If you live in Germany then it would be Interrail not Eurail you would qualify for.

Eurail/Interrail is only for trains, it is not valid on the vast majority of scheduled buses, trams, metros, ferries. Only on days you would travel reasonably long distances is it usually cost effective.

Your schedule may or may not be cheaper with regular tickets, the only way to really know which is better is to look up fares for your schedule and compare.

Reservations are required on long distance Italian trains and some International trains to/from Germany.

Hamburg to Milan is a very long journey for one day, Rome to Hamburg is even longer. I would not want to do either with a small child in a single day.

If you cross more than three countries, a pass is usually good value. Especially in high summer season with rather expensive ticket prices. In this case you travel through all of Germany, Switzerland/Austria and Italy. But to know for sure. You’ll have to compare a bit.

Passes cost about 60-50 EUR per travel day for adults per person (sometimes less, if you have more days), for some trains you need a seat reservation, like the high speed trains (13 EUR per seat) and Intercity (3 EUR per seat) for travel in Italy. Kids under 11 get passes for free.

To compare in a blink of an eye, use a website like  www.raileurope.com or www.trainline.com (which doesn’t mean you need to buy your tickets there, but they have good international ticket search engines). For Italy you can check prices on the website of trenitalia as well. You compare those with the cost of a pass + reservation cost for your plans. It’s highly dependent on when you travel. If you travel long distances on a week day in november, normal tickets probably will be cheaper. On a busy summer weekend, the Interrail/Eurail pass is your way to go.

Advance tickets may be cheaper, but have less flexibility, you’re bound to certain trains. Where-as the pass gives you a lot of flexibility enabling you to take any train you want, spontaneous rerouting, taking a break to stretch your legs or step out, and take the next train if you have an annoying neighbour.

You can also combine, e.g. use the pass for the large distances (Hamburg-Italy and back-, and buy ordinary tickets for shorter trips (Firenze-Pisa won’t cost much e.g.).

A pass is only valid for trains run by participating companies. About 95% of all mainline trains in Europe included, from Highspeed to Intercity, regional trains, local trains and S-bahn systems. You can all take it without any problem. Just some private operators and touristic railways are not included. City buses, trams, metro’s are also not included (since they’re not trains, aha). For some ferries, you get a discount, but not all of them.

Seat reservations can be bought on many different places, depends a bit on the train you take. But www.raileurope.com is a good place to get seat reservations for Italy. For Germany www.bahn.com indeed.

This topic also has a handy overview:

Thanks so much , yes even I feel the same as its very long journey.

Thanks for the detailed explanation. Hope it will help me and others as well :)