Your Questions Answered
Will they have the particular things I am looking for? Outlet shopping is hit and miss. You could be unlucky big time, you might not find a thing to buy,you might find something you'd never thought of. Nothing is certain. Even the staff at the outlet cannot be sure from day to day what stock they will have.
Can certain things be sent to me? Sending this type of merchandise abroad would breach all trade agreements and undercut the flagship stores. If you want outlet prices, you must make the effort to go to the outlet.
Will the staff at the outlets speak English ? Yes, they will also know all international sizing.
For outlet shopping, which is the most convenient airport to fly into ? The closest airports to the Prada and Gucci out lets are, in order; Florence, Pisa, Rome.
Can I get there by public transport ? Getting around by public transport is possible but not optimum. Take a train from Florence or Arezzo to Montevarchi. From there take a taxi to the outlets. You may want to ask it to wait for you whilst you shop or arrange for the same taxi to return for you at a fixed time as the outlets are all in quite remote areas.
Is a decent hotel near by to stay in and for a reasonable price?
We do not have hotels in area of the outlets on our books and so cannot personally recommend anything. If your goal is to outlet shop you could just arrive in the area and ask the locals where to stay - as it is not a tourist area you should find something. The outlets are about 30 minutes from Florence by car.
When is the best time to arrive ? It is best to arrive at Prada before it opens at about 9.00. At the door you take a ticket and then retire to the very chic bar/café next door, which has an electronic number counter to let you know when it's your turn. The choicest items are always there first thing and go quickly. Keep your ticket. Anything you think you might want to buy you can give to a sales assistant who will store it for you whilst you rampage on to the next discovery, at the end you have a second chance to re look at everything calmly and make your final selection. Do not bother going on weekends, public holidays or during the peak sale periods (when the best old stock is sent to the stores). As with all outlets, it can be hit or miss, some times you will be lucky and other times you will not find anything worth buying. At Prada 9 times out of 10 you will be stuck for choice 1 time you won't find a thing to buy, it depends on luck. At Gucci it is the reverse but that one time you are unlucky you will be so big time. Gucci never has lines/queues for this reason and so visit Prada first and then Gucci.
What about the sales in regular stores ? During sale periods (Early January and early July onwards) the bargains in the stores are almost as good as in the outlets. The outlets never have sales.
What about outlets in other parts of Italy ? We have visited very good outlets near to lake Como (Armani, Fendi, Iceburg) and Lago Maggiore (mainly pottery, china and kitchen ware)and in Legnano (mainly shoes, Fratelli Rosetti etc.) as it is far from us, we cannot give first hand information. The best idea is to check on before you leave or while at your To Tuscany villa.