One day the travel bug hit me and I realized that we had not really been anywhere as a family of three without friends or other family. Our lives were feeling more in control after adjusting to parenthood and for some reason Hawaii kept popping into my mind.

We are fortunate to travel to Paris and other destinations throughout the year, but I wanted to go in the opposite direction and find a contrasting atmosphere.

Considering we were thinking about Baby #2, I opted for a zika free zone. That meant many options were off the list.

Where to go in Hawaii was the first big question to answer. In the end I was between Maui and Kauai. There were so many attractive things about Maui and honestly, much of the research I did pointed me there. However, when I heard things like Kauai being known as “The Garden Isle” and that only 5% of the island was built upon, I couldn’t resist the urge to discover this more rugged place. Kauai also kept popping up on the world’s most beautiful places lists.

With a 2-year-old, I decided that we would be better off in a low-key environment and would enjoy an Airbnb close to the beach where we could cook without disturbing people at restaurants multiple times a day.

After making the decision to go to Kauai, the next step was where to stay on the island. Hawaii is a long trip from the Midwest, so we decided to stay for a full 10 days. It was glorious!

Not having any children in school, we were able to go over Labor Day Weekend. That was a great decision because the weather was nice (I hear that Kauai gets more rain in the winter months on the North Shore) and the crowds had died down a bit. Kauai is increasingly becoming busier.

I am a planner when it comes to vacations. Researching and planning each day is the way I get excited for a trip. It helps me feel like we aren’t missing out on anything and we can tailor our trip to our goals. Our goals this time were rest, relaxation, sun, good food and family time. It doesn’t sound like something you need to plan for, but for me it meant surrounding ourselves with great ambiance and making sure our schedule was conducive to seeing the island without wasting any time in a place we didn’t want to be.

In the 10 days, we stayed in 3 different places. My husband and I both agreed that we are glad we switched because we saw more and each had something special to offer.

From research, the North Side of the island seemed to be our speed, but the Grand Hyatt in Poipu looked beautiful and family friendly.

Here are the 3 places where we stayed:

  1. Grand Hyatt
  2. Airbnb Hanalei
  3. St. Regis Princeville
Grand Hyatt Poipu
Walking around the Grand Hyatt
Lagoon at Grand Hyatt Poipu
Lagoon at Grand Hyatt Poipu

We arrived on a Saturday evening, rented a car and headed to the Grand Hyatt. One piece of advice is that I do not recommend renting a big SUV. They told us that our midsize car we ordered was not available so they would “upgrade” us at no cost. The upgrade was a Ford Explore and far to big for the roads of Kauai. I would also recommend bringing your own carseat. We are used to cities with taxis and we never bring a carseat with us. It would have saved us some money and wouldn’t have been a real hassle.

We arrived to the beautiful Grand Hyatt, checked in and immediately ordered room service. I noticed a couple of bugs and didn’t think too much about it. We are on an island and the hotel is very “open air”. However, once we started eating we looked at the nightstand and saw mini cockroaches climbing everywhere, then we saw them on the wall, then in the bathroom. We were so tired from traveling with a toddler that both my husband and I were having a bit of a meltdown. I called guest services and they said they would send a cleaning lady. I insisted on a new room and they found us one that was a late checkout. We had to wait a while but they refunded us a few hundred dollars for the inconvenience. Everyone kept telling us it was normal to see these “sugar cane roaches” on Kauai. We were worried we might need to leave the island, because after living in NYC roaches did not sit well with us.

Fortunately, we didn’t have this problem for the rest of the trip! We don’t think that the Grand Hyatt is dirty and have an extremely fond memory of the hotel. Don’t let this piece of information scare you from booking. The staff was extremely accommodating.

On to our first full day. The beach outside of the Grand Hyatt is not really swimmable. However, their pools are amazing with the best feature being their lagoon. It is perfect for young children. It is a filtered lagoon with sand and salt water. We spent the entire day in the lagoon after the wonderful hotel brunch.

In the evening, we went to the Luau that the Hyatt held. I am not a connoisseur of Luaus but I thought the food was decent and the Luau was well done.

Before Luau at Grand Hyatt Poipu

The next day, we went down for brunch and enjoyed it so much. It’s fresh and delicious with many fresh fruits, juices. We checked out of the hotel and explored the South side of the island. Kauai is essentially a perfect circle, but the West side of the island is impassable by car, so the road system looks like a backwards C.

We went to the Kalalau Lookout. This is a slightly stressful drive in a large SUV. It’s winding and uphill with little to no shoulder. The view at the top is amazing and you can also stop to look at Waimea Canyon.

Kalalau Lookout

We headed directly to Hanalei Bay after this. It was a pretty long drive only because the speed limit is 35-50 mph on the Island. It was nice to take in the scenery and get more oriented on the island. 

For what it is worth, there is a mall on the Northeast side of the island. My husband broke a sandal and we stopped quickly to find something.

We arrived to Hanalei in the evening and it was already dark. Our Airbnb was amazing and incredibly clean. There was no AC, but it was not needed because it was very comfortable in the evening.

We walked into Hanalei and went to the local supermarket which was charming and then had the amazing Lava Flow pizza at the Hanalei Bay Pizzeria. It was incredible. We were so happy to be in our charming beach cottage with our delicious pizza.

Lava Flow at Hanalei Bay Pizzeria
Kauai Juice Co.
Processed with VSCO with c3 preset

The next day we cooked an awesomely fresh breakfast and hit the beach. Hanalei Bay is my all time favorite beach. First of all, the sand is great. It’s soft, perfect for sandcastles and great for kids. We were a block away, so we walked. The access is great. The parking lot was half full and the beach was not overly crowded. Again, no peak season but the weather was perfect. The waves on the beach were perfect for bodysurfing and surf lessons, but it wasn’t intimidating. We are not professional swimmers, so I appreciate a beach where I feel comfortable but also can catch some ways on a boogey board.

Hanalei Bay

Oh, and the view. The mountains surrounding Hanalei Bay are breathtaking. I cannot overstate the beauty of Kauai. There is something so prehistoric and majestic about the steep, green mountains that directly boarder the ocean.

After plenty of sun and exercise, we headed back to the cottage and the outdoor shower. It was so fun to be showering al fresco next to our very own avocado trees and mystery fruit trees. I still can’t figure out what fruit we had growing there, but it was beautiful and added to the mystery of the garden isle.

Outdoor showers make a vacation really feel like a vacation.
Avocado from the back yard of the Airbnb
Ready to swim again but enjoying that nice breeze in bed

We were starving and headed to Calypso for some eats. It’s not a fine dining experience, but I was confused by the amount of negative reviews. It’s what I expected for a sports/bar local eats spot and we just had some nachos and a variety of appetizers… and a mai tai. It’s open air and there are televisions. It’s a Kauai-an sport bar.

Kalypso Menu
Hanalei Town

We checked out some local shops and bought a beautiful butterfly garland for Constance’s room and a little turtle paperweight for my kitchen windowsill.

There are several food trucks in Hanalei that congregate together around some picnic tables. The only problem is the chickens, but the food was the best we had in Hanalei.

Trucking Delicious
Coconut Shrimp and Macaroni Salad

We slept so well and felt so good the next morning. We were both a little nervous, because we had a babysitter we had never met coming over to watch C while we took a boat tour of the Na Pali Coast.

Mystery fruit from the backyard of the Airbnb. Let me know if you know what this is!
Off to walk to town for dinner

 I will start with the babysitter. We used the Kauai Babysitting Company because of the excellent reviews. An absolutely wonderful woman showed up 30 minutes early to chat with us and get to know C. We felt so good leaving. I cannot explain it, but it was just a feeling. This woman was beyond responsible and C couldn’t wait to play with her all day.

Next we walked a block (location, location, location!) to register for the tour. This was my husband’s favorite part of the trip. We took a bus 5 minutes to the loading point of the boat and then were off for the tour. They guides were amazing and the ride was wonderful. Note that this weekend was about the last they would offer, because it starts to get rough on the Na Pali Coast during the fall and winter months.

Napali Coast Tour

First we took in the beauty of the mountains and learned a lot. We saw turtles and then went scuba diving, because it was the end of the summer season, the water was not very clear. I personally don’t like to swim in foggy ocean water. I may be completely crazy, but the lack of visibility gives me anxiety. 

We had a nice brown bag lunch and headed back. We found C and the sitter outside enjoying the garden. She was turning into a barefoot island girl before our eyes. She was big in her Moana phase and she was truly just living her truth in the garden.


The next day we took a drive as far West as we could. Unfortunately, I think this road is closed due to the massive flooding they had just after we left. The next day was another beach day and we tried a more fine dining experience after. The food was good, but the service didn’t really match. Everyone on the island was so kind and open, but the service here was trying to hard to be snobby. It’s a huge turnoff for me as a patron because I feel like true luxury experiences don’t have this strange complex.

Personally, the Airbnb was my favorite leg of the trip. We loved Hanalei, the location to town, the location to the beach, the excursion and we just felt extremely relaxed here.

Next we checked into the St. Regis in Princeville. It’s a beautiful hotel and property. The views are breathtaking. Because we had our little 2 year old. We couldn’t really just lounge in the lounge chairs and enjoy the fine dining. That is not to say that I would not recommend this place. We had a fabulous time. The spa is incredible and the rooms were fantastic. 

Hotdog on the beach at The St. Regis Princeville

We hung out in the pool in the morning and the other guests were so great. Everyone was friendly and open. People were enjoying cocktails, but it was definitely not a place that we felt uncomfortable having a young child. It was just a good atmosphere. The service was great and the pool snacks were wonderful as well.

The beach is a little rocky even though it connects with Hanalei Bay. My husband walked back to where we were before to swim.

Incredible Property

We had a rainy day while we were there and it was welcome. We did a room service and movie day. It was fabulous. While in bed, I ordered the St. Regis Princeville Room Spray and the pillows. 

We do not like to be the obnoxious family with the young child in the fancy restaurant, so we called down and said we have a young child but would like to enjoy a nice dining experience. We asked if it were possible to be seated far away from crowds and they were beyond welcoming and accommodating. We had great food in our private little booth in the back. It was wonderful.

Near our room at The St. Regis
Cozy under the clouds with a Bloody Mary

Kauai is a place that I would recommend with or without children. We personally want to go back again with our children because our family experience there was so memorable and we are at place where we truly enjoy spending time together.

After 10 days, we were beyond relaxed. It was time to go home and we were okay with that. We definitely felt like we were able to experience the island.