25 Fun Things to Do in Kailua for Guys

For those looking to escape the monotony of daily life, Kailua offers a treasure trove of adventures that are particularly appealing for guys. Nestled on the stunning windward coast of Oahu, this charming town is famed not just for its breathtaking beaches but also for its laid-back vibe and plethora of activities that cater to all interests. From exhilarating outdoor adventures to relaxing beach days, there are countless fun things to do in Kailua that promise to create lasting memories.

For the more adventurous souls, exploring the verdant landscapes and stunning shorelines can be a thrilling way to spend your time. Make sure to check out our guide on fun things to do in Kailua for young adults, which offers insights into activities perfect for those looking for a bit of excitement mixed with social interaction. If you’re traveling as a couple, or even just looking for great group outings, there are plenty of unique experiences detailed in things to do in Kailua as a couple.

Don’t want to break the bank? You’ll be pleased to know that Kailua is brimming with free fun activities that’ll keep your wallet intact. If you’re looking for budget-friendly options, our lists of cheap fun things to do in Kailua will help you make the most of your trip without overspending. As the sun sets, the adventure doesn’t have to stop; explore the vibrant nightlife with our evening guide at fun things to do in Kailua in the evening.

Whether you’re making plans for a quick getaway or an extended stay, we have you covered with recommendations for how to enjoy Kailua over a span of three days or even five days. No matter your situation—traveling with family, looking for activities with kids, or simply seeking some time alone—Kailua is bursting with opportunities to unwind and enjoy the great outdoors. So, gear up and get ready for some unforgettable experiences!

1. Kayak to the Mokulua Islands

Paddling out to the Mokulua Islands offers one of the best outdoor activities in Kailua. You can rent a kayak from local shops, as renting one is straightforward and suitable for both beginners and experienced paddlers. The crystal-clear waters provide an opportunity to explore Hawaii’s marine life closely.

This fun activity is ideal for a group of friends looking to bond while experiencing the beauty of nature.

“Remember to take sunscreen, water, and snacks for this adventure!”

2. Surf at Kailua Beach

For those who seek thrills, Kailua Beach is the place to be. Surfing here is one of the most enjoyable activities in Kailua. Whether you’re a novice or a seasoned pro, local surf schools offer lessons tailored to your skill level. The waves are consistent, making it an ideal spot.

In addition to surfing, relax on the soft sands or play beach games with friends.

“Try to catch a few waves in the morning for the best conditions!”

3. Hike to the Pillboxes for Stunning Views

Hiking to the Pillboxes is a must-do on your trip to Kailua. This hike not only delivers stunning panoramic views of the coastline but also gives you a sense of the island’s beauty. The trail is moderately challenging yet very rewarding, making it a fantastic group activity for guys.

Many hikers recommend starting early to avoid the heat and to enjoy the sunrise.

“Bring your camera; the view from the top is breathtaking!”

4. Explore Lanikai Beach and Its Lagoon

Lanikai Beach is renowned for its pristine beauty and is often considered one of the best places to visit in Kailua. With its soft white sand and crystal-clear waters, it’s an ideal spot for relaxation or adventure. You can enjoy fun activities such as swimming, sunbathing, or even kayaking in the tranquil lagoon.

Furthermore, the iconic view of the Mokulua Islands from the shore adds to this beach’s charm. It’s definitely one of the top things to do in Kailua for guys looking for a day of sun and surf.

A visit to Lanikai Beach is not complete without a morning swim!

5. Try Wind Surfing at Kailua Windsurfing

Experience the thrill of wind surfing at Kailua Windsurfing, one of the most exciting outdoor activities in Kailua. Whether you’re a beginner or an experienced surfer, the experts here provide lessons and equipment for everyone. The steady trade winds and beautiful scenery make it an exhilarating option.

Moreover, wind surfing grants you a unique perspective of the stunning coastline.

Pro tip: Take a lesson early in the day to catch the best winds!

It’s genuinely an unforgettable way to explore the waters while enjoying the sport.

6. Join a Stand-Up Paddleboarding Tour

Joining a stand-up paddleboarding (SUP) tour in Kailua is another fun activity that you shouldn’t miss. This activity is perfect for beginners and offers a fantastic way to explore the scenic waters at a leisurely pace. During your paddle, you can glide over coral reefs and spot colorful marine life.

Additionally, these tours often highlight the natural beauty of the area, making them ideal for photography enthusiasts.

Don’t forget to bring your waterproof camera to capture those stunning views!

Stand-up paddleboarding is a relaxing yet engaging experience that offers an entirely different perspective of Kailua.

7. Go on a Snorkeling Adventure at Kaneohe Sandbar

Embark on an unforgettable snorkeling adventure at the stunning Kaneohe Sandbar, a hidden jewel off the coast of Kailua. This vibrant underwater paradise offers a chance to witness a plethora of marine life, including colorful fish and beautiful coral reefs. Many local tour operators provide boat trips which are great for both experienced snorkelers and beginners.

Tip: The best time to go is during low tide when the sandy area is exposed, creating the perfect environment for snorkeling.

This activity is ideal for those seeking fun things to do in Kailua while enjoying the beauty of Hawaii’s natural surroundings. Remember to wear sunscreen!

8. Play Beach Volleyball at Kailua Beach Park

If you’re looking for fun activities that combine friendly competition and beach time, look no further than Kailua Beach Park. This popular spot offers several beachfront volleyball courts frequented by locals and visitors alike. Gather your friends or join a game with other beachgoers to enjoy the vibrant atmosphere.

Pro Tip: Don’t forget to bring your own ball, as shared equipment isn’t always available!

Playing volleyball is a fantastic way to contribute to your active lifestyle while embracing the scenic beauty of Kailua.

9. Enjoy a Scenic Bike Ride along the Coast

For those who enjoy hitting the trails, a scenic bike ride along the Kailua coast is a must. Rent a bike from local shops and explore the stunning views of turquoise waters, sandy beaches, and lush landscapes. The bike paths are well-maintained, making it easy to navigate.

Recommendation: The ride to Lanikai Beach offers some of the most picturesque sights, perfect for photo stops!

Biking in Kailua not only provides a fun way to get around but also allows you to absorb the local culture and natural beauty. Whether you’re with friends or solo, you’ll be sure to have a memorable experience.

10. Experience a Traditional Hawaiian Luau

One of the most fun things to do in Kailua is to experience a Traditional Hawaiian Luau. It’s a delightful combination of cultural performance and delicious food. Enjoy hula dancing, fire shows, and live music while savoring authentic Hawaiian dishes like kalua pig and poi.

Attending a luau is not just about the food; you’ll get a taste of Hawaiian history and traditions. Make sure to book your spot in advance, as these events are popular among visitors.

11. Take a Sailing Trip Along the Windward Coast

A sailing trip along the Windward Coast of O’ahu is one of the must-do outdoor activities in Kailua. Glide past scenic coastlines with breathtaking views of Ko’olau Mountains and the sparkling Pacific Ocean. Not only is sailing a great way to unwind, but you may also spot dolphins and sea turtles along the way.

These excursions are perfect for groups looking for adventure. Plus, consider bringing snacks to enjoy while taking in the magnificent views.

12. Visit the Kailua Farmers Market for Local Eats

For those looking to indulge in local culture, a visit to the Kailua Farmers Market is a great choice. Held weekly, this market features fresh produce, handmade goods, and delicious street food. It’s an excellent opportunity to support local farmers and artisans while enjoying tasty treats.

Don’t miss out on sampling local favorites like Hawaiian shaved ice and fresh fruit. This vibrant market also serves as a social hub for locals and visitors alike.

“Make sure to arrive early for the freshest picks!”

13. Check Out the Local Craft Breweries

If you are searching for fun things to do in Kailua, visiting local craft breweries is a must. Kailua boasts a vibrant craft beer scene with several unique breweries where you can sample locally brewed beers. Popular options include Kona Brewing Company and Island Brews, offering a variety of flavors and styles, from IPA to stouts. This is not only a great way to spend an afternoon, but also to meet locals and learn about Hawaiian brewing culture.

Pro tip: Many breweries offer tours, allowing you to see the beer-making process while tasting their best brews.

14. Go Fishing Off the Coast of Kailua

Fishing is one of the most enjoyable outdoor activities in Kailua for guys. You can charter a boat or rent gear and fish off the coast. Many local companies offer half-day or full-day fishing trips, targeting popular species like mahi-mahi and tuna. Fishing in the warm waters surrounding Kailua can be a thrilling way to connect with nature and unwind.

Tip: Make sure to get a fishing license and check local regulations before heading out!

15. Explore the Kailua Shopping Scene

Kailua has a charming shopping scene featuring local boutiques and artisanal shops. From beachwear to unique souvenirs, you’ll discover a variety of places to visit in Kailua. Don’t miss the Kailua Town Center, where you can find everything you need, from outdoor gear to local artisan crafts. After shopping, you can also enjoy coffee at one of the nearby cafes, making it a perfect day out.

Pro tip: Visiting on weekends allows you to experience the farmers market right in the heart of town!

16. Try Out the Local Food Trucks

Kailua is home to a variety of food trucks that offer everything from tasty tacos to delicious acai bowls. Each truck has its own unique flavor, making it a fantastic experience to sample different cuisines all in one spot. Head to Kailua Town, where local vendors gather, and indulge in the freshest options.

Pro Tip: Visit during the lunch hour for the best selection of local eats and to meet friendly vendors!

17. Relax at Kalaheo Park

After a day of fun activities, unwind at Kalaheo Park. This beautiful park is perfect for enjoying picnics, playing frisbee, or simply relaxing under the sun. With amenities such as volleyball courts and playgrounds, it’s a great destination for those seeking outdoor activities in Kailua.

Insider’s Tip: Bring along a beach blanket and snacks for a perfect afternoon!

18. Experience a Beach Bonfire with Friends

Nothing says summer like a beach bonfire! Gather your friends on one of Kailua’s stunning beaches and enjoy a night under the stars. It’s a fantastic way to unwind after a day of adventure. Fire pits are available at certain beaches, so plan ahead to secure a spot!

Fun Fact: Always check local regulations for bonfires to ensure a safe and fun experience.

19. Wander Through the Small Town of Kailua

Exploring the small town of Kailua is one of the most fun things to do in Kailua. Stroll through charming streets lined with unique boutiques, local art galleries, and delicious eateries. For instance, you might discover the perfect souvenir or an artisanal treat at a quaint shop.

This area is not only picturesque but also captures the spirit of the community. Moreover, transition from shopping to savoring fresh coffee at a local café. Don’t forget to check out Kailua’s vibrant street art!

Pro Tip: Visiting early in the day is ideal to avoid crowds and enjoy a serene atmosphere.

20. Join a Guided Scuba Diving Excursion

If you’re looking for adventure, joining a guided scuba diving excursion in Kailua is a top choice. Discover the underwater wonders of Hawaii, such as vibrant coral reefs and exotic marine life. This activity is perfect for both beginners and experienced divers alike.

Additionally, the waters surrounding Kailua offer excellent visibility and a plethora of dive sites. Make sure to bring your underwater camera to capture stunning underwater shots!

Highlight: Diving tours often provide all necessary gear, making it easy to jump right in.

21. Take a Helicopter Tour of O’ahu

A breathtaking way to experience the beauty of Hawaii is to take a helicopter tour of O’ahu. This thrilling adventure allows you to view stunning landscapes, from lush mountains to majestic coastlines. It’s undoubtedly one of the best ways to appreciate the island’s diverse scenery!

Specific tours may even include stops at famous landmarks like the iconic Diamond Head crater. Thus, you can soak in views that few get to experience. Book your tour in advance to secure the best times.

Tip: Opt for a sunset tour for unforgettable views and amazing photo opportunities!

22. Go Horseback Riding at a Local Ranch

If you’re searching for fun things to do in Kailua, consider going horseback riding at one of the local ranches. Experience the beauty of O’ahu’s landscapes on horseback, where guided tours take you through scenic trails. This activity is perfect for individuals and groups, allowing you to connect with nature while enjoying a unique perspective of the island.

Pro tip: Make sure to wear long pants and closed-toe shoes for a comfortable ride!

Horseback riding is not only a thrilling adventure but also a fantastic way to bond with friends or family. Plus, it’s a different way to explore the natural beauty that Kailua has to offer.

23. Play Golf at a Nearby Course

For golf enthusiasts, Kailua has several stunning courses that offer an unforgettable golfing experience. Whether you’re a seasoned player or just looking for some outdoor activities in Kailua, these courses provide beautiful backdrops and challenging greens. Enjoy the fresh sea air and stunning views as you tee off.

Tip: Book your tee time early to avoid the crowds and make the most of your day!

Additionally, many courses offer amenities such as dining options and pro shops, making it an all-encompassing day of leisure. It’s one of the must-do places to visit in Kailua for guys who enjoy sports and the outdoors.

24. Attend a Local Sports Game or Event

Immerse yourself in the local culture by attending a sporting event in Kailua. Whether it’s a football game, soccer match, or a little league championship, local sports events are filled with excitement and camaraderie. It’s a great way to experience the vibrant community spirit of Kailua.

Did you know? Attending local events gives you a chance to interact with locals and possibly make new friends!

Check community bulletins or local websites to find out what’s happening during your visit. Attending a game is one of the most enjoyable fun activities in Kailua, ensuring you soak up a bit of the island’s sports passion!

25. Capture the Sunset at Lanikai Pillbox Hike

The Lanikai Pillbox Hike is a must-do for anyone seeking fun things to do in Kailua. This moderately challenging trail takes you through lush greenery to the historic military pillboxes perched on a ridge. As you make your way up, you will be rewarded with stunning views of the Pacific Ocean and the Mokulua Islands.

For an unforgettable experience, try to time your hike so you reach the top just before sunset. The sight of the glowing sun dipping below the horizon is simply breathtaking.

“Don’t forget your camera! The sunset here is a photographer’s dream.”

While the hike is relatively short, it can be steep in some parts. Therefore, it’s recommended to bring water and wear comfortable shoes. In summary, the Lanikai Pillbox hike combines adventure with stunning vistas, making it one of the top places to visit in Kailua.

Kailua offers a myriad of activities for guys looking for fun and adventure. From water sports and hiking to local dining experiences and nightlife, this vibrant town provides countless opportunities for memorable experiences. Be sure to try a mix of adrenaline-fueled activities and chill moments to make the most of your time in Kailua. Share your favorite activities or experiences here!