To not go on this holiday

I would still go but I'd message her like you're going to and tell her you'll not e subbing her and if that's an issue she can stay at home.

Having read your updates, my advice is...
Cancel the holiday, ditch the bitch, enjoy life.

This. Absolutely no way would I be cancelling my holiday, but I wouldn’t be wringing my hands over restaurant bills and money because I wouldn’t be spending any time with her at all. I’d class the room as somewhere to dump your stuff (I agree a suitcase with a lock is a good idea), and somewhere to sleep, and that’s it. I’d send a message along the lines of ‘if you’re still planning on coming on the holiday, then please realise that despite sharing a room, we will otherwise be holidaying separately. None of my belongings are to be borrowed or taken, and I plan to spend every day alone, doing my own thing’. I probably wouldn’t even mention why, she knows why and it just gives her an opportunity to argue that she PROMISES to pay her way this time!

I wouldn't go I don't think. Just cant see how I"d enjoy a break constantly on edge that she'd 'forget' her purse when going out for dinner or whatever. I'd take the money that I would have spent (on myself, not on her!), and do something nice for a few days somewhere different, even if it's a bit low key and not what I originally wanted. Are you supposed to be sharing a hotel room? If so I definitely wouldn't go!

I used to have a friend a bit like this years ago, but at the time I earned a lot of money, and she was a good friend in other ways so I just sucked it up, even though I knew from her ex she had £50k tucked away in the bank! Now I wouldn't and couldn't do that.

It's almost like an illness with some people to find ways not to spend their own money

This break doesn’t sound like it will be beneficial to you, sadly. If you constantly have to enforce boundaries, lock things in your case etc, will you even have a chance to relax?

And a pp flagged that she may be able to charge items to the room, which you might be liable for as the main booker. I’d see if possible to cancel.

I wouldn't even think of going. If you had separate rooms and could completely avoid her it would be different but sharing a room with someone who is so awful isn't my idea of a holiday.

I think the reason she wants to go with you is because it'll work out cheaper than going with someone else. Let her go on her own and write it off.

I wouldn't have anything more to do with her and tell her exactly why

I’d go but not spend any time with her. So I wouldn’t be eating meals with her, for example. Also don’t take any new or nice cloths and keep things you don’t want borrowed in your locked suitcase.

I would definitely still go, but turn it into a sort of CF game. Obviously you need to update your thread every step of the way for advice and support (and our entertainment)

I agree with locking away your stuff so she can’t use it. Be really firm with her. And report back! ☀️

She then rather reluctantly went and bought some but complained how expensive sun lotion was !

I mean, everything is expensive when you're used to it being free!

If she’s a CF, you can bet she’ll still be going and trying it on again. I would give it a miss and avoid all the stress.

I came on here to give ideas of how to manage the trip but when I came to start writing I just thought - no, I couldn't do it if I were you, I'd kill her. Might be worth thinking about why you agreed to book a holiday with someone who had repeatedly stolen from you on a previous holiday. Are you perhaps a bit of a people pleaser? I note you also say you moved your toiletries into a wash bag, not that you confronted her. If you do decide to go I think you need to be willing to have confrontations even where it is embarrassing eg in front of a waiter - here's my €30 waiter for my meal. Oh CF says she has no money to pay? Sorry I have no spare cash - CF looks like you are doing the washing up/maybe call your mum and get her to do a transfer. Smile sweetly. Then walk out of the restaurant.

But this kind of person will always find a workaround to screw you. So I just wouldn't go.

I will add to the ‘ don’t go’ side. I made the mistake of going on a holiday with a friend (and sharing a room) despite dreading it, despite her telling me she wished she’d not booked, and informing me of all her routines she had to stick to (which were so different to mine). This was to Disneyland Paris and it was an utter disaster! For many many reasons - we both ended up losing our temper, I spent days in my own, came back to a darkened room when she was asleep so had to tiptoe around - I ended up booking a Eurostar a day early and leaving - it was so so bad and she upset me so much with her behaviour. (I had warned hee that I would go home and she challenged me to - so I did)

we never spoke again as friends - but had to work together and it was dreadful. I would have rather lost the money and had a civil relationship with her

It sounds like you don’t want to continue with the friendship, so I would see if you can get any sort of refund if you cancel. Give her half of what you get back and be done with it. If you do go, be polite, lock all your stuff in your suitcase (with a good quality lock) then just do your own thing. If you think she will still try to get you to pay everything just leave her to do her own thing.

Write it off .stuck on holiday with a Freeloader is going to be hell on earth for you.
She ain't no friend just a user.

There’s no way I’d even be considering going on this holiday. Leave her to it herself, she’ll shit herself when she realises you haven’t turned up and she hasn’t bothered bringing everything she needs and also has to pay full whack for herself.
The money is spent and long gone and by your own admission was cheap at the time - I’d write it off and move on.
Life is way too short to be dreading a holiday and I imagine she won’t have changed her ways.
Cheap people are not my ideal company.

Honestly if that's what she's like, I wouldn't bother going. I'd tell her before hand so she can decide whether to go or not. In no uncertain terms tell her why you're not going too. She doesn't seem to have to deal with the repercussions of her behaviour.

If you have time off work, still use the time off visiting places you've always wanted to see.

Me too! It won't be a relaxing break with you constantly having to watch out for her freeloading whilst guarding your toiletries

Everyone has made some great suggestions but I'm sorry- I just wouldn't go.
Lift is too bloody short for all this hassle and if you're dreading it ,it's completely pointless.
Have a good week at home doing whatever you feel like and avoid the stress and hassle of it all.

What’s the arrangement with paying for things in the hotel? If you can just charge things to the room I think there’s a massive risk she’ll run up a huge bill and you’ll be left paying it. You could lose even more than the cost of the holiday. Unless you’re very sure that can’t happen, I think it might be safest not to go.

I would forward her that app, with a cheery message saying ‘Oh look, this will make it so easy to split our expenses evenly. Don’t forget toiletries this time- money’s really tight at the moment so I might need to borrow a few things’. With any luck, she’ll duck out of the holiday

I also suggest you tell her you are going to use an app like Tricount, which tallies up what each of you have spent. It’s great on holidays with friends.

So when you do your message at the weekend remind her this means bringing or buying her own toiletries etc.

It'll be awful.dont go. She's got form for massive cheekyness so save yourself the hassle and tell her why.
And that's the end of the relationship..which isn't friendship.

What happened last time when she used your toothpaste and shampoo? Did you tell her this was out of order?

I think it's possible for you to have a good holiday with her so long as you both make an effort to get on, and she doesn't continue to take the piss.