My friends and I are planning a trip this summer to Europe. We want to visit Portugal, Spain, France, a quick stop in Amsterdam, Italy, and Greece. Firstly, is this an even remotely possible itinerary for an enjoyable trip? We'll be traveling for a month. Secondly, We want to get a Eurail pass. If we get a 1-month continuous global pass, is it realistic that we'll want sleep on the train often? Has anybody traveled like this? How would this compare to a flexi pass? Obviously we wouldn't be able to sleep on the train every night or we'd waste the pass. If we have only 15 days of train travel for example, we'd need to buy other ways of transportation unless we stay in only 15 cities. Would we be inclined to buy other forms of transportation with a continuous global pass anyway? Basically, we want to travel cheaply and w/o too much of a plan except a general route.
Personally, I would do half that in a month. Portugal and Spain make sense together. In a rush you might see a little of Southern France and Mediterrainean Italy - but it would reduce your level of enjoyment along the way. Maybe you could see some Portugal, through Northern Spain, some specific parts of Southern France and end in Italy - flying open jaw into Lisbon and out of Milan or Rome. When you build your itinerary, plan for no more than two major sites per day (throwing in other sites if time allows). Also plan at least a half day moving from one place to the next, a whole day if it's a long haul. It won't take long before you have exhausted your month. Trying to include Amsterdam and Greece significantly increases the time spent in transit and is a really bad idea IMO. If it's you and multiple friends, I would consider leasing a car rather than training - it may save you a significant amount of money you could then splurge on other things. Plus you can travel on your own schedule rather than wait for connections.