Oh dear, you just cannot visit 5 complete countries in 2.5 weeks. Impossible. Pick one or two places and then figure out what appeals to you.

This is a lot of traveling for 14 to 18 days. You should really limit your itinerary to either 1 country or perhaps 3 cities. In Italy alone you have 6 locations which could easily take up the entire time.

You mentioned hostels which leads me to believe you don't have a lot of money for the trip. Moving around from country to country will eat up more money than staying in one location.

First you determine your itinerary. Then check airfare pricing to determine the best prices, flying into one location and home from another. It doesn't really matter if you start in the north and move south as you'll only be traveling for 2 weeks and the temps will be moderate in May and it's not clear where you are going.

<<how should we plan our itinerary? >>

I'm not sure what you're asking. IMHO spend 4 or 5 days in major cities. Choose the places you want to see most. If they are close together then take a train; if not then fly.

How many cities, besides the 6 places in Italy, are you planning during your 14 days? Are you planning to get to a city and leave the next morning? Are you interested in zooming around or in experiencing the city/seeing the sights?

Well we don't know when we are going to be able to travel again. We know its a lot and we are prepared. If we have to eliminate one once we sit down and talk about it, then we will. But right now..these are our top picks.

ill have to look at my list and eliminate some places. thank you.

To help in your planning, most people on this forum will advise you that every time you change cities, even within the same country, it will take at least half a day to do so. . . . packing and checking out of the hotel, traveling to the train station/airport, waiting to board, the actual travel time, getting out of the station/airport to the next hotel, checking in. Often relocating can take even more time.

With 9 destinations on your list (without even considering if you plan to visit more than one place in France, Switzerland, Germany, and Croatia), you will lose about 5 of your days to traveling between the places. Also keep in mind that if you are traveling from North America, your arrival day in Europe will probably be jet-lagged and your departure day for home will probably not allow for any touring, just getting to the airport. Therefore, 7 of your days will be devoted to travel/jetlag.

Here is a sample. This does not represent in any way an actual itinerary I might propose. It is just a way to illustrate how the number of destinations you suggest would fit in the time you have. You will spend at least half a day traveling to place so you can leave the next morning. Does this look enjoyable to you?

Day 1: arrive France
Day 2: France
Day 3: travel to Switzerland
Day 4: Switzerland
Day 5: travel to Germany
Day 6: Germany
Day 7: travel to Croatia
Day 8: Croatia
Day 9: travel to Verona
Day 10: travel to Florence
Day 11: travel to Tuscany
Day 12: travel to Naples
Day 13: travel to Capri
Day 14: travel to Rome
Day 15: travel home

thank you all...again, i said we're new at this and this is our first time trying to plan anything this big. we might just travel around Italy and possibly croatia or switzerland

Croatia will cost more to reach than the other locations as flights from the US are expensive. It's also a bit more difficult to travel around on public transport as you have to bus more (not much train connections).

Switzerland is one of the most expensive countries you could have picked. There is nothing budget in Switzerland (a happy meal at McD's can run $12-15)although you can usually get reasonable flight prices into Zurich or Geneva.

Summer flight prices usually increase around May 15 so if you can depart before that, you might snag a few hundred off.

For Italy, I would prefer convents or monasteries over hostels. I don't want to share a dorm room or bath with other people. Most convents have private rooms and many offer private baths. Some have curfews if that's an issue.

>>>Italy (Rome, Naples, Capri, Verona, Tuscany, and Florence)<<<

This itinerary would use your 2 1/2 weeks if you want to see a couple of things in each place(no Venice?). It's possible you could spends a few days in Paris, fly to Rome or Venice and spend the rest of your trip visting Rome/Florence/Venice (no time for the rest of your Italy list).

You should be able to have a wonderful time traveling around Italy or Croatia or (if you can manage the costs) Switzerland! These are beautiful countries that hold so many different things that you should be able to come up with a plan that gives each of you a treasure of memories.

As kybourbon notes, it's a bit harder to get to Croatia, but once there, you can use public transportation - mostly buses, which are comfortable and have secure compartments on the side for luggage so you don't have to lug anything into the bus itself.

There's no reason to use a guided tour unless you want to - these are all destinations that are easily visited independently.

How lucky you and your mother are to be able to share this adventure!

why dont you just do France and Italy
what the others have said is true. the amount of time you have may not be enough for what you want to see, and it is going to cost you a lot more getting around to get to these places.
If I were you I would work on something like this:
fly into Paris(4)
train to Lyon (3) - can to day trips
train to Florence(2)
train to Rome(4)
spend time getting to Naples and Capri
train to Venice(3)
fly out to home

or of course you can do a tour.
there are quite a lot of tours out there that will go through all the countries/cities that you want to see. and it is possible that you could do it in the time frame you mentioned
check with a local travel agent. I live in australia and we have different tour companies.
however, these tours can be quite pricey.

One simple tip, alluded to by several of the previous posts: Fly into one city and home from another. It can save money, and what's more important to your hectic schedule, time. Most airline and travel agency websites have a multi-city function to put together such an itinerary.
More fundamentally, changing cities constantly can stress you out. Do you really want to come home with memories dominated by train stations and airports?
It's tough to give up dreams but better to truly enjoy what you do visit.

Thanks for your input everyone! I'm glad I asked these things while we're still in the planning process.

As far as visiting Switzerland--we would have a place to stay. It's crazy to know that even mcdonalds is so expensive.

And kybourbon--I forgot to list Venice. I think we'll probably stick with only going to Italy and visiting the Swiss alps for a weekend. I want to try and get the most and see lots of things before I start a family and have a full time career. Which is why I mentioned all those countries earlier.