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Travelers booking tours with completely unlicensed operators should be aware that unlicensed operators may only have normal car insurance and no additional insurance for cancelled trips. If unlicensed, it is possible (though not likely) that the tour could be stopped in progress, as happened in 2009 when some local operators lodged formal complaints with the police about two very successful foreign non-licensed operators.
When booking a tour package, you might want to clarify:
Any tour ‘package’ under Italian law involving transport, food and or wine and or biking and or guiding can only be offered legally by licensed tour operators. In the case of small operators, this is accomplished by being affiliated with a registed travel agency, since travel agencies are allowed to advertise and sell tours. Most minibus tours are offered by NCC-licensed drivers who are affiliated with a registered travel agency. These are completely legal. There are also some NCC-licensed drivers without travel agency affiliation who effectively give tours.
The law is grey on this because obviously no one can tell a driver not to talk to the customers, so as long as they don't advertise a 'tour package', there is no problem for them nor for you. No NCC driver can guide within a museum, and none of them do that. Their tours are strictly place to place and can legally include a tour of a winery conducted by an employee of the winery.
In 2009, one Tuscan wine tour operator and one bike tour operator, both run by individual foreigners, were fined for offering tours. The bike tour operator no longer advertises and the wine tour operator expanded in other more legally clear directions in the wine and tourism sector.
Many travellers to Tuscany have provided good reviews for completely unlicenced individuals and they undoubtedly are good. Just be aware that they might have less insurance than those with licenses and that there is a remote chance that your tour could be interrupted midway.
This is a link to an article about the two foreigners mentioned above.