Spending the holidays in Hawaii was a wonderfully different experience. Walking around the shores of Waikiki beach in shorts and a tank top while Christmas music played at a nearby food stall felt strange at first, but it didn’t take long for me to find the atmosphere relaxing, especially since this “vacation” was an all-expenses-paid trip.
My sister and I were unbelievably fortunate to have been asked to help nanny for multiple families on a seven day cruise around the islands of Hawaii. All that was asked of us in exchange for flights, lodging, excursions, and, of course, the cruise itself, were some babysitting hours. For seven days, we woke up and took care of kids who ranged from infant to preteen and explored around as much as we could.
If you want to see more from our week long trip you can watch our videos on my YouTube Channel!
Honolulu: Day One
Moving a party of 16 people, their 20+ bags, strollers, and car seats through security and onto a plane for a long, direct flight from Dallas to Honolulu was no easy task. Somehow, we managed without any issues, and it felt great to get to our hotel and know that our vacation was about to begin.
After a somewhat stressful check-in process at The Hilton Hawaiian Village – Waikiki Beach Resort, my sister and I were given the evening off to roam around. The first thing we did was watch the sun set for the night from the beach outside our resort.
On the way downstairs, we discovered that there is a weekly, seashore fireworks show launched from the hotel’s coastline. We decided to walk up the beach to grab a pierside, Polynesian-inspired dinner at Sun’s Up and claim a spot on the rocky ledges to watch the light display.
After a fairly decent program of explosions and sparkling streams, it was time to call it a night and prepare for our early-morning hike.
Honolulu and Pride of America: Day Two
My sister and I woke up early to climb Diamond Head Crater and catch the sunrise. It was extra challenging, thanks to the time change, and sadly a 6 am departure wasn't early enough.
Even though we weren’t at the top when the sun burst out, our view of the gleaming fireball as it peaked over the edge of the Pacific Ocean was more majestic than I could have ever imagined. (You can read and see more about this hike in my review: here!)
After many stairs up and back down, we headed back toward the hotel, but not before we stopped at a local farmers’ market on the campus of Kapi’olani Community College just across the street from the tunnel to Diamond Head.
We enjoyed some fresh pineapple juice and breakfast empanadas before going back to the hotel to help the family round up the children and head toward our cruise ship.
(You can see more details about both of our stops in Honolulu in this post!)
Luckily, the family had arranged transportation to and from certain places on the island so that we could all ride together with our luggage. Sometimes we were a little too proactive and over-estimated how long it would take us to travel places. A good example was when we boarded our ship, The Pride Of America.
Even after the ID checks, photo-ops, and payment stations, we were aboard the ship several hours before our room was ready. We eventually decided to claim stake at an unopened bar and keep everyone and their items there until the rooms were ready.
Finally, we unpacked just in time for the safety checks and a barbeque on the pool deck.
We had a calm evening getting accustomed to one another and preparing for the wonderful week we would spend together.
Kahului, Maui: Day Three
Cruise ship rooms are really small, but they seem extra small when you have to watch several children who crawl around and get bored easily. We spent the first day cooped up in the dorm-sized barracks of the cruise ship until the parents returned from their snorkeling excursion.
Since we only had two people to push three strollers, leaving the room wasn't really an option. When everyone returned, we grabbed a bite to eat and prepared for our sunset excursion.
Again, most things were pre-booked and that came with some unforeseen difficulties. Some of the parents didn’t know that car seats were required for any excursion requiring a bus ride or that children under the age of 5 weren’t advised to go to high altitude - excluding them from our current excursion.
Unfortunately, not everyone was able to travel to the top of Haleakala National Park to watch the sunset from above the clouds.
Luckily, my sister and I were able to go, and we got to check a National Park off our bucket lists!
We took almost an hour-long bus ride up narrow and windy roads to summit the volcanic caldera that is Haleakala. Being above the clouds when the sun set gave me a new perspective of the sun’s journey across the sky, and I was blown away by its radiance.
Once the sun had set, we hopped back onto the bus and made the windy journey back. We boarded the ship again, grabbed a bite, and hit the hay pretty early.
I found out that taking care of kids and hiking at high altitudes are exhausting after flying through several time zones.
Kahului, Maui: Day Four
The bus dropped us off around 9 AM, right at the public beach access point. We enjoyed ourselves a great deal that day by taking in the sunshine and good conversations. We played Frisbee, made sand castles, and swam in the ocean almost the entire time.
Around 2:30 PM, the bus came to pick us back up, and it was perfectly timed just before the clouds rolled in and the wind started to pick up.
Even though it was a short time in Maui, I laid out some of our details and shared more pictures in this separate post: Read more here!
Back on the boat, my sister and I got the night off, so we went to the formal dining hall, Skyline. We then tried to catch a show, but our timing was a little off, and we didn’t make it. We grabbed dessert on the deck and decided to go back to the room for some rest!
Hilo, Hawaii (The Big Island): Day Five
On day four, we didn’t have the same kind of lovely experience as we’d had in Maui the day before. My sister and I never got to leave the boat. Instead, we watched the kids from 7am to nearly 4pm while the families went on unplanned kayak and volcano excursions.
We were disappointed, because we weren’t scheduled to watch any kids that day and were planning to knock Volcanoes National Park off our bucket lists. We couldn’t complain, because this was, in fact, their family’s vacation.
Kona, Hawaii (The Big Island): Day Six
Even though our beach day on Maui was the most relaxing part of our trip, my favorite day was in Kona. We started the morning off early by catching a tender boat to another boat for our Big Island Snorkeling excursion.
The entire family, babies included, were able to go on this excursion. Luckily, the waves rocked the babies to sleep, so we took the older kids off the boat’s slides and diving boards and hopped into the water.
We spent all morning splashing, snorkeling, and looking at all the coral and fish below us.
After dozens of dolphin encounters and flying fish sightings, we headed back to the port area to have an afternoon walk around the town.
My sister and I found ourselves free to go shopping on the main street. We took a look around Hawaii’s oldest church, Moku’aikaua, before we checked out The Kona Brewery and Kona Coffee. Then, we went back to the boat to depart for another island.
You can read more about our day in Kona in this separate blog post!
Nawiliwili, Kauai: Day Seven
The further we got into our trip, the more comfortable the family became with my sister and I. On day six, we only had one child to watch, and they said we could take him off the boat if we wanted, so we jumped on the opportunity to explore the new island!
We spent the day carrying the baby on the Hop Off Hop Off bus and stopping wherever we could. The first stop was Wailua River for a river boat tour of the Fern Grotto where Elvis famously sang in Blue Hawaii.
The boat captain gave us a detailed history of the area's ecology and geology and shared how the area had grown and developed since the publishing of the movie in the 60’s. When we arrived at the grotto, a group of locals sang the wedding song made famous in the movie.
After their lovely show, we got back on the boat and returned to the dock we came from. Right on the other side of the parking lot was Smith’s Tropical Paradise, a nature park and preserve full of tropical birds and plants.
We fed peacocks, nenes, and dozens of other birds while carrying a sleeping baby on our bellies. We spent the afternoon wandering the beautifully kept, lush grounds until we had to head back to the cruise ship.
You can see and read more about our entire day on Kauai in this extended post!
Since this was one of our final evenings, the family had arranged a very special luau for all of us to attend at the Kilohana Manor House.
We took tours of the old sugar plantation and had rum tastings from their home-distilled liquor before sitting down for our delicious four course meal of local fish, fruit, and vegetables.
The luau performance was unlike anything we imagined. Its modern flare applied to a traditional story incorporated a bit of acrobatics with lights and music.
After the captivating entertainment, we got back on the boat and visited the Key West Bar on the pool deck for a night cap before the ship headed back to the port city of Honolulu.
Nawiliwili, Kauai and Na Pali Coast: Day Eight
We had a long night the night before, and we had lots of kids to watch on day eight, so my sister and I never left the boat. We ate burgers and mac n’ cheese at the Cadillac Diner and played games in our stateroom.
When everyone returned from their excursions and the boat departed, my sister and I headed to the top deck for a little quality pool time. We caught some rays before the boat drove past the Na Pali Coast.
The unique geology of the volcanic ripples was unlike anything I had ever seen. The lush yet barren-looking spires made me want to hike all of the coastal ridges. Sadly, our ‘drive-by’ only lasted for 20 or so minutes.
After the history lesson blared through the loud speaker system on the pool deck, our view of the Na Pali Coast diminished. My sister and I began to get ready for our last dinner and our last night of watching all the kids.
We packed up our things and left them outside the door, as instructed, before taking the kids to play ping pong and run around the arcade. It was a fun and relaxing way to spend our last night on the boat.
Honolulu: Day Nine
Our departure from the boat was just as hectic as our arrival, but the family had again arranged transportation from our boat to the airport. Unfortunately, though, the timing of the shuttle and our flight were slightly off, and we arrived at the airport about 6 hours too early.
My sister and I decided we would try to head out and go see Pearl Harbor while we were close. We extended an invitation to the party, but everyone else declined and chose to stay in the airport lounge.
My sister and I took a quick Uber ride to the monument and were instantly humbled when we entered. It is one thing to hear about and see reenactments of what happened on that infamous date in December, but to stand inside the port and see some of what those soldiers saw was a life changing experience.
We started our tour by visiting the USS Bowfin Submarine which has now been turned into a museum and memorial. We walked through the ship’s barracks and caught glimpses of what life was like for a sailor. We emerged from the submarine, and again, we were ever more grateful for our armed forces after seeing the sacrifices they made to protect our freedom.
After walking around the memorial’s grounds and reading the names of all of the soldiers on every ship, we were ready to see the USS Arizona.
Unfortunately, it was under construction, so we were only able to see it from the small trolley boat. What we were able to see was a sobering symbol of lives lost and a hard-fought battle. We were moved beyond tears remembering the sacrifices made that day.
We stayed as long as we could before we needed to head back to the airport. We could have spent days looking over and memorizing the names of those lost on that day. Instead, we called our Uber back, hopped on a plane, and made our departure back to the main land.
After a week of working hard and carefree vacationing on an all-expenses-paid cruise in paradise, we were back in the air heading toward reality. We could never thank the family that trusted us with their children and invited us on this trip enough, because we were provided the opportunity of a lifetime to go and do things we had never imagined.
If you want to see more from our week long trip you can watch our videos on my YouTube Channel - here!
Two Days in Maui
Haleakala National Park
Talkin' 'bout Tacos:
I'm Taylor, aka Tacos! I am sharing my journeys and experiences from across the world hoping to inspire travel and adventure in all who read.