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Language changes with time, we all know. What was once a common phrase becomes dated and a new word is substituted. Can a 21st Century Florentine understand what was written during the 19th, 18th, 17th or 16th Centuries? Can they read the works of Dante Alighieri, Boccaccio, Niccolò Machiavelli or Alessandro Manzoni in their originals? How far back can they understand their language?

EDIT - Clarifying - If a 21st Century native Florentine speaker can easily read Boccaccio, without notes or aids, then it's got to be an earlier date. If they can't, then the limit has to be some time after Boccaccio. I'm not asking for a specific year, but there have been so many writers during the past 500 years, that two of them must mark the limit between easily understanding and not understanding without notes or any help. The question is not whether the average Florentine speaker can or cannot understand "The Divine Comedy". It's when did the written Florentine language change that it cannot be immediately understood nowadays?

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    Related: italian.stackexchange.com/questions/8527/…
    – Hachi
    Nov 20 '20 at 16:45
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    Does this answer your question? Can native Italian speakers read The Divine Comedy?
    – DaG
    Nov 20 '20 at 17:15
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    The accepted answer to that earlier question informs us that Dante is mostly readable to present-day Italians. Dante is the first great author writing in Italian; hence, you are actually asking about authors preceding Dante, and 1) there are not a whole lot of them; 2) their texts are often preserved in a later Tuscanised form (for instance, this is true for most of the early Sicilian poetry), so for them most of what was said for Dante still holds.
    – DaG
    Nov 20 '20 at 17:26
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    @Centaurus The earlier material is typically written in Latin (with the exception of the poorly preserved Sicilian poetry and some religious literature). In fact Dante wrote a lengthy treatise (in Latin!) to justify his "unusual" choice of language.
    – Denis Nardin
    Nov 20 '20 at 17:37
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    The most ancient known commercial letter in Florentine is from 1291 (the same years as Dante's Vita Nova), and it is perfectly understandable to a contemporary Italian: wps.pearsoned.it/wps/media/objects/13367/13687937/…
    – DaG
    Nov 20 '20 at 17:45
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You seem to be interested in the oldest Italian text readable by a native speaker. Unfortunately the problem is that there just aren't many old Italian texts, especially from Tuscany. Here I'll list the main ones I could find (my source is Migliorini's Storia della lingua italiana), limiting to texts coming from Tuscany and neighboring areas, together with some comments about how easy or hard I found them to read.

The first document arguably in vulgar Tuscan I could find is the postilla Amiatina. It is just a short note at the end of a donation certificate in favor of a monastery on mount Amiata (dated 1087) that reads

Ista cartula est de caput coctu
ille adiuvet de illu rebottu
qui mal consiliu li mise in corpu

To be honest this looks a lot more like vulgarized Latin than Vulgar. Migliorini conjectures it is an attempt to "latinize" the following words

Esta carta è de Capucottu
e ll'aiuti dellu' rebottu
che mal consigliu i mise in corpu

Its interpretations is in any case rather obscure, because of the uncertain meaning of the word rebottu. To be honest I'm in doubt that one should even count this, and I'm including it only for completeness.

Next comes the Ritmo Laurenziano. This is a longer text, you can find it here. It dates to the mid twelwth century and it's not easy to read (mainly for the lacunae). It begins as

Salva lo vescovo senato, lo mellior c'umque sia na[to],
[. . .] ora fue sagrato tutt'allumma 'l cericato.
Né Fisolaco né Cato non fue sì ringratïato,
e 'l pap' ha·ll [. . .-ato] per suo drudo plu privato.

There are a few words that are definitely archaic and might require even a moderately educated speaker to open a dictionary (umque "never", drudo "friend"), and the spelling is definitely non-standard (cericato?). I would say that this is borderline readable. I suspect that without the lacunae and with a little more context it would be easier to guess the meaning of the unfamiliar words. It also uses several words in very "Latin-like" form, presumably because it was intended for the court of the bishop, where Latin would have been very common.

The next document is the Ritmo lucchese. This is a short poem describing a fight inserted in the middle of a history (in Latin). It is dated around 1213. It is too long to transcribe here (the complete text can be found here), but let me copy a portion here:

Stiano a mente, ben lo dico:
che a Lucca sempre sia schifato
e a Lucca sempre sia odiato;
aver di Lucca non i sia dato;
tolto i sia quel che a pilliato,
ka di Lucca l'à 'nvolato:
tutto fu dello sacrato!

In my opinion this text, while definitely archaic, is already perfectly comprehensible to an educated Italian speaker.

After this the next available documents in Tuscan are the literary works of the Dolce stil novo school. These are slightly more archaic than Dante's Commedia, but not significantly so and I would argue are already perfectly readable by any educated Italian speaker. Arguably we should lump with them the Tuscanized transcriptions of the poetry of the Sicilian school, which are either contemporary or shortly before them.

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    Reading Dante without comments/footnotes is trickier than you make it sound, in my view. I can parse most sentences, and get the general meaning, but there are enough archaic terms that it is difficult to get a complete understanding. Much less so for the other authors (also because they do not write in metrical rhymed lines). Nov 20 '20 at 15:59
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    @FedericoPoloni We agree that Dante is harder than Boccaccio, but I think I already said my piece about reading Dante (TL;DR requires some guidance, especially the parts that delve deep into Scholastic theology, but the language is mostly understandable), and I stand by it. I read the whole Comedy on my own, in middle school, and one gets used quite quickly to the language
    – Denis Nardin
    Nov 20 '20 at 16:01
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    Note: I completely rewrote the answer to focus on the pre-Dante period, as requested in the question.
    – Denis Nardin
    Nov 20 '20 at 19:32
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    @Centaurus I can speak only for myself, but I expect any educated Italian speaker to easily read B and D. They're basic high school curriculum! It's true that some Italian speakers have difficulties with them, that's why I'm using the weasel word "educated" (e.g. I don't expect someone like my grandfather with only a primary school degree to be able to read them easily, although maybe with difficulty). The reason is, as I wrote in the first version of the answer, that the Italian taught in schools since 1861 was actually modeled on D & B, so it's not surprising that people can read them!
    – Denis Nardin
    Nov 20 '20 at 19:36
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    I.e. the Italian taught in schools in 1861 was not based on some contemporary spoken Italian (which didn't exist) or contemporary spoken Florentine (Manzoni's proposal, rejected as impractical), but rather on the written language of the educated minority that was kept as close as possible to thirteenth century Florentine.
    – Denis Nardin
    Nov 20 '20 at 19:40

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