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Me and my wife are planning to travel Italy for two weeks. Here is the rough draft of our itinerary(23May-7June)

1. Arrive Saturday afternoon in Rome. Spend Saturday, Sunday and Monday night in Rome. The Sunday we will visit all the museums etc since on Monday all museums are closed(then we will do all the walks etc)
2. Travel to Florence via train (or possibly take the bus via Assisi). Spend Tuesday and Wednesday night in Florence. Spend the Wednesday visiting all the museums and sites.
3. Thursday - Hire a car in Florence and travel Tuscany for the next 5 nights. We have heard that San Gimignano is a great place to stay. We thought of staying in two different places over the five nights,what are your thoughts on this? Tuscany is our at leisure time where we want to soak in the Italian culture and very much interested in wine tastings etc. what are the best places to stay in to be able to experience the wine of the region? I have heard that you need to book for a wine tasting. Which farms should we be visiting? How much does a wine tasting go for? We would like to stay in farm houses if we can afford it(have heard they can be quite expensive). Any recommendations?
4. Tuesday - drive to Pisa to view the leaning tower etc and drive through to Cinque Terre where we drop the car off(if this is not possible we drop the car off in Pisa and take a train to Cinque Terre. Here we spend two nights to do some hikes and just enjoy the scenery)
5. From here we travel to Venice(not sure if the best is to take a train straight or first go back to Florence the to Venice. We spend the Thursday and Friday nights in Venice and leave afternoon back to South Africa.

Does this sound like a well balanced itinerary? Tuscany is our highlight and we have heard such great things about it. If you can advise how to make best use of our time I would really appreciate it.

Kind regards


The Tuscan Expert ;-)
Staff member
Ciao Stefanus,

It sounds like a very good plan so far! I agree with using trains as much as possible, renting a car only for your time in Tuscany so that you can travel around the area and the smaller town on your own schedule and leisure.

San Gimignano is pretty central and would be a good base, but really any place between San Gimignano, Florence and Siena would be good as it is very central.

Actually, a stay in a farmhouse apartment might end up less than staying in a hotel for the equivalent amount of nights. The only consideration is that many of them ask for 7 night stay minimum depending on the season, so you'll have to take a look and then contact them to get a quote on your 5 days. Cost also depends a lot on the property itself, whether it is set up as a resort and more luxurious or as a working farm offering accommodation with the chance to see Tuscany from a local, authentic point of view.

These are some farmhouses I'd recommend you take a look and contact - the form on there goes directly to the owners. For many of these types of lodgings owned and managed directly, contacting them directly is the best way to get the best rates as well as answers to any of your questions or concerns:
http://www.tuscanyaccommodation.com/agriturismo-montalbino.html - working farm
http://www.tuscanyaccommodation.com/agriturismo-vernianello.html - working farm, makes wine and olive oil
http://www.tuscanyaccommodation.com/fattoria-viticcio.html - winery
http://www.tuscanyaccommodation.com/villa-le-torri.html - makes olive oil, vinsanto
http://www.tuscanyaccommodation.com/apartment-la-roccaia.html - an apartment close to San Gimignano

These are villas and farmhouses run as a small B&B or boutique hotel so you stay by the night:
http://www.tuscanyaccommodation.com/casolare-di-libbiano.html - near San Gimignano
http://www.tuscanyaccommodation.com/palazzo-malaspina.html - B&B in a palazzo in the center of a medieval hamlet

Day trips to Siena, San Gimignano, the towns in Chianti would all need to be included. If you have a chance, add Volterra, the Abbey of San Galgano, Monteriggioni to your destinations.

The only part of your itinerary which you have to look at is the Pisa - Cinque Terre - Venice part ---- only because returning the car makes sense since you don't need it in Cinque Terre, but the train ride on to Venice is LONG by train. From 5 to 6 hours long, as all connections are regional and there are several train changes to make, whether you head north through Milan, through Parma or Florence. Check
trenitalia.com to see for yourself, putting dates closer to your travel times if nothing comes up for end of May. Car ride would be more like 4 hours.... my recommendation would be to either to do Florence, then Cinque Terre (train), rent car on your way back down, either in Pisa and then do your 5 days in Tuscany as planned, with return of the rental in Florence to then catch a train to Venice. It would just be simpler. Sounds complicated but it would be just be switching the order of Cinque Terre to earlier.

How does all this sound?

Oh, almost forgot - as far as wine tastings, once you're in the area you will find small estates nearby that do wine tastings with only a call needed. Ask the owners where you stay at, they'll know who and will call for you. Most tastings are not very expensive, from 5 to 20 euros, some include tastings of other local products like salamis and other regional cured meats. Then there are also wineries with shops along the roads that allow wine tastings on the spot, without reservations. Ask your hosts - they know their area very well and can recommend places you wouldn't find or try otherwise! Many, many wineries are so small they don't export at all so you might find some real gems while exploring the area in this way.