as introduced by the subject, I would like to have free shipping to Italy starting from 100 Euro and Free shipping to Germany or rest of EU starting from 150 Euro.
Can magento handle it with default setting or I would need external customization?
This isn't included in native Magento functionality but can be achieved with some customization or modules. For example, you can check out this one https://amasty.com/shipping-table-rates.html
I believe you can achieve it through a shopping basket price rule, putting a condition on the 'shipping country'.
You need to create 2 rules :
1 if shipping country is 'Italy'
1 if shipping country is NOT 'italy'