I will likely be traveling to Italy in February with my wife, my mom, my step-dad, my brother, and my brother's girlfriend. We're going in February because my brother is a public school teacher, and he has a week off of school in February for "February Break" (which I've learned is a New York / New Jersey thing). As a result, we'll only be able to go for 7 or 8 days, but my wife and I are thinking about staying longer after the rest of my family leaves.

The plan right now is to fly into Venice, spend a few days there, then travel to Rome / Vatican City, then Naples / Pompeii, then fly out of Rome. I'd also really like to go to San Marino as well, maybe on the way down to Rome.

If Kenzie and I stay longer, I think we might want to visit Florence, Pisa, and/or Milan as well, but the problem is the route. It would be weird to start all the way north in Venice, head all the way south down to Naples, then go north again. But I suppose that's really the only way to do it since my mom and brother want to go to Venice, Rome, and Pompeii.

Have any of there Europeans out there been to Italy (or either of the two countries within it)? Can anyone offer any suggestions about which cities are worth visiting, and what to do in those cities? Is it worth making a stop in San Marino? Is there anything worth doing there, or would the stop just be for the sake of saying that I've been to an additional country?

regardless make sure you enjoy the food.

I have personally not been anywhere outside of the United States. However, I have had friends that have gone to Italy. Two of my friends (husband and wife) live in Italy once or twice a month during the year as they have a house.

They love going to Milan and Venice. They also like going to Rome for the history. They have tried to go by the Holy Seas (Vatican) but that is heavily guarded.

As a meteorologist I will tell you Italy for the most part except for the higher elevations has a Mediterranean climate. November to March is their rainy season. Temperatures are climatology mild except for the higher elevations.

I've never been to Italy, it's one of the destinations still pending on my list. I know people who went, both back in time and in present days, but I only stepped on it for a flight connection xD

You basically mentioned all the main cities of interest in Italy, even I would have only included a couple more at most. Just walking through them is an entirely different feeling than cities elsewhere, history is at every corner they say. Specially in Naples and the fervor for Maradona, a soccer player, I was impressed when a friend told me how it's all over the city.

As for San Marino, all I know is that it's on hilly terrain, so much so that things like a flat street or path don't exist. The fortress atop the mountain is considered of important heritage, but beyond that it hasn't anything special to it as far as I know.

And yes, like classgame said, make sure to enjoy the food. Beyond traditional Italian dishes that have been exported globally, there are several local dishes in certain cities or regions that are absolutely worth the try, even recipes of the same dish may vary. Like Pokemon told us many decades ago, gotta taste 'em all!

Not going to list any cities since I've personally only been to Rome and the Vatican and that was in 2012 (definitely recommend it! my mom even got to sit in the Pope's personal chair in the lift due to her disability lol)

I do think since you're traveling North to South that you could experience a big shift. Italy has never been a great country when it comes to wealth distribution, the North is very rich and the South has historically been poor. I don't know how much of that you'll witness in the bigger cities on your list, so I think short road trips to see some smaller cities or towns in the surrounding area could be interesting.