Oahu for Winter Break: A Mom’s Guide

Two years ago, my husband and I decided to take the family to Hawaii during Winter break. My brother has a condo there (Waikiki) so we just had to book flights and a rental car and we were good to go. Per my brother’s tutelage, I visited the Hawaiian Airlines website daily and checked fares to find the least expensive flights. He was right fares really do change from day to day quite dramatically on Hawaiian Airlines. As a family of five, flights are a huge expense. I ended up finding flights for only $256 round trip for each of us. We left on January 1st for 9 days.

My brother’s condo was on the small side with one bedroom and one bathroom but it was perfect for us. He was blocks from Waikiki Beach and it was the ideal resting place for all the things we wanted to do.

Arrival Day – Honolulu Airport.

I ordered a Lei greeting a la “The Brady Bunch Hawaii Bound” style. Hawaiian Airlines had it available as an add-on option. Kids loved the lei so that was a hit. We were all tired from getting up at the crack of dawn in Los Angeles so we didn’t do much on Day 1 other than make a trip to the grocery store to get some snacks. Thanks to my brother we knew it was on Kapahulu Ave. just down the street from his condo.

Day 1 – Waikiki Beach.

I decided that instead of my normal MO of microplanning the entire trip we would just walk to the nearest beach and check it out, so we did. It took us until 11am to get ready and get out of the condo. You know the drill – bathing suits, sunblock, sunglasses, rash guards, towels, coverups, etc. We started off on our short 5 block walk to the beach. Along the way it was hard for me not to look in the shops but we made our way to Kuhio Beach Park on Kalakaua Ave at the end of Paoakalani Avenue near the Marriott. My brother was right it was a great kid’s beach. It had a jetty that created a protected area for the kids so I didn’t have to worry about them being taken away by waves. I assumed it would be crawling with millions of tourists that I didn’t want to have anything to do with but it wasn’t that crowded, and it was clean and fun for the kids. They played in the water all day. The great thing about Waikiki beach is you can rent chairs, surfboards, and paddle boards right there. It’s also a short walk across the street for food and snacks so it’s an easy day with the kids. We bought some $2 pool loungers and floated around with the kids. Lots of sunblock! Water was warm enough to hang out in even in January. Check out Waikiki beach reviews at Trip Advisor.

Day 2 – Hanauma Bay.

We decided to go to Hanauma Bay to snorkel because my brother told me I would love this place. I had no idea what a trek this would be and what would be involved prior to doing it. We left the condo earlier than the day before – 9am. We drove to a Snorkel Bob’s first to rent snorkel equipment for the kids, to save money on rental equipment. Then we drove to the bay – took about 30 minutes from Waikiki beach to go to Hanauma Bay along Highway 72. When we arrived at 10:30am it was closed – meaning too crowded and couldn’t enter parking lot. Lesson learned – go early. The line for purchasing admission tickets was at least 20 minutes long. We waited. I fed the kids at the snack bar — expensive. Lesson learned, bring your own food. It took at least 1 hour from parking, to waiting in line, to taking shuttle down to bottom before reaching beach. It was crowded but beautiful. There are an amazing abundance of colorful fish and occasional sea turtles. There is a lot to see even if your kids don’t swim. There are tons of shallow areas to just stick your head under water and watch the fish swim by. A mask is a necessity for anyone. The water was a little cold for me. If you are doing a lot of snorkeling and you get cold like I do you might want to have a wetsuit. Make sure you plan to be there during high tide, it’s easier to swim.

Day 3 – Back to Waikiki beach.


We decided since the day before was such a trek that we would stay near the condo again. We rented one paddle board today for the kids to play on in the protected area. My 10 year old had a great time paddling around the twins while my husband and I relaxed. We ate lunch across the street at Lulu’s Waikiki – it was very good and not too pricy. We hung out until about 3pm and headed back to the condo. The kids wanted to swim and go in the Jacuzzi and I reluctantly agreed. I couldn’t understand why you would want to swim in a pool when we basically had a huge pool in front of us but I conceded. While kids were playing I decided to look up a last minute babysitting service. I thought it might be nice to go out with my husband! I found a service called Happy Kids. They were great and a lot of great reviews from other parents. A little pricey at $20 an hour but the girl they sent over was amazing! The kids loved her and my husband and I went out for 3 hours from 7-10pm. We walked along Waikiki Beach – it was great. We stopped in at the Moana Surfrider for a Mai Tai at the beach restaurant. Very romantic with the banyan tree and the entertainment, a singer, was an added perk.

Day 4 – Back to Hanauma Bay.

We still had snorkel equipment as we rented for the week and I didn’t feel like we got the full experience because we arrived so late the last time. This time we arrived by 9am, skipped the video (only have to do it once) and went straight down to the bay (we walked). We took less stuff and brought our own food so we were prepared this time. We spent the day snorkeling and the kids had fun finding crabs under the rocks too. Overall it was a picturesque day. The weather was cooperating – warm and sunny. We decided we wanted to watch a movie that night. My brother only had a DVD player so our choices were limited. I found in Honolulu there aren’t any DVD rental places. We had a time finding anywhere to rent or even purchase DVDs. We finally found a Blockbuster that was closing so I bought a couple of DVDs to watch. We stopped off at the grocery store and cooked dinner at the condo that night. While kids watched TV, I researched what to do the next day.

Day 5 – Driving to Lanikai Beach.

I had seen many pictures of Lanikai and Kailua and this was on my must do list. Years ago I had been there working as a model for Eddie Bauer and I remember the turquoise water. Lanikai Beach is on Oahu’s Windward Coast and is often rated as one of Hawaii’s best beaches. National Geographic rated Lanikai #5 in their Top 10 Beaches of the world. They are not mistaken. This beach was incredible. Expansive white sands, sparkling turquoise water. It reminded me of some of the beaches in Sydney, Australia and the surrounds. The water is deep but we had blowup life jackets for the kids and a little raft that I pulled them around on. They loved it. It was windy that day but still beautiful. This is a great spot for couples and families alike. Read more about Lanikai and Kailua Beaches.

At the end of the day we drove back to Waikiki Beach as it’s only 30 minutes away and decided to get ready and go to dinner at a local place I had read about, Sam’s Kitchen. We like Garlic Shrimp – all of us – and this was the place to go apparently. Sam’s was definitely a shack – no real seating, and all seating they had was full. I’m sure it was good but we wanted to sit down so we decided to explore the area and find somewhere we could sit down to eat. I vowed I would come back later to try Sam’s. FYI Sam’s has since moved to a new location so I’m sure the seating has improved. We found this great asian fusion restaurant instead. I think it was mostly locals. We ordered all sorts of things and it was great. The Mai Tais were also great!

Day 6 – Surfing and Haleiwa.

I decided that we could not go to Hawaii and not surf. You know some sort of internal bucket list I have for the different places we visit. In Hawaii — snorkel and surf. So I did my research a few days ago and found a group of girls teaching families how to surf. They were in North Shore but if your going to surf, you have to go to North Shore right? right. We had to leave at 6:30am to get to North Shore for our surf lesson. We did the 2 hour private family surf lesson for $100 per person with North Shore Surf Girls. I would highly recommend them! 5 stars. My kids were 6 years old and 9 years old and they are not good swimmers. The twins did not swim well at all. They assured me that my kids did not have to know how to swim in order to surf, which shocked me but it was true. We met them at the beach for our 9am lesson. There were two women plus a photographer (their friend – added perk) One of them stuck with Axel and I and the other teacher and photographer stayed with the kids. We had a brief lesson on the sand about how to get up on the board and then we headed into the water. We all had wetsuits on (just the tops). The weather was great but it gets cold quickly in the water. We all got up. We all had a great time and got some great pix of us all surfing. For me it was probably one of the best things we did on the trip and I wouldn’t trade it for the world. They took us to a perfect spot to learn how to surf. It was not intimidating at all. I would say the only thing it was, was exhausting. I think we only made it to 1 hour and 45 minutes – we were all too tired to do the full 2 hours. It was money well spent.

After surfing, we headed to the town of Haleiwa – what an wonderful little town! I could have stayed there forever. We got some shaved ice for the kids and headed to the famed Giovanni’s Shrimp Truck on the side of the road for the garlic shrimp that I had read so much about. We all got a huge plate of shrimp – yes some of you may be disgusted but for those of you who like shrimp – it was mouthwatering! Yum!

We headed back to Waikiki just after lunch to beat traffic, etc. It’s a long drive from Haleiwa to Waikiki and we were tired.

Day 7 – Scarlett sick. Scarlett woke up the morning before we were leaving with a high fever. It was the flu. Axel took the boys down to the pool and I spent the day cleaning up the condo and packing. Around sunset Scarlett felt a bit better so we headed out to watch the sunset at Waikiki Beach. There was a large crowd gathered to watch the sunset. We headed down the beach to walk and watch. Along the way the kids saw lots of black crabs in the jetty rocks. It was really fun for them to watch the black crabs – they were everywhere.

Departure Day – Pearl Harbor and flight. It came to the last day and we had planned to all go to Pearl Harbor before the airport. Since Scarlett was now too sick to do that I decided to stay at the condo and Axel took the boys to Pearl Harbor. I’m sorry I missed that but they had a great time. It took much longer than we anticipated for him to get there, go on the tour and come back. We almost missed our flight! We made it in the nick of time. Scarlett slept for the entire flight home.

All in all it was a fun trip. We saw a lot of the island of Oahu and had a great family trip. The weather was perfect that first week of January. We bought my brother an Apple TV to thank him for letting us stay in his condo. He loves his Apple TV with access to unlimited movies in his condo and we had fantastic vacation.

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