there is a good reason for one item only per post - it helps to avoid confusion when the answers come in
So - reference your second tumbler..... I agree it has the same sort of curved bottom and therefore the assumption might be that it would have been partnered by a carafe.
But the cutting plus engraving are signs of a quality that isn't usually found on such sets, so regret I'm not confident of its intended use - it may well be a stand alone piece, and in view of the largish area of flat polished base it may well be Continental rather than British.
A point to bear in mind with engraved pieces is that whilst features such as cutting are almost certainly contemporary with the date of manufacture of the glass, the engraving could potentially be later. Such examples are where names and dates are applied for christening and marriage events on existing tumblers.
The vine and grape motif has very long history, and was still being used by Walsh around 1950 on their 'Fruiting Vine' pattern, so no great help there with dating.
Take it that you have scoured the base for any marks or names.
The type of cut lattice decoration on this second piece, plus the general looks, suggests to me very much the C20, but it's not an easy piece to date, but again attractive - the engraving looks to be well done.
If pushed I'd suggest somewhere around the 1920 - 1950 period, but have a feeling I'm guessing only.
Sorry it's probably not the answer you want - and have a feeling you won't feel pestered with replies