Adventure Awaits Your Family

We left Chicago in the early afternoon and had a stopover in LAX, eventually landing in Maui in the evening. We secured our rental car and drove to our Airbnb rental in Kaanapali which is about an hour away. We stayed at the Honua Kai, where we have stayed previously. It offers our family space as they are studio, one-, two-, and three-bedroom units complete with living room, full kitchen and washer and dryers. We stayed in a two bedroom mountain view this time and to be honest, you cannot go wrong with views in Hawaii so if trying to save money, island view is still great! 

We were all up early and decided to head to the Gazebo for breakfast. It is one of our favorite places to eat on the Island. It is a tiny gazebo at Napili Shores Maui by Outrigger ( 5315 Lower Honoapiilani Rd, Lahaina, HI)  overlooking the ocean with limited tables and no reservations. We always end up waiting about 45 minutes to be sat, but trust us, it is worth it! They are known for their macadamia nut pancakes and their fried rice (yes, for breakfast!). It is definitely worth a visit and we were even greeted with the most magnificent full rainbow! 

We spent the first day relaxing at our hotel and beach and then grabbed dinner at Duke’s restaurant which is located right in front of our hotel at the Honua Kai. Get the hula pie when there for dessert!

We made reservations for the kids to surf again and booked through Bully’s Surf School. Many of the surf schools lost their previous location in Lahaina due to the wildfires so we met them a bit further south. Unfortunately, the water was just too calm to surf. Instead of keeping our money and taking our kids out, they were honest and said they would rather refund our money – which we very much appreciated. We have surfed with them before and highly recommend though! 

We decided to pack up and head to the Sheraton at Black Rock to swim, cliff dive and relax. The kids love cliff diving and snorkeling here – there is always something to see and it’s a protected cove so its perfect for little ones too. 

For dinner, we headed to our favorite restaurant – Merriman’s. Not only does it offer the most spectacular views, but the food is amazing. It is a more expensive option on the island, but worth every penny in our opinion. We balance the cost by either making a dinner in our condo or eating at a few walk-up places during our visit. 

We woke and walked along the Kaanapali walkway all the way down to the Sheraton hotel. It’s a beautiful morning walk with views, and places to stop for breakfast or just a glass of pog juice. We spotted whales almost every day while here as it was whale watching season (December – April/May). 

We spent the day swimming, boogie boarding and sunbathing before heading to our room in early afternoon to change and head to a luau. We have done the Hyatt luau as well as the Old Lahaina Luau (which was not open due to the fires). This time, we experienced the luau at the Andaz in Wailea. It was about an hour drive and the scenery was beautiful right on the water. However, we much preferred the Old Lahaina Luau for the food, the show and the authentic feeling. Plus the Andaz was more expensive and in our opinion, the food did not justify the cost. 

We packed up the car with beach essentials, and drive to Makena State Park – Big Beach. This is one of our kids must see places when coming to Maui. As the name implies, the waves are big, but that also means a heavy undertow so this is not a great beach for little ones. There is a life guard on duty, but it is a beach I am constantly watching and making sure my kids are okay. 

After a full day in the sun, we headed back to Kaanapali but on the way, we stopped in Kihei for shaved ice. We stumbled upon which was almost as good or as good as Ululani’s Shave Ice. Peace Live Shaved Ice is worth a stop! 

We headed back to change and then grabbed dinner at Monkeypod in Kaanapali. It was good, but to be honest, we probably wouldn’t seek it out again as the food was just okay. 

We spent our last day in Maui snorkeling and boogie boarding and then we packed up to head to Kauai the next day! 

We drove back to the airport, returned our rental car and took an interisland flight to Kauai. We booked ahead of time with Hawaiian air and if you are traveling far to get to the islands, I highly recommend trying to see at least two while you are there. It is so easy to grab an inter island flight and inexpensive! Each of our flights were around $60 and the flight was about a half hour. We grabbed our car and drive to Poipu, which is the southern part of the island. It is known for being sunny and more dry than its northern counterparts of Princeville and Hanalei. 

We decided to stay at the Koloa Landing in Poipu as we are Marriott members. You can use points for your stay or a combination of points and cash. The property is gorgeous, and the staff is amazing! It was rated Best Pool in Kauai and for good reason. It features an infinity pool, waterfalls, water slides, zero depth (for littles), splash pads and more. We stayed in a three bedroom villa and were upgraded to a partial ocean view right by the main pool. The lanai was HUGE and wrapped around the unit – offering plenty of space for everyone. We had a full beautiful kitchen, a living and dining areas, three large bedrooms and three large bathrooms! It was one of the nicest places we have stayed at. 

We reached out to the concierge ahead of time and found they offer shopping services for necessities to be in your villa ahead of arrival. 

We were welcomed with a stocked refrigerator of waters and various drinks for our kids as well as pantry items including chips, cookies and a few other snacks. It was so nice to not have to run out to grab these things on our first day. Instead, we unpacked and headed right to the pool! The only thing to note is that this resort does not sit beachfront. You can see the ocean but it is across the street, but the beach is a five or 10 minute walk down the quiet road to the Sheraton. The hotel also offers shuttle service too. 

We made a reservation that night at the Beach House Restaurant. Definitely make a reservation ahead of time as it books up. I believe they open reservations 30 days ahead of time. We requested a table on the outside patio and the sunset views are spectacular. It was like the sky was on fire that night. We enjoyed the lobster deviled eggs, macadamia crusted mahi mahi and the Monkeypod Mai Tai! 

We headed to Poipu Beach. This is a public beach so it was a bit crowded, but we saw a beached seal which the kids liked as well as a bunch of turtles that came to shore for a break. There is a great cove protected by rocks for little ones to swim and then an area with larger waves. Brennecke’s Beach restaurant is right across the street for food and there are lifeguards at this beach as well. 

We ate at Brennecke’s this night, and while it was easy and convenient, we probably wouldn’t head back there on a future trip. 

This was one of our favorite days! We took the kids on an ATV tour at Kipu Ranch. It was aout 20 minutes away from our hotel. We took a guided tour – selecting the waterfall tour. We were with other people, but had our own vehicle which sat 6 people. It was a combination of off-roading and being on trails. We rode through the tropical forest and stopped along the way for some amazing viewpoints. It was a GREAT activity for older kids to experience and something we had never done before. 

After the tour we headed back to our hotel and ended up grabbing Bubba Burgers and eating in our villa that night while the kids night swam. 

We drove to Waimea Canyon – an activity we have never done before and it was definitely worth it! The views are spectacular while driving. It is a steep elevation and windy roads so just be prepared to drive slow and make stops along the way. While we originally intended to do a hike or two, we drove straight to the lookout, took in the views and learned about the area from a native who was there sharing stories with visitors. 

We headed to the beach and pool in the afternoon and then ate at Keokis paradise for dinner. The food was good here, but it does feel more like a chain restaurant than something local as it is situated in an outdoor mall. 

We drove to the Princeville and Hanalei area for our last full day. From Poipu it takes about an hour and a half, but it was worth every second in the car. In fact, if we go back, I would absolutely love to stay in the Hanalei area again. It is flanked by jagged peaks covered in green and turqouis beaches on the other side. The town is quaint and small but features restaurants and shopping. 

We went to tunnels beach and this was my favorite beach out of all Hawaii! It was very private and felt like no one else was there. Green covered mountains are situated behind you and the crescent shaped beach offered larger waves and a designated area to snorkel. There is a lifeguard on duty but there is not a restaurant or facilities here so pack snacks and waters. 

We headed to Hanalei Bay next. This is a large public beach with the iconic pier that jets out into the water. It was calm and shallow and offered a large sandbar which the kids loved. There are food trucks and facilities here as well.

We ate at Tidepools for our last night and it was probably our best dinner of the trip. We were seated at a table covered by a thatched roof hut and we were surrounded by the pools of the hotel filled with Koi fish swimming. It was raining all around us as we enjoyed the most delicious seafood and service. Highly recommend if you are staying in Poipu. 

One thing to note is that I would probably opt to stay more central next time – maybe closer to Lihue or Wailua areas as it would allow us easier access to the south and north shore of the island. Otherwise, I would have opted to stay in Hanalei area as it had such an amazing, authentic, low-key Hawaiian feel to the town.  

Day twelve was a pool day and travel day home.