Travel Exchange: Family Relaxation and Adventure in Hawaii

Post updated March 2020

It’s Travel Exchange time and I’m so pleased to have on the blog today Harmony Skillman with Momma To Go, an online lifestyle magazine dedicated to travel, fitness and parenting. Harmony shares her tips on family activities and parenting advice, and loves to talk all things travel! As soon as I heard she took an epic month long vacation to Hawaii that was it – I roped her in! Below is my interview with Harmony on what, where and how she and her family did Hawaii. I hope you find it helpful and enlightening the same way I have.

How did you decide on Hawaii as a destination to take a family vacation? Which islands did you stay on?

My husband works for an awesome company that gives its employees a one-month sabbatical every 5 years. In 2016, my husband celebrated his 10-year anniversary with his company and we knew we wanted to use that time to do a big trip. We originally had Australia on the brain! But realized that was probably not the best starter big trip. Then we thought about 3 weeks in Italy, since I have travelled there often. But… my husband has never been and would want to see all of the sights, which we weren’t sure our kids were ready for.

So one day I realized Hawaii would be the perfect mix of relaxation, adventure, big-trip, and experiencing a new culture! Hubby and I had visited Oahu in 2005 and hence decided to forgo Honolulu (where we could have flew direct from NY) and opted instead for Maui and the Big Island.

Who went?

Me, husband, little man (7) and baby girl (4, almost 5)

What time of year did you go and how was the weather?

We went for almost the entire month of August. It was hot. Not humid, but the sun in Hawaii is so strong. I would go out at 7 or 8am for walks, I had planned to do runs, but it was already hot and sunny in the morning. On the big Island we experienced those afternoon rain storms (especially as we traveled away from the coast) but the weather was warm. Funny story, we did travel to the Mauna Kea Visitor Information Center for stargazing one night. It was 41 degrees Fahrenheit at the summit! Needless to say we did not have the proper clothes for it, we were freezing!

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You might also enjoy: Ultimate Guide to Packing List for Hawaii

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Where did you stay and how did you discover it? What were the accommodations and amenities like?

We stayed in four places:

Maui – 1 Bedroom condo rental at Maui Kamaole. We loved this spot. It was walkable to the beaches in Kihei (specifically Kam II & III) and close to shops and restaurants. This property had a really nice pool and hot tub, where we spent a lot of time and met lots of other families! This I found on vrbo, but saved $80 by booking directly through the rental agency, Rentals Maui.

Hana– In Hana, on the remote east side of Maui, we spent one night in a traditional Hawaiian plantation home. This was called Mack’s Shack. I found it online and booked directly through the owner. This was a small one-bedroom house. My favorite here was we were in such a remote spot, spent all day driving the beautiful road to Hana, slept with the sounds of animals right outside our door, BUT this house had a giant satellite TV so we were able to watch the finals of the women’s gymnastics from the Rio Olympics!

Kona – for the first 8 nights on the big island, we rented a 2 bedroom, 3-floor townhouse in Keauhou. Here we had a lot of space to spread out! This property also had a pool (but sadly no hot tub, I love hot tubs). This property also did not have AC, which if I could do it again, I would opt for a place with air conditioning. It was hot. But the location of this condo was great, and we spent lots of time on the big deck out front.

Waiakoloa Beach Marriott – the last five nights of our stay, we treated ourselves to some time at a resort. We had one free night with our Marriott points. This hotel was under construction when we visited, but it kept the property sparsely populated which we actually liked! The pool was amazing- there is a huge waterslide that we spent many hours going down. The kids loved it! The hotel is a short walk to the beach, A-bay the locals call it. I love the beach so I went a few times, and took a Stand-Up Paddleboard Yoga class here. When we stayed at the resort, we returned our rental car, so we stuck close to the hotel. You could walk to various shops and restaurants, which we appreciated.

What kind of activities did you do on the trip?

Lots of time at the beach! Some of the bigger activities included a visit to the Maui Ocean Center, a snorkeling trip to the Molokini Crater, a drive up to the crater on Maui, Haleakala. We drove the road to Hana (and stayed over). On the big island we visited a coffee farm, Volcanoes National Park, I went for a hot tub soak and massage at Mamaloade, we went stargazing on Mauna Kea and we did a lot of snorkeling and boogey boarding. The kids made leis and bracelets at the Hawaiian Cultural Center in the Keauhou shopping center.

What were the highlights for you? And the kids?

I loved the beaches. I think one of our favorite days was when we went to Mana Kai beach in Maui and stumbled upon all of these amazing tide pools. Since we had just visited the Maui Ocean Center, we actually recognized the creatures we saw in the wild! We spent hours in these little tide pools seeing starfish, sea cucumbers, sea urchins and lots of fish. My kids also loved the Hawaii treat, Shave Ice!

How was the food? Did you discover some favorite restaurants?

In our condos, we tried to eat at home as much as possible. Everything in Hawaii is so expensive (including the groceries!). We try to always eat breakfast in the hotel room/condo when traveling. We would brown bag our lunch to the beach each day. Many nights we cooked or grilled at the condo. We did enjoy visiting Annie’s Island Burgers (twice) on the Big Island.

When we stayed at the resort, we ate cereal in the room for breakfast and lunch by the pool. We did go to the luau the last night. I think we enjoyed the show more than the food, although baby girl loved eating the pig! We also had a great Sunday brunch at the Lava Lava beach club, which you can walk to along the bay in Waiakoloa. The food was really good, and after eating we wandered onto the beach where they had a giant jenga, cornhole, and you could order drinks and snack from the bar!

What are your top tips for taking this kind of vacation?

Unless you have a crazy budget, think about what you want to splurge on (a snorkeling trip, a luau, a hotel stay) and where you can save (rent a condo, rent a small car, beaches are free, and eat at home). Utilizing some of these tips allowed us to stay so long, but yet not feel like we were missing out on the experiences that become life-long memories.

Were there any challenges?

The first day was rough with the jet lag. We arrived in Maui at 8pm local time, which was 2am at home. Our kids slept a lot of the second flight from LA to Hawaii, and arrived not that tired. They woke up at 2am ready for the day. Needless to say, the parents were not ready for the day. We kind of soldiered through the first day and stayed up until 7pm. By about day 3 we were pretty adjusted.

Did you feel the trip was good value for what you got?

Yes! I felt like we really got a lot for our money in terms of the condos and rental car. We probably should have stayed one or two less nights in the hotel. We had more room to spread out in the condos and we had a car and could get around. Plus we did the same activities more or less, beach and pool!

Would you recommend this vacation to others?

Yes, but coming from the East Coast at least, you need time to travel, time to adjust to the time change, and time to enjoy the islands. I think even a week would be rushed. Although in that vein, I would say don’t over plan. My cousin went and saw all four major islands and it was a lot of schlepping. I would say pick two islands tops and really enjoy those!

Ok, who wants to go to Hawaii?? Thanks so much, Harmony, for being a guest and sharing your fabulous experience!

You can find Harmony and her site Momma to Go on Facebook, Instagram, Pinterest and Twitter

To read more Travel Exchange experiences, see my posts:

A Family Vacation to Adventurous Costa Rica

The Allure of Turks and Caicos

Iceland: A Family Vacation

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