Our Family Trip | Hawaii 2020

Well, we are almost back to the island we call home after a full month of being away! The kids were absolute troopers and we’re not feeling defeated even after an 8 hour drive and 2 hour boat ride home. Hey, if we could do the 13+ hour flight with two sick kids, I think we can do anything! 

I guess I’ll just start at the beginning. We headed off island and started our winter vacation in Stowe, VT. It was the perfect winter trip before we escaped the cold. Our main goal was to get Willow on skies and get her used to the slopes. After spending a day exploring Stowe, a place that’s very special to me because I learned how to ski in Vermont with my friend’s family many years ago. It was truly special to be able to teach my little girl to ski in the same place I learned. Major difference was – she’s learning at 4 years old and I learned at about 13 years old! She absolutely loved it, was a little pro and didn’t want to stop. We can’t wait to try again! 

After checking out of the hotel I’ve been dreaming of staying at for a few years now, Field Guide, we hit the road and headed to Maryland where my family lives. 

Our gift to my sister for her 40th Birthday last year was a vacation somewhere warm. Since Hawaii was definitely on our must visit list again, we invited her on the trip and we all agreed that we couldn’t leave behind her kids, Auston and Bella. Our group of 7 were ready for palm trees and sun! 

The night before we left the kids started coughing, spiking a fever and just feeling horrible. PERFECT! We were supposed to fly out in just a few short hours. We medicated them up and hopped on the plane. We only had one stop in Chicago on our way over and honestly, the flight was pretty smooth except for a few of the adults getting a little restless. 

We arrived in Waikiki to a beautiful rainbow! Jon and I had arranged an SUV Limo to pick us up but we kept it a surprise – not easy for me to do! As we were walking out with our 50 bags I told the kids and Jess that I hadn’t ordered an uberX and that the car we ordered would most likely NEVER fit us all. They were so tired and now a bit concerned. I looked around for a bit, spotted the limo and then asked if they thought we’d fit. It was a fun surprise and honestly, extremely affordable with all the space we needed. I think an Uber would have been more, for sure! With traffic, it took us about an hour to get to our hotel. Auston was DJ’ing and we were all having a blast! 

We arrived to our first hotel, The Laylow – one of our favorite hotels!!!! and headed up to the room to unload. Next, was a trip over to Waikiki beach just a couple of streets away and then an early to bed kind of night. For the next few days we hung around Waikiki. The weather was overcast but not too bad and a good excuse to get some rest, recover from jet lag and let the kids heal up. After a bit of city life we were on to the North Shore. We rented a car on the day we were to head north as there was no need for one in the city. 

On the way north, we made a stop at the Ho’omaluhia Botanical Gardens for some touristy pictures and to take in the views then we headed over to Kualoa Ranch for some more exploring and fun photos! This was the same place we took our family photos last trip!

{Sick kid update – I honestly think that they both had the flu. After googling the 2020 flu symptoms, we realized they had them all! We kept them medicated and happy and they were absolute troopers, by about day 5 they were just about back to their healthy selves.}

For the next week we stayed up in the north shore at the beautiful Turtle Bay Resort. We stayed in the beach cottages like we did last time and it was perfect for all of us. The back porch overlooks the ocean and we were just steps away from the pools. The boys got some golf in and the girls had a spa day in between sitting in the sun poolside. No complaints here!  

We took an afternoon trip to Haleʻiwa for some shopping and one of the best açaí bowls on the island at Haleʻiwa Bowls. This little town is such a fun afternoon trip if you’re up in the north shore. If you time it perfectly, you can drive home and catch the most beautiful surfer sunset at Sunset Beach, which is exactly what we did! I would be remiss if I didn’t share our absolute FAVORITE food spot – SEVEN BROTHERS. Jon is still having dreams about this place and my mouth waters when I think about it. Best burger I’ve ever had and I say that without any hesitation. We couldn’t stay away – we went back for more and I tried their famous coconut shrimp the second night. UNREAL! If you ever visit Oahu, please do yourself a favor and eat at Seven Brothers! I can’t talk about burgers without talking about dessert. Just a few steps away from Seven Brothers, in the Food Truck area, Jess and I tried Ty’s Beach Bus and once again, I’m telling you – BEST DESSERT I’VE EVER HAD! I got the churro, drenched in cinnamon sugar with vanilla ice cream and NUTELLA. It was deathly and I actually got yelled at by the boys because I was in such a good coma I ignored their request for directions and we went the wrong way home. Sorry, not sorry. Needless to say, I gained back all of the weight I lost before the trip. 

The weather had almost fully cleared with a few days left at Turtle Bay. After checking out, it was time to head back to Waikiki – yes, right back to the Laylow! We couldn’t stay away! With complimentary shave ice every day, plenty of space and beds, perfect little cafe, and the most wonderful breakfast/lunch/dinner spot, the Hideout it really does have everything you need and more! 

The forecast was sun and blue skies for our last few days in Waikiki. On Jess and the kid’s final night, we took in the most beautiful sunset on the beach and splashed around in the ocean until dark. 

It was time for them to go home and we were so sad, especially because that great weather was going to stick around for quite a while! We kissed them goodbye and spent our last night in Waikiki before jumping on a plane and heading to Maui the next day.

We were ecstatic to arrive back in Maui and stay at the Kutcher Condo again! It was such a highlight of our last trip that we had to go back. They only had 3 nights available while we were there so we scooped them up. We spent the next few days soaking up the sun on Big Beach Makena – an absolute dream of a beach! It was major R&R time! After checking out of the Kutcher’s and having the most delicious breakfast at Kihei Caffe, it was time to head north to Kaanapali! We never visited Kaanapali or the adorable town of Lahaina on our last trip. Well, we were seriously missing out! It was amazing! Even just the drive – we stopped to do some droning along the way and immediately spotted dozens of whales! Breaching, spouting, they were everywhere! We had to keep going to check in to our hotel but we made a note to come back to that spot for more whale spotting.

We checked into our final hotel of our vacation, the The Westin Maui Resort & Spa in Kaanapali. We would be here for the next week. It was absolutely breathtaking. From the lobby, to the room, to the pools, to the beach. Whaler’s Village, an outdoor mall and tons of great restaurants were literally steps away from the hotel. Every day we’d stop to feed the fish and say hello to the flamingos on the way to the pool, and Willow even had one of their beautiful parrots jump right on her head! The hotel had crafts every afternoon that the kids could join in on. The pools had huge slides and basketball hoops, and when we decided to do a whale watch we walked right out on the beach in front of the hotel and onto the boat. Talk about convenience. It was our last week to soak up the sun and do whatever we wanted. We waited until 10am every morning to get the two-for-one breakfast because it was EPIC! I won’t go into details because I know I’ll get carried away but I’ll just say, if you stay there, definitely do the breakfast! 

If that wasn’t enough, we checked their event schedule and realized they had very elaborate and authentic Luaus every Thursday night. We had been wanting to go to one since we arrived but just couldn’t make it happen. This was the perfect opportunity. We got tickets and arrived before sunset for drinks and shopping before the actual event began. The show began and it was AMAZING! I give it a 10/10. It was so entertaining, the dancers were top notch and they even got Jon and I up and dancing, that is hard to do! Willow was a bit scared of all the drums and fire so she spent most of the show under the table. Poppy loved it! 🤣

On our last night in Maui, we went back into Lahaina for dinner and it was really nice to stroll around along the water and take in the sights, sounds and smells one last time. We headed back to our whale spot on the final day and then made a quick stop back in Kihei for a dinner on the beach. Alas, it was time to say MAHALO to the island we fell in love with 2 years ago. We had a red eye flight which couldn’t have worked out better. The kids slept through each flight (we had two stops) and got a nice little break in between. 

Back in Maryland, we got to go to two of my niece’s basketball games and one of my nephew’s college b-ball games. We visited with family, did laundry, watched the Super Bowl and celebrated Poppy’s first Birthday at my sister’s house.  Our month long adventure has finally come to an end as I sit on the slow boat with about 45 minutes left until we touch land. Willow to my right nodding off and Poppy in the back snoozing away. We can’t wait to get home and snuggle up together! Tomorrow, it’s back to the grind – the grind that we absolutely LOVE! So grateful and thankful to love what we do and do it together! We’re feeling recharged and ready for the year!

I mentioned a lot about where we went and what we did, but the most important parts of our trip were the priceless memories that we made along the way. We will never forget our time together in paradise, and to have my sister and her kids with us for part of the trip made it better than we ever could have dreamed. I’ve never been more thankful for photos in my life – the kids will be able to look back years from now and re-live the magical moments we created together. Thanks for reading and please hit me up if you’re planning a trip to Oahu or Maui, I would love to share our favorite places and things to do with you! ❤️ Mahalo friends!