Some words which I have problems pronouncing here, no matter how I try, plus coping strategies in case you have similar problems.
As in the number. Difficult because of the rolling “R” which I can do, but it takes some effort. Coping strategy: If you have to ask for 3 of something in a shop, buy 2 or 4 instead of 3. Hoping they’re not big, expensive or perishables. Trentatre is double difficulty. It’ll be hard when it’s my 33 birthday and I’m asked my age. Hopefully I'll have mastered it by then.
The “gli” is the hard bit. It’s supposed to sound kind of like “glee”. Imagine the problems I have buying 3 bus tickets. The tabacchi’s face fills with confusion thinking “What’s this crazy lady trying to say?”.
It is an English word, but if I say it in an Italian sentence the person will understand every word except that one. Coping strategy: “Andiamo per un caffè” Instead of “Andiamo al bar”
Again that pesky “R”. Again, it may be an English word but you won’t be understood unless you really roll that “R”. Try: “amburrrrrgerrrrrrrrrr. Coping strategy: Choose something else off the menu.
Near impossible to pronounce. It’s a beautiful country place in Tuscany where I went on holiday once. You can say you went “near to Siena”. It doesn’t cause me problems on a daily basis, but imagine if I lived there! One good thing about Napoli: It’s easy to pronounce.
Any words containing “R” in or “gli” are tricky. Double consonants are also a problem as in English you can’t tell the difference if there's one or two, but in Italian you can. Any English words used in Italian must have every letter clearly pronounced/exaggerated, and any “Rs": Roll 'em, roll 'em, roll 'em.
Hope this helps.