Aloha Hawaii: How to Plan a Vacation with Kids

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We are just a few days from our Hawaii trip and couldn't be more excited. Perry has always wanted to go to Hawaii and for his birthday, we decided to take the plunge and book a trip. The timing is perfect because Winter still flies for free. Despite her free flight, it's crazy to think that we are essentially paying the same amount for a two week vacation as we did for a six week one when we went to Cambodia and Thailand back in 2014. It's a tough pill to swallow how much our trip is going to cost, but we know that it will probably be a once in a lifetime trip and we couldn't think of a better time to do it.

When we went to Southeast Asia, we just sort of winged it. We would show up at the bus station or airport and hop on whatever mode of transportation to whatever destination suited us. We never booked accommodations in advance and had absolutely no schedule or itinerary. It was so fun traveling this way, but we know that this style of traveling won't work now that we have a kid.

Below are 5 things we did to get ready for traveling with a toddler:

1. Booked an Airbnb: My family is going to meet us out there and we will all be staying at a timeshare for about six days. But for the other days, Perry, Winter and I will be on our own. When we booked an Airbnb, we made sure to look to see if it had the following amenities:

  • Kid-friendly: The last thing we need is to be stressed out because Winter has her greasy paws all over precious artwork or expensive decor. When we did our search, we made sure to pay close attention to the decor and booked places that didn't have anything at her level or that could be easily moved. Tip: Type in “Kid/Family Friendly” into the search tool (located under “amenities”) to help you narrow in on potential places.
  • Playground/Grocery Store: We won't have a car in Hawaii. We decided to save the $500 it would cost to rent one and just stay in places that had good walkability. We made sure that each rental has a grocery store, park and restaurants within walking distance.
  • Entrance/Exit accessibility: While this isn't necessary a deal breaker for us, we looked for places that would be on a main level. We plan to pack light, but we will have Winter’s stroller, car seat and our luggage. We didn't want to get stuck hauling our things up 10 flights of stairs. Tip: A good keyword to enter is "wheelchair accessibility". If it is wheelchair accessible, you know that it's going to be good for a stroller.
  • Kitchen: We all know that going out to eat with a toddler is a crapshoot. We made sure that the places we rented had a kitchen that was stocked with basic cooking utensils, a fridge and a stove top.

2.  Bought Toiletries + Gear Ahead of Time: We know that prices are inflated on the island and things like sunscreen and snorkel gear can cost you a pretty penny. Before our trip, we went to Amazon and Target and stocked up on things like goggles, sunscreen, and our favorite snacks. We are still planning on packing light, but we figured we could cut down costs by bringing along some of the things we will know we use by buying them a decent price.

3. Checked Out Hawaii Blogs/Instagrams: I love learning about the what to do, where to eat and what to see when traveling from fellow bloggers. To get ready for the trip, I have been browsing this blog and this Instagram account for inspiration.

4. Packed Lightly: Now by light, I mean as light as you can get with a stroller and car seat. But we managed to get everything into one large suitcase, one carryon for the adults, a small backpack for Winter that holds all her toys, a stroller and a car seat bag that holds her car seat and some small blankets. We decided to opt out of a pack-and- play. While the Airbnbs didn't have pack-and-play or crib options, the hotel did. So for the few nights we aren't in the hotel we plan to co-sleep with Winter. This may backfire on us, however, so we are prepared to rent a crib if that's the case. Before you travel, see what companies rent out baby gear like cribs or highchairs so you don't have to worry about schlepping extra stuff with you. Most companies deliver and set up for you, so you don't have to worry about the transportation piece either. In Maui, we plan to use this company if we need to. (Tip: Most rental places won’t deliver a crib without an elevator if you’re not on the first floor. That’s another reason to make sure your Airbnb is accessible!)

5. Made a Hawaii live list: Perry and I don't want to have high expectations because you never know what it will be like traveling with Winter. But, we are also huge on setting intentions and creating a list of experiences that we hope to create. Below is a list of things we hope to see or do while in Hawaii:

  • Eat at a fresh fruit stand: Nothing screams island life more than eating the fresh fruit from the island. Winter has yet to try pineapple and I am secretly hoping her first bite will be in Maui.
  • Go on a sunset beach picnic: I keep dreaming of the sunsets in Hawaii. We want to spend as much time on the beach as possible and picnics are a free and easy way to get entertainment.
  • Do a waterfall hike: One day, Perry and I plan to leave little Winter behind and go on a hike, just the two of us. We don't get a lot of alone time, so we will fully be taking advantage of having the grandparents around.
  • Eat Hula Pie: I gave up sugar for the month of June and have been waiting to eat Hula Pie. It's probably the best dessert I have ever had.
  • Meditate on the beach: I cannot wait to close my eyes and get lost in the sounds of the ocean.
  • See a sea turtle: Last time I went to Maui, we saw huge sea turtles on black rock beach. I am praying that they will be around this time so Perry can see one.
  • Read a book: Both Perry and I picked out a book to bring on our trip. We plan to have less screen time during Winter's naps and read more. If you have any other good book recommendations, let me know!

Oh and if you're interested in what types of toys we packed for Winter, I wrote a post on the top 10 travel toys for kids, here!