Moving around and Itinerary


New member
We were thinking of flying into Rome for 2 days then go to Florence for 2 days (doing day trip to Pisa) then 2 days in Siena and another 2 days in Venice. We would like to know if this is a good itinerary and if you have any suggestions?

The other concern is getting around especially in the Chianti region. We will be relying on public transport between the towns but maybe to rent a car or explore by bicycle the wine region. We will be traveling in October and are big on wine tasting and would like to visit a couple estates during our stay. Mainly doing some tastings from Florence and Siena as part of a day trip. What mode of transport is best to explore the region? Any advise will be greatly appreciated.


Well-known member
From Rome to Florence and Chianti: a Tuscan Itinerary

Ciao Shaun and welcome to the Forum!

Your itinerary sounds great to visit the must-see destinations of Italy :)

As you are moving north from Rome and you soon meet Siena, I suggest you first visit Siena and then pass to Florence.

The best way to explore Tuscany is actually by renting a car, especially for getting around the Chianti region and do some wine tasting. A car will also allow you to move more freely and fully appreciate the beautiful Tuscan countryside and its unique landscapes.
The winding roads of Tuscany are then very charming!

Here you will find useful information about moving around Tuscany by car, while here on getting around Chianti, also by bicycle.
Chianti is famous all around the world for its superb wine production and Wine Tasting in Chianti cannot be missed from any Tuscan itinerary!

Among the best Chianti wine estates, I recommend a visit to Fattoria Viticcio, right outside Greve in Chianti, the beautiful and ancient Castello di Vicchiomaggio, and the famous Castello di Verrazzano, all giving the possibility to visit the wine cellars and taste their delicious Chianti Classico wine.

If you decide to stick to the towns you’ll not be needing a car at all; you might conveniently use the train to move from one city to another. Pisa can be easily reached from Florence in just 1 hour’s train ride. You can check train timetables as well as ticket fares at this link.

If you decide to not rent a car and wish to explore the Chianti region and its hill top towns, I suggest taking a guided tour like this one of Chianti and San Gimignano, that is great as you will visit all the most beautiful sights of the area, such as Greve in Chianti and Panzano in Chianti, taste the superb Chianti wine in a family run winery, and finally also visit the extraordinary medieval town of San Gimignano and its famous towers.

Another very good tour I highly recommend is the Chianti Wine Tasting Half-Day Trip from Florence.

In case you also need some good suggestions on where to sleep, please get back to us with more details and we’ll be happy to help you ;)

For now you may find it useful to have a look at the list of selected accommodations in Tuscany and lodgings in Florence.

Finally you may find this article on a 5 days Itinerary in Tuscany very interesting.

Enjoy planning your trip to Italy and its wonders :)

Post again for any further suggestions needed!
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Active member
Re wine tasting in Chianti

The idea of dropping in on a few vineyards for tasting is very appealing, and there is absolutely nothing to stop you from calling them up and arranging your own visit, however I would recommend booking some sort of tour if you really plan on relaxing and enjoying yourself. Drinking and driving is as strict, if not more so, than any other country in Europe and having to say 'no' when they bring out the reserve (why save the best til last??) is not much fun.

I would recommend Slow day in Tuscany for a tour including wine tasting in the Chianti Classico region.

Alternatively you could search for a tee-total travel buddy to do all the driving!! ;)

Buon Viaggio