Dfyjkt

My story is a bit complicated but I'll try to explain it to you. On January 9th I entered Portugal (Schengen area) and stayed until the 16th of January, on which I flew to Rome, Italy to study abroad until May 10th. I have/had a student visa for Rome, which lasts until June 26th despite my program ending on May 10.

I flew back to Lisbon on May 10. I'm wondering if I should apply for a visa extension in Portugal since my flight only leaves for the States on August 15th. I don't know if I'm still protected under my student visa until the 26th of June and then my tourist visa starts. OR should I leave the Schengen for a couple of days and then return to Portugal Or should I just extend my visa? I'm a little confused.

Assuming that you're not an EU/EEA national:

May 10 through August 15 is 97 days. That is more than you're allowed to spend in a Schengen country that you don't have a long-stay visa from.

So no matter what the various permutations of long and short visas (and whether your nationality does or does not require visas for short visits), you need to change your travel plans to spend at least 7 days fewer in the Schengen area.

There are no possible "visa extensions" that will help you in that situation -- other than getting a long-stay visa or residence permit from Portugal, which you most probably will not qualify for.

Those 7 days or more need to be complete days, counting midnight to midnight. They don't all need to be together, and don't need to be at the end of the period. But there must be 7 of them. They can be spent either outside Schengen, or in Italy while your long-stay visa is still valid.