Losing weight while on vacation

Hi there. I have about 5-8 pounds that I have been wanting to lose FOREVER (as in, years). I have been food planning for the last 6 months, and on some level have some shame that I have not been successful yet. In any case, we are now in Hawaii for the next two months (we is my family and me), and I am wondering what the best approach is to meal planning when we don’t have plans set for a day. For example, if we decide to spend the day driving to a part of the island that we haven’t been to, and planning to eat at a restaurant for example. I try to look up menus ahead of time, but we don’t always know exactly where we will be eating. I am typically very good at picking healthy choices, and I tend to do well allowing urges. However – my question is specifically pertaining to meal planning as I am having a hard time planning when I don’t always know what the options will be ahead of time (hence I leave some wiggle room to decide in the moment what I will have, like once we get to a restaurant) – but this doesn’t seem like it goes along with what would be ok meal planning. Typically, I try to pack my food ahead of time when I can, but logistically this isn’t always the best option for various reasons.
As a separate issue, I am a weight loss coach and have some degree of (1) shame as I mentioned above that I haven’t been able to get to my ideal weight and have answers to my own questions and (2) confusion on how to coach people as far as what to do when they go on vacation and the circumstances are different. Is packing a meal always going to be the go-to answer?
Thanks in advance!