There are quite a few English examples as well that I have come across, but in the heraldry lists they are usually given as 'tower' which may help you if you go searching. Cheers mate. Simaginfan 👍
Chess rook as a symbol in some medieval coats of arms & flags, mainly in Florence

There are quite a few English examples as well that I have come across, but in the heraldry lists they are usually given as 'tower' which may help you if you go searching. Cheers mate. Simaginfan 👍
I've found names, but not older photos or drawings etc, only new designs. Rookwood is I think a name I remember

Glad you've liked it tzimakos
It's quite strange this chessboard on the external wall of Sant'Agata di Scarperia e San Piero, isn't it???
@simaginfan a known English case of the 16th-17th cent. is John Mynne in https://www.british-history.ac.uk/survey-london/bk16/pp182-193, n.5, but the drawings are quite recent.

from the oldest I've found...
Switzerland [Germany?] 14th c.
https://www.e-codices.unifr.ch/en/list/one/snm/AG002760
France 15th c.
http://www2.culture.gouv.fr/Wave/image/archim/Pages/03082.htm
https://gallica.bnf.fr/ark:/12148/btv1b8470169b/f116.image
As a sequel thinking process from a previous forum, I've tried to check possible chess references in Florence of the middle ages. One motif that I've tracked is the representation of some chess aspect, mainly the medieval rook, on flags but mostly on coats of arms. [some prime info found in Antiche testimonianze degli scacchi in Toscana by Mario Leoncini, 2019]
Generally speaking, medieval chess rook is the most common or easy to track. Knight could be just a knight, Bishop & King a man, Queen a woman. And the checkered patterns are so common that I can't say that are of a chess reference, maybe only if it's presented on a 8x8 board.
And regarding the chess rook piece, this can be presented also as just a castle, something that maybe makes it difficult to identify, although there're few examples where a castle next to a medieval rook shape are given, making identification easier. The latter can justify that a chess rook piece, while being a chess reference, can be used also to represent a fortress-castle.
In any case, mostly under search is the shape of the medieval rook. The known shape of the piece with the two horns that sometimes maybe could be confused with an almost similar that can be found in the medieval coats of arms, this of the Lily flower [fleur-de-Lis]. And sometimes these two shapes could be combined in the same compilation; I've found some but I couldn't specify the exact dating of them.
Also must be said that Lily flower as an emblem was of Florence too! Called Giglio bottonato or di Firenze, since 13th century. Two examples are following for comparison, both from Palazzo d'Arnolfo, Tuscany near Florence...
....left stemma of Carnesecchi family [1491] with rook, right Giglio di Firenze.
Four coats of arms of families in Florence
I've tracked namely 4 Florentine families, having rook/s on their coats of arms, since late middle ages or early renaissance.
So in Florence there're 3 Guelf cases out of 4.
Some cases out of Italy
The medieval rook shape can be found and out of Italy of course. In these cases it is really usual that the coat of arms, that includes a chess-rook, corresponds to a family or location name including some word like "roc[h]", "roche", "roque" etc. Something that could imply a castle but also a rock!?!
France
Regarding France I could say that I was lucky tracking the volumes of Armorial général by Charles-René d'Hozier, but they are 35 of over 1000 pages each! So I limited my search only in the 14th [Languedoc 1st], but I had some good findings. In over the half, a word containing "roc*", "roque*" etc could be found, while in the rest there wasn't certainty, as they were for persons. It also must be said that these volumes were written around 1700, so many of the presented images show later phases... Just two
Roquemore
It's of the town Roquemore, 12km north of Avignon S.France, next to the Rhone river. The name Roccamaura [or Rocamora] and a nearby castle is mentioned since 12th century. It's also an example of rook & Lily flowers combination.
Roquefort
Possibly it's about the famous cheese place
, as the volume is on Languedoc district! But maybe after middle ages. Marie's one surely relies on chess...
Germany
Two cases...
Rochlitz
Rochlitz is a town of Saxony. Its coat of arms is presenting a castle while the two horns of a medieval rook is left and right. This compilation is said that's firstly tracked in a seal of 1364.
Rochow family
Rochows is an old family of Brandenburg. The appearance of chess rooks on their coat of arms is mentioned at least since 1353.
Spain - Rocaberti
The name Rocaberti can be found since late 10th century, used by the viscounts of Peralada, while as a title-name surely since 13th century. I couldn't track since when the rooks entered their coats of arms.
And getting back to the Florence area but getting away from rook theme, the following is from Sant'Agata di Scarperia e San Piero, Tuscany. The church started being built in 10th century. But I don't know when exactly this 8x8 chessboard was added or what exactly is trying to say.... & in google maps