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Explore our Travel guides by island:
1. Lock In Some Dates
6 months to a year in advance
Considering factors like flight/drive time, jet lag, time differences, and downtime, I suggest a full seven days for one island. If you plan to visit two islands, opt for ten. Hawaii is not a place you want to rush! I can’t tell you how often people beg me to extend their vacation, so plan accordingly and if your schedule allows, round up.
You likely already have some travel dates in mind, and the good news is that there truly is no bad time to visit Hawaii! Do not sweat it if you’re working around your kid’s school schedule. If you do have some flexibility, here are some things to consider:
2. Make a Budget
6 months to a year in advance
I’m not going to sugar-coat it, Hawaii is expensive. Oahu is the cheapest island to visit and Maui shows no mercy. A family of four can expect to pay around $10,000-$15,000 for a ten-day vacation to Oahu. Here’s how I factor in costs when arranging a budget-conscious vacation to Oahu.
10 Days on Oahu (Family of 4)
This estimate is based on a $400/night hotel stay, which is technically still a mid-range “budget hotel” according to Hawaii’s standards. You can easily stay somewhere clean and central in Waikiki for this price. On the flip side, incredible luxury resorts on Oahu (like Turtle Bay on the North Shore) can easily set you back around $600-$1000 a night.
While there are several ways to save money (book with points, fly before your kids are two years old, stay at a vacation rental with a full kitchen, and opt out of the rental car), it’s best to be realistic. If you’ve ever endured the special kind of nightmare of budgeting for a wedding, you’ve likely already learned this lesson: overshoot and plan for the unexpected.
Take a deep dive with our
Ultimate Guides By Island
Island Hopping
If you have the time, consider visiting more than one island! Most inter-island flights are 40-45 minutes but remember that we’re still dealing with airports, rental cars, and kid meltdowns here. I block out at least a half day to travel and settle in.
Molokai and Lanai
While you’re here, you may want to visit the lesser-known islands of Molokai and Lanai. While Molokai is beautiful and rooted in deep history, it is generally less welcoming of visitors. Lanai can provide a luxurious, low-key experience for the right family (hello bougie Four Seasons).
Alternatively, you can visit Lanai for the day via ferry from Maui. If your kids are older, it’s possible to forgo a car and walk from Manele Harbor to Hulopo’e Beach (great for snorkeling and sunbathing), but renting a jeep is the best way to explore Lanai.
4. Book your Flights
6 months to a year in advance
Let’s make this vacation official! I have been using Skyscanner to find the best flights since I was a poor, travel-obsessed 20-year-old. Almost everything about how I travel has since changed, except for this because they’re still the best in the industry. Here are the leading players I book with and why:
Airlines I Book With and Why
Airports In Hawaii
5. Figure Out Where to Stay
6 months to a year in advance
This is my favorite part! Some things to consider:
I also have articles written about the best family-friendly hotels on each island.
6. Decide on a Rental Car
6 months to a year in advance
To rent a car or not to rent a car? It depends on your travel style, island of choice, and age of your children. If you plan to chill by the resort pool for most of your stay, you can certainly get by without one!
But in most cases, I suggest renting a car while visiting Hawaii. Oahu is the easiest island to navigate without one, but Maui, Kauai, and the Big Island make it much more difficult with kids in tow. Rental car shortages do happen, so be sure to reserve a vehicle early.
My family travels inter-island often, and we almost always find the best rates through Discount Hawaii Rental Car. These guys are awesome. They require no prepayment or cancellation fee. They also allow an extra driver and reduced young driver fees, which is rare.
Be sure to find out if your hotel charges a cheeky parking fee! Many charge $40 or more a night. If you’re on a budget or want to spend most of your time at the hotel, consider renting a car for part of your trip and planning your excursion days around it.
Transportation guides
8. Reserve Spas, Tee Times, and BabySitting Services
3 months in advance
If you’re in the mood for some self-care (you’re a mom, yes you are), it never hurts to book ahead.
Large resorts often keep a few daily spa appointments open for new guest’s arrival. Smaller spas hire fewer massage therapists, and the best ones tend to book up quickly.
If golf is on your itinerary, reserve early morning slots a few months in advance. Tee times before 2:00pm are more popular and also more expensive. Some golf courses offer shuttle services, so reserve those as well.
Large resorts often offer Kid’s Clubs to registered guests and don’t require any pre-registration. However, clubs like Aunty’s Beachhouse at Aulani Disney Resort on Oahu book up quickly and accept reservations 90 days in advance.
9. Make Important Restaurant Reservations
1-2 months in advance
It’s possible to book a reservation at most restaurants by calling a few days in advance, but some exceptions do require a certain level of moxie to get your foot in the door.
Call a month ahead if you’re traveling with a group and want to celebrate at popular places like Duke’s or Merriman’s.
The character brunch at Makahiki (another high-demand activity at Aulani) books up insanely fast, and dedicated moms have been known to stay up until 12 a.m. (Hawaii time) 30 days out to secure a spot.
Mama’s Fish House on Maui is arguably the most well-loved restaurant in Hawaii and accepts reservations 18 months in advance. (I once made a miracle happen and scored a table a few weeks out! Allow at least six months to play it safe.)
If you’re on a strict budget but love to eat out, avoid sticker shock by doing your research beforehand. Watch happy hours for the half-price pupus (appetizers), and remember, this is still America—portions are huge. Your kids probably don’t need their own $30 entree.
Restaurant guides
10. Map Out Kid-Friendly Beaches, Hikes, Parks, and Excursions
1-2 months in advance
Get a rough idea of where your excursions are located so you can map out a few fun days without driving all over the island. Some landmarks in Hawaii restrict the number of daily visitors to help protect natural resources.
Popular Landmarks:
Here’s a list of the most popular landmarks that require an entry ticket and when they are available for purchase.
The Perfect Itinerary for Your Family
Be sure to schedule plenty of downtime—especially if you’re a meticulous travel planner like me! A good rule of thumb is 70% structure (yes, even for relaxation) and 30% unstructured time to do whatever feels right. The right kind of planning melts away the hustle and gives you more freedom to simply be with your family in paradise.
If you’re feeling overwhelmed, I can help you decide if a customized travel guide or a done-for-you itinerary is the best fit for your family.
