I made 9 blunders on our first family vacation to Hawaii with my 1-year-old. Here’s what I’d do differently

I planned a trip to Oahu, Hawaii, with my husband and 1-year-old daughter this summer. It was our first family vacation to Hawaii.

I stayed at the Hilton Hawaiian Village Waikiki Beach Resort with my spouse and children.
Emily Hochberg/Insider

All pandemic, I yearned for an isolated tropical escape. But I kept postponing it, either because COVID-19 transmission rates were too high and I didn’t feel safe flying, because I was too overwhelmed while taking care of a baby, or because I was too preoccupied with a cross-country transfer from New York City to California.

This summer, the timing finally felt right. My family was now located on the West Coast, and Hawaii seemed like the ideal vacation spot.

We planned to spend a week at the Hilton Hawaiian Village Resort on Waikiki Beach in Honolulu, Disney’s Aulani Resort & Spa in Ko Olina, and the Royal Hawaiian Hotel in Waikiki before departing from Honolulu.

We had some wonderful memories, and I’m pleased we went, but if I could do it all over again, I would manage a few situations differently.

As a parent, I first discovered that traveling with a little child is not a vacation, but a trip. I should have had this attitude from the beginning.

On “holiday” with my daughter in Hawaii.

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What was our greatest error in bringing a one-year-old to Hawaii? Likely to bring a one-year-old to Hawaii.

My kid is a toddler, and toddlers are notoriously difficult. Traveling with a toddler is more difficult.

Due to the pandemic and the nature of having a newborn infant, we have traveled with our daughter only on a few short trips close to home since her birth. This was our first major trip outside the United States, and I was excited.

And while that is not inherently negative, I should have begun with lesser expectations. We were on our way to paradise, but I had no intention of sipping cocktails by the pool, reading a nice book, or working on my tan.

Instead, I spent the majority of my time corralling and entertaining a jet-lagged 21-month-old with a short attention span who had no desire to see the beach, quickly became sick of the pool, and refused to eat in restaurants.

I yearned to sink into a lounge chair or dive into the water as I grew increasingly exhausted and exasperated by the number of outbursts.

Next time, I’ll expect the worst and hope for the best. I’m still delighted we went, but I’ll expect the worst and hope for the best.

I wish I had planned better for our flights and brought a few essential carry-on items.

My daughter is seated on my lap and looking out the aircraft window.

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I spent considerable time refining my checked-baggage packing list for our seven-day trip. On our 5-hour flight from Los Angeles to Honolulu, I wish I had paid the same kind of care to my carry-on.

My daughter was exhausted by the time we made it through security and to our gate for our 8 a.m. trip. The queue at Starbucks was so long that we would have missed our flight if we waited, and there was nowhere else to eat in the airport terminal. Naturally, she refused the goods I had on hand, leaving me to deal with a toddler who was irritable from hunger.

Thankfully, she fell asleep on my lap shortly after takeoff. However, this meant I had to sit in an awkward posture for the next few hours while attempting not to disturb her. I wished I had brought a sweater or a neck pillow to act as a cushion for my numb elbow.

Additionally, the aircraft cabin felt stuffy and overheated. I was perspiring profusely from carrying my daughter through the airport when I realized I had also forgotten a water bottle and a hair tie.

On the return flight, I made sure to be more prepared, although I should have brought my daughter more diversions. I hoped I had more distractions to keep her from kicking the seat in front of her on the way back, as she was less interested in the iPad on the way there than on the way back.

When we arrived in Hawaii, we rented a car, which I believed would provide us with the freedom to explore and travel between hotels. Reserving transfers would have been less expensive.

My daughter was in the vehicle.

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I rented a car for a week through Costco Trip for $476, which I deemed reasonable given the summer travel dates.

I desired a rental automobile so we wouldn’t be dependent on anybody else for transportation and so I could install my daughter’s car seat only once.

I initially believed that it would also be the least expensive alternative. I forgot about parking, however.

The self-parking fee for registered hotel guests at Hilton Hawaiian Village is $57 per night; our three-night stay was $171. Self-parking is $37 per day at Aulani, a Disney Resort & Spa, but valet was the same price, so we opted for it; for two nights, it cost $74. Self-parking for our two-night stay at the Royal Hawaiian was $45 each day, totaling $90. During our trip, we spent $335 on parking fees.

We did not drive much and stayed primarily at our lodgings. We simply drove the car to drive to and from the airport, exchange hotels, and visit the Honolulu Aquarium in the afternoon. The one positive aspect was that we only had to fill up the petrol tank once before returning the car, which cost only $21.

If we had utilized airport and hotel transfers, I believe that we would have saved approximately $100. Charley’s Taxi, a popular service recommended by each hotel where we stayed, offers flat prices to and from the airport to Waikiki Beach for $31 each way and to the Aulani resort for $95 each way. The service would have cost us approximately $252 dollars. Even with increased gratuities or fees, I believe it would have been less expensive and someone would have assisted us with our stuff.

While I loved the flexibility of being able to set our own schedule, Hawaii is expensive and a car wasn’t necessary for our agenda.

I tried to eat at restaurants too frequently. Everyone’s journey would have been less stressful if we had ordered takeaway.

Attempting to entice my daughter to eat with an iPhone (L) and her hiding under my dress at our hibachi supper (R).

Emily Hochberg/Exterior

I am well aware that expecting a child to sit quietly at a restaurant for an hour-long dinner is impractical.

But because I hadn’t sufficiently lowered my expectations on vacation, I erroneously believed it would be simple to dine by the sea if we choose a low-key, non-fancy restaurant.

On our first night at the Hilton, we dined at a casual beachfront restaurant, but my jet-lagged daughter found it too stimulating. She was unwilling to watch videos or remain motionless. The time change also affected her appetite, and she refused to eat foods she generally enjoyed, which contributed to her irritability. I had to carry a screaming, kicking child out of the restaurant, much to the disgust of my fellow diners, while my husband avoided eye contact and ate his lunch by himself.

Later, I chose a hibachi restaurant because I believed she would enjoy the flames and motion. Unfortunately, I did not expect that the presence of strangers in a group dining setting would cause her to become timid and flee the table. The entire supper was spent in the corner, with my husband and I taking turns standing with her.

And on our last night, I thought we would enjoy a quick meal and mai tais. However, before we could place our orders, she requested to flee onto the beach with my husband and refused to return.

We would have been better off ordering takeaway and eating in a park or on the beach so that we could actually eat together.

When we arrived at our first hotel and found that our room wasn’t ready, I made one of my biggest blunders. I failed to bring day bags to the pool.

Waiting for our room to become available.

Emily Hochberg/Exterior

We arrived at the Hilton Hawaiian Village Waikiki Beach Resort weary, perspiring, and quite elated.

The hotel features five swimming pools, a lagoon, and a prime beachfront location. We were ready to immediately take advantage of its beauty. After leaving our luggage with the valet and waiting in a lengthy check-in line, we discovered that our room was not yet ready. We were permitted to use the facilities while we waited, but our luggage, including our swimwear, was already in storage.

I could have requested for the luggage back, but my toddler was ready to leave the lobby and I didn’t want to display our enormous suitcases in the midst of the crowded check-in area.

So instead of immediately getting to the pool, I sat at a table in my dirty aircraft leggings until our room was ready. By that time, my daughter need another nap, and we missed our afternoon pool time.

When arriving at a tropical resort before check-in, I have now learned the necessity of always carrying a day bag including swimwear and a change of clothes.

I should have had a better plan for napping on the go.

My kid slept in her stroller on a rare occasion.

Emily Hochberg/Exterior

My daughter has always had difficulty sleeping. She requires a lot of assistance from me or her father, as well as a dark, chilly, and quiet room, in order to go asleep. When on vacation when your room isn’t ready, none of these options are available. She is also one of the only infants on the planet who will not sleep in her car seat or stroller without much fuss. And in the unlikely event that she does, it is brief.

I knew we’d arrive at the Hilton around naptime, but I assumed her plane nap would prevent her from needing another one. Due to our early departure and the time change, she was so fatigued that she fell asleep in her stroller for the first time ever, just as we were informed that our room was ready.

When we entered the room, we attempted to remove her and place her in her cot. We failed dreadfully. She was really distressed, and I was unable to get her back to sleep or calm her down for over an hour, much to the concern of our hotel neighbors.

I was in the same position when we transferred hotels to Aulani. Instead of attempting to get her to take a sleep, I let her play in the splash pad for as long as she wished and praised myself for being such a kind and accommodating mom.

Then, all chaos ensued. Due to exhaustion, she began to weep about anything and everything. She was unhappy that she couldn’t swim in the lazy river because she doesn’t know how to swim, angry that I offered her anything other than the lazy river, and infuriated that I wouldn’t allow her to walk face-first into a pool of water. I was unable to soothe her while I walked, strolled, and hushed her.

The fact that we were at a Disney resort was my only consolation throughout the public outburst. Is it even a Disney trip if no one throws a tantrum? We fit in perfectly.

Given our plan, this was largely unavoidable, but next time I’ll look for ways to assure early or late checkout, or better still, stay in just one hotel for the duration of the trip to prevent this from occurring many times.

When our room at Aulani wasn’t ready upon check-in, I should have contacted the hotel service sooner.

Trying to comfort my girlfriend in Aulani.

Emily Hochberg/Exterior

My daughter’s meltdown at Aulani as a result of her missed nap was entirely avoidable. I was simply unaware.

I was instructed to download the hotel’s app upon check-in in order to be informed of activities, services, and more. The staff gave me my room keys and informed me that they would be activated when my room was ready, so I would not need to return to the front desk. I was also informed that the front desk will contact or text me when my room was ready. I never did.

When I opened my app while waiting that afternoon, a room number appeared. I believed this to be usual procedure. I was unaware that it meant my room was genuinely prepared. I repeatedly waited for a phone or text message. I returned to the front desk at 3 p.m., the official check-in time, only to realize that my room had been available for hours, as shown on the app.

While the hotel apologized and offered me a $50 resort credit for the inconvenience, my daughter’s nap was over and I was angry with myself for not questioning when I saw the room number published.

Next time, I will surely inquire more frequently about the condition of my room, especially if a meltdown is imminent.

My daughter loved the pools, particularly the kids waterslides. I wish I had a phone holder that was waterproof so I could have caught more memories.

The waterslide at Hilton Hawaiian Village Waikiki Beach Resort was a favorite of my daughter.

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We experienced some of the most enjoyable moments of our trip splashing about the pool.

My daughter enjoyed dipping in the shallow end of each hotel pool, running back and forth through the splash pads at Aulani, and zipping down a waterslide for children while sitting on my lap at the Hilton Hawaiian Village Waikiki Beach Resort.

I doubt I’ve ever seen her more joyful, and I wish I had more pictures of her in the water. We got some, but if I wasn’t so afraid of getting my phone wet or putting it in the pool, I would have gotten so many more shots! I realized that I had made a mistake when I did not get a phone case after observing other parents carrying their phones on lanyards with cases.

I especially regretted not having one when three of us rode a raft around a lazy river at Aulani successfully and safely. It was a beautiful family experience, but without a waterproof case, there was no way to enter and exit the raft.

During this journey, we made numerous errors. But I have no regrets whatsoever.

I will appreciate both the positive and negative experiences created on this trip.

Emily Hochberg/Exterior

My trip to Hawaii was neither a vacation nor the picturesque island escape I had anticipated.

But recalling everything that went wrong makes me chuckle, and the memory of seeing my daughter’s face light up when listening to Hawaiian music or sliding down a waterslide brings a grin to my face.

When I look at images from our vacation, I now think, “I’ve largely forgotten the tears and the frustration.” “What a fantastic time! We should repeat that action.”

The next time we travel, though, I will hopefully have a better strategy for naps, check-in, and food. As parents, we all simply do our best.