Depends what you want for your 1 month. Just idyllic relaxation with a modicum of conveniences? Kauai is probably your answer. I expect it's the right answer almost regardless of the question.Before I was 30 I was a bit of a travel cool kid wannabe who thought Hawaii was a bit too main steam touristy. I finally had to go for a wedding in my 40’s and boy was I wrong. If I had to pick one place as the most beautiful in the world that I have seen I think I would go with Hawaii. I want to get my family there for 10 to 14 days soon. I keep getting push back but I have to make it happen.
One of the layers I would like to add to my eventual travel routine is at least 1 month a year in Hawaii. I just need to get over more to figure out where I might chose as my home base?
I first went to Hawaii with my parents in 1974 and again in 1976. Think first iteration of Hawaii 5-0. Crowded didn't mean crowded, even on Oahu. Makaha beach seemed a million miles away and utterly remote, never mind the North Shore. Now it's nearly continual housing to Makaha.
I next went in 1988 on my way to Australia and we only spent 4 days on Oahu. It had morphed very much into a big city by that point. Next time I was on Oahu was around 2008 I think and that's when my Freeway story happened and the housing extended to Makaha.
I did a day on Maui with my parents on that 1976 trip and there was nothing really in comparison to then "bustling" Oahu. It was remote, Lahaina was quaint, Kaanapali and Kapalua likely existed as cane fields and not much more. I returned to Maui in 2002, staying in Kihei and it reminded me a lot of Oahu sometime in the interim between 1976 and 1988. It was still easy to get around but lots of development had occurred. Felt nice to be there, small, personal, locals didn't fully resent you for being Haole. Now it is very busy, notably in season (which is American Thanksgiving, December 15-end of February, summer months for those from south mainland where it is too hot). On our most recent trip last Christmas it was very busy, with plenty of traffic and beaches were crowded (well, those that are easiest to access for tourists anyway; if you know where to go it's not that tough to find nice, uncrowded beaches, even at Christmas). So at this point, much as I love Maui, it is very much looking more and more like Oahu.
The Big Island is big, very big. Where we typically stay is about 30 minutes north of Kona. But it's 2 hours drive from Volcano National Park, regardless of which route you take. It is incredibly varied in terrain and temperature with tons and tons to do and see. But you need a car, absolutely. Lots of great beaches, though it's harder and harder to get to some of them because of the exclusive/expensive communities being built near them. This has long been the case but it is expanding. If you like the rain more, the Hilo side of the island might be for you - far less touristy, portions perpetually threatened by volcanic activity but very tropical, serene and peaceful. I would love to move there but it will never happen.
Kauai I've never been too (ask me in five months) but it is the least populated of the bunch and least visited. But it has a Costco, imminent sign of a pending downfall (I believe they are selling Brondo now). Very small island and winter is very wet for much of the island. Least safe island to swim at as well due to winter swells, currents, etc. though there are safe beaches of course. You can drown off any beach and many do on every island each year.
We had always thought of getting a condo in Hawaii (real estate doubled in Hawaii during the pandemic btw) but never took the plunge, largely because we didn't want a second full mortgage worth more than our current house - probably foolish in hindsight. For us the costs of spending 2-3 months there is probably prohibitive, even though we'd thoroughly enjoy it. And I'm not talking staying beachfront, this is well away in a residential setting. So now Central America is more where we're thinking due to affordability. Even Mexico is on the radar - I have a retired friend who rents a 3 bedroom condo in a gated community for ~1600 CAD/month, easily affordable for me.
We're still not sure if we'll stay in Canada or not once we retire. On this I'm talking permanently. There are a variety of reasons for that.
Don't get me started on Westjet....This is encouraging and might tip the scales for me using Westjet allot more. The lack of direct flights coming out of Covid has been pretty tough just because connections have become less reliable.
AC is no different really, but my most recent disaster was Westjet.