March 21, 2018
Jon and I have unintentionally vacationed ONLY to islands over the last 5 years. We never purposed to be island hoppers but living on Nantucket has somehow made us obsessed with island life. We’re not mad about it. We had always wanted to go to the Hawaiian islands and decided 2018 was going to be the time we finally went for it! We slowly planned our trip starting with our plane tickets and then booking hotels over a few months. I normally like to plan out most of the details of our trips before we go but we decided to just kind of wing it and go with the flow to start off the new year. We wanted to make the long flights worth it so we went for just about 3 weeks right after Christmas. It was the perfect amount of time and the weather was ideal. The 14-hour flight with a toddler had us a bit nervous but thank the Lord and stars above, our Willow was an angel and made US feel like the babies.
We started our trip in Kauai at a little Inn close to the airport. It was love at first sight. We rented a Jeep Wrangler and adventured around the lush island the first two days. First stop was Wailua Falls. Jon ran into a local while we were viewing the falls from above and he showed him a path through the fence that would take him right down to the base of the falls. Willow and I took one look down the steep hill and decided Jon would be on his own for this one. Maybe when she’s a little older we’ll go for it. About an hour later Jon emerged from the path covered head to toe in mud. He said the view was worth it but it was not the kind of trail you should go down in flip-flops. Definitely a good first hike. The next stop was the Kileauea Lighthouse. Gorgeous views and birds flying from cliff to cliff made for a pretty epic scene on our way to Hanalei. Last stop of the day was Hanalei Bay Beach. This is where Jon decided to break out the drone for the first shot of the trip. Within about 10 minutes…DRONE DOWN! He had lost it over the ocean and when he tried to bring it in it crashed into some trees down the beach. We miraculously got it back and salvaged the parts. It wasn’t flyable for the rest of the trip but he did get it fixed when we got home. There’s only one thing to do when you crash your drone on the first day of your Hawaiian vacation…go to Target and get a new one, duh! We had to wait until we were in Maui to do that but my camera was all we needed for the rest of our Kauai adventure. Hanalei Bay was definitely one of my favorite spots of the trip. The little surf town, beautiful beaches, and pier to watch the sun set every night was just heaven. It offered convenience, great eats, including one of the best Acai bowls I’ve ever tasted, and just a really relaxed vibe. We will definitely be back!
Maui was island #2 and I was beside myself with excitement about our accommodations. We stayed at the Kutcher Condo in Kihei. The airbnb is owned by one of my favorite photographers & marketers, Jenna Kutcher! I have followed her for a long time and I listen to her Goaldigger podcast every chance I get so to have the chance to stay here was pretty exciting for me! The condo couldn’t have been a better choice for us. It was steps away from the beach, perfectly located in an area with shops and restaurants we could walk to and a pool (that we never used). The condo itself had everything you could ever imagine you’d need – towels, beach gear, beach bags, full kitchen, tv with every app you could think of, a lovely deck with an outside eating/sitting area. It was just perfect. We decided to drive about 5 minutes down the road one night to the very fancy town of Wailea and eat at our favorite restaurant, Ruth’s Chris. It was fun to change it up from the little Surf Inn in Kauai to a little fancy livin’ in Maui. We tried out a few different beaches but we ended up loving the one right outside our condo the most. It was never too packed, nice calm waves and just all around convenient!
Our Maui adventures included a beach day in Paia. LOVED this town. Jon wasn’t up for spending too much time here but I could have spent an entire day exploring. We decided to do the Road to Hana. We had heard so much about it. Some people said don’t do it, some said it was a must. We had to at least see what it was all about. I downloaded the Road to Hana app on my phone – THIS IS A MUST if you’re going to make the trek. If we hadn’t had the app, we would have had NO IDEA where we were or what we were passing/seeing. It was super helpful. We definitely didn’t start early enough so we never made it to Hana as we weren’t feeling driving the 620 curves and 59 one-lane bridges in the dark but we made it pretty far. The highlights of the drive were Paia, the Garden of Eden (this is where you can see the famous Jurassic Park rock!) and the Three Bears waterfall. Willow was such an incredible trooper during this almost 8 hours in the car! She never cried or complained – seriously, NOT ONCE. So thankful for that.
After our amazing time in Maui, we were off to Oahu for the final 9 days! We started in Waikiki and stayed at the Laylow, Autograph Collection. I feel like I’m saying everything was the BEST but this hotel really was THE BEST! Again, it had everything we needed and was located in the perfect area (about a 5-minute walk to the Waikiki Beach). Complimentary ukelele lessons and shaved ice by the pool were a couple of the awesome bonuses of this hotel. We had a Junior Suite and it had plenty of room for all of us. A huge bathroom, king bed, couch and great living area. We could have eaten every single meal at their restaurant, the Hideout – it was THAT good! Waikiki Beach was pretty packed and definitely not our favorite beach by a long shot but the color was breathtaking and to see all of the hotels along the shore mixed in with the palm trees was kind of a fun change.
After loving life at the Laylow, we were off to the North Shore for the rest of our trip. We booked a cottage at Turtle Bay Resort (the one in Forgetting Sarah Marshall). We didn’t want to be in a hotel for our last leg of the trip so the cottage was the perfect alternative with panoramic views of the ocean from our bed. We wanted to completely veg out since we were nearing the end of our trip. We had done a lot of hiking, exploring and traveling around the islands, now it was time to put our feet up and soak in all the beauty. After a few days of R&R, we decided to try out the horse stables on the property. Willow road a little pony and couldn’t have been more thrilled. We also hiked to the Banyan Trees (the ones from LOST). I have to admit, I was a little worried that Turtle Bay would be too touristy for us but it really was an amazing place. The staff was excellent, carting us around in golf carts wherever we needed to go. There’s a beautiful golf course, great restaurants, 3 (or more) pools and a lovely cove for beach time. Their spa is worth the money. As I checked in for my massage, I was directed out to a patio overlooking the ocean. I sat out in the open air listening to the waves crash in my robe and slippers until I was ready for my massage. It was relaxation to the max.
We booked a family photo shoot with Rae Marshall during our time in the North Shore of Oahu. We met her at Kualoa Regional Park and she took us down the beach to one of the most beautiful spots we had ever seen. She took photos of us on a dock with the green mountains surrounding us. You can also see the Chinaman’s Hat from this spot and walk some gorgeous secluded beaches. We loved the spot so much that we took our friends here the next day to shoot some maternity photos for them!
We made one more trip out of the Resort to check out Haleiwa – LOVED this town! If you visit, you’ll definitely want to stop by Haleiwa Bowls for an epic Acai bowl and this is also a perfect little town to pick up all of your gifts before heading home. We watched a gorgeous sunset over the ocean on our way back to the resort. On our final day of the trip, we stopped at The Hoʻomaluhia Botanical Gardens for some photos and one last breathtaking view. We were ahead of schedule and our flight wasn’t scheduled to leave until 9 pm so we also made the last stop at Pearl Harbor. It couldn’t have been more perfect timing as they were about to close so we just strolled right in. No tickets needed. It was absolutely surreal to see maps of where my grandfather had served in World War II, to see some of the submarines they used, the airplanes. Next time, we’ll spend a bit more time visiting the other exhibits but we were so thankful to make it before closing time.
I know I’m forgetting so many details but I think this is a nice start! We are already anxious to go back. The islands are truly magical and we can’t wait to see more of them. If you have any questions about any of the spots, accommodations or really anything at all about our trip, I would be so happy to answer them! Comment below or email me! Here are some of the highlights of our Hawaiian adventure. Mahalo!
Here are some of our family photos by the ever-so-talented Rae Marshall! We had such a blast taking these and we’re so thankful for memories she captured for us!
Love this❣ I’m going to order a few of these.
Let me know which ones you want!
These photos are magical! Loved reading about your trip ❤️
Aw! Thank you Jenna! It was a blast! XO