In Mid-October 2008 my girlfriend and I are going to meet a group of 30 in Florence. Our travels will take us to Assisi and we'll leave the group in Rome after 2 weeks together. We are all from the United States.
My friend and I wish to arrive a week before and stay a week later than the others to take in other areas of Italy/Europe. Any suggestions as to 'must-see' sites, cheap, but safe/clean hotels/hostels. Will probably enjoy resting the last week along the coast (Amalfi?).
Your best choice of airlines? What city to enter and exit Europe?
We were thinking of landing in Milan and taking a train trip through the Alps en route to Florence the first week.
We are on a conservative budget.

Need to check your maps. It is a little hard to go to Milan/Florence via the Alps. It could be done but it is a long trip. Why not go to Rome and come home from Zurich?

Unless you particularly want to spend time in Milan, I would fly into an airport in a city you want to see. For example I would suggest flying into Rome and out of Venice, or the other way around to avoid cost and time backtracking on the ground.

Choice of airlines depends on where you are leaving from in the U.S.

If you want to see the Alps you're going to have to go significantly further north than Milan - and see no reason to land there unless you're mad to see it for some reason.

If your group is going from Florence to Rome I would land in Geneva or Zurich so you could see a little of the mountains and something of Switzerland before Italy, then head south, meet your group in Florence and end up in Rome. October is sort of shoulder for Amalfi Coast (you can;t swim but restaurants and hotels will still be open and ferries running so you can see Capri - and definitely Pompeii and the Museum in Naples. I believe you would have to return to rome to fly directly home.

Hi Rudolph,
If you want to see any of the Alps at all, then fly into Zurich and out of Rome. If you do this, make sure to go over to Lucerne which is very close to Zurich. It's a beautiful town. But, if that's not all that important, then fly into Milan instead. I did this last year but in reverse, flew to Rome and home from Milan. At the end of the trip, you could pass some time in Sorrento and then go back up to Rome to fly home. Pompeii is a good place to see as is Naples and Capri. We flew Alitalia last year and got a really good price, but not everyone likes that airline and it's always on the verge of bankruptcy, but I had no complaints. Look for fares on Kayak.com. You also might want to check out Swiss Airlines. By the way, you won't be taking the train through the Alps if you land in Milan and go to Florence, that's why Zurich would be the better choice if you want to see the mountains. I don't know of about hostels, but there is an international hostel association or something like that that you can join and they give you lists of them in the places you're going to stay. Check out some of the travel books and websites for reasonable hotels. Tripadvisor.com is a good site because they list most of the hotels in any given town and in all price ranges and then there are tons of reviews you can read about each place. I've used this site often.

Good Luck

I suggest you research airfares and itineraries to start your planning. Because that's such a big expense, you want to plan it first IMHO. It sounds like you have lots of time, so you can find many itineraries that would be fun. Especially since you're never been to Italy.

It sounds like a great opportunity. There are good hostels, but also convents have cheap lodging (if you don't mind a midnight curfew at most of them).

Have fun planning. Ask back on this forum with detailed questions.
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One approach to this is to work with the cities that are definites. For your two weeks group travel, it seems that Florence is yor starting point and Rome is the end. So you can get some books and research what desirable cities might be resonably close to Florence and Rome (you could pst that question here if you wanted to). The most convenient (easiest) intercity connections would be 4 hours to 5 hours by train, this might be a guide for you.

You need to think about what specific interests you have. What would be cool to see.

In late October,the weather in Amalfi might disappoint you. You might look at some temperaturs and webcams for an idea.

Enjoy your trip.