25 Things to Do in Kailua for 5 Days

Planning a getaway to the beautiful shores of Kailua for five days? You’re in for a treat! Nestled on the windward coast of Oahu, Kailua boasts stunning beaches, lush landscapes, and a myriad of activities that cater to everyone from families to solo travelers. Whether you’re looking for thrilling outdoor adventures, relaxing beach days, or romantic outings, this idyllic location has something for you. For a head start on your itinerary, check out our curated list of fun things to do in Kailua.

If you’re a young adult seeking excitement, you’ll find plenty of ideas in [this guide]. Couples looking for a romantic escape can also tap into a selection of enchanting experiences outlined in this resource. Don’t worry if you’re on a budget; you can explore a plethora of free things to do or cheap activities that won’t break the bank but still offer unforgettable memories.

As the sun begins to set on this charming town, the fun doesn’t cease. From delightful evening options found in evening activities to exciting pursuits for families with kids, as detailed in this family-friendly guide, you’ll never run out of things to do. So pack your bags and get ready to discover the many wonders of Kailua—you won’t regret it!

1. Relax at Lanikai Beach

Lanikai Beach is often hailed as one of the best places to visit in Kailua for a day of relaxation and stunning views. With its soft, white sand and crystal-clear waters, it’s the perfect spot to unwind. Not only can you sunbathe, but you can also take leisurely swims in the beautiful turquoise sea.

Moreover, the beach is less crowded compared to other locations, making it an ideal getaway.

“Arrive early to secure your spot, and don’t forget your sunscreen!”

2. Kayak to the Mokulua Islands

Kayaking to the Mokulua Islands offers an adventurous way to explore the natural beauty surrounding Kailua. You can rent a kayak right from Lanikai Beach and set out on the calm waters. The journey provides picturesque views of the islands, and once you arrive, you can enjoy stunning views and soak in the tranquility.

This outdoor activity in Kailua is an excellent way to immerse yourself in the stunning scenery and wildlife.

“Pack a picnic to enjoy once you reach the islands!”

3. Hike the Lanikai Pillbox Trail

For those seeking outdoor activities in Kailua, the Lanikai Pillbox Trail is a must-visit. This relatively short hike rewards you with breathtaking panoramic views of Lanikai Beach and the Mokulua Islands from the top. The trail is steep but well worth the effort.

Build your strength and stamina with this hike, especially if you go in the morning for cooler temperatures. “Bring water and enjoy the incredible sunrise views if you can!”

4. Visit Kailua Beach Park

When exploring Kailua, one of the top places to visit is Kailua Beach Park. This stunning beach is known for its soft, white sand and picturesque views of the Mokulua Islands. It offers a variety of fun activities like swimming, sunbathing, and picnicking. Additionally, there are facilities such as showers, restrooms, and picnic tables available for visitors’ convenience.

Moreover, the gentle waves make it a perfect spot for families.

“Don’t forget to check out the beautiful sunrises – they are simply breathtaking!”

5. Explore the Kailua Farmers Market

The Kailua Farmers Market is another exciting spot for those wondering what to do in Kailua. This vibrant market takes place every Thursday and Sunday, featuring a variety of local vendors selling fresh produce, handmade crafts, and delicious local cuisine. It’s a fantastic place to immerse yourself in the local culture and taste authentic Hawaiian flavors.

In addition to food, you’ll find live music and a lively atmosphere, perfect for exploring.

“Arrive early to get the freshest fruits and the best parking!”

6. Discover the Beauty of Maunawili Falls

Just a short drive from Kailua, Maunawili Falls offers a stunning waterfall hike perfect for adventure seekers. The hiking trail winds through lush rainforest and leads you to a magical viewpoint where you can take a refreshing dip in the natural pool beneath the falls. The hike is relatively easy, making it a suitable activity for most skill levels.

Don’t miss the opportunity to snap some gorgeous photographs along the way.

“Bring water shoes for the slippery rocks near the falls for a safer experience!”

7. Enjoy a Day at Kailua Bay

Kailua Bay is renowned for its breathtaking beauty and serene waters, making it a perfect destination for those seeking fun things to do in Kailua. The beach is ideal for sunbathing, swimming, and simply unwinding on the soft sands. Additionally, the bay’s gentle waves are perfect for various water activities. Grab your beach towel and enjoy a picnic while soaking up the stunning views of the turquoise waters.

For families, Kailua Bay offers ample outdoor activities, ensuring every member has a fantastic day. Don’t forget to bring sunscreen and stay hydrated! We recommend visiting early in the day to avoid crowds and secure the best spots on the beach.

8. Try Stand-Up Paddleboarding

If you’re looking for outdoor activities in Kailua, stand-up paddleboarding (SUP) is a must-try. This fun activity allows you to explore the calm waters of Kailua Bay while giving you a workout at the same time. Rentals are available at various spots near the beach, and beginners can find lessons easily.

The gentle swells and beautiful surroundings make it an unforgettable experience, ideal for any skill level. Pro tip: Early mornings are the best time for paddleboarding to enjoy peaceful waters before the winds pick up.

9. Take a Surf Lesson

Surfing is an iconic sport in Hawaii, and Kailua is no exception. With its consistent waves, taking a surf lesson is one of the best things to do in Kailua. Beginners can learn from certified instructors in a safe and friendly environment while picking up essential skills.

As you paddle out, you’ll enjoy the thrill of catching your first wave. If you’re already experienced, you can find some challenging surf spots nearby. Don’t forget your swimsuit and a positive attitude! After your lesson, relax on the beach and take in the stunning views of the Pacific.

10. Experience Windward Oahu’s Scenic Drives

One of the most fun activities in Kailua is experiencing the breathtaking scenic drives of Windward Oahu. Make your way along the Kamehameha Highway, where vibrant views of lush mountains and ocean vistas will leave you in awe. This drive offers numerous picnic spots and is dotted with scenic lookouts, making it perfect for stopping to capture those Instagram-worthy moments.

“Don’t forget your camera; the views along the drive are spectacular!”

This scenic route is a great way to explore the charm of Oahu’s coastal and country landscapes. To fully enjoy this outdoor activity in Kailua, plan for a day where you can take your time and soak in the natural beauty.

11. Stroll Through the Kawainui Marsh

The Kawainui Marsh, one of the largest estuarine marshes in Hawaii, offers a peaceful retreat in Kailua. This lush habitat is perfect for a leisurely stroll or a more vigorous hike. Birdwatchers will especially enjoy spotting native bird species that call this area home, such as the Hawaiian Black-necked Stilt.

“Arrive early in the morning for the best birdwatching experience.”

As you walk the wetlands, look out for the unique landscape, complete with native flora and historical sites. This is one of the best places to visit in Kailua for those who love nature and tranquility.

12. Visit the Uluniu Nature Reserve

The Uluniu Nature Reserve is a hidden gem in Kailua, offering visitors a chance to connect with nature. Explore its scenic trails that wind through diverse habitats, including coastal forests and wetlands. The Reserve is perfect for outdoor activities, whether you’re hiking or birdwatching, and families will appreciate the educational signs scattered throughout the area.

“Pack a picnic; the peaceful spots in the reserve are perfect for relaxing.”

This nature reserve reflects the beauty of Kailua’s environment, making it a must-visit for nature enthusiasts. You’ll leave with unforgettable memories of your time in this stunning part of Oahu.

13. Explore the Local Art Scene

Kailua boasts a vibrant local art scene that showcases the talents of its artists. Wander through local galleries and studios where you can find stunning paintings and intricate crafts that reflect the Hawaiian culture. Throughout the year, various art shows and exhibitions are hosted, making it an ideal time to explore the artistic community.

Don’t miss the chance to visit the Kailua Art Walk, held every third Friday, where you can interact with artists and purchase unique works!

14. Try Local Cuisine at Snuggles

If you’re wondering what to do in Kailua, dining at Snuggles should be on your list. This local gem offers a menu filled with Hawaiian and American comfort food. Their delicious pancakes and fresh poke bowls are favorites among both locals and visitors alike.

Additionally, Snuggles has an inviting ambiance that enhances your dining experience. Be prepared to arrive early, as this spot can get busy, especially on weekends!

15. Visit the Pillbox Hike for Sunset Views

The Pillbox Hike, offering stunning views of Kailua and Lanikai, is a must-visit for outdoor enthusiasts. This hike leads you to historical military bunkers, known as pillboxes, perched on the ridge, providing breathtaking panoramas of the coastline and lush valleys. The trail is moderately challenging, making it suitable for most hikers.

For a memorable experience, try to hike during the late afternoon, allowing you to catch the sunset from this spectacular vantage point!

16. Explore Kailua’s Historic District

Wandering through Kailua’s Historic District offers a glimpse into the rich culture and heritage of this charming town. The area showcases notable buildings with historical significance, alongside beautifully maintained storefronts and galleries. As you stroll, you’ll find unique shops selling local arts and crafts, making it a delightful place to explore.

This neighborhood not only highlights the past, but it also serves as a hub for local culture. Don’t miss the opportunity to grab a bite in a cozy café. Visiting in the morning is ideal; this way, you can enjoy a quieter atmosphere and meet local artisans.

17. Visit the Mokulua Islands for Birdwatching

The Mokulua Islands, located just off the coast of Kailua, offer some of the best birdwatching opportunities in the region. Home to a variety of seabirds, including the rare Hawaiian Laysan Albatross, these islands make for an unforgettable outdoor activity. You can either kayak or take a boat tour to reach these serene islands.

Birdwatchers will appreciate the diverse avian life, especially during the migratory seasons.

“Bring binoculars for a closer look at the stunning birds in their natural habitat.”

Visiting early in the morning increases your chances of spotting more species.

18. Experience a Luau

Experiencing a traditional Hawaiian Luau is a must-do when in Kailua. This cultural event is not just about delicious local cuisine but also showcases vibrant music, hula dancing, and storytelling. Attending a luau provides insight into Hawaiian customs and traditions while enjoying a festive atmosphere.

Various venues around Kailua host luaus, often set against a stunning ocean backdrop.

“Be sure to wear comfortable clothing and bring your appetite!”

Booking in advance is highly recommended for the best seat and meal options, making it one of the top fun things to do in Kailua.

19. Take a Scenic Bike Ride

Exploring Kailua by bike is one of the most fun activities you can enjoy during your trip. Rent a bike and pedal along the beautiful coastline, taking in the stunning views of Lanikai Beach and the turquoise waters of Kailua Bay. The bike paths are well-maintained, making it an accessible way to experience outdoor activities in Kailua.

Be sure to stop at various scenic spots along the way, where you can take pictures or enjoy a quick swim. Families and solo travelers alike can find joy in this activity.

Pro tip: Remember to wear sunscreen and hydrate well during your ride!

20. Check Out the Kailua Art Walk

The Kailua Art Walk is an event that showcases the creativity of local artists and musicians. Occurring on the last Friday of every month, visitors can walk through Kailua Town and enjoy art galleries, live performances, and food from local vendors. This vibrant community event is a fantastic way to connect with the culture of Kailua.

Additionally, art enthusiasts will appreciate the variety of artwork available for purchase. Whether you’re strolling to look or hoping to add to your collection, this is a great spot to kick back and enjoy local talent.

Don’t miss trying out some delicious local snacks while you walk!

21. Discover the Unique Shops in Kailua Town

Kailua Town is filled with unique shops that offer everything from local boutiques to surf stores. You can spend hours browsing for artisan crafts, clothing, and Hawaiian souvenirs. Make sure to explore the local eateries that often serve delicious Hawaiian cuisine.

This activity is especially great for those seeking to take home a piece of Kailua. Walking through the charming streets of the town allows you to soak up the local culture while engaging in fun activities.

Tip: Check the local calendar for any special events or sales in town!

22. Go on a Dolphin Watching Tour

One of the most exciting things to do in Kailua is embarking on a dolphin watching tour. Book a spot on a charter boat that takes you out into the beautiful waters off Oahu’s coast. During the tour, you’ll have the chance to encounter spinner dolphins and possibly even some whales, depending on the season.

These tours offer not just a chance to see these magnificent creatures, but also a wonderful opportunity to enjoy the stunning ocean scenery. Remember to bring your camera!

Tip: Early morning tours often yield the best chances for dolphin sightings.

23. Visit the Hawaii Waterfall Adventure

The Hawaii Waterfall Adventure is a must-experience when you’re in Kailua. This guided eco-tour will take you on a journey through Oahu’s lush landscapes to discover hidden waterfalls. As you hike through tropical forests, you’ll witness stunning vistas and various local flora and fauna.

This adventure combines the beauty of nature with the thrill of discovery, making it one of the best outdoor activities in Kailua. And, of course, don’t forget your swimsuit for a refreshing swim!

Pro Tip: Wear durable shoes and pack snacks for the hike to keep your energy up.

24. Take a Car Trip to the North Shore

A road trip to the North Shore is undoubtedly one of the best places to visit in Kailua for a day full of adventure. The scenic drive along the coast will entice you with views of beautiful beaches and lush greenery. Once there, you can explore famous surfing spots like Waimea Bay and Sunset Beach.

Along the way, visit local food trucks for a taste of Hawaii’s famed shrimp plates or acai bowls. This trip is perfect for both adventure seekers and those looking to relax and enjoy the culinary scene.

Reminder: The North Shore can get crowded on weekends, so consider going during the week for a more peaceful experience.

25. Enjoy a Relaxing Day at Enchanted Lake

For those seeking serenity, spending a day at Enchanted Lake is one of the most peaceful activities in Kailua. Nestled away from the hustle and bustle, this picturesque freshwater lake is perfect for unwinding and connecting with nature. You can take a leisurely stroll along the shores, or simply sit back and enjoy the beautiful surroundings.

During your visit, consider renting a kayak or paddleboat to explore the calm waters. This will allow you to appreciate the tranquil setting even more while engaging in fun outdoor activities in Kailua. Additionally, the area is rich in birdwatching opportunities, making it a delightful spot for nature enthusiasts.

“Bring a picnic and spend the day! The lush landscape and peaceful vibes make it a perfect spot for relaxation.”

Best Times to Visit Enchanted Lake	Activities	Tips
Morning (7 AM – 10 AM)	Kayaking, Birdwatching	Arrive early to avoid crowds.
Late Afternoon (4 PM – 6 PM)	Picnicking, Strolling	Sunset views are spectacular!

Whether you’re in search of fun things to do in Kailua or a peaceful retreat, Enchanted Lake will provide the perfect backdrop for a memorable day.

Kailua is brimming with enticing activities that cater to diverse interests, from beach lovers to adventure seekers. Whether you’re kayaking to the islands or savoring local delicacies, these five days in Kailua will leave you with unforgettable memories. Don’t forget to share your favorite activities or comment on your experiences in Kailua!