Tentative itinerary for upcoming trip in May

[Disney_Fan_01]

we have a trip planned for the 4 of us including a 3 year old and a 5 year old for our 10 year anniversary in May. I am planning to set some kind of a schedule and need some assistance. We will be staying for a total of 9 nights split into 3 nights at waikikki followed by 6 nights at Aulani. We will be renting a car for the entire trip. This is our first visit to Hawaii so we would like to explore the island along with some relaxation. Our trip is around the busy Memorial Day weekend (May 22nd through May 31st), so I am trying to factor that as well as I set my itinerary. We are coming from Dallas, TX so there is a 5 hour time difference, which will take some time to get adjusted. I will appreciate it if any of you could provide feedback on my plan. Am I missing something, trying to do too much with little kids or any other similar experiences you may have had.

Day 1(May 22 - Mon): Arrive at HNL around 12:30. Head straight to hotel near waikikki beach after picking up rental car. Relax after a long flight, maybe explore the waikikki beach area in the evening based on how everyone is feeling. Early bedtime
Day 2(May 23 - Tues): Plan to go to Diamond Head early morning maybe around 8am. Will my 3 year old be able to do the hike. My wife is planning to take a carrier to carry him at the back should he get tired. I feel my daughter who is 5 should be fine. Suggestions from people who have done this with little kids. After Diamond head, we are planning to go to Kailua beach. May stop by for brunch at Cinammon restaurant on the way there. Plan to relax at the beach for a couple of hours and then head back to the hotel for naps. Plan to do something around the waikikki area for the evening. Any suggestions? Nice family friendly dinner places that you would recommend.
Day 3(May 24 - Wed): Plan to go to Hanauma Bay early morning. Get there before 8:00. Plan to do snorkeling here. Will there be opportunities for little kids to snorkel in the shallow area or are all the cool fish and other stuff at the deeper end. Thinking if I should rent snorkeling gear for my 5 year old as well. We may be done with the beach area by 11 and will try to head out for some lunch spot. Are there good places that you would recommend for lunch around the Hanauma Bay Area? I know that there are no lunch options at Hanauma Bay. After lunch, we plan to use kids strollers and go to Makapuu lighthouse hike. We may head back to the hotel after that for naps. In the evening, explore waikikki shopping area.
Day 4( May 25 - Thurs): check out at the hotel and head to Pearl Harbor. Plan to spend a couple of hours there. Head to aulani after lunch. Check in to Aulani in the afternoon and relax in the room. Explore the resort in the evening.
Day 5(May 26 - Fri): resort day at Aulani. Breakfast reservation at 7:30 at Makahiki. Other than that open time.
Day 6(May 27 - Sat): resort day at Aulani. I believe there is a new Lua scheduled for Saturday evening. Is it worthwhile to do with a 3 year old and a 5 year old?
Day 7(May 28 - Sun): resort day. Dinner reservations at Ama Ama other than that open time.
Day 8(May 29 - Mon): resort day. This is also Memorial Day and there is some lantern floating festival at Ala Moana beach. Should we plan to venture for this or will it be too crowded?
Day 9 (May 30 - Tues): plan to go to North Shore. Leave early morning and head to Waimea Bay. Hike around the waimea valley which opens at 9. After the hike, spend some time at the waimea bay beach. I plan to jump off the cliff(looks super cool). Head over to sunset beach for lunch at Ted's bakery. After lunch, we plan to head back and go to laniake a beach for a quick stroll to spot turtles. Head back to Aulani. Maybe stop by Dole plantation if kids are not too tired. In the evening, we have dinner reservation at Makahiki restaurant.
Day 10 (May 31 - Wed): breakfast reservation at Ama Ama. Open time at the resort. Out flight back is at 9:20PM. What time should we start heading back to the airport?

 

[buffettgirl]

Just a couple of suggestions / comments:
-Diamond head with your 3 year old: really depends on how active/agile a child he or she is. Same for the 5 year old. It's a combination of flat dirt or paved areas, stairs (lots of them) and rocky bumpy paths. Really depends on your kids. Mine wouldn't have been able to do it at 3, or 5. They just weren't very coordinated kids. haahha.
- Family friendly in Waikiki , definitely try take out at Steak Shack. You either sit on the beach or at a few tables that belong to the little shopping area. It's just before you get to Fort Derussey. You can eat and watch the sunset if you time it right. Otherwise Cheeseburgers is always pretty good (there's one on beachwalk which might be closer to where you are staying)
- Hanauma bay - all the fish are close to shore, all pretty shallow. Lunch options would be Kona Brewery in Hawaii Kai, (good ice cream over there too at Bubbies). You might be pretty warn out to also hike after that.
- Your pearl harbor day - watch the traffic as you are heading to Aulani. It's the start of a long weekend and traffic can start to pick up as early as 3.
- the lantern thing at Ala Moana gets very very crowded and parking is crazy bad.


Otherwise, have fun!

 

[lizard1]

-One thing with your plans for Pearl Harbor on the way to Aulani- make sure that if you are going to have all of your belongings in the car that they are able to be hidden.
-I have heard that holiday weekends are very crowded at Aulani. I would maybe consider moving your Tuesday (30th) plans to either Saturday or Sunday as maybe there will be fewer people around the resort on the Tuesday making it more enjoyable.
-Make sure that when reservations are available that you get them signed up for Auntie's activities if you are interested. They do fill up and you may not be able to switch their spots or even get into an activity once you are there.

 

[buffettgirl]

Also, to take on to the above: yes, make sure all your belongings are hidden, however, even then rental cars are easy to spot and they'll go right for the trunk.
And, most hawaii schools will be out on Memerial day weekend, so it will be extra busy everywhere, but certainly at aulani as people get away for the summer.

 

[Looptyloo]

My family restaurant suggestion for Waikiki is the Barefoot Beach Cafe, down close the the Aquarium. It's all outdoor seating right by the water, you would have the option to play with kids in the grassy areas or in the water a bit while you wait for food and such. Good food, with some good kid friendly options. Good prices and large servings.

On your way back from Hanauma Bay/Makapuu, check out Uncle Clay's House of Pure Aloha for some great shave ice. SO good (and a bit less syrupy sweet tasting than many other places).

 

[Lizzards]

Depending on your desires and what suites your family, Pearl Harbor could be way more than a couple of hours. My kids loved the Bowfin submarine tour. They could touch everything which they loved!

My children also loved the Dole pineapple plantation.

My children also just loved staying at Aulani. There were so many fun things to do there as a family. They never wanted to leave!!! But when we "forced" them to leave the resort they enjoyed exploring Hawaii.

Have a fun time!

 

[Disney_Fan_01]

Just a couple of suggestions / comments:
-Diamond head with your 3 year old: really depends on how active/agile a child he or she is. Same for the 5 year old. It's a combination of flat dirt or paved areas, stairs (lots of them) and rocky bumpy paths. Really depends on your kids. Mine wouldn't have been able to do it at 3, or 5. They just weren't very coordinated kids. haahha.
- Family friendly in Waikiki , definitely try take out at Steak Shack. You either sit on the beach or at a few tables that belong to the little shopping area. It's just before you get to Fort Derussey. You can eat and watch the sunset if you time it right. Otherwise Cheeseburgers is always pretty good (there's one on beachwalk which might be closer to where you are staying)
- Hanauma bay - all the fish are close to shore, all pretty shallow. Lunch options would be Kona Brewery in Hawaii Kai, (good ice cream over there too at Bubbies). You might be pretty warn out to also hike after that.
- Your pearl harbor day - watch the traffic as you are heading to Aulani. It's the start of a long weekend and traffic can start to pick up as early as 3.
- the lantern thing at Ala Moana gets very very crowded and parking is crazy bad.


Otherwise, have fun!

Diamond Head - Thanks for your suggestions. I was having doubts about the Diamond Head myself. Most probably, we may skip that this time. How about the Pillbox trail near Lanikai beach. Should we try to do that instead. Is that slightly easier. Does anyone know?
Pearl Harbor - great tips on avoiding theft. We may check out and leave our bags at the hotel to pick up after our visit to Pearl Harbor. We will plan to leave waikikki area before 2 heading towards Aulani in order to avoid early long weekend rush hour traffic.

 

[Disney_Fan_01]

My family restaurant suggestion for Waikiki is the Barefoot Beach Cafe, down close the the Aquarium. It's all outdoor seating right by the water, you would have the option to play with kids in the grassy areas or in the water a bit while you wait for food and such. Good food, with some good kid friendly options. Good prices and large servings.

On your way back from Hanauma Bay/Makapuu, check out Uncle Clay's House of Pure Aloha for some great shave ice. SO good (and a bit less syrupy sweet tasting than many other places).

Appreciate your suggestions!

 

[Disney_Fan_01]

Depending on your desires and what suites your family, Pearl Harbor could be way more than a couple of hours. My kids loved the Bowfin submarine tour. They could touch everything which they loved!

My children also loved the Dole pineapple plantation.

My children also just loved staying at Aulani. There were so many fun things to do there as a family. They never wanted to leave!!! But when we "forced" them to leave the resort they enjoyed exploring Hawaii.

Have a fun time!

Thanks for your feedback. We will try to do the Dole Plantation tour in a seperate day instead of fitting it with our North Shore excursion day. Maybe too much for the kids to handle. We will have to weigh the options of staying in the resort for the morning or going to dole plantation. I know what the kids would prefer to do

 

[Disney_Fan_01]

-One thing with your plans for Pearl Harbor on the way to Aulani- make sure that if you are going to have all of your belongings in the car that they are able to be hidden.
-I have heard that holiday weekends are very crowded at Aulani. I would maybe consider moving your Tuesday (30th) plans to either Saturday or Sunday as maybe there will be fewer people around the resort on the Tuesday making it more enjoyable.
-Make sure that when reservations are available that you get them signed up for Auntie's activities if you are interested. They do fill up and you may not be able to switch their spots or even get into an activity once you are there.

Great suggestion on Aulani being busy during the long weekend. We may move our plan for the 30th up by a day or two. Depending on the crowds, we may plan to venture out maybe in the afternoon if it gets too crowded. Will keep options flexible and play it by ear

 

[CaliAdventurer]

1) remember, it will be HOT that time of year and the sun will be punishing. Rash guards for all, all the time. Plan accordingly. Hikes, keep them light.
2) Go to Leonards on your diamond head day for malasadas. touristy but yummy and the kids will love it
3) Tommy Bahama cafe will be a happy medium for dinner that's both beautiful, yummy, and has live music but still ok with small children.
4) When you go to the Northshore, Waimea beach can be very crowded- its a locals beach too and the break can be right into the shore in spring. We go to pipeline instead for its serenity. Def go to Haleiwa and get snowcones and the little shops are so quaint. A great burger place there also. The Dole Plantation is easy to do on the way to or from (its off the hwy).
5) Cinnamons will be packed but is a good time and my favorite bfast so far on the island off the resort. Homey. went to some other renowned places and was not impressed by the flavor.