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Doing the math... 10 people times $3500 is $35,000. Holy hell. You could do it exponentially cheaper by renting a villa in Tuscany, hiring a cook / chef and driver / car / SAG well for under $10-15G's (and split among 10). Having ridden all over France and Northern Spain and Italy (tuscany - sienna, florence, san gimingano) I personally would not use a Sag. There are towns all along the way providing great food and beverages (red wine bein one of them). You could just ride from your villa, and trust me, there are killer Villas and roads all over the place! you do not need a guide. just a map!
actually have looked into the whole villa rental in Tuscany but not gotten very far other than dreaming and googling
very economical way to go if you're gonna be based in one locale.
I did a gig cycling in Tuscany, really fun -- albeit hilly! But who cared how long it took to get to the top when a fine wine was awaiting :)