We will be in Florence for 5 days in October and have another 9 days before we fly out of Milan. We wish to visit Venice (2 days) and Cinque terre and Milan(2 days) We would have been travelling by train up to this point and dont mind train,bus or tours.Could you please advise us which way would be the most convenient way to cover this distance. It appears we will cover some ground twice. We are two sixty something sisters traveling together.

I'll give you my ideas, but I also suggest you repost with a country tag for Italy.

So you're in Florence > train to Cinque Terre > train to Venice > train to Milan.

Yes, you will pass Milan and central Italy on your way from the CT to Venice, but since you leave from Milan, and since Venice and the CT are on opposite sides of northern Italy, it just has to be that way.

Your longest distance will be from the CT to Venice. The rest isn't too bad.

If you weren't started in Florence, I would perhaps suggest a more circular route, but that's set, isn't it? Or that's the way I read your message.

So nine days for me would be two in the CT, 4 or 5 in Venice with a day trip or two, and 2 in Milan. I think the more time in Venice the better because there are so many things to see, and there are so many great day trips.

If you did 3 days in the CT, there are a couple of good day trips from there, too, but they aren't as easy as those from Venice. The CT pretty much requires that you get in and out of there via La Spezia by train, but there are boats, say to Portovenere, but that is very weather dependent.

Pack light.

Yes, I'm afraid you will have some backtracking involved! We're it me, I'd head straight to Venice on an express train from Florence. Then make my way to the CT. The fastest way if using public transport may be to take that same express train back to Florence and then catch the train that will take you through Pisa and on to La Spezia (where you disembark to catch a train that goes to the five villages). There are many folks with more expertise than me on this board, so I recommend "topping" your thread in the morning so that more folks will see it. Also, your title isn't very specific, so you could consider re-posting with a title that has more info about your question.
Happy Travels,
TA

Trenitalia schedules
Www.trenitalia.com. Look for the English flag icon for the website in English.

To go to the Cinque Terre, for the least doubling up and backtracking you should at first fly into Genova, then move to Florence, then to Venice, then to Milan.

Florence to Vernazza (picked at random from among the Cinque) takes about 3 hours, on the way you can interrupt the journey for a look around Pisa, well worth it. So count half a day to get to Cinque Terre, hoping for good weather, otherwise don’t go.

Vernazza to Venice - trains go along different routes (via Genova-Milan, via Parma-Bologna, via Pisa-Florence, via Rapallo-Milan, via Sestri Levante-Milan), count on between 6 to 7 hours (slow regional trains for some of the way), in other words the best part of a full day.

When I read the OP's post, I took it to state that the beginning point (Florence) and the departure point (Milan) were fixed.

If you are not including Lucca and Pisa in your plans for your five day in Florence, consider adding a day for Lucca, and then stopping in Pisa on your way to CT. And/or a day trip south to Orvieto while in Florence.