If I may share my thoughts on a Rolex...
Rolexes are in very high demand, and you will need to order one and wait. It's just the way it is. It's worse than VCA. Rolex purchases are not like 15 years ago when your cousin purchased a Daytona. As FYI, over the past 10 years,
I have purchased half a dozen Rolexes, and not one was an in-stock purchase. I have had to order all of them.
For me, I like to buy my Rolexes at my local AD. You can build a relationship, and you can be sure to get what you want. If you really want a Daytona, I would go to your local AD. There is a super long list for the stainless Daytona, and that is even if the boutique will put you on the wait list. I am sure you've heard stories where people are told they cannot even get on the wait list. Since you already have Rolexes, I am sure you can get on the wait list. If you want a two-tone Daytona, that is a bit easier, but you still have to wait. As FYI, I had to wait a little over two years for my stainless Daytona. Even if you do not want a Daytona but want a GMT (Pepsi / Batman), you will need to order and wait. My point is, it's almost zero odds you can walk into any store and "try on" a Daytona or a GMT which are high demand watches.
If you want Rolex or VCA, I personally would not compromise and go to Tiffany or Cartier just to get something locally on your vacation. You'll still end up wanting that Rolex or VCA piece. Maybe decide what you want and just order it. That would be the best way to secure it. Plus, you won't be wasting your time chasing these items which really are commodity goods that do not need to be purchased in Hawaii.
You can spend the time enjoying your wonderful vacation! There are so many sights to see in Hawaii.
I am sure you will have a great time!