Here are some Siena-centric Tuscan holiday tips. I’ve tried the same approach in most other Italian regions, and had a lovely time as well.
Sightseeing
“Every street is a sight,” wrote F. H. H. Seymour about Siena in 1907, although the same could be said of many Tuscan towns. In fact, you can soak up just as rich a cultural experience exploring them—and maybe a more authentic and original one—as you can at the Uffizi. Steer clear of the corsi or main streets, which have lately been contaminated by Occitane stores and Calzedonias (an Italian stocking chain), and follow your nose down the cooler, often deserted side streets to glimpse the stone-based buildings (once towers), their gothic windows, the extraordinary iron work of the lamps or horse ties built into the façades, the arcades over streets, the hidden cloisters, minor chapels, fountains and gardens, and the often-empty museums. Standing in front of a fresco of an obscure local saint, in a church you have all to yourself, the walls covered in plaques listing those Tuscan, i-ending names, the ubiquitous Chigi and Piccolomini coats of arms carved in wood and marble and bronze—all of that does more for me any day than thronging through the Duomo in Florence.
Food
I have a Sienese friend who is fond of saying, “It’s not authentic unless you have to haul them out of bed and talk them into cooking for you.” The Tuscans don’t have much of a restaurant tradition, and at least until recent generations didn’t often go out for meals—they have it so good at home. Despite the new trend to post a “Light Lunch” sign in the window, restaurants haven’t figured out the tasty, hearty sandwich or salad, so lower your expectations, don’t sweat overpaying for the dry, dull panini on the central piazzas and sit back and enjoy the splendid scenery.
Recommendations
One exception to the sandwich situation is the San Paolo Pub on a tiny ally leading down from the corso to the Piazza del Campo in Siena (http://www.sanpaolopub.it/). It’s where all the students go. They have delicious, creative, inexpensive, abundant sandwiches that absolutely hit the spot.
I have two spots where I go out dinner in Siena. Osteria Le Logge (http://www.giannibrunelli.it/italiano/osteria_osteria.html) because of the beautiful room, the wine list, and the staff. The dishes are always creative and often superb. For the Tuscan (and other) classics, served up in all their simple glory, try Enoteca I Terzi (http://www.enotecaiterzi.it/). I like the reserved service, the deep-voiced owner is a personaggio of the wine world, and their tagliata is the best steak I know.
But, still, I urge you to cook. Go to the butcher and see what appeals, ask how to prepare it. You can manage the instructions in Italian—corraggio!
Where To Stay
There are so many nice places these days, and the web sites show much more clearly than they used to what each is really like. Still, try calling the owners instead of sticking to email—you can learn a lot. Also, check distances in kilometers not driving times; remember, the times were calculated by Italians! It’s key to be 5 km or less from a grocery store, because milk spoils in three days here and bread (take the Tuscan, unsalted guanciale) goes stale in one. The properties with one Italian and one foreign owner give you authenticity and warmth. Here are my go-to recommendations, my winery’s agriturismo (of course!) and two properties owned by friends.
Castello Poggiarello: www.castellopoggiarello.it
Casa Cernano: www.casa-cernano.com Pretty, hilltop B&B with great breakfast in an original farmhouse building.
Luxury villas just outside Montalcino: Siena Dream http://www.sienadream.com/
The Seaside
The Tuscan coast is worth the trip. There are public beaches, but why not go for full immersion and reserve at a bagno? Call in advance or get there really early (before 9:00a), and rent an umbrella or two for the day (60 Euro per, and forget the rows nearest the water unless you’re there for the season). My favorite is Bagno Alessandro in the Le Rochette area north of Castiglione della Pescaia (http://www.bagnoalessandro.altervista.org/), but in Castiglione itself, over the bridge from the old village, is a whole string of nice bagni, each one favored by a different Sienese contrada.
Just so you know, the Italian beach routine is as follows, no sun block required:
9:00a Kids to the beach with Granny.
10:00a Mom and Dad join them, Mom to chat with friends, Dad to read the papers.
11:00a Snack for the kids (prosciutto sandwich or ciacciano (a Sienese focaccia)).
12:00n Kids forced in under the shade of the ombrellone.
1:00p Four-course family lunch (antipasti, pasta, fish, dessert and coffee, with white, slightly frizzy wine by the carafe) at the bagno’s bar/restaurant.
3:00p Siesta.
5:00p Granny and kids back in action.
6:00p Mom and Dad wake up too, for the best hours of the day.
Getting Around
If you want to do Florence or any other busy town, why not splurge on a driver? They’re allowed in the historic centers and know just where to go. You will save so much time and hassle and can fit much more sightseeing in. Try http://www.mytours.it/.
General
Touring is like parenting: let go of your expectations and let the child emerge. So give up your agenda, just this once (Isn’t that what vacation is for?), turn off the main road and again off the side road and onto the dirt one, especially if it’s marked VIETATO. You may not find a thing worth seeing, but it’s never happened to me.
The Truth About Tuscany 