Top Things to Do in Kailua: Beaches, Bites & Boutiques Near Waikiki

Are you interested in seeing the world’s most beautiful beaches?! We thought so!

In this FIRST CABIN INTERNATIONAL HAWAII post guide, we’re helping you curate the perfect escape to Kailua – beaches and beyond.

The Kailua coastline is on the island’s windward side where the weather is prone to rain, wind, and clouds. However, rain or shine, Kailua is worth the day trip from Waikiki!

Let’s dive into the details and plan the perfect day trip to Kailua!

Traveling to Kailua Town from Waikiki Beach

Kailua is located on the east side of O’ahu, 12 miles from Waikiki. There are two ways to get there, both offer stunning views, so consider going one way and returning the other.

The direct route is over the Pali Highway, approximately 30 minutes from Waikiki, boasting an impressive lookout point.

South of Waikiki is the longer, arguably more scenic drive, along the Kalanianaole Highway.

Drive along the coast and stop at various vistas including the Halona Blowhole Lookout and the Makapu’u Lighthouse.

While both drives are beautiful, beware of commuting during traffic hours.

Fun in the Sun: Exploring Kailua’s Coastline

Suntan, swim, and snorkel at two of the island’s most beautiful beaches.

Whether you want an action-packed adventure or a relaxing beach day, it’s all possible in Kailua.

For impressive views, and a pre-beach workout, hike the Lanikai Pillbox Trail.

Remember to watch for man-of-war jellyfish eight days after the full moon.

Kailua Beach

This crescent-shaped beach stretches 2.5 miles with gentle waves breaking onto the sand.

Post up for the day to work on your tan, have a picnic, surf the shorebreak, or snorkel to Flat Island.

Lanikai Beach

The turquoise-colored waters, powdery soft sand, and two offshore islands make this a postcard-perfect beach.

This slice of paradise is ideal for beach days, snorkeling, and ocean adventures.

Spend the Day on Kailua’s Crystal-Clear Waters

Get out onto the windward side waters with bodyboards, surfboards, standup paddleboards, snorkel gear, or kayaks.

There are adventures for all skill levels.

Below are places to rent water equipment for fun in the sun!

Kailua Beach Adventures

130 Kailua Rd

Located within walking distance to the beach, this place is the spot to rent kayaks to paddle out to Flat Island or the Mokulua Islands.

Go on a professionally guided tour or opt for watersport lessons.

They rent everything from snorkel gear and beach chairs to bikes and surfboards.

Aaron’s Dive Shop

307 Hahani St

The only dive shop on the windward side has offered scuba diving classes and charters since 1971.

Whether you’re looking to rent scuba gear, get certified, or go on a snorkel tour, it’s all here.

Hawaiian Watersports

171 #C, 171 Hamakua Dr

In the heart of Kailua town, this shop has a variety of equipment rentals including skimboards, kiteboards, windsurfs, and foil boards.

They offer lessons of all kinds.

If you want to try surfing, foiling, or kiteboarding, head this way!

Shop Kailua’s Locally Owned & Boutique Stores

Kailua is a quaint and quintessential beach town boasting restaurants and shops.

Make the most of your day with bike rentals from The Bike Shop and get around town on two wheels.

Pop into Manoa Chocolate Factory for a chocolate tasting and factory tour by day or live music and a natural wine bar by night.

The great Farmer’s Markets have local cuisine, souvenirs, and produce.

Every Sunday the Lokahi Market showcases unique artisans and small businesses.

And, bookworms will appreciate the selection at BookEnds.

For new bikinis or beachwear stop into BikiniBird or HIC.

Discover original art and textiles made by local artisans at the Lauren Roth Art Boutique.

Shop at the high-end boutiques Olive & Oliver for curated textiles, menswear, and home goods.

And, at Classic Waves Boutique, you’ll find handmade jewelry, clothing, and artisan goods.

Feast on Delicious Food in Kailua Town

Yes, fantastic beaches and cute shops are in this quaint little beach town, but there are also some delicious places to eat!

There’s a little something for every style of dinner, for breakfast, lunch, and dinner.

Here are a few of our favorite places to eat in Kailua.

Buzz’s Original Steak House

413 Kawailoa Rd

This iconic restaurant has served the community deliciousness since 1962.

Right across from the beach, stop in for the famous Mai Tai, a tasty lunch, or a special dinner.

Lanikai Brewing Co.

167 Hamakua Dr

Sip on locally made beers at this casual brewery.

The drinks pair perfectly with Valentina’s pizzas, salads, and sandwiches.

The staff is friendly and the vibes are good.

Kalapawai Market

750 Kailua Rd

This family-owned business has four locations across O’ahu but the original two are in Kailua.

During the day you can grab a sandwich to-go, but the Kailua Town Market offers an award-winning full-service dinner in the evenings.

Moke’s Bread & Breakfast

27 Hoolai St

Start your day with scrumptious lilikoi pancakes, house-made corned beef hash, farm-fresh omelets, or a Local Moco.

This family-owned and operated laid-back eatery has been serving Kailua for over 20 years.

Kailua is the Perfect Little Getaway from Waikiki

Explore a different side of the island and get to know Kailua because it’s a quick hop over from Waikiki.

This beach town boasts some of the island’s most beautiful beaches.

No matter the weather, Kailua has things to see, do, and eat.

For more tips and resources for your trip to O’ahu, check out our blog!

We’ll see you at the beach.