OK, I’m etiquette-challenged, please help!
I’m meeting with my former boss tomorrow. She is
very nice and we always had a great relationship but strictly work-related. Since then, her husband landed a very high position and they moved out of town. We’re visiting the city where they live (in a fancy downtown condo) and I suggested a meeting. She enthusiastically accepted and we (DS and me) are coming to their place and then she wanted to show me the city (so no meal at their place). Is it appropriate to bring flowers, or anything else? I want to show warm feeling towards her but not come across as too formal or too casual. I guess she already knows I’m socially awkward anyway 
Of course, such a thoughtful gesture is always appropriate! You could think of it as a small housewarming gift. Flowers, a potted plant, bottle of wine to enjoy in her new condo, whatever else you know she would enjoy. Express your pleasure at being able to meet up, see the city with her and wish her the best in her new situation.
Agree. And if you have any concerns, it doesn’t need to be a large bouquet. This is a tradition in some European countries, a lovely one.
But I think the next question is, if you do stop for coffee or lunch, who offers to pay? I would be prepared to, as a thanks for her effort. Just don’t worry too much, enjoy.
I think flowers are always a nice gift. Nothing over the top. Just a nice bouquet.
I think it is lovely to bring flowers, not too personal and always appreciated, unless you know she has allergy. If you know she likes certain chocolate, cookies, coffee, etc then it may be good too.
I remember when someone brought me a dozen NYC bagels when I lived abroad, they were very much appreciated.
I am not a flower person. I actually forgot to order a bouquet for my own wedding. I think a nice picture frame is a good gift. No worries about allergies, diets or food preferences and can easily be re-gifted. I am currently looking for a nice one to bring to my D’s bf’s parents when I visit them this summer.
I am in the minority - love to get and give flowers but I would only bring them if someone was in some way my host - bringing her flowers when you are just meeting up at her apt seems awkward. I would, however, try to arrange to take them out to lunch or dinner as part of your tour. Sounds like fun and I am sure it’ll be fine either way.
Another vote for flowers. IF you are going up to the condo and not just meeting in the lobby.
Or, if there is anything from the area you live in (where you two worked together before she moved) that is special, you could bring that. Something from a local shop, vineyard, bakery, etc. like @oldfort mentioned.
Keep it simple! Have a great time! I also agree with @lookingforward to anticipate “who pays”.
If there is something from your home area that you know she particularly loves and is unlikely to get where she now lives, you could bring that without making undue fuss. (A box of Frango mints for a former Chicagoan, for example.) Otherwise, if you are just meeting up at her apt it seems a bit much to me to bring flowers: tends to put too much weight on the occasion. She is not inviting you for a meal.
I would definitely suggest refreshments while out, and pay for them.
Let’s not overthink this. I think flowers are a lovely idea.
Flowers are nice, or a small box of fancy chocolates.
CaMom13 " I would only bring them if someone was in some way my host…"
OP said, “…coming to their place and then she wanted to show me the city…”
That’s hosting, to me.
I’m in the camp of thinking a kind gesture of a small hostess/housewarming gift is never out of place just like a thank you note is never in bad form.
Another who likes the flower idea if you are going into the condo.
No to the picture frame.
No to a picture frame. She just downsized.
No to flowers. I hate to have to locate a vase which is usually in an out of the way place since I like the simple life on my counters.
Yes, Yes to a small food item from her former city and your current city.
If you like tea service, which I guess you don’t that would be fun.
Pay for her ticket on a a boat or walking tour.
Treat her to dinner or a light lunch.
If you get home and think her hospitality overdid your efforts then you can send a fruit basket.
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Don't overthink it. Most people do not offer to do things they do want to do.<<<
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Unfortunately we are not in our hometown now. I had this idea of bringing something local, but couldn’t really think of anything besides chocolates, and these wouldn’t have survived the long trip. I’m leaning towards small unpretentious flower bouquet.
I’m perfectly OK with paying for her meal, coffee or whatever, but wouldn’t this sound a bit odd to offer considering that we both know they have tons more money than we do (not that it would put a strain on my budget either)?
I think if you’re just meeting at her condo and then leaving that bringing a gift is overkill. I would do my best to pay the bill when you go out to eat/coffee. She may insist though. I always told my kids to offer twice and if the other person truly insisted, to let it go (unless splitting ends up being an option). If that’s the case, I would follow up with a written thank you note. If I was able to pay for lunch/coffee, I still might follow up with a thank you email – more along ‘so great to see you’ over a true thank you note.
An offer to pay shouldn’t be based on who has a larger bank account, IMO.
No. @doschicos is correct. Plus, you are the one doing the inviting, so you should pick up the tab. I agree with @collage1 that the other party may offer/insist to pay, and then you can agree to split the check. But skimom always taught us that the one who invites should pay (or make the offer at the very least).