Hawaii was a “bucket list” destination for me from childhood; I have wanted to visit the “Aloha state” for as long as I could remember and just never pulled the trigger for one reason or another. When I heard that Southwest Airlines was going to start flying to Hawaii, I knew I would be watching those flights closely since we had a companion pass, and sure enough, we scored a DEAL on flights! (ahem… meaning I can spend more on resorts, fun activities, and great food…).

For those less familiar with Hawaii, there are six major island destinations to consider for tourists: Kauai, O’ahu, Moloka’i, Lāna’i, Maui and the island of Hawai’i. Each island is unique in what it has to offer, and we knew with only eight nights we did not want to split our time between more than two locations. We ultimately chose to spend five nights on Maui for the diversity of family friendly activities; as well as for the time to visit close friends who live there. Then, for the remaining three nights we decided to visit O’ahu with the opportunities of visiting Pearl Harbor and including a little Disney magic (more on that later!).

The trip is entirely too much to cover in one blog post; so I will follow this first blog with several additional blog posts to detail specifics like: driving the Road to Hāna, visiting the Polynesian Cultural Center, our experience at Aulani, A Disney Resort & Spa and a few other fun trip components!

But first – let’s touch on some of our adventures in Maui!

The first big decision we had to make in planning our Maui time, was where to stay. The island itself is fairly large so we knew we wanted to be somewhere that was centrally located, but also in an area with fantastic beaches and beautiful resorts. We ultimately landed on the Wailea beach area – a lovely section of town with gorgeous resort after gorgeous resort. It is also only about 30 minutes from the airport, 45 minutes from the Lahaina harbor, and about 30-40 minutes to Ho’okipa Beach in the other direction (which is where we would be kicking off our Road to Hana day). We opted to stay at the Fairmont Kea Lani – a family friendly resort with all-suites, amazing pools and a kid’s club. You can read more about the Fairmont Kea Lani in Kacie’s detailed blog post. For our family of six this was perfect as we were able to get two guaranteed connecting suites (hard to find sometimes!) and had more than enough space for everyone to spread out. We loved the resort and I would stay there again without hesitation!

So, what is there to do on Maui for a family vacation? The answer is – more than you can possibly fit into five days! But we did our best and I’ll touch on a few of our favorites. We will definitely need to plan a return trip to round out this list in the future though.

Journey to the Haleakalā Crater

This was something I had thought about briefly before our trip as a “maybe” activity, but really wasn’t sure if it would be easy enough to do with the kids or worth the drive. Thankfully our friends encouraged us to make the impromptu drive up to catch the sunset one night and it was breathtaking! I would recommend without hesitation. Sunrise is actually the more popular time to go, but with a driving time of over an hour and a half from the resort before sunrise, the early morning sounded like a struggle to me (note: we are NOT morning people in my house). Our friends suggested sunset as being their favorite time to go because it tended to be much less crowded and (in their opinion) equally beautiful. We arrived to the summit with plenty of time to spare before sunset and had a chance to explore a bit. It is so high up (at 10,023 feet above sea level) we were literally looking down at the clouds and the views were just unbelievable. A few tips for a happy visit:

It is COLD – do not head up in your shorts and flip flops from the 80-degree weather at the beaches (rookie mistake on our part since we had not really planned on doing this). Wear long pants and jackets – I promise you’ll thank me.
If you do want to go for sunrise, you must plan ahead. The park requires parking reservations for sunrise. These reservations can be made at 60-days in advance of your visit (or we can help you book this as an excursion with a local guide or tour group).
If you are prone to motion sickness, be aware that most of this drive is a long winding mountain road and you are ascending to high elevations. Be sure to plan accordingly!

There is an entrance fee as you are entering the Haleakalā National Park (private vehicle was $30 at the time of this writing). Your entrance ticket is good for 3-days, including the date of purchase, if you are planning to also drive the Road to Hana (or the reverse) – KEEP your ticket! The end of the Road to Hāna actually ends at the Kīpahulu District of Haleakala National Park, which is the coastal area of the park. Your ticket can be used for both if within the three-day period. All considered this was absolutely a highlight of our time on Maui and not to be missed on your visit!

Atlantis Adventures Submarine

This was another activity that we planned on the fly and we were so glad that we did. Atlantis Adventures departs from the Lahaina Harbor and takes you out on a ferry boat to where the submarine surfaces. You get to watch the submarine emerge from the water, and once the first group of guests have disembarked, you climb down into the cabin of the submarine yourself. Once everyone is safely onboard, the hatch is closed and the submarine dives down to the ocean floor (at depths of 100 feet) to view an active coral reef area, and then over to a sunken ship that was anchored to become an artificial environment for marine life. We saw small sharks, rays and various schools of tropical fish. The kids had a blast knowing we were in a “real submarine” underwater and were excited to find and identify the different marine life as we explored. Once we completed our exploration of the reef areas, we returned to the surface and made our way back to shore. This was a perfect way to experience the underwater world with group members who were not old enough yet for diving or snorkeling. The kids unanimously voted this as their favorite Maui adventure!

Food and Drinks

Now we get to the important stuff…. Because really isn’t traveling all about finding the best food and drinks…? We had so much good food on this trip – but a few things really stood out and you must be sure to include them on your #foodgoals list:

Monkeypod Kitchen by Merriman – This is actually a local chain restaurant and you will find two on Maui (on in Wailea and one in Lahaina and then another on O’ahu-just across the street from Aulani!) – The food here is fantastic – but what you really come here for are the Mai Tais. I promise this will be the best Mai Tai you have ever had. Their version features all fresh ingredients and a unique Honey Liliko’l foam on top!
Ululani’s Hawaiian Shave Ice – Shave ice is a MUST DO when you visit Hawai’i and you will find many options to choose from. Ululani is a classic favorite though – with locations in both Kihei and Lahaina. The ice is shaved to a pillow of soft fluff and you can choose a flavor or combination of flavors from their endless list. I strongly recommend you include the scoop of ice cream in the middle (macadamia nut was fantastic!). TRAVEL TIP: It is always SHAVE ice – not SHAVED ice.
Nalu’s South Shore Grill – This was the perfect spot for a casual meal. The pricing was very reasonable, the food delicious and the service fantastic. We opted for a table on the patio and I enjoyed a traditional Hawaiian dish - Loco Moco served with mac salad.

Other honorable mentions have to go to Café O’Lei (Pacific Rim dining in Kihei) and Ama Bar and Grill at the Fairmont – All fresh ingredients, beautifully served and I fully enjoyed every single dish I tried.

Two of our other big adventures – Road to Hāna and our Discover Lanai sailing trip - each deserve their own blog posts – be sure to check those out individually!

Whether you are a frequent visitor to the Hawaiian islands, went once for a honeymoon and planning to go back with the family, or maybe looking to plan your very first trip, I hope this blog series will provide inspiration in your planning. I also know there is much more to designing the perfect Hawaiian vacation, than I can possibly outline in just a few blog posts, and that is why we are here to help guide you and answer your questions every step of the way as your travel advisors. Mahalo for reading!