Tour 2 - From San Gimignano to Siena, Florence and through the Chianti area


  • Duration: 1 week
  • transport: Car or bus on site
  • Accommodation: in one central location

Cities rank among the must-see addresses in Tuscany Florence and Siena at the top. But vacation only in the city? So, off to the countryside and day trips to where all the other tourists are. You have to have been there at least once and it's really worth it.
Our tour suggestion can serve as a rough guide and recommendation. Since we cannot take all interests into account here, we leave it to you to round off your individual travel program accordingly. You will see that after the first impressions on site it will not be difficult for you!

Starting point in San Gimignano

Saint Gimignano

An ideal starting point to reach both cities in a short time is San Gimignano (Click here for map view). This place is also one of the hip, world-famous sightseeing addresses. So what could be more natural to look for cheap, stylish accommodation in the immediate vicinity, e.g. B. a winery on our partner site: (overnight stays around San Gimignano)

They usually arrive on Saturday evening and need some rest and relaxation first. So before unpacking your suitcase, sit down on your terrace and look forward to your arrival. It is advisable to bring a bite to eat with you or, better still, to go shopping in Italy on the way. First arrive, breathe the vitalizing air of Tuscany and enjoy the view of the vineyards and the multicolored hilly landscape of the surrounding area.

Just no stress ...

pool vacation

Stay at home on Sunday and enjoy the amenities of your holiday apartment and the pool. Your children, if you have them, will thank you. And relaxing is good for you too, which is available here at no extra charge. In the evening, after 18.00 p.m., you will be rested enough to go into town. The last tourist buses leave the world-famous city of towers San Gimignano and it almost suddenly becomes quiet and homely. The locals have their city back, meet in the piazza for coffee and gossip and you are right in the middle of the hustle and bustle. By now you will start to be happy that you are here, that the shops are open and that you are being served in a friendly manner.

Excursion to Siena

siena town hall

The next morning it's off to Siena (click here for map view). Siena because the historical center is easy to understand and rich in sights. Follow the signs to the center and drive as far as you can and finally to the parking lot or the multi-storey car park on the edge of the center. You have already read in the travel guide that “Piazza del Campo” is probably the most beautiful piazza in Italy. When you get there and let your eyes wander, you will know why. Just drink a latte macchiata and let the architecture, perfect in its beauty, sink in. This image will be burned into your memory. Then walk up and down the pedestrian zone, have an espresso in Café Nannini, visit the Duomo of Siena with its chessboard floor, one of the 103 world heritage of Italy. Then inspect the many small shops with a wide range of products. At lunchtime they go to the trattoria "da Dino", near the Piazza del Campo, where you can get fresh specialties at family-friendly prices. In the Piazza del Campo you can drink your cappuccino or spoon an ice cream and think about whether you would rather go shopping in the afternoon or take further sightseeing. Then, finally, after a few hours of Siena, you understood why the whole world comes to Tuscany. In the evening you drive a little tired and tidy inside the 50 km back to your apartment and look forward to the evening dip in the pool.

You must have collected a lot of brochures in Siena and maybe also bought a German newspaper. You can see all of this in peace on Tuesday. Let your children run around and treat yourself to a day's rest, or prepare yourself with your guide for Wednesday, because now it's time to go to Florence. It's about 60 km, think about whether you really want to drive your car or rather take the public bus from San Gimignano. Parking is very difficult in Florence and if you are noted as a parking wrongdoer, the fine will be sent to Germany. It is best to speak to your landlord or to the tourist information office in San Gimignano, German is also spoken there.

Excursion to Florence

florence cathedral

The highlights of Florence (click here for map view) are diverse and definitely cannot be accommodated in a single day. So think about what you want to see beforehand. Recommended is the way from the main train station (Stazione di Santa Maria Novella) to the cathedral and on to the Uffizi, past the Arno and over the Old Bridge to the Palazzo Pitti. Even though your eyes almost pass over everything that can be seen, you have only seen a small but beautiful part of Florence. The queue of tourists in the middle of it pushes you along. At first you don't even know what to photograph first. You can climb the world-famous dome of the cathedral with a good level of fitness, there are 463 steps that lead to the top and give you a total, unforgettable panoramic view of the city on the Arno. You will also pass many small restaurants on your walk, pay attention to the prices. A good offer is a tourist menu for around € 10-15. It usually includes three courses with drinks. When you get back to your apartment late in the evening, you have to review what you've seen. The display images of your camera will help you with this. And you absolutely need rest and relaxation the next day.

Excursion to the Chianti area

On Friday you finally go to Chianti. Our suggestion is the route via Poggibonsi to Monteriggioni (30 km), further to Castellina in Chianti (15 km) and as a destination Greve in Chianti (20 km).

tuscany chianti tourData from OpenStreetMap - Posted under ODbL

You will pass a multitude of wineries, make arrangements in advance who will drive and should definitely stay sober. The Italian police know no mercy when it comes to alcohol sinners. That would destroy all nice holiday impressions in one fell swoop. Otherwise, try the wines, which are superb across the board. It is a good opportunity to purchase fine wines directly from the producer. The small wine towns that you pass through are picturesque. You can eat and drink at reasonable prices and have time to savor the beautiful surroundings and the relaxed joie de vivre. You will notice that the time goes by far too fast until you turn back towards San Gimignano.

And then the week is already over, you have to pack your suitcase, tidy up and discuss the upcoming departure with your landlord. I bet you'll be back!

Last updated: 06.02.2024

Affiliate links / advertising links
The links marked with an asterisk (*) are so-called affiliate links. If you click on such an affiliate link and shop via this link, I will receive a commission from the online shop or provider concerned. For you the price doesn't change!