Train travel

It is probably cheaper to buy individual advance purchase tickets for each train, not a pass.
If you are starting out with planning this, you have a steap learning curve to climb.

I suggest you start with the "Main Seat 61" website, specifically this page: https://www.seat61.com/Europe-train-travel.htm
This site has pages for each country, and many for each route, explaining who the operators are, what the service is like and the best way to buy tickets.

Tickets are generally on sale 90-120 days in advance (varies depending on train company and route), and it is always cheaper to buy early, prices never go down, only up as you approach the date. So you need to be deciding on dates and times, and buying tickets, in the next few weeks.

Italy train travel is dirt cheap with point to point tickets. Germany has some great discount passes available such as the Bavarian Pass which allows travel all through the Bavarian Region for super cheap price and multiple people can use the same pass.

Your story sounds like the typical new traveler (not a bad thing) with a knee jerk action of buying a Eurail Pass. It’s such an overpriced and outdated mode of travel that you’ll spend way more than you need if you go that route.

If you have extended stays in Italy, it would seem to me that a pass wouldn't make sense. I just got back from Italy. We traveled from Tirano to Lake Como to Cinque Terre to Florence to Siena to Rome to Sorrento (via Naples) and back to Rome. I prepurchased Lake Como to CT for a small savings and Rome to Naples for a larger savings. All other travel was done by local train or bus in which the prices are fixed so there is no advantage to prepurchase. And even these routes with a savings for pre purchase, you do have an option of taking a cheaper local train with the fixed price. Relatively speaking, Italian train tickets are cheap. The Italian train company, Trenitalia, has a super easy website for ticket purchase.

I can't speak much for train travel in Germany except that I've used trains for travel in Bavaria twice. The Bavarian trains are inexpensive. It is my understanding that other regions in Germany do also have value train options, but I won't swear to it. Like Chris F said, Seat 61 is an excellent resource. As long as the tickets you purchase can be printed from home, DBahn is an easy site to use.

If train travel is new to you, you will want to do a fair amount of research by each country that you need tickets for. I have done most of my travel in Europe by train (including several long trips thru multiple cities and countries) and with help from Seat 61 and the forum, I don't believe you will have much difficulty, but start your research early.

You might want to check Google Maps to see how far it is between cities. It's a long, long way from Amsterdam to Naples.
We've taken quite a few train trips, and I'm only good for about 3 hours at a time. With the advent of budget European airlines, we're more into flying into a central location and taking day trips out of there via rental car. Then moving on down the line to the next city that compliments the first city--traveling in an efficient straight line. We often also stay in apartments with laundry facilities that allows us to travel with half as many clothes (travel lighter.)
Few people are using Eurail passes any longer.

In my experience, passes cost more than all but the longest point to point tickets. I haven't purchased a pass this century. I still price it occasionally. So far point to point is a much better deal unless the flexibility to get on and off is really important.

If hopping on and off the train is important, Germany has day pass options that are worth understanding. They're only for local trains (the ones that stop at every small station) so not the best option for a long leg but great for multiple short trips in a particular area.

For long-distance trains buying you tickets well in advance brings you considerable discounts. The cheapest ticket for Amsterdam to Berlin, for example, for tomorrow is EUR 109,90; for a same weekday and a same departure time on a date begin December it is EUR 59,90.
Regional trains have a fixed price, but as said above are already cheap.

While some Amsterdam-Berlin direct IC tickets for tomorrow are still available for €109.90, the 2nd class fare on that train can be as high as €130.20. If most of your longer travel is within Germany, the German Rail Pass with twin/pairs discount is convenient and pretty cheap (e.g., 10 days of travel within a month for $300 per person). While you'd have to pay separately from Amsterdam to the German border, the German Rail Pass does cover the daily direct train from Munich to Venice, or to a closer stop such as Bolzano or Verona.

Train tickets in Italy are relatively cheap even without advance purchase for the distances that tourists typically travel in a day. Medium-speed or faster trains in Italy also require a paid seat reservation in addition to a pass, making it less convenient.

The answer to this question is always, IT DEPENDS. The first thing I would suggest is to map out your stops from Amsterdam to Naples. You will then have to go to each countries website and get a quote on what the cost is to go from point to point. Add them up and compare to the Eurail pass cost.

If it is close within a couple hundred dollars, I prefer the pass (Only the monthly pass). I prefer this because I take a lot of day trips and day trips add up because they are round trip. I also like the flexibility of changing plans and don't have to worry about wasting money if I have already pre-purchased a ticket. I can also change the day I travel as well. I also don't have to buy a ticket at every stop. Passes mean convenience to me and there is a price point I am willing to spend for the convenience. I think they are something to be considered. However, it is a financial decision for you to make, but do look to see if they work for you.

js,

I haven't read all the previous replies, but a few points to mention about rail passes. These do not include the seat reservations which are compulsory on some trains, especially in Italy. You'd have to buy these separately out-of-pocket. Even with a rail pass, if you're caught without valid reservations for the trains you're riding on, you'll face hefty fines which are collected on the spot! One other point to note is that the seat reservations are specific to train, date and departure time so can only be used on the one train listed on the ticket.

I haven't looked at the costs for tickets from Amsterdam to Germany and within Germany. Others on the forum can provide good information on those. However for travel within Italy, Regionale tickets are very inexpensive, but don't forget to validate locally purchased tickets or again hefty fines! That also applies to Metro and Bus tickets.

For travel on the express trains such as the high speed Freccia, you can save a lot with advance purchase Super Economy or Economy tickets but you MUST be willing to commit to specific departure times. Super Economy tickets are non-refundable and non-changeable after purchase and Economy tickets have limited flexibility. You can also travel on the competing high speed Italo trains on the high speed routes.

To buy tickets in advance, you might consider www.trainline.com as they sell tickets for many rail networks around Europe, including the two main networks in Italy. You'll have to register on the website first, including payment information, but after that the process is very easy. I haven't checked recently but I believe there may be a small surcharge on some purchases. You could also have a look at Loco2.

Thank you for all the advice and information it will be very helpful and I will continue to check into the websites that were provided. We have traveled by train in many countries throughout Europe and really enjoy traveling that way very relaxing. But I always think its good to get advice from others who have traveled via train especially in countries I haven't traveled especially for an extended period of time. Always welcome more advice. We plan to spend a couple weeks just taking our time through Germany and then 3 - 4 weeks in Italy. Thanks again for your replies.