Zimlich

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