Quick itinerary: Landed Florence Sept 8 to meet with daughter/SIL for 5 days biking around Lake Garda area, then transferring to another bike hotel at Cesenatico on the Adriatic coast. Daughter/SIL returned Florence the 19th and back to Bellingham today 9/20 (FLR-CDG-SEA). My BIL/SIL independently had booked a biking/cooking class in Pisa, then also headed to Cesenatico and the same hotel. We had one night's overlap and no, we didn't actually coordinate this.
Daughter/SIL and I took the .Italo high speed train from Florence to Verona, arranging a car transfer from Verona to the hotel in Peschiera del Garda. The train from Florence was 40 minutes late, due to "unspecified system delays."
There was no reasonable way for us to get from Peschiera del Garda to Cesenatico by train. It could have been done but would have involved transfers through Bologna, etc. We arranged a car transfer between the hotels (which was actually offered).
My BIL/SIL were taking the HS train from Pisa to Bologna, then transferring to the local for Cesenatico. The local train was cancelled due to a scheduled strike. They had to arrange private transfer. There was no notice given by Trenitalia.
Leaving Cesenatico, daughter/SIL were returning to Florence, taking a local from Cesenatico to Bologna, then transferring to a HS train to Florence. I was taking the train to Naples (because Pompeii). As it turned out, we booked the same regional train out of Cesenatico. I booked from the main train station via Trenitalia, 5 km from the hotel. My millenial daughter used Google maps to find that there was a station just on stop up the line, just a few blocks from our hotel. So when leaving Cesenatico, we all went to the same station and I bought a 1,50€ ticket for the one stop.
This turned out to be a wise move, as when we got to Cesenatico there were a big bunch a Ironman triathletes with multiple bike boxes trying to board PLUS 200-250 teenagers trying to cram on. It was a massive sardine crush and we were delayed 20-25 minutes. Fortunately the teens detrained a few stops up the line. We arrived in Bologna 15 minutes late.
Bologna Centrale: All the multilevel complexity of Berlin's Hauptbahnhof with none of its elegance and combined with the opaque confusion of Frankfurt airport. Still, if you were alert to follow the signs you eventually got to the correct track pair. My train switched between tracks 18 and 19 twice before it arrived (either side of the same platform, but do try to keep up).
My Trenitalia business class / silent zone fare to Naples was 47.90€. It included a bottle of Prosecco to welcome me aboard. Later there was espresso, but cappuccino was not available. Two demerits. The train arrived more-or-less on time.
From Naples this morning I took the 40-minute "Circumvesuviana" train to Pompeii. Fare for 3€ one-way. I had a 10:30 tour, the 9:00 train was absolutely packed. Sardines time again. The return train early afternoon was fairly full but seats were available. The train was loud and bumpy.
My final train for this vacation was simply Napoli Centrale to Roma Termini, again quite comfortable Trenitalia business class. Fairly expensive this time around because I forgot to book it until the last minute.
A few takeaways:
Book in advance like airline tickets. Italian trains are demand priced. The 47.90€ from Bologna to Naples was a saver fare. Booked late, just Naples to Rome was more.
When taking HS into Naples, note that many trains only stop at Napoli Afragola and do not go all the way into Napoli Centrale. Don't make my mistake. There is no taxi service from Afragola. You can, however get a train from Afragola to Centrale for 15€ same day purchase.
Be aware Italian trains (in my experience) are not spot on time like I've found on the Austrian ÖBB, German Deutsche Bahn, or French TGV. You might consider padding your connection times a bit.