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How to Plan a Family Trip to Hawaii

Hawaii is one of the most near-perfect anniversaries or honeymoon destinations in the world, but the Aloha State can actually be great with the kids and family, too. Logistically, it’s a breeze, allowing everyone to dig into a unique culture and jaw-dropping landscape without having the hassle of juggling everyone’s passport, interview with the customs, or dealing with the currency exchanges.

There are four major islands here namely Kauai, Oahu, Maui and the Big Island that offers a countless options of resort and a luxury houses in Hawaii that are ready to welcome your entire family with an all-inclusive type of experience, but of course, it’s also easy to create your own itinerary and tailored it exactly for your family. In this guide, we’ll give you an idea on where to dine, stay and look for an adventure just off the beaten path.

How to Get To Hawaii

From the mainland, Hawaiian Airlines offers most of the flights and between each island and they also partner with airlines such as American, JetBlue, and United in point sharing. There are airlines like Delta, Virgin American, Alaska, United, Allegiant, WestJet, and Delta also offers nonstop flights from major cities across the western U.S.

Sometimes it’s really overwhelming to book the flight of the entire family, but you can break up the process. You can secure the flight from the mainland first then take your time to book the flights between the islands, which should make things much easier.

If you feel like upping the luxury quotient a bit and don’t mind spending a little extra, then you could also consider taking a private jet flight with your family. Traveling to Hawaii and moving from island to island while you’re over there can become easy that way. Not to mention that you won’t have to stress out about having to book various flights and getting lost in the details. This will leave more time for you to relax and enjoy the vacation.

Getting Ready

The next thing you need to figure out is the number of an islands you’d like to visit. Depending on the length of your stay, it’s worth going to at least two islands (but preferably as many as you possibly can).

If you’re going on multiple flights throughout your travel vacation, you need to pack as light as possible to avoid baggage fees, which can really add up over the course of several flights. You don’t need heavy clothes because Hawaii has a tropical climate, not unless you’re going visit places like Haleakala National Park on Maui which have a much higher elevation.

Renting a car is a great idea also as there isn’t another easy way to get around the island you’re on. It’s more comfortable to travel from hotel to different sites and beaches.


You’ll likely end up in the capital city of the state since most flights to Honolulu are frequent and less expensive. It’s definitely worth staying a while to experience a uniquely laid-back urban you can try here that isn’t possible on the other islands.

Places to Stay

Staying somewhere near Waikiki beach and all its towering resorts is ideal. This will give you access to a lot of the nearby shops in Waikiki and most importantly to the beach. It’s an easy walk to wherever you need to go and is ideal if you have a young family that don’t want to be walking all the time. There are a number of delicious food places nearby too, but let’s talk about that in our next point.

Where to Eat

You should never miss out a hot and fried-to-order malasadas from Leonard’s Bakery. Try their more flavorful and almost chewy dough hole-less doughnuts. During lunchtime, go to Ono Hawaiian Food. They serve a meal for two that’s good for a family of four and good for your pocket too! Their specialty is the traditional dishes like lomi lomi, kalua pig, and haupia (a Hawaiian dessert made with coconut milk). The best of all is the steamed taro leaf wrapped pork lau lau and the kids will be sure to love these amazing dishes.

What to Do

Pearl Harbor and Diamond Head are two of the iconic sites for reasons. But they are not just for educational experiences and academic sense only. The USS Arizona Memorial is undeniably moving in a way that kids of all ages will appreciate, even if they don’t fully understand its significance. If your family is up an for adventure, you can try hiking in Diamond Head, where you’ll get the best view of the island that your kids will definitely remember well into their adult years.


This is a place filled with volcanic activity and adventure and is the epitome of everything that Hawaii has to offer. It is also one of the most beautiful of the islands too, it should not be missed.

Where to Stay

On the west coast, there tends to be the most places to stay in Ka’anapali and Lahaina, or on the southern coast in Wailea. There are also some more secluded spots if you are looking for a more private and less hectic family holiday.

Where to Eat

Sam Sato’s gives you an office vibe with its low-slung beige building far from the cool and glitzy tourist stops. Try their signature dry mein, it’s a touch thicker than ramen with a killer al dene chewiness and is tangled with scallions, bean sprouts and slivers of barbecued roast pork. The local delicacies are also something worth trying, with many traditional Hawaiian dishes that are absolutely delicious. My favorite is definitely anything cooked in an Imu, which is a type of underground oven. Slow roasted pork is definitely a highlight of this magical method of cooking.

What to Do

Never miss out the beautiful and mind-blowing sunrise at the top of Haleakala National Park. The crater itself is absolutely beautiful and it must be because if you don’t get there at 5 am or earlier the chances are that you won’t get a parking spot. There is also a lot of beautiful native plants to see too, but make sure that you bring some warmer clothes because the temperatures can really drop in the park. You can also find the best private boat charter maui has to offer because it’s a beautiful island and going on a journey around it won’t be an experience you’ll ever forget.


Another island on our list is Kauai, this is an island of valleys, green mountains, and little farm stands. You can feel a funky and super chill vibe on this island, where harmless chickens roam the roads. It is one of my favourite places, especially if you are looking

Where to Stay

Getting your own home is one of the best places to stay in Kauai, especially if you want to experience a bit more peace and quiet with your kids. Kauai is definitely the place for this for a more secluded and private holiday and your kids will absolutely love playing on beaches and exploring the nature with practically nobody else around.

Where to Eat

Try the daily farmers’ markets, known as “sunshine markets”. This is a good place to bond with your kids and a place to introduce to them some exotic fruits. They can also enjoy that fruit in a form of dessert at Jojo’s Shave Ice, where they use homemade syrups. You can also try an ice cream at Lappert’s Hawaii Iceam and Coffee. They have a Laua Delight sorbets that taste so creamy from coconut milk.

What to Do

Kauai is known for its phenomenal scenery along with its hiking trails and most especially those that hug the Napali Coast. However, that particular route is not advisable for kids, but still, you can enjoy its amazing scenery. Your second option is to drive to the scenic lookouts of Waimea Canyon and check out the Canyon Trail to Waipoo’s Falls, which are absolutely incredible.

The gentle waves and warm water of Hanalei Bay are great for first-time surfers. If you don’t know how to surf, Titus Kinimaka’s Hawaiian School of Surfing offers a lesson for the entire family.

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