The Ultimate Hawaiian Island Hopping Adventure Day 1 & 2

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Day one of our island hopping adventure in Hawaii was AMAZING! We hope you enjoy these reviews and of course, special thanks to Hilton Hawaiian Village for hosting us.

We have one of the later spring breaks and it feels like everyone is already like “been there, done that” and we are over here like “doing it now”. That’s okay because although we technically are in spring break right now, we already took spring break 1.0 and then two weeks later, we took spring break 2.0. 

Today I’m sharing about our OG spring break and why Hawaii is the PERFECT place to go this summer, fall, winter and of course spring. 

Now I’m not advocating for just any Hawaiian vacation… instead think bigger and better with a first-class island-hopping family experience. Stay longer, explore more island and do it all in a big way!

Here is how we spent day 1 of our awesome Hawaiian Island Vacation! 

We started the fun flying first-class from LAX to Oahu. Our flight landed in the late evening and as soon as we stepped foot on Oahu, we felt that familiar island air. We made our way to the car rental counter and had the best experience ever with our partner, Advantage Rent-A-Car. 

They reached out right before our vacation and it worked out perfectly to rent their vehicles on the islands. We were provided a brand new minivan to drive which was awesome, but the real stand out was their stellar customer service and friendliness. It was the perfect welcome to Hawaii!

We were swiftly in and out of the airport and on our way to Waikiki! 

We arrived at the Hilton Hawaiian Village (which is about 20 minutes from the airport) later in the evening and we were all ready for bed then. We slept very well and woke up to this view!

When I was a teen, we took our first family vacation to Hawaii and we stayed at the Hilton Hawaiian Village, so I was SO EXCITED to show my own girls around and to stay here with my own family. We stayed in a different tower this time, the Rainbow Tower with a true ocean view all the way to Diamond Head. 

We had connecting rooms, mine and Pete’s had a king and the girls had two queen beds. The views though stole the show. When we were planning this vacation, it was all about the views and this was exactly what we were looking for!

We had a lazy start to the day, which we haven’t had in f-o-r-e-v-e-r and it was just what we needed. Because the Hilton is right on the beach, it is perfect for exploring Waikiki. We love how alive the area is with shopping, dining, and fun. But really, there is all of that and more in the Hilton Hawaiian Village itself. You don’t ever have to leave to pack your days with fun and relaxation. When I came here with my family as a kid, we didn’t leave!

The afternoon was spent at the lagoon. The Hilton has this huge lagoon with a little ornamental island in the middle where you can rent all sorts of water fun things. 

While I sat under an umbrella reading a book, Em played in the water and then joined Pete and the girls on the Aqua Trikes and paddleboats.

Remember how I mentioned that the village has everything, well it totally does. There is an ABC Store with all the convenience store offerings plus snacks and grab and go meals. 

There are also restaurants, an ice cream and coffee place and shopping galore! 

Em found a pearl stand where you can pick an oyster and then they open it to reveal the pearl. This is where I bought my very first pearl too!

Since it is so close to Waikiki, we headed out that way and explored.

We truly love it here!

Pete even made a new friend!

Since this vacation was all about above and beyond experiences, the Hilton surprised us with a dinner we will never forget! 

Every Friday night they have fireworks over the ocean in front of the resort and we had a front-row view during dinner at Bali Steak & Seafood.

The chef made some amazing vegetarian and vegan dishes for us to enjoy. They were equally beautiful as they were delicious.

When the fireworks were just about to start, we were escorted to the patio right next to the famous rainbow art.

It was a truly spectacular display of colors!

Afterward, we returned back to our table for dessert… but before it was served, we looked over and found Emmy like this! Ha! She is carrying on her tradition of falling asleep at dinner on vacation. She is 8 now, and I wonder when it will stop? 

Pete carried her up to her room while she was dreaming of how we are going to spend our next day in paradise! 

Heather Reese
the authorHeather Reese
Heather Delaney Reese is the storyteller and photographer behind the lifestyle and family travel blog, It's a Lovely Life®! For the past decade, she has vacationed over 150 days a year with her family. She is a vegan, and loves being by the water, spending time with her children, husband, 2 Shih Tzus and Cat.


  • This sounds like such a fun and interesting day! I’d love to do something like this. The pictures are other-worldly. My sister went to Hawaii and she loved it. I need to plan a trip there. Thanks for sharing.

  • This, seriously, looks like heaven on earth! I have always wanted to visit Hawaii! Hopefully, I will be able to take my family someday!

  • Oh. My. Godness.!!! I need to visit here and take awesome pics and have loads of fun like you! Love the look of the lagoon and all the food!

  • Looks like a wonderful experience. I visited Hawaii 17 years ago. I think I need to start planning another visit!

  • I sadly have never been out of the continuous United States. I would love to get to Hawaii someday, and the Hilton Hawaiian Village looks fabulous for a family!

  • Anything Hawaii makes me kind of sad in all honesty. And the reason behind this is because that’s where my husband and I escaped to quickly after we got married and while we did get a little bored, we still had an amazing time and I will never ever ever ever forget that!

  • We went to Hawaii for our honeymoon. We hope to go back with the kids at some point.

  • Oh Hawaii! I hope to visit soon. It looks like an amazing time. And first class…what a great way to start a vacation .

  • I have never flown first class, it looks so roomy up there! Everything in Hawaii looks so vibrant and clear. I am obsessed with fireworks, so I would really enjoy myself.

  • The food looks amazing! I bet it taste as good as it look. Hawaii is a place I hope to visit someday. I like that there’ are so many fun things to see and do.

  • I’m dreaming of how I’ll spend my time in paradise also! I’ll be honest, the traveling part of travel stresses me out a little. But it looks so easy with the right airline and rental companies booked. I’m not sure how you managed to pull yourself away from the islands.

  • Oh wow! Everything looks perfect and fun! Hawaii is one of the places I am dreaming to visit but seems impossible for now. Love the photos!

  • I am envious. I have always wanted to travel to Hawaii. I am going to be intentional now about making my way there.

  • I’ve wanted to go to Hawaii for as long as I can remember. I’m not sure if we’ll ever make it over there, so I’ll live vicariously through your photos 🙂

  • That does look like a pretty place to see with your own eyes. My mom wants to go there someday, I am not a fan of flying so its not for me but I love to see pictures!

  • We have only been to the big island so far but hope to cross this one off the list soon and you gave me the idea of a perfect place to say when we do!

  • Those are some very beautiful photos. This makes me want to take a vacation right now. I would love to go there. I haven’t had a nice vacation like this ever.

  • What an incredible trip you had. Hawaii is so on my bucket list with the kiddies soon!

  • Oh my gosh I am so happy you posted this! I have ALWAYS wanted to go to Hawaii honestly and wanted to see pictures of it. How awesome is that. It looks so amazing there.

  • Looks like you guys had a fun family vacation! Hawaii is so beautiful, Ive always wanted to visit!

  • This looks like the dream family vacation. The location is just beautiful and the accommodations are perfect for families to enjoy every single moment of their stay.

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