This is will vary completely on depending on:
- How well you know the SW
- Where you are going
- What you expect from the SW
Approx. 10 years ago I had a SW accompany me to a conference in New York.
She found out I was going and made a joke about joining me.
The next day she texted and we discussed a scenario where she would join me.
We agree about everything from how often we would have sex - private time - she wanted to visit friends and explore New York while I was in the conference.
I paid for flight, meals, entertainment and she shared my accommodation (no separate room). I upgraded the room so we a suite with a large King bed.
We also agree upon a few that she suggested and we both felt was reasonable.
I would never go with anyone who I didn't know well and felt comfortable with.
It was great having travelling with her and we are still in contact even though she has long since retired.
I was working abroad recently and was thinking of inviting another one of my long term SW to join me as I go flights once a month and had an apartment I was staying in but due to many reason it didn't work out.