San Gimignano is a cute little town just over half an hour from Florence and Siena. Locals will always complain that is far too touristy for them (and that’s reflected in some establishments’ prices) but nevertheless, everyone fully agrees on one thing: it’s an absolute gem.

I’ve been lucky enough to visit San Gimignano both in summer and in autumn and it’s difficult to choose which is the best season to visit but, price and color-wise, autumn would definitely be my choice; weather should still be sunny and warm, the biggest hordes of tourists have gone (you will still get plenty of day buses, though) and you can get an excellent double room with views right on Piazza della Cisterna for less than 80 Euro at Al Pozzo dei Desideri (we didn’t stay here but we saw all the rooms and they were absolutely lovely!). We stayed in their sister accomodation A Spasso nel Tempo in Via Matteotti, 37. Excellent price, walking distance from the centre of San Gimignano, lovely young and helpful lady at the check in: it was absolutely perfect! They do not offer breakfast but they are walking distance from a couple of cafes/bakery.

Parking in San Gimignano can be expensive and can be an issue, particularly in peak season. Personally, we have never paid car park once there. A few tips where to leave your car for free (if you don’t mind a bit of walking):

• If you are coming from Poggibonsi and following COOP supermarket sign, you can try to find a space on the big roundabout and on the roads that goes to San Gimignano.
• Coming from Poggibonsi, after the roundabout turn the first road on your left into Via G. Matteotti and go till the end. It’s a residential area and there are always some spaces.
• Coming from the SP1, there are some free spaces near a bus stops between Via Martiri di Citerna and Via di Fugnano.

In any case, always check the signs before parking, in case something has changed!

Food-wise, San Gimignano offers plenty of options for all budget. Being such a famous destination, it can get a bit pricey so be careful where you choose if you are not in the mood of splashing out! Eating in the main square (Piazza della Cisterna) is pricey all year round so I would avoid it but, if you’re trying to catch the last autumn rays, it’s a good spot to get them. There or at Enoteca di Vinorum.

Not many places can boasts this stunning view: get a glass of Vernaccia white wine, share a bruschetta (grilled bread with varied toppings) and relax in the sunshine with lovely views on the surrounding countryside. It’s a WOW place, you’ll see what I mean 🙂 For a more substantial meal, head to Ristorante Il Pino: we were recommended this place and it was a great choice. They had a 35 Euro tasting menu lunch that included welcome bubbles, antipasti, local soup ribollita, pappardelle with wild board, tagliata and dessert. We hardly managed to finish it all and we “had” to skip dinner.

On another occasion, we tried Perucá and were not disappointed; their fagottini del contadino (home made pasta filled in with pecorino and pear) and their gnocchi truffle and porcini were to die for. The restaurant is lovely and cosy in a narrow alley in San Gimignano downtown. We tried Osteria I Quattro Gatti (Via Quercecchio, 9) as well for a bowl of pasta and it was a good choice; it’s a nice restaurant with a lovely outdoor romantic area. Recommended for couples.

If you find yourself in San Gimignano on a Friday during summertime, head to Il Museo del Vino (Via della Rocca) for the sunset;  for a very small price they offer a tasting of local wines and cheese (what Italians would call aperitivo) on a lovely outdoor terrace. Possibly one of the few things not overpriced in San Gimignano and surprisingly quiet. A walk up to the walls of the city is one of the best free things you can do while in town.

Echoes (Vicolo Mainardi, 10) is another good bet for a good glass of wine and a delicious bruschetta (no outdoor seating though). They may look a bit pricey (for Italians) but believe me they are massive and one could be perfectly shared for lunch. They have over 60 types of toppings so take your time….The owner is a Pink Floyd lover (Echoes…) so with your meal you will get a nice playlist too.

Do not leave San Gimignano without trying the “best gelato in the world” (as they claim) at Gelateria Dondoli in Piazza della Cisterna. Being Italian and having eaten my body weight in gelato, I can truly say it’s one of the best I’ve ever tried! Go for the unsual flavours such as champelmo (champagne and grapefruit), rasperry and rosmary and check out their seasonal new entries. Don’t worry: all gelato flavours are translated in English, so you can’t go wrong but, if you do, it will be still delicious.

When it comes to arrange a visit to San Gimignano, the rule n. 1 is of course to try to visit the town before the hordes of buses and minivans arrive (or just after they leave); a walk in the evening down the narrow alleys that open to beautiful secluded squares is breathless.

As far as shopping is concerned, I have to say I would avoid any San Gimignano shop any time (overpriced and all selling exactly the same items) but if you are looking for something a bit different…have a look at J Gallery: 2 young artists (brothers from Belgium) manage 2 galleries/shops in town where they display and sell their works (and some other pieces). Amazing hand made and unique design jewellery and art pieces. I’ve dragged my boyfriend in a couple of times, hope he got the message!