Never Been to Hawaii--Need Help Planning

[DisneyStarWisher]

My DH and I are planning a trip to Hawaii next September/October to celebrate our 30th anniversary and my retirement. Here is what I have planned--
Day 1: fly to Seattle (do some sightseeing in Washington)
Day 2: drive to Portland (do some sightseeing in Oregon)
Day 3: fly to Honolulu (spend time at Waikiki Beach)
Day 4: Diamond Head/start 7-night cruise
Day 5-10: Cruise
Day 11: Pearl Harbor/Check in to Aulani
Day 12-14: Aulani
Day 15: Dole Plantation/North Shore/Fly home (late flight)
Day 16: Arrive home
Since I have zero experience with planning a Hawaii trip, I could use some pointers. Anything I need to change?

 

[Firepath]

We are doing the cruise next week for our 30th and also flying in from Portland. Your trip looks great to me.

 

[DisneyStarWisher]

We are doing the cruise next week for our 30th and also flying in from Portland. Your trip looks great to me.

How neat! Have a great time!!!

 

[Daisy7425]

Sounds like so much fun! What time is your cruise check in? I thought they are usually pretty early in the morning and Diamond Head could take a while. Will you have a rental car?

 

[DisneyStarWisher]

Sounds like so much fun! What time is your cruise check in? I thought they are usually pretty early in the morning and Diamond Head could take a while. Will you have a rental car?

Well, I haven't booked the cruise yet. I figure I need to book Aulani first to know what dates I need to book for the cruise. I will have to wait until 7 months out to book. I hope that's enough time to be able to book the cruise. All I know right now is that it departs at 7 p.m. I figured we would be up extra early that day due to the time change, so Diamond Head would be good to do that day. From what I've read, it takes about two hours, and it opens at 6 a.m. I figured that would give us plenty of time to get to the ship?

 

[thedogatemyhomework]

if you do diamond head when it opens and the cruise leaves at 7 pm...you may want to add some extra things to do to pass the time.

extra time exploring waikiki, or maybe a couple of hours at one of the beaches from hawaii kai to kailua.

could also consider doing pearl harbor on that day as well as that will let you go straight to aulani. but that will depend on how much time/how many things you want to do at pearl harbor.

 

[DisneyStarWisher]

if you do diamond head when it opens and the cruise leaves at 7 pm...you may want to add some extra things to do to pass the time.

extra time exploring waikiki, or maybe a couple of hours at one of the beaches from hawaii kai to kailua.

could also consider doing pearl harbor on that day as well as that will let you go straight to aulani. but that will depend on how much time/how many things you want to do at pearl harbor.

Good to know! I would love to do Pearl Harbor that day, just so we can get to Aulani faster. I definitely need to research Pearl Harbor to see what all we would like to do there. If we stay around Waikiki the night before the cruise and then do Diamond Head and Pearl Harbor the day the cruise departs, would you say I would need a rental car, or is everything close enough we could just Uber?

 

[DVCjj]

Can't offer suggestions as we just did a quick Aulani and Maui (and late Jan/early Feb didn't cooperate for us) but wanted to tell you that your itinerary sounds like a dream to me. I'm sure everything will be a memory you'll treasure.

 

[thedogatemyhomework]

the uber bill may cost you a bit...but it does offer the advantage of not having to drive (diamond head isn't particularly difficult to hike...but it can be tiring). renting a car means you don't have to wait for the driver, or worry about surge pricing, etc. but also means you have to deal with traffic (if there is any), as well as finding parking.

its mostly a pick your preference kinda deal.

diamond head/waikiki isn't too far from pearl harbor...maybe an hour at most drive around mid morning (probably closer to 20-30 minutes), but its much much closer than aulani to pearl harbor. depending on what you want to do at pearl harbor and how much time you want to spend at diamond head...you may be able to uber/drive to/from your hotel in waikiki to do diamond head and book a tour for transport to pearl harbor (just gotta make sure you check what time the tour ends, etc.)