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How To Plan A Family Trip To Hawaii

How To Plan A Family Trip To Hawaii

Seeing the gorgeous luxury homes in Hawaii set against its beautiful landscape should only encourage you to go on that well-deserved family vacation. After all, your kids will only be young once in their lives, as with you. Now comes the hard part: planning the vacation. It might seem like a terribly daunting task, and might at times discourage you. Don’t let it, because here comes help! Let this assist you as you organize the best family vacation of all time.

When to go

HawaiiBefore getting this show on the road, you need to decide the when. If you are on a tighter budget, you might want to consider travelling during the off seasons, which are from late April to early June and from September to mid-December. Traveling off-season will mean perhaps a bit less sun, but it will also mean accommodations and fares will be a lot cheaper than they usually would be during peak season.

Unfortunately, going on an offseason will mean taking the children will have to take a leave from school;if you travel in early June, perhaps you can talk to the teacher and see if you can arrange for your child to take on extra work and early final examinations in order to permit your child to leave school a couple weeks early.

Since there are numerous islands in Hawaii, you might be thinking of visiting a few of these. If this is the case, book your tickets to the main island you will be visiting and then you can arrange the flights or boat trips between the islands.


It is important to ensure that all your travel documents are in order and you have copies of both digital and physical copies. If you are a foreigner, make sure you have a copy of your passport (if not, your actual passport) with you. When it comes to clothing, pack light and just bring light clothing; now’s the time to bring out those floppy hats, tank tops and shorts! Don’t wear boots or else you’ll just develop fungi and instead, stick to slip on shoes or sandals.

Make sure you have enough sunscreen for everybody or just buy it when you get to Hawaii. Bring travel sized toiletries or just like the sunscreen, purchase it when you get there. There’s a big chance you’ll be getting into the water, so bring ziplock bags for your gadgets. If you’re planning on island hopping, better check if there’s public transportation on the island you want to go. If there is none, try to make reservations for a rental vehicle.

Where to stay

Everybody has needs when it comes to accommodations. For example, your teenager will definitely want a place with a good and steady wifi connection while your five-year-old might want cable tv while the wife will want somewhere with a view. In addition, you have to think of the places you want to go; do you want to be within walking distance to the market or the beach? Luckily, these days your options for your accommodations are endless. If you’re a small family, a hotel will do the trick. If you’re looking for something with a little bit of everything, perhaps a resort will be your best option. If you’re a rather large family, try Airbnb. If you want to go all out and splurge, try luxury mansions for rent.

Choosing an island

Hawaii Molokaii

Hawaii is an archipelago and choosing the islands (hopefully as many as possible) you want to visit will probably be one of the hardest decisions you will have to make for this vacation. You’ll have so many demands, so here’s the lowdown on some of the islands:

Oahu – If what you want is that classic Hawaiian vacation, then Oahu is for you since there most activities here are quite Hawaiian. Oahu is also perfect for families who do not want to travel far since the state capital, Honolulu, can be found on this island as well as of Daniel K. Inouye International Airport, so it’s likely you’ll be arriving in Hawaii via that airport.

Big Island Hawaii – Adventurers will love the Big Island; after all, how often will you get to say you’re staying on a growing island? You can witness the continuous eruption of Kīlauea, a volcano that’s been erupting since January 3, 1983, in Hawaiʻi Volcanoes National Park or opt to go underwater with the dolphins.

Maui – First-timers might want to check Maui out, with its expansive beaches and activities perfect for both older and younger kids. The one negative to this island is due to its popularity, it can be a bit crowded, but I would definitely still recommend it.

Lanai – If you’ve got a bit of cash and are willing to spend on accommodation, then you might like Lanai. It’s definitely not a pocket-friendly island and not for the tots, but a day trip to the island might be the trick to check it out. Naturally it is a bit quieter due to the higher prices.

Kauai – It might be a bit rainy here compared to the other islands, but perhaps the green of Kauai may be owed to that rain. Active families will enjoy this island with its many hiking trails and waterfalls.

Moloka – Some say there’s not much to see on Molokai, but it’s the island to go to if you want your family to have a taste of Native Hawaiian culture.

What to Do


It might be a small state, but you will never run out of activities on Hawaii. First up is surfing, which was invented in the state. Next is hiking one of the trails scattered all over Hawaii. Little kids can even participate since Diamond Head Crater is not that much of a hike and can be managed by them.  There’s also the Pearl Harbor  Memorial,  Dole Plantation, and Polynesian Cultural Center. Of course, attending a Luau with your family must be on your list to complete the Hawaiian experience.

Hawaii is known to be the friendliest state, which is why it’s also perhaps the best place for your family trip. Remember, kids grow up fast so cherish every moment you spend with them.


nb: this article has been written in collaboration with Luxury Retreats.