Planning a Hawaiian Family Vacation? Check out this Itinerary!

This post may contain affiliate links. See disclosure page for more information.

Planning a trip can be stressful and sometimes you just don’t know where to start because it can seem so overwhelming.  By sharing our itinerary I hope to be able to give you travelers at least a little something to start with.  Here is some information to get you started in planning your amazing Hawaiian Vacation.

Day 1 Travel day!

Depending on your home city, you will be dealing with at least some sort of jet lag.  It may not be as evident the first day but it will be sure to set in even a little at some point. The island of Oahu is in the Hawaii-Aleutian Time Zone which is 3 hours behind the West Coast and 5 hours time difference from the Midwest.  Plan to not over do it this day.

We arrived at 4:00pm and then drove to the North East corner of the island to a town called Hauula.  This part of the island was chosen because we wanted to be near the Polynesian Cultural Center, which we would be visiting the next day. We wanted to be close so we did not have to drive the narrow windy roads at night back to Waikki after the evening show at the Cultural Center. This was also a great location as a base for a few days to visit the North Shore. It took about 1 1/2 hours to drive to our rental from the airport.

We had a wonderful rental through TripAdvisor called the “Sandy Beach Cottage with Breathtaking Beach Views”.  Listing #FKN2129337.  This was a one room ground floor unit with a screened in porch.  It was very small, with the queen size bed nearly in the kitchen.  To sleep 5, two people had to share an opened up futon and one slept on a couch.  It may sound inconvenient, but actually it was one of the greatest rentals we have been at. Having our own space and just steps from the Hawaiian beach made the sleeping accommodations worth it! It was like sleeping in a cabin right where the land meets the water.  There are not many affordable places in Hawaii that can offer this!  There are other options in this area like condos and hotel rooms but this was perfect and cozy for our family.  I think it helped that we camp as a family so we are used to sleeping in small places together. That night for dinner we had not planned ahead with groceries but had read on the reviews of our rental that there was a shrimp food truck that was a few blocks away.  Delicious!

Day 2  Polynesian Cultural Center

This was a great day to try sleep in, to regulate the time zone sleepiness! But how much can you sleep in when you are all in the same room? That was okay because the rental is right on the water so even though we woke early, it was amazing to relax and watch the sunrise over the ocean.  The rental was right on the beach so the kids could start off early, playing in the sand.  Even teenagers still like to make sand castles!  The Polynesian Cultural Center opens at 11:30 am and it is best to get there early because there is so much to see and do there, you will not have time to do it all, even being there all hours they are open.  Check out my review post HERE.  As I mentioned, the first full day may still be lingering with jet lag sleepiness, especially the kids.  Two of ours did end up falling asleep at the evening show, but we only had a few minutes drive back to the rental.

Day 3 Kualo Ranch and North Shore

By the third day we were all energized and ready to go!  We wanted to do something active so checked out Kualo Ranch and did an ATV ride.  This was about 15 minutes from the rental and we did have to do a little back tracking as we were driving east. (Towards the way we came from the airport) If you plan ahead there are also horse rides and water activities, but they were all sold out when we called the day before. We also checked out Ahupua’a ‘o Kahana State Park and did a little hiking on one of the two hiking trails there.

We then went back to the condo and enjoyed the beach.  This rental was on an area of the beach that the waves break far out so was safe for us to snorkel.  Again this place amazed me in location- sandy beach and able to snorkel right outside the door.  It seems to me there are not many places you can rent like this in Hawaii unless you want to pay huge amounts.

Early in the afternoon we took another drive, but this time west towards the “North Shore.” We used the GyPSy Guide touring app (which I talk more about in THIS post- available in App Store) and it was wonderful and gave us recommendations where to stop.   We had planned to spend an hour and a half at the Waimea Falls.  If you pay the fee to enter, you can also swim at the falls so bring your suit if you think you might do that.  The walk past all the plants and flowers is mostly uphill until you reach the falls.  You can pay a fee to take a tram, but it was a nice walk.

Then we continued our drive and stopped at a few different beaches as directed by our touring app.  We stopped at a fruit stand, a shrimp truck, and at Laniakea Beach beach where sea turtles come rest on the shore.

We then continued on to the famous Matsumoto’s Shave Ice in Haleiwa.  It is amazing how much more developed it has become in 10 years since I had been there.  The menu is enormous and you have the option of adding condensed milk, Azuki Balls (sweetened bean paste- they let us try some first) or  Mocki balls (sweet rice cake).  You can also add ice cream on the bottom.  We discovered the best shave ice places in Hawaii were the ones with homemade syrups!

We drove on to Waialua which is where the road turns south an goes inland towards Pearl City. If we would have continued on this road, we would have run into the Dole Plantation and looped back towards Honolulu. We also did not plan to drive the entire loop back to our rental so we turned around and did have to backtrack some of the way we came.  What made it great is that even though we saw the same scenery, we had different information being told to us from the Gypsy Guide App. We ended up driving past the Polynesian Cultural Center again so chose to eat at the restaurant located in their market place and check out the shops since we did not have time to do that the previous day.  

It is a fun place to people watch and shop.  This would be our last night at the rental on the northeastern part of the island.

Day 4 Waikiki, Pearl Harbor

This is the day we would be moving to a different type of accommodation. We moved to Waikiki so that we could experience another part of Hawaiian life.  It is much busier with tall buildings along the beach, where as the cottage was a more lazy and laid back type of place. We wanted to make the most of our time so planned our route carefully.  We were moving on a Sunday so it was perfect for visiting the Swap Meet at the Aloha Stadium on our way to Pearl Harbor.  The Swap Meet is flea market that is open on Wednesdays, Saturdays and Sundays. It is the cheapest place to buy all souvenirs.  If you hold out and try to buy the same thing on Waikiki beach you WILL pay more. We found this out buying a beach towel!  This market is just a few minutes away from Pearl Harbor so it makes it convenient to visit them consecutively.

The Pearl Harbor Historic Site itself is free to visit.  There are tickets to purchase for the boat that takes you to the USS Arizona Memorial where can see the oil is still leaking from the ship and the memorial to all those who lost their lives. Because I had not booked tickets for the USS Arizona exactly 2 months ahead of time, there were no slots open for any days we would be there.  I did find out though, that you can call at 7 am the day before you arrive and tickets become available. The third option is to get there by 7am the day you want to visit and hope that there are tickets available.  You buy them from Recreation.gov.   If you find yourself in the same situation and cannot get tickets ahead of time, don’t sweat it. There is still a good chance to get them. Make your plans for which day you will visit and call at 7 am the day before.   When I ordered tickets on the phone, we chose the ones with the audio tour.  This greatly helped to keep the kids interested and actively participating. They listened and looked for the numbers along the way that correlated with what was being said .  I think we would have not had the same experience without the audio tour.

Then it was time to head to our hotel.  We chose the Hyatt Place because it is walking distance to Waikiki Beach  and so that we could use Hyatt Rewards Points to save money. It also offers a free breakfast.  With three kids and two of them being teenage boys, this saved us a lot of money.  There was a Hyatt down the road that was much fancier but just not worth it to us because there was no breakfast.  Also, the Hyatt Place is one of the only hotels that we could find that actually allows 5 people to be in it, without having to rent a suite or a 1 bedroom condo like at other hotels.  If you book early enough and can even get an ocean view room. In the evening we could walk the block and a half to the beach to swim, watch the surfers and eat dinner.

Day 5 Huanau Bay, Many Beaches

This day we toured another whole part of the island, the Beaches and Volcano tour on the Gypsy Guide App.  We started early (8 am) so we could arrive at the Huanua Bay before the parking lot was full.  We stayed and snorkeled for a few hours.

We then drove a loop heading away from Waikki beach and followed the recommendations of the touring app.  The App told us of other great beaches to stop at so we spent 30 to 60 minutes at a few others, checking them out,  They were all so very different!

We then reached our favorite, Kailua Beach where we spent more time body surfing.  This beach was a little off the route but was recommend by the Gypsy Touring App so we decided to go there.  We were so happy we did!  The app even helped us find the best parking and this beach was perfect because of the flat sandy bottom and the amazing waves for body surfing.  My kids were so happy we found it!  In fact no other beaches for the rest of our trip lived up to this one.

On the way back we took a short detour to the Nuuanu Pali Lookout,  which is another place we would have missed if it were not for our amazing touring app.

Final Thoughts

This was a great itinerary because we got to experience two parts of Oahu.  The laid back north shore and the hustle and bustle of Waikiki.  It was a vacation within a vacation. We visited a majority of the island in just 5 days and were able to discover our favorite places so that if we return again we will know what they are.  We also minimized backtracking, and got to drive on all 3 roads crossing Oahu to get from Honolulu to the East side of Oahu.  (Interstate H3, Likelike Highway, and Pali Highway.)  All three of them have different tunnels and are unique in their own way.

Ways to Save Money

Use your own touring  guide.  By using the Gypsy Guide touring app it only cost us a few dollars and we could stop when we wanted to instead of on a bus with a large group of people.  We also were able to learn a lot along the way.

Car rental- check prices at Costco (if you have membership) and AAA.  Keep checking and rebook as prices drop.

Choose a hotel with a free breakfast and an opportunity to use points.

Stay in a condo where you can cook some of your meals.  Check VRBO, TRIP ADVISOR, and Booking.com

I hope this gives you some ideas for when planning your own trip to Hawaii, or at least gives you ideas to think about.  Having a plan to start with and then modifying it to fit your own likes and family is always helpful versus starting from scratch.  If Hawaii is still on your bucket list, Pin this for later! Please comment below with your thoughts and suggestions.

Happy Travels!

Jennifer