If you have 5 days and youre interested in shopping go to Rome. You wont be able to see half of what Rome has to offer in just 5 days but theres plenty of shopping. If you want a change of scenery: take a day trip up to Pompeii. Or take 2 days, fly/drive/train up to Venice, spend the night and head back.
If money is no object, call a travel agent and tell them what youre interested in (shopping, history, beaches).
If you want to keep an eye on the costs and since you have 9 months make a budget for what you want to spend each day (flight, hotel, meals, tips, etc). Then keep an eye on kayak.com or any other travel website until you find a flight that youre happy with or that is below your budget. Do the same for your hotel. Research your hotel on Tripadvisor.com before you confirm a reservation.