It’s much easier to be a sail training vessel than a passenger vessel.
I sail a sail training vessel and it is registered as a passenger ship.
There are nevertheless specific rules for the ship and the trainees are considered as such and not passengers. They are expected to work the ship at the direction of the crew etc and we have various minimum manning requirements which can include trainees.
We also carry volunteers who have some experience aboard the ship but not necessarily maritime qualifications. Some are highly experienced working the ship and act as watch leaders capable of taking charge of a watch of up to ten in all ship activities including climbing aloft, steering, handing sail etc.
We sail with up to a 100 paying passengers on day sails which we use to raise funds.
We sail with five paid professional crew, and on an overnight or longer (usually seven days), we carry ten volunteers and 40 trainees, a total of 55.
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I realized awhile after I posted that officially being a “sail training vessel” may only be a USCG thing. I guess the rest of the world just registers them as passenger vessels. Here your vessel would have to be both a ‘sail training vessel’ and a ‘passenger vessel’ to conduct the operations you described.
Because the Cutty Sark - and clipper ships in general - were specialized ships that needed a large crew to carry a relatively small amount of cargo at high speeds. They were more like high-strung racing yachts than commercial cargo ships. They made sense when carrying high value cargo at high speeds or carrying illegal cargo and not getting caught was the mission. In the 21st century these cargoes are not going to be on sailing vessels of any kind.
Kind of like why we don’t use Ferraris for taxi cabs 
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