Unsure about my itinerary...


New member
My husband and I are planning a trip to Italy for August of this year to celebrate our 25th anniversary. We plan to fly into Naples and spend 6 night in Positano. From there we plan to spend two nights in Siena, then 4 nights in Florence before leaving for 4 nights in Venice. I am so excited about this trip and have been thinking about it for years. We like slow travel with lots of time to sit at the cafes, drink wine and eat the wonderful food. We are the type of people that hate having busy schedules and rushing around from one thing to another. We like to wander around the cobblestone streets and discover what ever comes our way. I am not really into visiting all of the tourist sites although I will feel like I have to see some of these things when in Florence because it would be unforgivable if I don't see some of the museums. My husband and I are more into soaking up the culture and atmosphere around us and wine and food.

My concern is are we making the right choice to stay in Florence or should we stay in Chianti or Lucca. I would really like to experience the Tuscan countryside but at the same time we do not want to stay anywhere remote. We do like to be within walking distance of restaurants and cafes. Everyone has a different opinion on where to stay and they keep asking me to choose base on what I like. It is really hard for me to make this decision before getting there what I will like. We have booked Residenza d'Epoca Campo Regio Relais in Siena and in Florence we are staying at Hotel degli Orafi. We will not be renting a car while we are there and will have to rely on public transportation or tours. Some of the places I really want to see are Lucca, Chianti, San Gimignano, Valdorcia and possibly Monteriggion. If you could suggest the best itinerary for seeing these places that would be great. Also suggestion on if we should stay with our original plan or if we should consider staying in Lucca for a night or so. We want this holiday to be laid back and romantic not exhausting. Recommendations on tours would also be good. Thanks in advance.


Well-known member
If you have a car I would recommend staying someplace between Florence and Siena on SR222 like Greve or Castellina. We stayed in Castellina last September and it was a great base location. We drove to Siena, Florence and Pisa without any trouble at all. If you are still looking for a place to stay we stayed at Poggetto and it was wonderful. The owners, the apartments, the view and the location were all amazing, so much so that we are going back next June.


New member
Thank you JMFell for your response. We really hoped that we would not have to rent a car. We are interested in doing a tour or using public transit. We really want to sample the wines do I don't think driving would be a good idea after some of the wine tours.


The Tuscan Expert ;-)
Staff member
Ciao gypsyinme,

I think you already have a good idea of what you like and what you prefer to do, so I'd stick with your plan, particularly since you want to stick with public transportation and tours it makes sense to base your stay in Siena and Florence and use those as the starting points for any day trips you make.

You will also find ample wine shops in both towns where you can do wine tastings as well as find great food and wine everywhere you go both in Siena and Florence, so it isn't a requirement to go out and about to get a taste of great food and wine. But the countryside..... that is another matter! :D

Two nights in Siena and 4 in Florence are actually not that many days. Tours will be a good way to see most of the places you want to see because they allow you to relax and not worry about driving anywhere, as well as being able to drink at lunch and dinner ;-). You will only need to use public transport to get from Siena to Florence (take the SITA bus).

Looking at your itinerary, these are some options:
- 1 whole day to see Siena
- 1 day from Siena to the Valdorcia (Pienza, Montalcino and Montepulciano are the main towns in the area - there are some wine tours that will only focus on Montalcino or Montepulciano since they both produce two different DOCG wines, Pienza is famous for its cheese made of sheep milk called pecorino.)
- 2 days just to see and absorb Florence - get to see a museum or two, the churches themselves are museums as well. Definitely recommend the Santa Maria Novella church.
- 1 day trip from Florence into Chianti - I've listed some tours below that offer several options, some include San Gimignano and main towns in Chianti, such as Castellina and Greve, another includes Monteriggioni as well but not San Gimignano.
- 1 day trip from Florence to Pisa and Lucca - this you can do on your own. Take the train to Pisa in the morning, most of the sights are concentrated in the Piazza dei Miracoli where you'll find the Leaning Tower. Have a nice lunch, then take the short train ride (get train at the San Rossore station near the Piazza dei Miracoli) to Lucca and spend the rest of the day there. Return to Florence before or after dinner.

I don't think you need to stay in Lucca at all considering you're then heading off to Venice and all fast trains depart from Florence. If you're back in Florence for that night, you can just head off to Venice the next day at your leisure.

Ok so these are some tours to look at -- none are operated by us, but the first two are links to Viator, a travel tour consolidator we have partnered with. The rest I found through web searches to give you an idea of what is out there (lots!)

General tours, mostly using Florence as a starting point

Montepulciano and Cortona from Rome

DISCLAIMER: As I said before, we are not affiliated with any of the following, I am just showing you some options that came out through some searches. Take a look at them, see which ones best meet your interests and budget, contact them for more info and hopefully this will make it easier for you to decide for one or the other. Actually, if you end up using any of these, we'd like to know how it goes!! Any recommendations made on this forum by our users get votes and we in turn recommend them again to others ;).

Valdorcia Day Tour

Chianti Wine Tasting

Pienza and Montepulciano

Best of Chianti - Greve, Montefioralle, Castellina and Monteriggioni

Great way to see Tuscany is through wine tours, such as the various options offered on here
and here http://www.verbenabluviaggi.com/tuscany_trips.php?tipo=Tuscany day trips

Hope you find these suggestions useful, let us know if you need any more help! :) Hope most of all you're enjoying planning it all :)


New member
Thank you so much for your response.....I kept checking and hoping that you would reply. I love the information that you have been providing.


The Tuscan Expert ;-)
Staff member
Thank you so much for your response.....I kept checking and hoping that you would reply. I love the information that you have been providing.

You're very welcome! :) Feel free to ask any other questions you might have as you plan your itinerary, hope you're enjoying the planning :)