Help With My Italy Itinerary

I’m headed to Italy with my family in less than two weeks and I’m beginning to feel a bit unprepared. I’ve got the basics covered – plane tickets, lodging, rental car. But have yet to flesh out the itinerary with things to do, places to visit, and most importantly… where to eat. Here’s an outline of my itinerary. If you have some input, please let me know by sending me an email or posting a comment.

October 29- October 31

Staying in an apartment right off the Duomo square.

November 1 & 2

We’ll be lodging at Il Borghino

Novemnber 3 – 10

Well, not exactly in Siena. But in the Tuscan village Vignale . We’ll be using this as home base to explore numerous hill towns in Tuscany.

Update (Oct. 22, 2007) : The Red Sox are in the World Series. So if you know places this obsessed fan can take in the games while in Florence, please let me know!


2 responses to “Help With My Italy Itinerary”

  1. Eli Sava Avatar
    Eli Sava

    Hey JJ,
    Have fun on your trip. We haven’t met, but this is kind of up my alley and I was able to fill in some details with maps and emails.

    I mostly know Siena and the hill towns. It is hard to go wrong with sights, since it feels great just to be there. You might do a minute’s worth of reading on the medieval feud between Siena and Florence, since the Sienese and neighboring locales logged most of their history around then. To summarize: they fought a lot. There is a fun story about the Gallo Nero and how Florence/Siena settled their territorial dispute using roosters. Do a web search on “black cock Siena Florence” (seriously, it works fine as long as you include Siena and Florence). Also important background are the Guelphs and Ghibellines,, especially if you go to San Gimignano, which you should. I won’t go on about the Piazza del Campo and the Palio horse race because you can’t really avoid them if you go to Siena. I recommend city tours — the standards for city guides are really high.

    Now, food.

    If you walk across the piazza towards the Palazzo Pubblico (town hall) and turn right a few hundred meters on the right side is Il Carroccio. Yum. Don’t forget to eat wild boar (cinghiale) at some point. Top gelato there is Il Gelato. When you are standing in front of the Palazzo Pubblico looking up, it is at the top, slightly to the left of center. Enoteca Terzi on Via Termine is good for wine, so is a little one on the corner of a building on Via Montanini near Banchi di Sopra. Those are streets.

    Closer to where you are staying, try the pizzeria Da Michele in Radda (the pizzaria across from the entrance to the town, not really in the town walls). Monteriggione a little farther away is pretty, though small. Nearby is Bar del Orso that is FANTASTIC for lunch — you go to the counter and tell them what you want, then pay when you leave. Super crowded, bear paraphenalia, man I wish I was there now. The gelato in Castellina is very memorable, but my impression is confounded by an hour up hill on the bicycle.

    For hill towns in wine country, I like San Gimignano, Montepulciano and Montalcino. In Montepulciano, for very rustic food go to Osteria Acquacheta and for more refined Le logge del Vignola. There is a little wine dungeon there called Cantina del’redi. In Montalcino try Boccon del Vino – restaurant and enoteca. For lunch there is a little place just under the main piazza called Baccus (look for crazy good deals on Brunello). There is a beautiful Abbazia di Sant’antimo that is near Montalcino.

    Drink odd years of Brunello and sangiavese wine(97,99,01).

    In San Gimignano, try the gelateria in the main piazza (coming from Porta San Giovana, entering Piazza del Cisterno, it is on the left. You can’t miss it because you’ll see lots of signs for ‘gelato world champion’, or something to that effect. A fairly gourmet restaurant in SG called D’orando. SG is gorgeous and the story of the tower building among the aristocracy there is interesting.

    I don’t know Lucca super well, but it seems pretty obvious. Stroll around the city walls, walk around the city. For simple fare, Da Giulio in the north end is a family-style trattoria that has a great reputation. I didn’t think it was miraculous, but the food people swear by it.

  2. Sarah & Dante Avatar
    Sarah & Dante

    Let me know if this link works. I created a google map of all my old haunts and must sees. to watch the world series, go to the lion’s fountain in florence. they’ll def be playing it, and it’s near a great sandwich and gelato place.

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