Family advice

My nephew’s girlfriend and her sister are planning a trip to Tuscany in September. We have been asked for some advice on where to stay and what to do in and around Tuscany.

It sounds as if the girls are looking for an authentic experience so rather than staying in hotels they are keen to get closer to the locals and try a villa for a week. They also want to know what to do and see in Tuscany. Here goes…

Where to stay?

Tuscany isn’t huge but basing yourself in the right place makes seeing the sights much easier and cuts down on driving time. We have traditionally based ourselves around Siena or just north of Siena in the Chainti region. This means that Firenze (Florence) is only an hour away to the north, Cortona is a little more to the east and some of the finest Chianti vineyards are on your doorstep.

It’s also an easy drive to the popular villages of San Gimignano to the west and Pienza, Montalcino and Montepulciano in the south.

Pisa is about an hour on from Firenze if leaning towers are your thing. And the eternal city of Rome is only two and a half hours south on the A1.

The villa

Tuscany is full of villas for rent and companies who rent them out. There are big operators like “Tuscany Now” ( and “Cottages to Castles” ( who have hundreds of properties on their books. We’ve used both of these and have not been disappointed but our first point of contact will always be “Chiantimania” ( and the lovely Olga and Francesca who run the business.

They are a small company with a collection of exclusive villas largely located in the Chianti region between Siena and Firenze. The villas feel more like homes rather than rentals and they have villas that can cater for all size groups. Chiantimania can also organise vineyard tours, olive oil tastings and Tuscan cooking classes. Olga found us our cottage last year in the Crete Senesi region just south of Siena. Given our modest budget she really had to hunt to find it but did a superb job.

And when dealing with Olga and Francesca nothing is too much trouble.

Things to look for in a villa:

  • A swimming pool – September will be hot
  • Air conditioning or insect screens on the windows.

Top tip: villas are rented from Saturday to Saturday. Many shops are shut on Sunday so make sure you visit the local Supermercato on Saturday afternoon and stock up for the next few days at least.

Getting Around

Tuscany is a part of the world that can only really be seen by car, bus or Vespa. There are trains running between some towns but for a truly independent experience a car is the best option. One word of warning, the major motorway system in Italy is superb but beyond that, roads can be a mixed bag. In a number of ways:

1) The quickest way between two points is a straight line – this is not a philosophy used much in the Tuscany countryside. Quite often what may look like a short trip on a map is a winding, twisting road. Generally in the countryside averaging 40km/h is pretty good. Having said that, the locals seem to be able to average twice that on the same roads so maybe it’s just us.

2) A road on the map is not always what it seems – in fact many roads marked on maps are what are called “white roads”.In kiwi speak that would be a dirt road. It’s not unusual but you just have to be aware that sometimes the asphalt turns to gravel and 80% of the time that doesn’t mean you’re lost or about to drive up someone’s driveway.

Of course the other 20% of the time it does.

Places to see

Where do you start? Based on our own experience and comments made by our visitors last year, the places liked most were:


Take a full day to explore Siena. Places to see include the main piazza in the old part of the city called the Campo ringed by buildings and dominated by the Torre de Mangia (tower). A climb to the top of the torre is a great way to see Siena and the surrounding countryside – but with it being 400 steps, it’s something for the fit and healthy.

It’s only a short walk from the Campo to the Duomo (cathedral) and even the non-religious should take a tour. Siena is also great for shopping which can be followed by a drink a Al Mangia bar on the edge of the Campo. This is a prime spot for that most Italian pass time – people watching.

Dinner choices in Siena are multiple. Al Mangia in the Campo is the place to be seen. The food is good but expensive and the view across the Campo is superb. Our favourite place is Osteria di Bigelli also in the Campo around the northern side (see Siena map). The food is very authentic, beautifully cooked and always a pleasure to eat. The service is friendly and helpful and the staff speak excellent english.

Top tip: parking a car in Siena can be difficult, particularly on Wednesday as that is market day. We use “il Campo” underground carpark (see Siena map). It’s about a 5 minute walk to the centre of Siena through the university grounds – very pleasant.


Or Firenze as the locals say. Firenze is definitely a day trip, possibly two days if you really want to get the most out of it. Visit the Duomo, the real David in the Galleria Accademia, Piazza della Signora with the other David, the Ufizi gallery, the Ponte Vecchio or as much as you can fit in.

If seeing David is your thing then make sure you book a ticket on the internet in advance to avoid the queues. Standing in line in the hot sun for hours is a sure way to sour a visit to Florence.

Florence is also great for shopping – gold, leather and anything designer. The area between the Ponte Vecchio over the Arno River, and the Duomo is packed with stores. When it comes time to eat we suggest getting off the main streets as the quality of food increases noticeably and the cost reduces dramatically.

On the way into or out of Firenze visit Piazza Michelangelo on the hill overlooking the city for the perfect photo opportunity. It will be you and about 1,000 other visitors to Firenze but it’s worth it.

Top tip: if driving to Firenze parking can be tricky. We always use a garage called Garage Ponte Vecchio at 46 Via de’ Bardi (see Firenze map). It’s a stones throw from the Ponte Vecchio and is located on the left of the road just before the roads become closed to public cars. It is expensive (8 Euro an hour) but it is right in the middle of Florence so saves a huge amount of walking time. There are many other carparks in the city but they can be hard to find and can be a twenty minute or half hour walk to the Ponte Vecchio. That’s a long way on a hot summer day.

San Gimignano – see Tuscany map

The quintessential Italian hilltop village famous for its towers of which 7 of the original 40 remain. It’s about 30 minutes drive from Siena and has impressed everyone we’ve taken there. It’s full of shops, bars and restaurants and is a mecca for tourists. In September the tourist rush is abating so it’s even better.

Top tip: Try gelato from the shop in the main piazza. It has won many, many awards – all displayed around the shop entrance.

Castellina/Radda/Panzano/Greve – see Chianti map

A cluster of small villages in Chianti which are worth a day trip. Traditional Chianti hilltop villages with Greve, built along a river, being the exception. Greve has a large triangular piazza worth wandering around. A must see/smell/taste experience in Greve is Macelleria Falorni, the butcher and deli on the far side of the piazza – look for the pig shaped sign hanging outside.

Castellina and Radda in Chianti are what you have always imagined Tuscan villages to be. Narrow streets and open piazza’s with a mix of local merchants and tourist shops vying for your attention. Washing hangs from second story rails above your head and there is always the clatter of dishes, the smell of food and the sounds of families enjoying siesta.

Buonconvento/Montalcino/Pienza/ San Quirico d’Orcia/Montepulciano – see Tuscany map

South of Siena this was very much our “home turf” and a trip through these villages can be done in a long day. This is the typical rolling hills, sunflowers, cypress tree part of Tuscany so take a camera and don’t be afraid to stop on the side of the road for a shot. Pienza is stunning with views over the valley below and is also the home of pecorino cheese – you have to try some. Montalcino is famous for Brunello wine. Expensive but like velvet to drink.

Top tip: if you can be in Buonconvento for dinner then eat at Marios on the main street in the old part of the town. If it’s warm ask to eat in the courtyard out back. The food is simple authentic Tuscan and delicious. Be adventurous – pheasant, quail, duck or local boar are all great.


We’ve been to Cortona twice and both times it has rained so we aren’t huge Cortona fans. It has caché from the book “Under a Tuscan Sun” so is worth a visit if you have time. The book also means it is a mecca for tourists – mainly American.

Frances Mayes villa Bramasole is behind the town. Apparently she has sold it because of all the tourists arriving to say hello to her.

Assisi and Lucca

Both these places have been recommended to us but we have not got there yet. Assisi is actually in Umbria but apparently is amazing. In a week these might be a drive to far.

Other stuff

1) Learn some Italian and don’t be afraid to use it, the locals will appreciate it. To arrange for lessons – or even a single lesson contact the delightful Mauro at Saena Aiulia, our language school in Siena.

2) What about visiting a hairdresser in Italy. We have tried a few and they are all artists, doing things with scissors that would baffle most kiwi hairdressers. Our favourite is Salvatore Sangiovanni who owns System Parrucchieri in Siena. He can perform wonders – everyone who walks out looks like a model. Jean swears by him and would fly back for her next cut and colour if she could.

System Parrucchieri is located on Via Giovanni Dupre, 28 – Siena, it’s marked on the Siena map.

3) Try buying meat from a local butcher or deli rather than the supermercato. The experience is fantastic and the meat they supply is a cut and a half above the supermercato.

4) GPS is a miracle. Accept that and use one to get where you want to go. But keep a good old fashioned map handy as they are great for context.

But the best part of Tuscany …

will be the part the girls discover for themselves, and that’s what it’s all about.

5 thoughts on “Family advice

  1. you simply HAVE to write for our INSPIRE Mag G. Your summary is fantastic and you clearly have the passion of the area at hear. kNowing how often you have been there and how much you love it does not escape me and I am so lucky to know exactly where to go if ever I need the low down.

    can’t wait to see you and Jean back in Welly and get more of the low down.

    when will that be? your return to the cutest little capital in the world?
    Let me know as i feel a DOckside lunch coming on!!


    • Petra,

      We must get together. We move back into our house at the end of March so I would be thinking a Dockside catchup soon after that would be a plan.


      PS: I have a half written article that I will finish in the next week.

  2. Pingback: Advice for Italian travellers – Part 2 | toscanakiwi

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