Stay in Florence or Siena?

Regarding Florence versus Siena, it depends on your interests. If you enjoy art or have a particular interest in the Renaissance, definitely stay in Florence. The medieval influence is more prominent in Siena. I far prefer Florence, primarily for the reasons noted above. Also, in Siena, I felt like the modern city intruded more, although that may be a function of the area in which I stayed (at the convent at the site of the home of St Catherine of Siena, near San Domenico church).

We spent a week in Florence and my husband, much to my surprise, said he could have stayed longer there because there was so much to see and do in such a pleasant location. My first trip to Europe, I spent 3 weeks in Florence, so I know what he meant. I've seen many amazing churches, but for some reason Santa Croce is at the top of my list. We stayed in an apartment right across the street from it (and the Leather School).

We took a (long) one-day coach tour that included Siena, San Gimignano, lunch at a "wine estate" and Pisa. I normally don't like big bus tours, but our daughter and grand daughter (age 5 at the time) came up from Sicily for the weekend and it was the most efficient thing we could do. The 5-year old did great. So did the rest of us.

The tour was the Walkabout Florence "Best of Tuscany" one -- https://www.walkaboutflorence.com/tours/best-tuscany-tour. It gets very good reviews from Trip Advisor. We certainly enjoyed it. Both the guide on the bus and the Siena tour guide were excellent.

I highly recommend it if you want to see a lot in one day with good guides. It left from the Florence train station and returned there at the end of the day.

Lo, thank you so much for the info about the Day in Tuscany Tour. I've bookmarked it for next year's trip to Italy. It sounds perfect for us with our limited time.

Ben,

You may be moving around throughout Italy too much even though you are planning 18 days. You may wish to eliminate Venice or Amalfi coast.

As far as your specific questions, a day trip to Florence is probably not long enough. I've been to Florence 3 or 4 times and have still not seen all the sights. A day trip to Siena may be possible to get a flavor of this town, but there is no direct train, so public transport would be taking a bus or two trains.

I really love both towns and was just in Tuscany and missed Florence this time and spent time in Siena instead.

I don't think that I would stay in Pisa, you could visit the Leaning Tower and Duomo in Pisa on your way to Cinque Terre (the train station had a checked luggage service in the past).

If you are really into hiking, I can recommend some specific all day hikes in the CQ.

Nick

Stay in Florence. From there you can visit both Siena (by bus or train) and Pisa+Lucca (by train) in two separate day trips. Florence deserves more than just a day trip from Siena, and going to Pisa/Lucca from Siena is a longer trek. So Florence is the perfect hub.

Taking as a base your itinerary you should do things in this order (via train):

Venice (3 nights, with day trip to Murano and Burano or Padua)
Florence (4 or 5 nights, with a couple of day trips in Tuscany)
Cinque Terre (2 nights)
Sorrento or Amalfi Coast area (4 nights)
Rome (4 nights, with possible day trip to Orvieto)
Fly home from Rome.

The total is 17-18 nights on the ground.

I agree with Roberto, Florence is a better base to do daytrips and has more to offer with a longer stay. I definitely would not stay overnight in Pisa. For the most part, Pisa is about the cathedral complex. Lucca would be a better overnight choice. I would not try and do both in a day. Siena can be done as a daytrip, although it is better with a couple of nights.

I've spent weeks in Florence, and that would definitely be my choice. IMHO Siena can easily be done in a day. I haven't been to Pisa, mostly because I have had multiple friends go there and they all said "skip it." Maybe one day I will work it into the itinerary! A good friend of mine does bicycle tours of Tuscany, (He's actually a friend of my young son) and he always tells me to go to Lucca. He's lived in Italy for years, and has "been there, done that" at his leisure, so I tend to listen to his advice, because he knows I only have a few weeks as opposed to his entire year. He still recommends basing in Florence, because there's just so much THERE! I agree with Roberto's itinerary, especially since your wife has not yet been to Italy, and I think she'll enjoy seeing these cities. Do Either CT or Amalfi, 18 days really isn't enough for all of it -- unless you want to see Italy from the window of a train or bus.

PS: Nothing beats sitting in a piazza in Florence at night, having a little wine, and enjoying the beautiful fountains all lit.......so, cut your itinerary down to just three locations and actually enjoy just being there -- which is what Italy is really about.

I think your entire itinerary is doable if you want to see it all, assuming you have at least 17 nights (better if more, of course). Just follow my advice above on number of nights on the ground.
Of course different people have different travel styles. Some (like me) would get totally bored staying too long in the same place. My rule of thumb is to avoid one nighters (too much hassle changing hotels), therefore I try to stay at least 2 nights in the same hotel. However unless I'm in a place with plenty of day trip opportunities (like Tuscany or the Gulf of Naples area), I can't stay more than 4 nights in a place, not even in New York.

I just about always agree with Roberto since he's from Florence. And Donna's also very well versed on Italy.

We stayed in Florence for a long weekend and then moved to the countryside south of the city--NW of Poggibonsi on an agriturismo. So many great tourist sights are off the train lines, and Tuscany is best seen via rental car on day trips. We turned our rental car in at Hertz in Orvieto--another great hill town that's 70 minutes north of Rome via train.

I would say, given the time allotted, that you choose either C/T or the Amalfi Coast. There are so many great sights in Northern Italy that you could see with the extra time.