The Ideal "Family" Day In Kailua

Hawai’i is all about spending time in the great outdoors. If you like to stay up late and sleep in, a trip to Ibiza may be more fitting. Around here it’s up with the sun, maximize your day and have dinner when the sun goes down.


Everyone knows Waikiki is famous for sunsets. Crowds of tourists taking selfies on the beach, fighting for space to get the perfect angle. The colors are beautiful and its a surefire way to inspire FOMO with your friends, but is there a better option? YES! What goes down must come up, and on the windward side the sun comes up in spectacular fashion every morning.

Kailua and Lanikai are incredible beaches to watch the sunrise from, and you won’t have to fight any crowds! It’s late March so you’re going to want to hit the beach by 6:15am to really get the full experience. If you stare at those islands long enough though, you will eventually get the urge to paddle out. But don’t get ahead of yourself, grab breakfast at a favorite local spot!


(Also famous for brunch, but you’re getting an early start)

1. Cinnamon’s  Eggs Benedict fans rejoice, they have an entire page of their menu dedicated to this delight. Try the Crab Cake Benedict for a twist on this traditional dish.

2. Boots & Kimo’s These guys are a local phenomenon with a line out-the-door every day but Tuesday (only because they are closed). They have a winning formula with their mac nut (macadamia) pancakes. We don’t know if it’s still worth the wait because every time the line is too long, we end up walking down the block to #3.

3. Crepes No Ka ‘Oi If you want to bet that you can’t put a Hawaiian twist on french crepes, you’re about to be “out some money”. These guys bridge the gap not only from Europe to Hawai’i but from confection to savory. Try the “Haole Boy” and experience Maui Gold pineapple with ham on this unique adaptation.

4. Over Easy One of Kailua’s newest breakfast joints has come out of the gates swinging. Locally sourced eggs from Waimanalo create the foundation and then it’s up to you to build your dream breakfast of kalua pork, Portuguese sausage, candied bacon and a huge variety of fresh veggies.

Kayak Rental Snorkel Gear Kailua Bay

Full? Perfect. You are gonna need those calories for the trip ahead. Drop into our shop and grab some free parking. Lockers for keys and wallets are available so you don’t have to worry about planning too far ahead. We’re going to start by asking a few questions (what’s your experience level, adventure level) and going over the weather conditions. We’ll help you formulate a plan and go over everything you need to know to have a kick butt day. A good package for the family would be two double kayaks, a dry bag for your phones and cameras and snorkel gear for some turtle seeking while you’re out there (comes to $57/person).


Launching into Kailua Bay is an amazing experience, whether it’s your first time or your thousandth time. The offshore islands encircle you and the outer reef keeps the bay relatively calm. Head out to either of Kailua’s offshore islands for a surreal ocean experience. Popoi’a or Flat Island will take about 20 minutes and is a good destination for family fun with kids. Moku Nui, the larger of the Twin Islands is a more advanced destination taking upwards of 1 and a half hours, but the view of Oahu’s windward side mountain ranges will be worth it! On the way back, make sure to stop off at breathtaking Lanikai Beach for some much deserved rest and beautiful snorkeling. Let the trade winds bring you back to Kailua Beach and spend some time reflecting on mother nature…

Hungry again? I thought so. Grab a bike ($20/four hours) and take an easy bike ride to one of




1. Teddy’s Bigger Burgers There’s no way around it, there’s just something about their buns. With dozens of ways to dress your burger, Teddy’s offers a fun experience for the carnivores in your family. Kids will be stoked.

2. Lanikai Juice is what Jamba Juice would be if it was born of Hawaii, with Peruvian roots! This trend setting local smoothie shop made acai bowls famous in Hawai’i and started the pitaya (dragon fruit) craze with its mesmerizing deep red rouge. You’ll learn about the health benefits of all of their ingredients and add boosts of what your body needs to tackle the day.

3. Whole Foods Kailua Has been great at locally sourcing fruits and vegetables and products made in Hawai’i. Their hot bar and salad bar combo goes on sale every Wednesday but we still seem to end up with $30 worth of food piled up. There’s a bar in Whole Foods. This is not a typo and is unbelievably a favorite hang out for Kailua locals. They bring in seasonal micro-brews and always keep our very own Lanikai Brewing Co. on tap!

4. Paniolos is a local burrito shop, inspired by the Paniolos or Hawaiian Cowboys. This is a cool part of our history, further expanding the diversity of the islands. Show up hungry and leave with your wallet fully in-tact.

5. Buzz’s Steakhouse It is impossible not to include Buzz’s on any list of recommended restaurants in Kailua. Grandfathered in as one of the only businesses close to the ocean, Buzz’s has been a go-to for lunch and dinner since your daddy was a baby. Calamari steaks with a lemon caper sauce will change you for the better. Both Clinton and Obama have dined here while they were active presidents, look for their dedicated table in the back. Buzz’s is also canal side and offers one of the few vantages from their parking lot of the sun setting over the Ko’olau Mountains in Kailua.

Kayaking through Lanikai’s coral garden

If you follow these instructions exactly, we can guarantee you’ll fall asleep with a smile on your face and a hankering to wake up in the morning and crank up the ol’ adventure motor bright and early the next day. So what are you waiting for? Come see the windward side!

When you’re ready to go, start by booking your kayak online here: 

Book Now

(Psst… Coupon code “kailua” will save you 15 percent…) Or give us a call at 808-262-2555.