Top Tips for Your Best Hawaii Vacation with Teens

Headed to Hawaii with teens? To quote Dickens, you may find traveling with teens “the best of times . . . and the worst of times!” Here are few tips to make Hawaii with teens fulfill your “best of times” dreams!

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What to Pack

A good trip to Hawaii with teens starts with a well-provisioned suitcase! We fly Southwest when we can, so we always have the ability to take two suitcases each. We don’t take it that far, but we always pack an extra suitcase with the things that will make our trip better or that will expensive or a hassle to buy on-site. For Hawaii, our packing list includes:

Hawaii with Teens

What to Buy Upon Arrival

Groceries in Hawaii are EXPENSIVE! We are talking $5.99 for a loaf of bread or a bag of chips. It’s really crazy. That’s why you want to bring as much as you can in your suitcase! But no matter how much luggage you can carry for free on your flights, you will need to buy some provisions upon arrival.

You will find the best prices at Walmart. There are usually only 1-2 locations on each Hawaiian Island, but they are near the airports. So no matter where you are staying, make sure to swing by Walmart to get most of what you need when you arrive. We typically buy bread, chips, sodas, water, milk, yogurt, and some sort of bakery treat like brownie bites or cookies. Just make sure your accommodations have a refrigerator before you buy items that need to stay cool.

Walmart is also a great place to buy the beach gear you couldn’t bring with you like boogie boards. We always gift our boogie boards to a family we see at the beach on our last day. My teens enjoy this ritual and making other kids happy. Walmart stores in Hawaii also have a great selection of inexpensive Hawaiian souvenirs and rack after rack of $39.95 Hawaiian shirts!

There will usually be a Safeway or other grocery store located near your hotel for things you run out of or forget. Safeway has a membership club you can join when you are checking out that will save you a dollar or two on some purchases. Go ahead and join – it’s easy at the register – to save a few bucks.

What to Eat

There are restaurants everywhere in Hawaii, but you may find that they are randomly closed on certain days or have long waits. You may also find yourself on the road between places to eat and want food immediately.

Plus, food in Hawaii is expensive. What would cost my family of four on the mainland $60 may well cost more than $100 at a typical Hawaiian restaurant. Unfortunately, my teens are no longer satisfied with the offerings on the kids’ menu, but they don’t like anything too exotic. We bought many $20+ hamburgers on our trip. At one seafood restaurant, my daughter chose the $25 chicken pasta which was the most expensive thing on the menu. Then she didn’t like it and only ate a few bites!

To spare yourself this, always be prepared with picnic foods. In fact, if your family is game, plan to eat breakfast in your hotel room and one picnic meal a day. If you limit your restaurant meals to one a day, you don’t have to worry so much about sticker shock when reading the menu!

To make up for the daily picnics, make sure to add in a treat each day. I highly recommend seeking out shaved ice or other frozen treat daily. We also enjoyed stopping at a roadside stand for an exotic fruit platter. These treats are not inexpensive, but they are definitely less than a full meal and your teens are guaranteed to like them!

Hawaii with Teens

Where to Stay

I typically prefer hotels over home or condo rentals. Hotels typically have more reviews and ratings available, and they offer a more standardized experience. However, when traveling with teens, I find it better to book homes or condos with at least two bedrooms and two bathrooms.

You and your teens probably have different sleep schedules, so you will be able to go to bed and get up at different times. Plus, having extra bathrooms means that two people can shower at once. This is great after an afternoon at the beach when you all need to shower and get ready for dinner! Finally, you probably aren’t used to spending 24 hours a day with your moody teens. Having a bit of space helps everyone.

Rental houses or condos also often have provisions to make your trip better. Our condo rental on the Big Island came with boogie boards, beach towels, and even sunscreen! And you have a full kitchen to more easily prepare meals and store food.

This being said, I do recommend staying briefly in a resort hotel with terrific amenities. Perhaps plan to spend 1-2 nights in a beach resort prior to departure. You can spend the day lounging on the beach in a comfy lounge chair with an umbrella and someone bringing you fruity drinks while your teens enjoy the great pools and activities!

Hawaii with Teens

What to Do

Your trip to Hawaii with teens can’t just be driving around and enjoying the views. Teens like to feel like they are “doing” something. They won’t be happy if you aren’t intentional about planning at least a few activities they can look forward to. Here are some great options for the four major Hawaiian islands.

Oahu

Kauai

Big Island

Maui

One thing offered on all Hawaiian islands that your teens are sure to love is a luau. Although touristy and kitschy, teens love this safe environment to try new foods, learn a bit about the culture, see native dancing, and hear the local music. Plus, they are likely to meet other teens during the experience as you are usually seated at a table with other families.

Making Travel Better

Even if you focus more on adventure activities, Hawaii with teens will involve a fair amount of travel. Your teens may never have experienced such long flights. And there is a lot of driving if you really want to see the entire island you are visiting!

To make flights better, make sure your teens are prepared in advance. Your airline will likely offer free movies, but your teens may be happier with some shows or movies downloaded on their own devices. Make sure they have a portable chargers (and remind them to charge these in advance). They may also appreciate having a neck pillow for cat naps during the long trip. See our related post The Great Travel Pillow Search.

Most trips to Hawaii will involve a lot of driving if you want to see all the major sites. While you may be tempted to book the smallest rental car to save some cash, go ahead and spring for a larger vehicle like a SUV. Your teens will enjoy being able to spread out in the backseat, and you will all have better views with a vehicle that sits a bit higher. One caveat – some of the roads on the islands are pretty narrow, so make sure your car insurance is up for the challenge. I recommend booking your rental car with a Chase Sapphire Preferred card to get primary car rental insurance for free. This will protect you if you happen to scratch up the sides of the car on a rock wall or lose a side mirror!

For long drives around the island, we love the GuideAlong app. It has itineraries for all of the Hawaiian islands as well as other locations. The app uses your GPS signal to identify where you are and narrates sights, activities, points of interest, and facts about the area. We’ve used it for Grand Teton National Park, Yellowstone, the Big Island and Kauai. My kids enjoy the narrator’s stories and wit, and they love trying the foods and things he suggests. We learn a lot more about the destination than we would if we were just navigating from place to place with online map apps.

Finally, challenge your teens to create a playlist of songs that blend their favorite music with their favorite oldies, which are likely some of your teenage favorites. Some of my best memories are driving down the road on our vacations singing Bohemian Rhapsody or Sweet Caroline with my kids!

What are your top tips for traveling to Hawaii with teens?

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