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I can highly recommend Italy - beautiful art, architecture, scenery and music, interesting local festivals, great people and food. Beaches, mountains, lakes, the ocean, historic sites, world class museums and galleries and a lot of varied things to see and do. The best part is the wonderful Italian people. It's very easy to get out and explore Italy and further in Europe using the trains or budget flights. Mid-April to mid-June or September to October are good times to go. The peak summer season can be very hot and crowded
Nobody can tell you with any certainty what the prices will be like that far into the future. Prices depend on exactly where you're starting from, when you go (prices vary a lot), how long you stay, where you go in Italy, how you get around, the kind of places you stay in and what you see/do/eat. People who backpack generally can get by for $100 per day staying in cheap hostels and carefully watching their budget (not including airfare). However, if you stay in hotels, it will cost you more. I usually spend 100 to 150 euro a night for a hotel just for myself, but there are cheaper places.
Here are some resources that can help you plan and check options and current prices for your trip (expect prices in the future to rise):
http://www.kayak.com/ - airfares & hotels; the explore function is useful for finding the less expensive places to fly into from your starting point.
http://www.trenitalia.com/tcom-en - Italian train schedules & prices. You can find links to the various national train sites on the Man in Seat 61 site above.
http://www.venere.com/ - hotels/B&Bs - prices for the same hotel can vary hugely depending on the season and what local events are going on.
http://www.hostelbookers.com/ - hostels.
http://www.monasterystays.com/ - monasteries & convents that offer accommodations
You can also look into camping or couch surfing as cheaper alternatives for accommodations, but you don't need to with your budget.
http://www.backpackeurope.com/ - information & advice
For sightseeing prices: check the websites for entrance fees for the museums & galleries you're interested in. I spend anywhere between nothing and 40 euro a day depending on exactly what I go to see when out exploring. For food, I spend around 25 to 50 euro for a meal, but you can eat for less. A pizza is 8 to 13 euro and a panino or wrap is around 3 to 6.50 euro in many places. You can often get food at festivals at a relatively low price. You can also shop in the markets and put some meals together for yourselves. When I travel, I like to try the local specialties and the good restaurants.