MotoGP Trip to San Marino

What is your home airport?
The Cinque Terre deserve 2to 3 nights. Rome about 4 nights.
Bologna can be easily visited in a day.

We're flying into Rome and out of Milan from/to San Francisco. The MotoGP race takes us off the beaten path from the 'common' itinerary of Rome, Florence, Cinque Terre, and Venice. We're limited to 14 days, which includes travel, but I know that we can do it without having to rush through everything!

I'm going to say something radical and somewhat blasphemous here.

Plan your trip around the MotoGP race. Get your lodging squared away for that first. We didn't decide to go to Le Mans until about 6 months before the race. By then, the closest lodging was an hour drive away.

Stick to the eastern side of Italy and go to Venice instead of Cinque Terre. I was in the Cinque Terre in July. I think it's way overrated, especially if you are familiar with the west coasts of Canada, the US or Mexico.

It's too early for specific train schedules for September at Trenitalia, but you can put in some dummy dates to see routes, times and potential costs for anywhere you want to go. Make those dates about 3 months from now. Stick with fast (Frecce) trains as much as possible. I made the run from Roma Termini to Bologna in June. There's something pretty cool about seeing that you're going 250 km/h on the digital monitor.

Take a closer look at any options with only 1 change. Sometimes those with 2 are actually faster.

In your case, it will probably be faster to go through Bologna to Rimini and back a bit to San Marino. The 2 changes could be to local slow trains or to 1 slow train plus a taxi. Use Rome2rio to see what I mean by that and to see a map of the route.

Two weeks that include flights is not really much time. I'm assuming you meant the following: leave the US on day 1, arrive in Italy on day 2 ... leave Italy on day 14, arrive US on day 14. Remember that to have a full day in a location, you need 2 nights.

For your last night in Italy, I highly recommend the Hotel Berna, almost across the street from Milano Centrale. I wouldn't stay at the airport unless I had a very early flight. You really do need the 3 hours that they say are required for flights back to the US. Malpensa is large and it seems like a very long distance to walk from the entrance to check-in, through passport control, through security, through many opportunities to buy duty-free stuff and finally to your gate.

Our initial plans for our recent Fall trip included going to San Marino for the race. Needless to say, the couple that was most motivated to see the race, backed out and then Rossi got injured prior to the race so, we didn't miss much. Biggest issue during initial planning was discovering San Marino is a bit isolated on the Eastside of the country. San Marino itself and Ravenna I was most interested in, nearby Remini I understand is a somewhat low-brow riviera. If you can keep your visit to the Eastern portion of the country, that'd save a lot on the travel and maximize your time; Rome is several hours and train changes away, Milan's two airports I really like flying in/out of but, it's a bit of a train ride away.
Here's a possible itinerary:
fly into VCE
Venice 3nts
Bologna 2nts
Ravenna/San Marino/Remini 2-3nts
Ferrara 2nts
Verona 3nts
Padua 2nts
return via VCE

Thank you all for such great recommendations. We're adding a day because of the train travel, but here's our tentative schedule...additional feedback is greatly appreciated!
- Trastevere: 3 nights
- Bologna: 2 nights
- Rimini: 2 nights
- Cinque Terre: 3 nights
- Milan: 1 night
With the exception of Rimini, every lodging accommodation is through Air BnB.