Sept / Oct. Itinerary/Train travel

Richard, you itinerary looks just fine. From Milan to Vernazza, it will take about 3.5hrs and you will be on 2-3 trains depending on the run. You can buy the tickets online. You will receive one ticket for each train that you will be on. If you are traveling after June 8, you won't be able to see schedules as Trenitalia hasn't fully u-p-dated their schedules and will do so on June 12. The website is www.trenitalia.com From Vernazza to Florence, and for most runs, you will be on Regionale trains all the way. Again, another 3hrs. You cannot buy tickets for the Regionale trains online more that 7 days out from the time of travel. You can buy them in Milan if you want. Regionale tickets are good for 60 days when you buy them in Italy. No trains listed on the ticket. You can get on any Regionale train making the run shown on the ticket. You must validate this ticket in the little machines in the station before boarding. From Florence to Venice and from Venice back to Milan, you most likely will be on the very nice high-speed trains. You can buy tickets for these runs online 119 days out once you get by the u-p-date barrier of June 12. You can even get reduced fares for these high-speed runs if you are willing to accept non-exch/non-refund tickets. Seat reservations will be provided with the purchase of the tickets.

My only suggestion would be that you not circle back to Milan to leave. How about flying into Venice and out of Milan? (Only reason I'm suggesting reversing the direction is that it can be challenging to make really early flights in Venice, but into Milan and out of Venice is possible.) Since you've got a nice span of time in Venice, I suggest being certain to explore some of the smaller islands (beyond the Murano/Burano trips that most do). Torcello has lovely very early churches and a tiny population, and there are a number of other interesting islands to explore.

Thank You for the information. Richard