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Planning a Trip to Hawaii? Tips For a Vacation That Actually Feels Like One

Updated: Nov 28, 2023

The one good thing about jetlag: catching the sunrise. Pounders Beach, Oahu

"Focusing on enjoying simple pleasures allowed us to really connect as a family and not have the feeling we need a vacation after our vacation."

Our vacation priorities include: connecting as a family and keeping an easy and free vibe going (this pretty much always involves nature and other simple pleasures). We don't like to spend a ton of money on eating out, hotels or admission fees and are usually guided by local recommendations. Over the years I noticed the kids felt pressure to like the meal and behave properly at a restaurant or pressure to have fun at a crowded tourist attraction, and sometimes it just added up to exhaustion and no fun at all. Focusing on enjoying simple pleasures allowed us to really connect as a family and not have the feeling we need a vacation after our vacation. If this resonates for you and you're going to Oahu, then read on! I have a bunch to tell you.

We've stayed on the North Shore of Oahu twice. We have not yet ventured to other islands because of 9+ hour flight times just to get to Honolulu. Also, my husband likes to surf, and, as you've probably heard, the North Shore is surfing's holy land. Plus, there's so much more to love about Oahu! We have gone swimming with sea turtles, tried shave ice, enjoyed walks in the botanical garden and ate amazing, fresh food.

When to go:

During fall and winter the surf is enormous. Like, 20ft waves. These are the breaks that make the North Shore famous. The big surf competitions take place between October and December. Also note this creates traffic on little two-lane roads. Even with the traffic, it's still pretty easy to get to all the towns along the North Shore without too much delay. Temps in the fall and winter are mostly in the 70s. The ocean still felt warm.

Our previous trip was during April, and the weather was delightfully warm and sunny (although we were told it can be very rainy) and the waves were super chill.

The locals say September is the best time to visit because it's still warm like summer and there is a lull in tourism and waves.

We were there in November and had to find little bays for the little one to swim. Pounders Beach (pictured above) was across from our Airbnb. It had some waves but was OK for the little one to wade in as long as there was an alert adult with her (not naming any names, but a certain husband was holding our daughter with his back to the ocean, and both got taken out by a rogue 6ft wave. They reappeared a few seconds later and were OK. Never turn your back on the ocean! My wrath might have been worse, though.). On the plus side, my son got to enjoy body surfing and boogie boarding all week. If you are looking for some calm water, Kawela Bay is the place.

Snorkling in Shark's Cove (there were no sharks--not sure why it's called that!). Nice place to collect shells. Lots of sharp coral, so wear water shoes.

We used VRBO and Airbnb for our stays and had a great experience both times. We stayed in a cute little house in Waialua the first trip. This area is very residential and chill. We shared a large house in Laie with my husband's family on our second visit. Laie felt less residential but was perfect for our family reunion (my husband's family lives in Australia, so we met halfway).

Pounders Beach in Laie.

Having a kitchen when we travel is a must for me. And what's better than local fruit and macadamias for breakfast and BBQ, fish and salads for dinner?! For lunch, we stopped at taco joints and food trucks, which are plentiful and SO GOOD. I will list my favorites below.

My morning stroll in Waialua.

When we stayed in Waialua during April, the surf was low and was great for swimming and snorkeling. My husband had a magical morning surfing Haleiwa Beach. The ocean was clear, and he saw sea turtles gliding under the water and popping their cute heads up for air.

There are places to rent surf boards, etc. at all the beaches. We rented at Haleiwa Beach. There are also stand up paddle board sunset adventures at Haleiwa that I'm super excited to try next time when my daughter should be a strong enough swimmer.

One of the highlights of our trip was watching sea turtles (and swimming with them!). The sea turtles weren't around last November, to our disappointment (I'm guessing they stay out to sea more when the waves are big). The best place to see them is Laniakea Beach.

Volunteers keep people away from the turtles as they come and go. Laniakea Beach

For groceries, we shopped at Malama Market in Haleiwa. They had a good selection of fish, vegetables and some of the regular snacks the kids like from home. Organic options are limited on the North Shore. If organic is important to you, stock up at Whole Foods in Honolulu or Kailua on your drive up from the airport. I say this because we wasted a morning trying to get to Whole Foods in Kailua's traffic.

Delicious roasted chicken in the Malama Market parking lot. Great place to grab lunch on the go.

Kids love Hawaiian shave ice. It might look like a snow cone, but it's not! It's all the in the preparation of the ice. And, apparently, kids are experts in this department. Both of mine were offended when the "shave ice" truck at a food truck festival here in New York's Hudson Valley was clearly serving snow cones NOT shave ice!

Haleiwa has two famous shave ice spots: Matsumoto's and Aoki's. I think the shave ice tastes the same at either place. We have an affinity for Aoki's because we saw it in all its former kitsch glory years ago. The owner is super nice, as well. It has since moved locations and had a major makeover.

Aoki's 2013. Old fashioned Hawaiian style.

The new Aoki's has a deck with lots of outdoor seating. A nice place to hang out in town.

We found an organic option for shave ice (also lacking in neon food dyes) at the Old Sugar Mill in Waialua. This is a great spot to stock up on souvenirs and gifts, as well. They have tons of locally made items and great Hawaiian coffee. If you're headed out to Waialua, check out Killer Tacos and also Giovanni's Shrimp Truck.

All the major surf spots have food trucks nearby. We stopped by Sunset and had great lunches and desserts a few times. Other Hawaiian staples to enjoy: bullet coffee and papaya bowls.

Post beach day ritual: roadside fruit stands for fresh coconut water. Nice ladies open the coconuts with machetes!

Other than sea turtles, going to the beach and eating lots of beautiful fresh food, we like Waimea Botanical Garden. Lots of lovely walks and SO MANY amazing flowers. They have cultural and sacred sites you can see and read about. There is also a waterfall, and you can swim in it! They have life jackets there.

My husband and son in the waterfall in 2013. Wai (fresh water) is considered sacred to Hawaiian people. Known as life giving waters, fresh water in the form of rivers, streams, springs and ponds represents life, purity and health.

Not your average shoulder ride.

Never too many flowers! We didn't pick these at the botanical garden, by the way.

My last recommendation would be to hire a photographer. We worked with Heather from Little Bird Photography and are so glad to have all the great family shots from our trip. At the very least, buy some leis at Malama Market and do your own photo shoot!

Mahalo and have a magical trip!

From the photo shoot with Heather

P.S. Underwater cameras are also a great idea to capture some epic moments!

And don't forget the obligatory beach foot photo.



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