When we moved to Kailua I knew NOTHING. I’ve learned everything from experience and some personal recommendations. I’m here to fast track your research with info you won’t find on Google about things to do in Kailua, Hawaii.
You’ve booked your trip to paradise (aka Oahu) and you’re smart enough to know that sunrise beach photos in Lanikai or Waimanalo are absolutely worth the early wake-up call. Whether you’ve booked me to capture your family’s sun-kissed memories (smart choice!) or you’re DIYing it with your iPhone, let me—a transplanted mainlander with four wild boys—guide you through things to do in Kailua, Hawaii after those sunrise shots.
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Post-Photo Session Morning: Sunrise to Sunset Without Moving Your Car
After those dreamy sunrise photos at Lanikai Beach (sand still in your toes but memories captured forever!), don’t rush back to your hotel—the day is just beginning! Leave your car right where it is and stroll over to Kalapawai Market for their heavenly macadamia nut coffee and egg sandwiches. If you’re feeling extra indulgent, The Sunrise Shack is across the street, with their famous bullet coffee and tropical smoothie bowls that taste even better when you’re already beach-ready.
When lunchtime hunger strikes, walk a few steps to Bob’s Pizzeria for massive New York-style slices that’ll fuel your afternoon beach adventures—my carb-loving boys can demolish an entire pie in minutes!
💡 Mom insider tip: if your kiddos are still sandy from your photo shoot, grab your breakfast to-go and head right back to the beach where they can play while you enjoy that caffeine fix with your toes in the sand.
You can even head over to Kailua Beach Adventures to rent boogie boards, snorkels or kayaks for the day.
Best Breakfast in Kailua Hawaii: Feed Those Hungry Beasts ASAP
Listen, I learned this the hard way with my four boys: nothing ruins that post-photo high faster than hangry kids (or husbands). After you’ve captured those dreamy sunrise moments at Lanikai or Waimanalo Beach, your crew will be STARVING.
My top recommendation for grab-and-go is Kalapawai Market because its RIGHT next to Kailua Beach. You’ll drive past it no matter what. They make incredible breakfast sandwiches. Snag them and head back to the beach for an impromptu picnic while the crowds are still minimal.
💡 Bonus: keep your parking spot.
For a sit down experience go to Moke’s Bread & Breakfast on Hekili Street. Their lilikoi pancakes are basically Hawaii on a plate—sweet, tangy, and utterly Instagram-worthy. My boys devour them like they haven’t eaten in days. Pro mom tip: get there before 8:30am or prepare for a wait that might trigger meltdowns (and not just from the kids).
Kailua is full of sit-down breakfast options:
Top Beaches in Kailua, Hawaii: The Real Reason You Came to Hawaii
After breakfast, it’s prime time to enjoy Kailua Beach Park before the midday heat kicks in. Unlike Waikiki (which is amazing for other reasons), Kailua Beach offers:
- Calmer waters perfect for littles
- Fewer crowds (usually)
- That powdery white sand that doesn’t get scorching hot
- Plenty of natural shade from pine trees for fair-skinned kiddos (speaking from experience)
💡 Pro tip beach essentials I wish someone had told me about when I moved here with my boys ages 8, 10, 11, and 13:
- Rent boogie boards from Kailua Beach Adventures – cheaper than buying and no need to lug them home
- Bring water shoes (those rocks hiding in the sand are no joke)
- The public restrooms are… serviceable. Lower your expectations accordingly.
Free Things To Do in Kailua Hawaii for Families
Let’s be real—Hawaii isn’t cheap, and after dropping serious cash on flights and accommodations, you might be looking for ways to entertain the crew without emptying your wallet. As a mom of four hungry, growing boys, I became an expert at finding free Kailua adventures that are actually worth your time.
Lanikai Pillbox Hike costs exactly zero dollars and delivers million-dollar views. It’s steep at the beginning but short enough that my boys didn’t have time to start the “how much loooonger?” whining. Bring water and go early before the heat kicks in because there is zero shade. The Instagram-worthy panoramas of the Mokulua Islands make this one of the most popular free things to do in Kailua. When we first moved here, this hike became our weekend tradition—even my hesitant 8-year-old managed it like a champ!
The Kailua Farmers Market (Thursdays at 5pm) is technically free entry, and while you’ll probably end up buying something delicious, it’s a fun cultural experience even if you just browse. My boys love watching the coconut opening demonstrations, and vendors often offer free samples. It’s become our Thursday night dinner spot!
The Kawainui Marsh Trail offers an easy, flat walk where my kids actually spotted Hawaiian stilts and coots—a mini wildlife adventure that costs exactly zero dollars. Pack water and bug spray; I learned both lessons the hard way after one particularly itchy afternoon with four complaining boys.
Kailua Regional Park has sprawling grassy areas perfect for burning off energy. Bring a soccer ball or frisbee and let the kids go wild while you enjoy the mountain views.
Want a cultural experience? Ulupo Heiau State Historic Site is a sacred ancient Hawaiian temple that’s free to visit. It’s a quick stop, but it sparked fascinating conversations with my boys about Hawaiian history (and they actually listened!).
Things To Do in Kailua Hawaii With Kids: Beyond the Beach Bliss
\When I first moved to Kailua with my four wild boys, I thought it was just a beach town. WRONG. Kailua activities range from low-key explorations to adrenaline-pumping adventures, making it perfect for families who need variety (and let’s be honest, which family doesn’t?).
For water-loving families, Kailua Sailboards & Kayaks rents everything from kayaks to SUPs. My personal recommendation? Their guided kayak tour to the Mokulua Islands. It’s pricier but worth every penny when you see your kids’ faces as they paddle into that crystal blue water.
💡 Pro tip: Book the morning tours when the water is calmer—afternoon winds make for a workout that might lead to family “discussions” (ahem, arguments).
If shopping is more your style, Kailua Town itself is packed with boutiques that beat any mall experience. My personal favorites are Lauren Roth Art Boutique, Mokulua Surf Shop, and the Salty Babe. SoHa Living offers home goods that’ll make you want to redecorate island-style when you get home. I’ve bought birthday gifts for almost every mainland friend here!
Got a rainy day? HI Kids indoor play space is a total lifesaver! When we first moved here, I had no idea Hawaii actually gets rain (sometimes lots of it). They have giant building blocks, climbing structures, a toddler zone, arts and crafts, and—most importantly—coffee for parents. Worth every penny of the admission fee when cabin fever strikes and the aloha spirit is wearing thin after days of rain.
Things To Do in Kailua When It’s Too Hot: Indoor Afternoon Options
Personally, I think this is the best time to be floating in the ocean! When the sun is high, the water is most brilliant shades of turquoise and blue! But if you’re sunburned and need a break I highly recommend food and shopping!
Whole Foods in Kailua Town has an incredible poke bar for lunch, plus air conditioning that feels like heaven after a morning in the sun. The Windward Bar has daily happy hour specials from 4-6 on food and drinks.
Maui Brewing is also a family friendly, open air bar and restaurant right in the middle of Kailua Town. The food is better than you’d expect from a brewery. You can watch the rain, the people and just relax in the shade while catching up on recent surf competitions.
After refueling, check out BookEnds bookstore. It’s small but mighty with a fantastic children’s section. My boys actually put down their devices here (miracle!) to browse Hawaii-themed books. Tokyo Central has loads of Japanese snacks and knick-knacks, and of course my favorite shops: SoHa Living, The Salty Babe, Lauren Roth Art Boutique, and Mokulua Surf Co. are just around the corner, offering everything from tropical home décor to stylish beach apparel.
Best Shave Ice in Kailua Hawaii: The Afternoon Sweet Spot
No Kailua day is complete without shave ice from Island Snow. Yes, it’s where Obama goes when he’s in town, but more importantly, it’s where my sugar-loving boys declare “this is better than Christmas!” with every bite. Get the snow cap (sweetened condensed milk) on top – calories don’t count on vacation, mama. We’ve tried every flavor combination between the six of us, and my personal recommendation is lilikoi, coconut, and pineapple with condensed milk on top. Island perfection!
Where to Eat in Kailua Hawaii: Dinner with(out) a View
As the day winds down, grab dinner at Buzz’s Steakhouse right across from Kailua Beach. It’s casual enough for kids but still feels special with its old Hawaii vibe. There is no beach view because the dunes are so high. But its the closest sit-down dinner spot to the beach on the Windward side. The coconut shrimp is worth every penny of the tourist pricing.
If you’ve somehow managed to book a sitter (that deserves a victory lap!), Kalapawai Café is perfect for grown-ups who need a moment of sanity and a good glass of wine.
My personal favorite is Maui Brewing. Its elevated fare or a bar and right in the middle of town with live music some nights.
The Scenic Drive Back to Waikiki: Kailua to Waikiki via Waimanalo
Here’s an insider tip that literally took me MONTHS to discover: When heading back to Waikiki from Kailua, skip the Pali Highway and take the long way around via Waimanalo. This coastal drive along Kalanianaole Highway is hands-down the most gorgeous route on the island and worth every extra minute – during the day. You can’t see squat at night!
The road hugs the coastline, offering jaw-dropping views of turquoise water and the Na Mokulua islands from angles you won’t see anywhere else. My boys actually stop fighting in the car because they’re too busy pressing their faces against the windows (small miracles, right?).
Make sure to stop at Makapuu Lookout for a quick photo op—you can often spot whales during winter months. We’ve made it a family tradition to grab one last shave ice at Waimanalo Shave Ice (try the pickled mango flavor if you’re feeling adventurous) before continuing the drive.
Sandy Beach is another perfect quick stop if you need to let the kids burn off some energy before heading back to your hotel. Just don’t let them swim there—it’s known as “break neck beach” among locals for a reason. The massive shore break is for watching.
💡 Pro tip: Download the Shaka Guide app before you go! It’s like having a local tour guide in your car, telling you where to stop and sharing fascinating stories about the places you’re passing. You’ll actually learn Hawaiian history without realizing it! The app uses GPS to trigger narration about sites as you drive by, pointing out hidden gems you’d otherwise miss. When we first discovered it during our second month here, it completely changed how we explored the island. The Eastside Oahu tour covers this exact route and is worth every penny for the hidden beach recommendations alone!
Family Photography in Kailua Hawaii: Why Professional Photos Matter
Can I get real with you for a second? When we moved to Hawaii, I thought my iPhone photos would be enough to capture our new life here. Four years later, I have exactly TWO photos with all four boys AND me in the frame—both awkward selfies with half my face cut off.
This is why I became a family photographer in the first place. Because moms deserve to exist in their family’s visual history, especially in a place as spectacular as Hawaii.
My sunrise sessions in Lanikai and Waimanalo aren’t just photo shoots—they’re experiences designed specifically for families who might be wrestling with jet lag anyway (hello, 5am wake-ups with mainland kiddos!). We capture that magical light while the beaches are empty, and then you have the ENTIRE day ahead of you to explore Kailua like a local.
The best part? You’ll have quality photos that show everyone together, looking their best with that heavenly Hawaii glow—not just the standard “dad or mom is missing because they’re taking the picture” vacation album. When clients tell me how much they treasure having photos of their WHOLE family in paradise, it makes my photographer-mom heart so happy.
Kailua Hawaii Local Tips: Mom-to-Mom Advice
- Bring a change of clothes for everyone. Hawaiian sand gets EVERYWHERE. My car still has sand from our first beach day four years ago.
- The trade winds in Kailua are no joke—hair ties are essential unless you want to look like you stuck your finger in an electrical socket in your photos (learn from my mistakes with my boys’ hair flying everywhere in our first family photos).
- Pillbox Hike offers incredible views but is NOT stroller-friendly. Save it for when the kids are older or you have carriers for little ones. My 8-year-old managed it, but we took lots of breaks.
- The parking situation at Lanikai is challenging. If you book sunrise photos with me, I’ll share my secret (legal) parking spots that took me months to discover.
Whether I’m your photographer or not, I hope this helps you navigate Kailua like a local mom instead of feeling overwhelmed by the tourist traps. Your family deserves a magical Hawaii experience—one that you’ll actually be in the pictures of, looking relaxed instead of stressed!
Want more insider tips or curious about booking a sunrise session while you’re here? Drop me a line through my website. This mainland mom turned island photographer has plenty more secrets to share!
More Things to Do in Oahu & Travel Resources
- The Ultimate Things To Do In Kailua Hawaii: Perfect Day After Sunrise Beach Photos
- Oahu Easter Events 2025: Spectacular Egg Hunts & Festivals
- The Best Turtle Bay Photography for Families Oahu, Hawaii
- Everything You Need To Know About Ko Olina, Oahu From Ko Olina Photographers and a MOM
- Best Oahu Beaches for Boogie Boarding
- Lanikai Beach – Ultimate Run Down For the Best Experience
I'm a USMC spouse, South Carolina native, recovering homeschool mama of a 4 boy circus. They've taught me the most important facet of family photography: KEEP IT FUN!
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