Which tool to choose
You don't need "the absolute best", you need the one you already have at hand for your case.
Just want a quick draft, no account and no worrying about limits? Go to Microsoft Copilot (copilot.microsoft.com). Under the hood it uses the same GPT models as ChatGPT and it's free with no daily cap in Italy. It's the best choice if you need occasional answers and don't want to pay.
Do you write lots of emails and want maximum care with formal Italian? Choose Claude (claude.ai). On the nuances of Italian (complex grammar, idiomatic expressions, formal registers) it tends to be a bit more precise.
Do you live inside Gmail for work? Use Gemini. The integration that writes directly in your inbox, however, requires the paid Google One AI Premium plan. The free version of the Gemini chatbot writes the draft that you then paste yourself.
Already have a ChatGPT account? Keep it. The free plan includes GPT-5 with a cap of about 40 messages every 3 hours: for a few emails a day that's plenty.
For most people, free Copilot solves everything. The procedures below apply to each of these: only the site where you paste the prompt (the instruction you give the AI) changes.
How to do it
The mistake that wastes time is asking "write me a follow-up email" and stopping there: you get a generic text full of blanks to fill in. The difference is made by the concrete details you give the AI.
- Open the site of the tool you chose. From browser or app it's much the same: you find a text bar where you write.
- First gather the four pieces of data that are always needed: who you're writing to (name and role), what you're asking for or following up on, when it was due, what tone you want (cordial, neutral, firm).
- Paste the prompt below filled in with your data.
- Read the draft. If it convinces you 80%, fix the last details by hand. If not, ask for a revision (step 6).
- Check names, dates, figures and amounts by hand: the AI can get them wrong.
- To adjust, reply in the same chat: "Shorter", "More formal", "Add that this is the second follow-up".
The operational syntax for a request (something you're asking for the first time):
Write a professional email in Italian.
Sender: Marco Rossi, purchasing department.
Recipient: the sales manager of the supplier Beta Srl.
Goal: ask for an updated quote for 200 office chairs, model X.
Useful information: we need it by June 30 to close the quarter's budget.
Tone: courteous and professional, direct, no beating around the bush.
Length: maximum 120 words. Include the email subject.
Do not invent data I haven't provided: if a piece of information is missing, leave a flagged space in brackets.
The operational syntax for a follow-up (something already requested and left without a reply):
Write a follow-up email in Italian.
Sender: Marco Rossi.
Recipient: the administrative manager of the client Gamma Spa.
Situation: I sent invoice no. 145 on May 3, payment due June 2, today it still shows as unpaid.
This is the first follow-up.
Tone: courteous but firm, professional, without being aggressive. I want to keep a good relationship with the client.
Length: maximum 100 words. Include the email subject.
Close by asking them to confirm a payment date.
Do not invent amounts or dates I haven't provided.
That "do not invent data" at the end is the line that saves you: without it, the AI fills the gaps with made-up numbers.
A concrete example
A real situation: you lent 80 euros to a colleague a month ago, they haven't mentioned it since and it embarrasses you to write to them. Open Copilot and paste:
Write a short, informal email message in Italian for a colleague.
A month ago I lent them 80 euros, they haven't paid me back yet and haven't mentioned it again.
I want to remind them without creating embarrassment, with a light and friendly tone.
Maximum 60 words.
The result is an email that opens with a joke about how time flies, recalls the loan as a mutual oversight and closes with a "let me know whenever it's convenient for you". You change the name, check that the figure is right, and send. The problem that had been blocking you for weeks is closed in two minutes, without the awkward sentence you would have rewritten ten times.
When it does NOT work (and how to fix it)
If the AI invents the numbers
It happens: amounts, invoice dates, mangled names. The way out: always add the line "do not invent data I haven't provided" to the prompt, and reread figures and dates by hand before sending. Don't blindly trust the numbers written by the AI.
If the tone sounds fake or too "American"
Generic drafts slip in pompous formulas ("I hope this email finds you well") that sound contrived in Italian. Reply in the chat: "Rewrite it without American courtesy formulas, get straight to the point as an Italian would write". Alternatively, pass the draft to Claude, which handles the formal Italian register better.
If you've run out of free messages
On ChatGPT free, when you use up the quota you fall back on the base model. Don't get stuck: alternate between ChatGPT, Copilot, Claude and Gemini throughout the day. For emails Copilot doesn't impose practical limits on you, so keep it as a reserve.
If the AI gives you a very long text
A 300-word follow-up email = nobody reads it. Always indicate a cap ("maximum 100 words") right in the prompt. If it ignored that, reply "Halve it, keep only the essentials".
A tip from someone who actually uses it
Create your own base prompt and save it in your phone notes. The first time you build it carefully, then every follow-up email becomes "paste, change three details, send". The value isn't the single well-written email: it's never starting from scratch. And one fixed rule: the AI writes the draft, the final read is always yours.
Frequently asked questions
Do I have to pay to write emails with AI?
No. To write a few emails a day the free version of Copilot, ChatGPT, Claude or Gemini is enough. The paid plan only makes sense if you use AI intensively every day for work.
Can I have it write directly inside Gmail or Outlook without copying and pasting?
Yes, but it's a paid feature. In Gmail you need Google One AI Premium to have Gemini compose in your inbox. In Outlook, Copilot's assisted writing is reserved for the paid Microsoft 365 plans, not the free one. Until you pay, the free method is to write the draft in the chatbot and paste it: a few extra seconds, zero cost.
Does AI write as well in Italian as in English?
Yes. These tools handle Italian with quality comparable to English. Write the prompt directly in Italian: the assistant recognizes the language and keeps the register you ask for.
What's the most convenient tool for someone who only writes occasionally?
Free Copilot. It doesn't have the nuisance of daily limits, in Italy it works without a mandatory account and uses the same GPT models you'd find paid elsewhere. For occasional use it's the clearest path.
But if I use AI, will the recipient realize I didn't write the email myself?
It's the most common fear, and it's unfounded if you do one thing: personalize. A draft pasted exactly as-is sounds generic and shows. A draft where you change the opening, add a detail only you and the recipient know and cut the artificial formulas becomes indistinguishable from one written by hand — because in fact you did write it, starting from a base. The AI saves you the blank page, not the thinking.