5 Best Tips You Need to Plan a Family Vacation to the Hawaiian Islands

Who doesn’t dream of going to Hawaii?

After all, it’s the ultimate family-friendly destination, offering something for everyone in your travel tribe—no matter if you prefer to be lounging on the beach or by the pool, or out exploring the great outdoors for some serious adventure.

But, what in the world could be holding you back from handpicking dates, submitting PTO time, and re-working the family calendar to make time for a memorable experience? Well, there are so many things—from knowing which island(s) to call your home away from home to transportation, weather conditions, and, most importantly, time and money involved.

And, you’re not alone. For that reason, I’m here to help you say “aloha” to your dream getaway by dishing out my best tips to plan a family vacation to the Hawaiian islands! Take a read and get to packing your bags ASAP.

1. Know That “Hopping” to Multiple Islands is an Option.

plan a family vacation to the hawaiian islands

One of the most daunting tasks of planning our Hawaiian vacation was having to choose just ONE island to visit. But, when we found out that we were able to “hop” from one island to another in less than an hour and at less than $100 per person, we were ecstatic. This would allow us to see all four of the main islands on one extended 16-night visit.

Now, that doesn’t mean it was all a bowl of cherries. One of these flights was on a “quaint” little nine-seater plane. Yikes! But, the others were on large commercial jets, which were offered through Hawaiian Airlines or Mokulele Airlines. And, the good news? The airports are small and very easy to navigate. So, we could easily leave one island after breakfast and be checked in at the next island resort by lunch.

On the other hand, I realize that not everyone travels for a living or has just one kid to manage. Not to mention, can take 16 nights off of work and real-life responsibilities to see all four islands. With that…

2. Pick an Island Based on Your Travel Style.

plan a family vacation to the hawaiian islands

When you do need to pick just one Hawaiian island, I would offer the following insight as a very generalized overview of the four main islands after having spent four quick nights on each.

The Big Island was made for the adventurer. It’s definitely perfect if you want to have a diverse and dramatic experience. In a single day, you can swim with sea turtles, walk through lava fields, hold a baby seahorse, and stroll through a rainforest. You may even be able to squeeze in a luau for dinner. Ultimately, it has all the natural beauty, Hawaiian feels, and adventure you can handle. Because this is not a “resort destination”-type vacation, however, it might be best suited if you have older kids in your travel tribe who will appreciate venturing out and exploring. If this speaks to you, be sure to check out this post where I run through the top 10 places your family needs to explore while on the Big Island. 

What the Big Island offers in adventure, however, Maui offers in resort luxury for the paradise seekers. Maui’s all about paradise. Think gold, shimmery beaches, luxury resorts, golf, and shopping. Wailea, in particular, is a pristine, tropical area with some of the island’s most famous resorts, dining, and shopping. Not to mention, the rainbows and sunsets! If you’re looking for a beach resort destination-type experience, Maui is it! If you want to learn how you can enjoy a stress-free, luxurious vacation on this island, add this post to your reading list.

Next up, Oahu is a shopper’s dream! Every high-end store you can think of can be found in Waikiki. It’s a full-on major city (including the crowds) just blocks off the famous Waikiki Beach. Other resort areas on the island will get you out of the city and closer to the beach, if that’s more your thing. Additionally, this island is home to the hip, laid-back North Shore (think Banzai Pipeline). Curious what the kid-friendly gems are on Oahu? You’ll want to read this blog post I put together!

Lastly, if you’re looking for a more laid-back, less crowded, true island experience, than Kauai is your place. This island is ideal for nature lovers and outdoor enthusiasts. My head is still spinning from the whirlwind of sights including rainforests, the Waimea Canyon, Na Pali Coast, hundreds of waterfalls, roadside stands, and roaming chickens. I say go and hike, kayak, snorkel, or lay on a beach! And, if you really want to splurge, take the helicopter to Jurassic Park Falls. Truly mind-blowing! And, I unveil a mini itinerary on what to do and see when visiting this island here.

3. Don’t Be Afraid to Explore Via a Rental Car.

plan a family vacation to the hawaiian islands

Man oh man… did a rental car come in handy on every island, or what? The investment for one came to about $300 for 5 days/4 nights. Why’d we decide to get one? Well, there’s such varying climates, topography, and experiences throughout each of the islands. So, you really have to get out and explore to get a real sense of all that Hawaii has to offer!

And, you’ll want the freedom to stop at a fruit stand, hop out for a roadside coconut, take a quick swim in a waterfall, or capture a family selfie from a scenic overlook. Trust me on this one. The mid-size base-level car rental did fine for us, with the exception of recommending a Jeep if you’re going to Maui on the Road to Hana. You’ll appreciate a narrow wheelbase for the 600+ tight hairpin turns!

4. Mind the Weather.

plan a family vacation to the hawaiian islands

The weather can vary dramatically depending on where you stay on each island. For example, up in the northern region of Kauai, it rains approximately 350 days per year. Wowzers!

Ultimately, it can often be beautiful and sunny on one end of the island and raining buckets on the other – as is the case throughout most of the islands in Hawaii. For this reason, I recommend doing some research on the island regions before making your hotel or resort reservations. This is something we hadn’t considered, and we ended up on the rainiest side of the island during hurricane season.

5. Keep Your Travel Budget & Time in Check.

plan a family vacation to the hawaiian islands

I know what you’re probably thinking right about now. This all sounds great, but what about the time + money?

Am I right?

The two things that kept us (and maybe you and your family) away from Hawaii was our preconceived notion of the costs and estimated travel time. So, I’d be remiss to not share my own experiences on these two topics with you.

Being that Williamsburg, Virginia is our home base, we spent about $550/per person round trip on plane tickets by driving three hours to Baltimore and flying out of that major hub. This really helped! One small disclaimer, however: my husband is a ninja at finding good flight deals. We flew about 3.5 hours to Dallas and another 8.5 to the Big Island.

Coming back home, all the flights are overnight. So, we hopped on a 7 p.m. flight (Hawaii time) and landed in Baltimore the next afternoon after a layover in Denver. That sounds awful, I know. Honestly, though, it wasn’t that bad (thanks Melatonin!), and it was totally worth it. We were all adjusted to the six-hour time difference within two days on both ends.

Actually, after returning, I told myself I’d do it again in a heartbeat for a 7-8 night vacation. But, 10 (or forever) would be ideal.

Now, the second greatest expense will be your accommodations. You can save a lot of money here, and also on food, if you go with a vacation rental. For example, a two-bedroom deluxe with a full kitchen that sleeps a family of six on the Big Island at Wyndham Kona Hawaiian would average $1,900 for a seven-night stay. That brings room and airfare for a family of four to the Big Island for seven nights to just under $5,000.

Keep in mind, however, food is certainly more in Hawaii than back on the mainland. And, it’s not unusual to spend $16 for a salad or sandwich or $35 for an entree when eating out. Though, there are convenient grocery stores, and you really can keep costs down if you eat meals back in the suite, shop from street-side fruit stands, and eat out only occasionally. Oh, and for having a rental car, gas ran $4.19/gallon, on average.

plan a family vacation to the hawaiian islands

Tripbound Traveler Tip: Shopping at local grocery stores makes a big difference! For example, on the Big Island, you can stop at the local Foodland grocery store and grab a pound of poke (fresh raw tuna sliced in cubes) for $10 per pound. This is the main delicacy of the islands, and will run you $25 on average for 4 oz. when dining out.

Ready for the good news? Once you arrive, there is so much to do that will cost you nothing at all! So much adventure and natural wonder without spending a dime (or, at least, very little). You can spend a week playing and adventuring without forking over much of your hard-earned cash on activities the whole family will love and treasure for a lifetime.


So, what do you say? Are you ready to make this Hawaiian getaway a reality for your family so you can set your sights on all the natural beauty and wonder the islands have to offer? Your Tripbound Resort Specialists are here to make it happen! Give us a call today at 1-888-816-5214, and we’ll match you with the perfect family vacation.

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