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None of us are qualified to answer that question, so I would highly recommend contacting the Embassies of the countries you'll be visiting.

Based on the situation here in Canada, travellers with medical marijuana permits in their home jurisdiction regularly arrive at the border, only to be told that their permit has no validity here. They are subsequently placed under arrest and the drugs confiscated! Whether they're charged or just deported is at the discretion of the CBSA and RCMP. I expect this is similar in other countries. The same situation occurs with Canadians travelling to Washington and other states which now allow marijuana. They fail to recognize that they're dealing with Federal laws when crossing the border, and not the laws of the state.

Are you talking about marinol or unregulated marijuana?

There is no international treaty of reciprocity of marijuana laws, so if he is caught, he will be considered in the same context as a drug smuggler.

I absolutely would not do it. Talk about ruining your trip from the outset!
Drug laws vary from country to country and even the more liberal ones have a level of tolerance for controlled substances that won't allow you to just bring them it to the country.
Marijuana is easily accessible in Amsterdam but it is still regulated. You can use it in designated areas such as coffee shops but it is still illegal to transport it - coffee shops are one of the only places that have an exception to this rule. Any amount above 5 grams for personal use is still illegal. You cannot transport it or bring it into the country from somewhere else. That said, there is a relative high level of tolerance for use when compared to most countries.
Italy has some tolerance for recreational cannabis but it is still illegal. Using it while there isn't really the issue though...it's bringing it through customs. Since this is your point of entry into Europe you should have none with you. Too risky.

Medical Marijuana cards are not even recognized by the U.S. government or states other than the one where the referrals are issued let alone other countries. If his condition is so dire that he can not go without than I would restrict your travels to Amsterdam.

I would be careful even with Amsterdam because they have laws that are different if you are a citizen or visitor. Marijuana is still illegal in the US federally. I believe TSA and customs would come under Federal law. We are always careful even with regular medications to have our prescriptions properly marked.

I sure hope you wouldn't follow the advice of a stranger on a topic that has the potential to land you in jail. I'm assuming you're looking for help finding a definitive (government) resource that would answer your question. How about asking your marijuana provider if he/she knows of any such references.

In Italy having cannabis under a certain amount for personal use it's not a criminal violation rather an administrative violation similar to a traffic violation. However crossing international borders with them may have more serious consequences which I don't know. But I would listen to what Judy writes above. Someone who lives in a town called Grass Valley must know more than most of us.

Living in the UK I don't have a lot of knowledge of new US laws, but I do have a question:- what's a medical marijuana card?

Does it give you permission to go around under the influence? Or carry drugs in the car?

Also, surely you will have to get from Italy to the Netherlands. How will you travel? If flying, all airports are full of drug sniffing dogs, and if taking the train, many train stations are regularly visited by the same drug teams.

Italy announced that will introduce medical marijuana during 2015; it will be produced under strict controls in the military pharma plants in Florence. But details are still to be worked out. In Italy any medical drug that could give dependance is strictly controlled - and importing the thing instead of buying from an authorized source is wholly another matter.

Even in the UK it is possible to be prescribed a medical cannabis product - Sativex. An EU resident can take such drugs from one country to another supported by the prescription. This is not something open to a non resident or someone without a prescription issued in the country.