Florence & Tuscany - Thoughts on this plan

First time to Italy… I wouldn’t go too crazy with the day trips. Three nights in Florence will barely scratch the surface of this great city. Siena can mostly be covered in two days so you might have a day there for a quick trip. I’d focus on the major sites in your three primary cities, Venice, Florence, Siena.

First time in Florence we spent five days. One was a day trip to Pisa. And we still found plenty to do our second time there, and can’t wait to return. Don’t waste your vacation traveling all over the place when there are amazing sites within walking distance.

I’d do three nights in each city, skipping Bologna. You’ll find plenty to do without day trips. If you tire of the crowds, sure, venture off for a day. But you’re trying to squeeze in a lot in 10 days.

Have a great trip. I cannot wait to return to Tuscany!

What time of year is this trip going to be?

I have to agree that you are planning too many side trips for such a short trip. I commend you for not trying to stay in too many places but trying to take too many day trips can have the same effect of making the trip all about transportation and not enjoying.

I like the general plan but remember that 3 nights is only two full days on the ground so even with 4 nights/3 days in Florence the city deserves 2 days and then maybe a day trip. Pisa and Lucca make a nice loop by train from Florence. You could also do Bologna as a day trip from Florence but you seem to be concentrating on small towns instead which is fine.
Viareggio is really just a very blue collar beach resort town with the usual distractions and I'm not sure I would spend a day of a short trip going there unless you really want to see a beach.

Siena is beautiful, if very touristy, and deserves at least a day one it's own. San Gimignano and Volterra would make a good - if long - day trip from there but you'll need someone else to work out the transportation to do both in one day. The Pienza/Montepuliciano area is at least an hour and half away and is on the very edge of what I would consider enjoyable as a day trip and I would work to visit something closer instead.

The cities you're staying in have their own charms so don't forget to explore them rather than planning to just use them to see other things. I know these things seem completely reasonable on paper sitting at home with a long list of places you want to see but part of it is enjoying the places you've travelled to see. Especially in rural Tuscany part of the experience is slowing down to experience the lifestyle that depends more on season and weather than the hour of the day. As tourists it's hard but remember to leave some time to breathe. I think something as simple as a languid spritz (or two) in Siena's el Campo as dusk falls across the piazza is one of Italy's real experiences. And if suddenly a contrada based flag throwing and marching band procession breaks out while you're there that's a real Sienese evening.

Lastly what time do you fly out of Venice? Early morning flights out of Venice can be tough so I would suggest cutting out the vaporetto and staying within walking distance to Piazza Roma so you can head directly to bus/taxi to get to the airport if your flight is early.

Hope that helps, have a great trip!
=Tod

To avoid a split stay in Venice- first see if you can change departure flight to Florence.
If not- consider traveling onward at arrival to Florence or perhaps Bologna.
Put all your Venice nights at end.

With just 10 nights stick to 3 locations if possible. Each location change eats up at least a half day.

Tuscany- the places you have listed for day trips are not all easily done without a car.
Lucca/Pisa is easy by train from Florence
Siena by bus- better than train as bus drops you up in town.

SG- easier from Florence- train to Poggibonsi then bus
Volterra- no train- so bus from Siena or Florence or SG- will take some time.
Pienza no train station- bus only
Montepulciano- train station is outside of town so it’s a long train ride from Siena then a bus

All of the above better done with a car or a private driver.

Check toursbyroberto.com- gets good reviews here- he books up early.
He can take you to a few hill towns, wineries, etc.

Try this
Arrive Venice
Train to Florence- fast train about 2 hours
Florence 3 or 4 nights with maybe 1 day trip
Bus to Siena
Siena 2 or 3 nights with maybe 1 day trip (w/Roberto)
Train back to Venice thru Florence
Venice 4 nights
Depart Venice

Make sure you have your transportation to/from Venice airport worked out.
Morning flights out of Venice can be an issue- if your flight is past 10-11 it’s fine- you just need to know how to get to airport on time!

Some info here (Pat’s post sharing Aussie’s advice)
https://community.ricksteves.com/travel-forum/italy/venice-suggestions-where-to-stay-and-what-to-do

Thank you! I have made notes from each response. ChristineH, I took your advice and changed order of towns to visit. Our flights do need to remain in and out of Venice.

I have a few questions for our new itinerary:
Upon landing in Venice end of March, will high speed train to Florence.
Can someone please share the name of the train line so I can pre-purchase our ticket? Is the ticket good all day or do I have to choose a specific train time?
4 nights - Florence

3 nights - Looking for town in hills to experience staying in quieter area w vineyards, wine tasting, good restaurants. I think Siena is too busy.
- maybe San Gimignano and day trip to Volterra one day. Is there a bus from San G to Volterra?

3 nights - Venice (Will plan for return to airport for 11am flight)

Trenitalia and Italotren are what you need for train tickets. Be sure to use the Italian spellings for searches (Firenze, etc.)
You lose out on the advance purchase discount, but I don't buy tickets in advance for arrival because your flight could be delayed and they are not refundable or changeable as far as I know.

I would consider renting a car for your Tuscan stay.

Here is a map of the Tuscan towns easily visited by train and the bus for other towns.
https://www.chianti.com/greve-in-chianti/what-to-see.html

The issue is that in general smaller towns in rural Tuscany are not well served by public transportation. One example is that there is a bus between SG and Volterra but I believe it is only a couple of times a day so any trip is dictated by the earliest and latest bus on a given day. So it's an hour each way for the direct bus and you're stuck with the available times - and Sundays are even worse. Siena is an easy recommendation since it is pretty, interesting and one of the local hubs for transportation and tours.

If you want a smaller place there are train+bus combos like San Gimignano and Corona of Under the Tuscan Sun fame. Both are very pretty and very well touristed. Arezzo is about the population of Siena but much less touristed and the old town section is certainly smaller than Siena so it has modern Italy as well. Arezzo has always played second fiddle to Siena through out history but it has it's charms, is easily reachable by train and is close to Cortona some of the towns on the other side of the valley from Siena.

If you really wanted to concentrate on wine centric areas you could check out Greve in Chianti which is in the middle of excellent wine country and I believe has continuing bus service to Radda in Chianti which is another wine centric town and both have tasting rooms. I've never been but the Casa Chianti Classico wine museum and tasting room (which is in a restored convent) gets rave reviews and I would love to go as some of my favorite wines come from this area. Also Castellina in Chianti and Gaiole are on the same bus line I believe. Greve is easily reachable by bus from Florence (1hr) along with the other towns but it is an isolated valley so to get to Siena without a car you would probably have to go back to Florence or find a way to the inevitable Poggibonsi.

Hope that helps, even if it's not great news.

Have a great trip, rural Tuscany is as beautiful as advertised,
=Tod