I think it would be very nice to fly to northern Italy for this weekend. The weather will be very ni

I would go for the first short break to Venice - better than Milan for sure as a first visit, as another Fodorite commented. If you have some free time you can visit Verona from there. Fly in or out of Venice Marco Polo Airport, or Venice Treviso Airport (Ryan Air lands there as well, or alternatively Verona) Regarding your shopping for suits - there are plenty of high-end shops in Rome, or to suit your budget - so buy your suits on your second trip.
I would go to Rome for the other break. You can do a day trip from there if you feel you need to get out of this city for a day - even as far as Florence (which is doubtful as you are only going for a few days.
Is it because of business reasons that you have to do two trips in two weeks to the same country? - or do you simply have these slots available for two short breaks and intend to take maybe low cost airlines? - or is it your intention to choose one of the two breaks you have available. If it is the latter, I would go for Rome, since you have more days at your disposal, there is plenty to do there, car rentals phoenix az and you would fit in the shopping spree for suits.
If you want suits you will generally find off-the-peg "Brand" suits in Milan, so rubbish like Armani etc (just near the Opera). If however you go down the side streets near the main railway station you could find a tailors who would make you a proper suit but not over a weekend (they take a week or two once you get out of Hong Kong etc).
Do Venice for the first trip, Rome for the second. If, in either place, you feel the need to get out and see something different (I'd wager you won't), from Venice head to Verona or Vicenza or Padua; from Rome head to Ostia Antica or down the coast.
The reason I ask for advise again is because the city may be changed between the suggested since i have more days and you guys may just recommend to travel once to Italy from the 7th onwards and not travel back and forth as originally planned.
I think it would be very nice to fly to northern Italy for this weekend. The weather will be very nice. If you stay in Verona, then you can visit both Venice and Milan or Lago di Garda if you feel like it. There are many airports you can use.
Maybe to avoid the hassle of travelling twice to Italy in such a short time, you might take a flight to Venice, spend 3 nights there, then train (or take low cost internal flight, check out Easyjet or Ryan air - they both do internal flights in Italy) car rentals phoenix az to either Florence car rentals phoenix az or Rome and spend the last 3 nights in the city you chose.
Alternatively, if you do not mind travelling for a holiday in such a short time span, go for the first weekend break to Venice, and during your second holiday do either Rome and Florence (or anywhere else in Tuscany or Umbria) or stay for the six nights in Rome.
It always depends on whether you like to include countryside car rentals phoenix az or prefer cities, whether you are more into culture and history and whether you would prefer to visit a city thoroughly, or prefer visiting multiple cities. It is all a matter of personal choice.
just travelled by train in italy, it would have been great had the train not broken down on us several times, once leaving us stranded at night in this town which had no open hotel rooms...we had to sleep outside the train station that night. i recommend if you are going to use the trains, to travel in the morning/afternoon, in case the train breaks you will have time to find another route.