Maui Travel Guide- Island Hopping from Oahu

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We woke up to this view. I feel like I should say more… but there are no words for how you feel when you open your eyes first thing in the morning and you get to look over and see this! The picture below is a look at the girls’ room. Ours connected to theirs and had a king bed instead of two queens.

Since this was our last day with our partner, Hilton Hawaiian Village, we didn’t stray far before our flight over to Maui. We had breakfast, went to the pool, walked down to Waikiki further and just relaxed. It was awesome!

The beach off the Rainbow Tower.

Oh, and Pete and I stopped for a snack by the pool too.

And some Hawaiian coffee! The coffee here is the best!

We also did some shopping…

Then it was time to fly over to Maui.

I was so excited to go to a new island that I’d never been to before, but also a tad sad to leave Hilton Hawaiian Village. The good news is that it was everything I dreamed it would be for Pete and the girls. They LOVED it just as much as I did when I visited with my family as a teen. We all have decided we want to make it an annual vacation spot for us and to bring our extended family with us too. It is perfect for multi-generational vacations. We also want to stay in The Ali’i, the resorts boutique hotel within the resort so we will be back soon!

We arrived at the airport a couple hours before our flight because it is a popular airport. We made it through security in minutes, so we hung out in the Hawaiian Airlines lounge that we had access to with our first class tickets. Then it was time to go. 

I can’t even tell you how much we enjoyed flying up front. It made getting on and off the plane so easy and it was great having our luggage off the plane first. It definitely added more vacation to our vacation! My only complaint about this flight was that it was too short! This is coming from someone that is a nervous flyer (or was before this trip). The views from above would make me want to book flights over the islands alone.

We finished off a drink in the air- POG, our favorite, and then we were on the ground again!

A quick shuttle ride to our partner, Advantage Rent-A-Car and we were off exploring. They had us in and out fast and the car was perfect. It was clean and ready to go. I’m still in awe of how friendly everyone is that works there too. They are so professional and really show the Aloha spirit!

Right after I took this picture of Pete, the real adventure started with non-stop whale sightings right off the coast of Maui. 

We saw lots of whales…so many Emmy stopped counting.

They were jumping into the air, playing in the calm waters and just floating by. Maui is so mellow all around and we could have just sat on our balcony all day watching them swim by.

Oh gosh, then there was the food.

We ate very well in Maui even though we weren’t enjoying any seafood. From smoothies to tofu on forbidden rice (I had this twice)…there were so many options. 

We would go every day to get fresh kombucha on the island and really just took it easy.

Oh and the sunsets. They were magnificent! We made sure, like most people on the island, to plan meals around the sunset. Either by dining oceanfront, while they were happening, or to congregate on the beach to enjoy them.

Ash decided one night to go for a sunset run along the beach. I can’t imagine a better view to exercise alongside.

Much like on Oahu, we found ample breakfast buffets too. Those are our favorite way to start the day since everyone can have their own favorite foods.

Let’s talk coffee for a bit. This was one of the things I was a little disappointed in. Not that the coffee wasn’t good- but that it wasn’t as readily available as I had hoped. You all know that Pete and I run off coffee, so we had to get strategic and scope out where to get our fix ahead of time.

Sweet treats, on the other hand, were not a problem. We had that covered tenfold. I even found a place with vegan banana bread.

We were also very specific about our dining requirements. It had to have an ocean view or something else that made it special. I would highly recommend asking locals when you are on the island for recommendations. Those are the best!

One morning we got up early and had breakfast at a place where you can make your own pancakes at the table. Not my idea of taking a break on vacation, but Emmy thought it was the best so that made it worth it. Plus the pancakes were really good and they had vegan ones!

We were on the island for Pete’s birthday, so we went to an eclectic restaurant that had a dog as a greeter and some pretty cool food like this pasta- yep. We ate well on the island!

Shave ice too. I promise we did do more than eat!

Hop on over and see part two of our family vacation to Maui.

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.


  • Both the view and food looks amazing! I bet it was a relaxing getaway. I am personally ready for a getaway myself.

  • This brings back memories of my honeymoon. We went on a trip that hit 4 islands and it was 20 years ago so I have forgotten most of it. You showed so many fun times I want to go back.

  • What an amazing trip! The water is so blue there and everything is so beautiful! It’s like a dream vacation, for sure!

  • This brings back such memories I was in Hawaii for my honeymoon and went to 4 islands. I love the ways you enjoyed the islands and hope to go back some day.

  • Hawaii would be a dream destination! I don’t see anything in any picture I’ve ever seen of Hawaii that isn’t beautiful! I bet the you and the kids had a lot of fun island hopping, as well as the whole experience!

  • WOW! This trip looks absolutely beautiful… the food, the adventures… and I can’t even imagine seeing the non-stop whales! What an amazing life experience!

  • Such a nice place to visit and the beach is amazingly beautiful. I would love to be there and enjoy the beautiful views of Hawaii.

  • I’ve been to both but didn’t hop. It was nice seeing your photos as it reminded me of the times I was there. Your girls are very lucky.

  • What a fun and great experience you had. Looks like a great place to visit. I’ll definitely go here one day with my family.

  • Oh! We’re planning on doing a Hawaii trip this year and I absolutely can’t wait! These photos are fantastic! I love how the colors stand out in your pics! All so lovely!

  • For a second, I put myself in your shoes. I read the first paragraph and imagined myself walking out on the balcony as the sun was coming up. I think having a balcony suite next to the ocean is magical, something about the view releases feelings of euphoria.

  • This looks like it would be a fantastic trip. That hotel looks absolutely beautiful!

  • Oh my goodness, first your kids are the cutest. I love this article with insights on how to do Hawaii with kids. I’ve desperately wanted to go back since my honey moon but haven’t really known where to start. Thank you so much. xoxo

  • So much fun for the whole family! I would love to experience Hawaii too. The beaches are calling my name! Your daughters are fortunate they get to travel extensively with you. What a great learning experience for them.

  • It looks like you and your family had an absolutely amazing time. The views are gorgeous and it definitely looks like a vacation to remember.

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