He should write to the court where he was convicted. He should also make sure that he can travel in the places he wants to go with his conviction record while on probation. The country may not let him in, which can be a real financial bind.
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Any judge of the court that placed him on probation can approve the request. While I do believe that a lawyer would probably be beneficial, it is technically possible to do it with one. Simp,y write a letter to the judge explaining the circumstances, where you want to go and for how long. Point out that you've been doing well on probation up to this point and that you will continue to do so.
Each retired judge in Montgomery County has a regular judge assigned to hear his or her Violations of Probation matters or in the case, a probation modification request.
Your friend does not have to hire a lawyer but it could be helpful in getting this issue before the correct judge and heard as quickly as possible.
Your friend can look at Maryland Rule 4-346(b).
This is not an unusual request and will usually be granted.