Waikiki, Hawaii Itinerary – traveling with toddlers

At the beginning of this year our family took a 6 day trip to Waikiki with our 3 year old! We traveled from Delaware and I had lots of requests to share our Hawaii itinerary. We consider ourselves pretty experienced travelers and love a good deal so I thought it probably would be helpful to write the Hawaii Itinerary up in a blog post!

Hawaii Itinerary Flights

We ended up flying out of Newark which is a 2.5 hr drive but for some reason it was the shortest travel day at about 13 hours with reasonable ticket prices. The other airports closer to us only had travel times of 17+ hrs for the days we needed. We booked one ticket with our Chase points (we have a Chase prefered card). Then we used Delta points (Delta reserve card) to book the second ticket plus a bit of the third, leaving us with about $400 to pay TOTAL for the three of us, which was amazing.

PS – Reading this blog post is going to make you think we have a ton of credit card debt but I promise the ONLY debt we carry is our mortgage. If you are smart about opening credit cards you can easily hit the rewards minimums by putting regular expenses on them and paying your bills completely and on time. Anywhoot, onto the rest.

For air travel with Emme, we typically bring her carseat in the plane but now that she is 3.5, we do not. I usually bring her a small pack of playdough, an animal figurine, water coloring book, and an ipad. We have found that overnight flights are way better. Mostly because then you don’t have to feel guilty watching them watch their ipad for 12 hours they will just sleep. 🫠

Hawaii Itinerary Hotels

Now if you have a frequent traveler in your life (AD AF Pilot in our house) and don’t have the Hilton Aspire card, you are missing out on LOTS of free vacations. We almost always use Hilton points when we travel. I legit cannot remember the last time we paid for a hotel room. We stayed 6 nights in the Hilton Waikiki Resort for FREE thanks to points, their free weekend resort night certificate, and free night when you book 5. I can totally recommend this resort if you are a Hilton member! It has slightly older/well-loved hotel rooms IMO but for somewhere free to sleep, it was GREAT, lol. Plus it is walking distance to the fun stuff in Waikiki.

Because that Aspire card automatically makes you a diamond member, my husband asked at check-in if there were any free upgrades, and there were! We got upgraded to an ocean view room in the Lagoon tower which was PERFECT. You also get $36/day of food credit that works at particular places on the resort. Starbucks is one of them and we had a Starbucks in our tower. We ate for free every morning on the $36. Some mornings we went $1-4 over pending what everyone chose but it was so worth it. We enjoyed the routine of waking up and heading downstairs for breakfast. We like to think our toddler thrived on this daily rhythm as well since everything else about each day was so different and new.

Rental Car

We went an untraditional route for our rental car and used Truro. This is basically a car sharing service where real people let you borrow their cars for an amount per day. Think Uber meets Rental car, lol. It sounds crazy but it is actually a very well-oiled system and our owner was amazing! We picked up our car right at the airport, met our driver, then took photos of the vehicle status and checked in on the app. You can chat or call the owner if you need them directly in the app.

You do assume some risk, as many insurance agencies do not treat these vehicles as a true rental but you can add on some extra coverage with Truro if you want. We did not because we knew we wouldn’t even be driving it everyday. Drop off was just as seamless, our owner met us at the departures drop off which honestly saves so much time!

DAY 1

Alright let the actual itinerary begin! Day 1 we landed around 5 pm and by the time we got checked in it was about 7pm and we needed dinner! The Hale Koa Hotel is a military family resort in walking distance to the Hilton resort. We popped over to Happy’s Snack bar and got dinner and beer for $40. Which if you’ve eaten in Hawaii you know how inexpensive that is! It was quick and efficient fast-food. It is associated with Hale Koa so I think you need to be an ID card holder to eat there. Then we popped over the Exchange/shoppette in the bottom of the Hale Koa and bought waters, snacks, sandwich supplies, and alcohol and loaded them into our stroller. You must be a military ID card holder to purchase here.

We went into the trip knowing that we would only be eating out for dinner each day. We packed lunches for the afternoons in our small yeti cooler we brought as one of our carry-ons. (Amazon affiliate link). That yeti cooler was definitely clutch everyday! We bought a 4-pack of large waters at the exchange and my husband would refill them before he left the hotel gym every morning. I know how lame that sounds but it did save us money, as did buying alcohol at the shoppette for day-drinking, lol. We did splurge at the pool one or two days but otherwise mostly drank at dinner or whatever we had in the cooler.

Day 2

On our first full day we decided to check out Waikiki on foot! We got up super early (thanks to a 5am toddler wake-up) and were on the Hilton resort beach by sunrise which was fun! We did a nice walk along the main strip and stopped in Kona Coffee Purveryors for some espresso beans. The line is always out the door at this place. My husband showed me a great hack for if you step to the right where the bean tasting and retail is. If you are purchasing beans or other retail, you can also order a coffee with it and skip that giant line! This probably saved us an hour, lol.

Next we hung out on the beach and in the resort lagoon, eating a cooler lunch. The beaches here are all pretty open, so you don’t need to be staying at the resort to access the lagoon. There is no one checking hotel cards or anything. Afterwards we rinsed off and changed and had dinner at the Waikiki Brewing Company before grabbing ice cream on the way back and passing out at the hotel. This brewing company was great! It is up on the second floor and mostly open-air and has some space for a toddler to run around. lol.

Day 3

On second full day we decided to hike Diamond head. We did not know you need reservations to do this! We showed up and were turned away, so we parked at the scenic spot just before the park entrance and then got a walk-in reservation. If I could do it over I would have booked that ahead of time, but we got lucky and it worked out fine for us. The hike is about a mile and half, and you cannot bring a stroller. It gets pretty rocky but our 3 year old hiked most of it herself so I wouldn’t say it is challenging. There is a nice view at the top and it wasn’t too crowded when we went on a Saturday.

The second half the day we hit the beaches again and attempted to go out to dinner but BOY was our toddler done for the day. This was one of only two “dang it” moments we had on the trip. She recently dropped her nap so we are in a sort of transition phase where if she naps she is happier in the afternoons but then won’t fall asleep until after 10 pm which is crazy, lol. So anyways we were on the way to dinner and she fell apart. We decided to turn around and go back to the hotel and everyone passed out–ha!

Day 4

This was one of my favorite days. After breakfast we drove over to Lanakai beach which was breathtaking and incredibly less crowded than the Waikiki area. There was no one within at least 50 ft of us. We brought our sun tent and prepared to be there until the afternoon which was glorious. If we ever win the lottery and move to O’ahu we would live in this area, lol. The beach has a no consuming alcohol or playing loud music rule but we had a shade tent that gave us some privacy and I did not see anyone enforcing rules. I think the real rule is just to be respectful.

That evening we hit the “historic” Duke’s for an early dinner. We sat our on the patio which is a more casual menu but way more our speed. There is live music out there there isn’t too loud and if you stay long enough you will catch the sunset. We showed up right before they started seating folks down there so we got a great shady table. Emme was a huge fan of the “fancy drinks” AKA smoothies and enjoyed her food. She also did a bit of dancing by the stage, lol.

Day 5

This was the day Edgar was super excited about! My friend from our time in Japan and Manual Mode for Moms Student, Meghan, gave us a tour of Ford Island, where she lives. Ed is enjoys WWII History and Meghan has become quite the expert on the history of Ford Island and surrounding military bases! We met up with her and got a driving tour on base, saw her adorable house, and checked out historic locations. It was incredible and we are soooo grateful Meghan reserved her day for us!

We got back to the hotel late that night but scooted over to Maui Brewing Co. which Edgar was not a fan of (he ordered a jalapeno beer like a weirdo). I thought my beer was great and the food was good but Ed says he will never go back, LOL.

DAY 6

Meghan recommended we hit Hale Koa beach which is on the Marine base (so you need ID). There wasn’t a soul there and lots of gorgeous shell remnants to dig through so we stayed for the morning and then headed out to brunch. The water was very calm and would be good for kids who want to swim. Over Easy was our brunch pick while we were on that side of the island again. I cannot recommend this place enough! Edgar said hen he has been there in the past they waited a while to be seated but we were seated right away and I swear we were out of there in like 15 minutes. Literally inhaled our food it was SO good! Parking is limited so we parked at McDonalds and walked over at the risk of being towed which worked out since the service was so fast.

On our last night we went back to Duke’s (because why not), and then played on the beach during sunset before sadly dragging our little butts back to the hotel for one more night. We arrived later this time so we had to grab a drink at the bar and putz on the beach a bit before our table was ready. Honesty, that was not a bad option. It helped Emme burn a little energy before sitting down for dinner.

DAY 7

Our last day in Hawaii we had time to hit the beach once more before checking out of the hotel. Then we went back to base and ate at the Lanai where we had a view of the ocean and airport. The base shares a runway with the airport which is kind of wild! There is a nice little beach next to this restaurant too. Our Truro driver then met us at the airport which was super seamless and easy! Then we arrived at Newark to cold, grey weather and made the depressing trek back to the hotel to pick up our car (this hour of our life was the worst of the trip by far, lol).

Other Ideas

Other things we did not get to do but would have enjoyed are listed in this section. Many of these were recommended by my local friend Meghan who gave us the amazing tour! Other places were things that were on our list of interests that we just didn’t get to. There are literally endless places to play and eat, you cannot get bored on O’ahu–especially if you are an ID card holder!

Food:
Kid/Other places:

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