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View of the ocean in Kailua.

8 of the Best Things to Do in Kailua

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Are you looking to explore Hawaii off the beaten path? Located on the windward side of Oahu, the town of Kailua is one of Hawaii’s best-kept secrets. In addition to lush rainforests and beautiful beaches, this hidden gem offers a quiet escape from the hustle and bustle of the island’s larger cities. To help you plan, we’ve compiled a complete list of the best things to do in Kailua. From secret beaches to waterfall hikes, there’s so much to do when you visit Kailua. What will you explore? 

When you’re ready to start planning your trip, request our free Vacation Guide. This planning tool contains local insight into the best things to do on Oahu and the Big Island! 

Top 8 Things to Do in Kailua 

1. Kailua Beach Park View of Kailua Beach Park

With white-sand beaches and turquoise blue waters, it’s hard to envision a more gorgeous paradise than Kailua Beach Park. This 2.5-mile stretch of shoreline is one of Oahu’s top beaches, and for very good reasons!  

This spot is a prime destination for kayaking, paddleboarding, swimming, snorkeling, diving, and beachcombing. Lounge on the beach and soak up the sun, enjoy a picnic lunch, or dive into the crystal-clear water and swim among the colorful fish. At the end of a perfect day, make sure to stay and watch the sunset. We guarantee you have never seen anything more beautiful! 

2. Lanikai Beach 

While there are many great beaches on Oahu, Lanikai beach is the best. The name Lanikai means “heavenly sea,” and this beach absolutely lives up to its name. Miles of tranquil blue water reaches as far as the eye can see, and tall palm trees line the half-mile stretch of shoreline. There are no posted signs leading to Lanikai Beach, but there are several beach access points located off Mokumanu Drive. 

3. Hiking Couple exploring on a waterfall hike.

In addition to beautiful beaches, Kailua offers miles of picturesque hiking trails. If you’re looking for fun and free things to do in Kailua, Hawaii, you’ll want to add the Lanikai Pillbox Hike to your Hawaii bucket list. This uphill trek is short but steep, and the incredible views are well worth the climb.  

Along the way, you’ll see colorful wildflowers, two historic military bunkers, and panoramic views of Mokulua Islands, Kailua Beach, and Lanikai Beach. If you look out into the distance, you’ll also see Makapu’u Lighthouse peeking out of the water!  

Maunawili Falls is another great hike to add to your Oahu itinerary. This moderate hike winds through the jungle, leading to a waterfall and a great swimming hole. Make sure to wear great hiking shoes, as you’ll be traversing muddy areas, large tree roots, and rocky streams. Don’t forget to bring your camera! Afterward, be sure to try a few of these other amazing waterfall hikes on Oahu. 

4. Dining 

When it comes to dining in Kailua, the hardest decision you’ll have to make is where to go first! From casual beach bars to fine dining, there are several excellent restaurants throughout town. If you are craving fresh seafood, we recommend reserving a waterfront table at Huggo’s in Kailua Kona. Enjoy a spectacular sunset while you dig into the catch of the day.  

For a more casual experience, head over to Bob’s Pizza for some of the best slices you will ever taste. Then, stop by Manoa Chocolate Hawaii for a sweet treat! Check out our dining guide for more great recommendations about restaurants on Oahu. 

5. Shopping 

There’s plenty of great shopping in Kailua if you know where to go. Whether you’re on the hunt for one-of-a-kind treasures or the top brands, you’ll find it all in Kailua Town. Take your time browsing the trendy boutiques, unique island stores, national retailers, and art galleries. When you take home all of your great finds, you’ll be glad you stopped by! 

6. Kailua Town Farmers’ Market Woman at farmers market holding an assortment of fruit.

If you’re looking for things to do in Kailua when it rains, a trip to the market is a wonderful option. The Kailua Town Farmers’ Market is open every Sunday from 8:30 a.m. until noon, rain or shine. Here, you’ll find local produce, delicious food, live music, and tons of fun family activities.  

Another option is to visit the Kailua Night Market, which is independently owned and offers a completely different experience. Open every third Friday from 5:00 p.m. until 9:00 p.m., this market features diverse culture and food, incredible local artwork, and exciting entertainment. Entry and parking are free, and pets are always welcome! 

7. Paddle to Mokuleia Islands (The Mokes) 

When searching for things to do in Kailua Kona, kayaking to the Mokuleia Islands should be at the top of your list! Nicknamed by locals as “The Mokes,” these two islets are located just a few miles off the shoreline of Lanikai Beach and Kailua Beach Park. The island on the right is closed to the public. However, the one on the left is a great spot for kayaking, paddleboarding, snorkeling, cliff-jumping, or simply lounging on the powder-soft sand.  

To paddle to The Mokes, you’ll need to launch your watercraft at the canal in Kailua Beach Park near the bridge. The journey to the islands typically takes anywhere from 45 minutes to two hours. There are also several tour companies that can take you on a guided tour of the islands. Keep an eye out for turtles, seabirds, and dolphins! 

8. Halona Blowhole View of the Halona Blowhole at sunset.

Formed thousands of years ago, the Halona Blowhole is one of Hawaii’s natural wonders that you’ll have to see to believe! The scenic outlook overlooks the unique lava rock formation and the crashing waves of the Pacific. When the water rushes into the lava tubes below, the Blowhole erupts, shooting sea spray high into the air like a geyser. You can hear and feel the rumble just before an eruption.  

While you’re there, make sure to check out Halona Beach Cove. Several movies have been filmed in this idyllic cove, revered for its natural beauty. When the waters are calm, this is a great place to go swimming and snorkeling. 

Stay Nearby with Private Homes Hawaii 

Now that you know all the best things to do in Kailua, it’s time to start planning your tropical getaway! Located just minutes away from all these incredible attractions, Private Homes Hawaii offers the ideal accommodation for your stay. Each of our Oahu vacation rentals is fully equipped with top-notch amenities to ensure that your vacation is a relaxing one. From spacious oceanfront estates to casual beach homes, we offer a wide array of lodging options to choose from! 

Browse a complete catalog of our Oahu vacation rentals to start planning your trip to paradise!