The one island (other than Ni'ihau) I have never set foot on despite having lived in the state for three years. My military reunion will take place on Oahu in May 2020 and this time around I am determined to get to Kauai! Will have about five days and nights and will have a rental car. I had thought about the Hyatt but am having second thoughts given some reviews. Do not particularly want to return to the Big Island but could do that instead. Obviously prefer to avoid rain and would appreciate food opportunities besides something at the hotel.

I appreciate recs with a little rationale and thank you.

Hi Dukey, We spend a month each year in the Poipu area. The beaches there are swimmable, and there is a great variety of eateries in the area.

I have trip reports here from the last two years, with a fair amount of detail on restaurants. Ask if you have questions.

Kathie & Cheryl's notes from Kauai 2017

A month on Kauai, 2019

Quick report on new Japanese Restaurant in Hanapepe, Kauai

Kathie, Thanks very much I will look at the links. And I did so. Again, thanks. Still considering at this point.

I live on Kauai's North Shore. This May, we had amazing perfect weather and calm seas. Hanalei Bay, Ke'e Beach, Tunnels, Anini Beach ... all swimmable and GORGEOUS!
In May, I would definitely stay on the North Shore. Most lodgings are condos, but for hotels/resorts check out the Hanalei Bay Resort; the Westin; the St. Regis.

THANK YOU for those specific property recs. It is helpful to have them and no I am NOT using you as my personal Google and would not think of doing so, either.

What type of lodging requirements? 2* 4*? Kitchen? Cottage?Condo. for how many or are you flying solo.
As a repeat visitor I'd be happy to share my thoughts and recommendation. Ask away.

Since this would be a probably five-night max stay (coming over from a several-night stay on Oahu just prior) would much prefer a hotel situation as opposed to a condo. However, if a condo is more likely to be available than a regular hotel then not adverse. Will definitely have a rental car regardless of accommodation type. As I mentioned up thread, we keep getting diverted from Kauai, from Iniki onward and since we are flying over specifically for the reunion on Oahu and only for that reason, and spending that kind of money just to get there, I remain determined somehow. Besides, I'm going to be unable to travel or dead someday so thanks for the kind help and thoughts.

I might consider North Shore in a rental. Princeville has many options of all prices. It's a planned community and some find it beautiful, while others find it sterile. But it puts you in a great location for short exploration.
with maybe a daytrip west.
I've used Kauaivacationrentals.com and Napaliprops.com. Parish Rentals to get you started if you care to look.Or Charo's old place, The Hanalei Colony Resort. https://www.hcr.com
For me it would be important to have a washer and dryer ofter Oahu.
https://www.kauaivacationrentals.com/#q=*%3A*. https://www.napaliprop.comwe've stayed at plantation cottage which is a wonderful little cottage on a large lot https://www.napaliprop.com/Plantation-Cottage-2.html
I'll have more thoughts.