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Tasty Tuscany Trails


I will be in Tuscany in early September, so I am starting my food and wine plans now. This will be my first trip to Tuscany, not to Italy, but I am not real knowledgable on Italian wines.

I think I will spend a few days in Venice first, rent a car, then head to my "home base" in Loro Ciuffenna (Arezzo). I will have a car and will be within an hour of all the terrific cities and towns for great food and wine. We are in a great location.

Any "must see" or "must try" ?
Anyone been tasting on the Chianti Wine Trail recently ...in the past few years?

I am open to experiencing high brow to low brow....we are pretty "laid back" folks and don't like to rush around, are not "fussy", appreciate great views, and prefer wandering around rather than being on a guided tour. However, I am a bit concerned about wine tasting and driving, so I would like to look into a wine tour for "a bigger tasting day" or maybe just hiring a driver if we need to hit more than 2 tasting rooms in a day :/

All advice is welcome!

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  1. Try the winery and estate Monterinaldi in Radda or Restaurant Lamole outside Greve. Both terrific.Gives you a chance to check out the beautiful scenery.

    1 Reply
    1. re: patmolloy

      We were thinking about attending the chianti Classico wine festival in Greve. Have you ever attended that, patmolloy?
      It looks like fun, albeit a bit of a more crowded atmosphere than what we usually care for.

    2. Be aware that many (if not most) wineries in Italy do not have a tasting room with dedicated staff to accommodate drop-in visitors, as you would find in Napa/Sonoma. You should try to make appointments at the wineries you are planning to visit. A large winery like Banfi is likely an exception to that norm.

      Also know the Enoteca Italiana is in Siena, where you can taste wines from a wide variety of Tuscan wineries and from the rest of Italy.

      4 Replies
      1. re: DavidT

        Yes. I understand I need to make plans! I am interested in the minivan and driver thang....

        Have you been to Enoteca Italiana? I saw that it has like ...over a thousand wines! I am not sure where I would start.....I am trying to "bone up" on Italian wines before I go.

        There will be lots of italian food and wine tastings at sedimental's casa this summer...prepping for the trip!

        1. re: sedimental

          Here is a recent thread on the Italy discussion board about visiting wineries in Tuscany.


          1. re: DavidT

            Also be aware that a number of Tuscan wineries have a tasting room in a village/town nearby rather than it their winery. In addition, there are some villages that have tasting rooms (enotecas) where you can sample wines from a number of wineries in the area.

      2. Hi, sedimental:

        I suggest you include Avignonesi on your drives. Their Vin Santo is legendary and very expensive. They offer a a good tour and fine dining wine-paired lunch on the estate, which is excellent. When I was there, I believe lunch included some Vin Santo, or perhaps at a greatly reduced price.

        I also have a soft spot for Contucci on the Piazza Grande in downtown Montepulciano. The head winemaker there, Adamo, is a stitch.

        If you make it to Montepulciano, a highlight is always to duck into the Mazzettis' copper store, Bottega del Rame. Serious cookware, and serious eye candy abounds.

        There is an enoteca on the main square in Cortona that is excellent, although its name escapes me.

        Have Fun,

        1 Reply
        1. I'll answer the tourist side of this question. I too will be in Tuscany in September, but for the second time.

          Must see - and I skipped them the first time, are Florence and Lucca. The other three must see's are Pisa, San Gimignano and Siena.

          1 Reply
          1. re: collioure

            Yes, we will be within easy distance to all. I might skip Pisa, I think I have been there as a kid, but I was a nomad..so...who knows.
            I had not planned on Lucca....?

          2. Badia a Coltibuono in Gaiole in Chianti is a spectacular place. They make wine and olive oil, and also have cooking classes. It is also a B&B. One of the most beautiful places I've ever seen. And the wine is tasty, too!

            1 Reply
            1. Just to give you an idea, I’ll tell you what I did last year when I got tired of all those speed cameras they have stuck along the main roads. I took to the single-lane, paved & dirt back roads of the Chianti Classico district. Some were a little slippery in early March but not real bad; I had no problems. We just drove slowly and enjoyed the countryside without disturbing anyone. There are wineries everywhere. Just type “winery near Siena, Italy” into Google Maps. Move the map to the north and they pop up like fleas. I go to the websites of those that interest me to see about visits and check them out in the Gambero Rosso. Many wineries sell their products on-site (they put a sign out by the road); it is becoming more and more common in Tuscany along with speaking English.

              1. Be sure to go to the Italy board and do a search for Tuscan wineries. There have been threads there on visiting wineries in Tuscany.

                Here is one thread from that board that may be of interest:


                1. Montepulciano is a sweet little hilltop town with what seemed to be dozens of small winery tasting shops - cantinas. We were there maybe ten years ago and it was wonderful. You can wander drunkenly from one cantina to another all afternoon. I'd love to go back, actually.

                  1. Not sure how far a drive from Arezzo - but IMHO the must do day trip is going to Montalcino, Sant Antimo Abbey and a visit to Ciacci Piccolomini D'Aragona winery, lunch at Il Pozzo in SantAngelo inColle. Bring your camera for the drive on SS146 for a photo of Capella diVitaletta . and you will not be disappointed

                    5 Replies
                    1. re: Boston Bob

                      I also recommend a visit to Montalcino, one of the great wine towns in Tuscany.

                      The Sant Antimo Abbey is a VERY special place.

                      1. re: Boston Bob

                        Via Michelin directions from Arezzo says 1 hour 39 minutes though the Crete Senesi - a beautiful drive that is not hard on the eyes


                        1. re: Boston Bob

                          Thanks Bob! It appears there are many places around the area that are easy on the eyes!

                          So hard to narrow it down!

                          1. re: sedimental

                            Hi, Paul:

                            Another tip: See if you can upgrade your rental to a convertible. I was comped an upgrade, to a cute little Peugeot 5 cyl. turbodiesel drop-top, and it was a BLAST on both the backroads and the Autostrada. Never hurts to ask!

                            Never did get any photo tickets... There were cars passing me, so maybe 185 km/hr on the Autostrada was too slow?


                            1. re: kaleokahu

                              We spent some time in Tuscany in October of 2010, based ourselves in Montalcino for four days. The one thing I recommend is that you get a relatively small car. You would not believe how tight the streets and byways of some of those hill towns are. We also found that exploring the "white roads", meaning the dirt roads was the best way to find all kinds of interesting places. Our GPS (updated in the US for Italy) would go silent when we got on them and then start talking to us again when we finally got back on a paved road. I commented to my wife that it was the best way to shut it up.

                              Highly recommend the Sant Antimo Abbey. Had a great visit to both Ciacci Piccolomini D'Aragona and Conti Costanti but I made arrangements in advance.

                              I would recommend Sienna, but don't go on a Wednesday. That is market day and it is absolutely impossible to find a place to park a car unless you are there very early.

                              Montipulcino was great, even though it was raining on and off. Fantastic little tasting rooms and nice places to get lunch and a glass of wine to relax.

                      2. I am heading to Italy in September also (first time) and greatly appreciate the suggestions already on this thread.

                        We had planned 6 nights in Florence from which to do day trips, but I wonder if we should instead find a place to stay in the small towns/winery areas for the last night (6) before we head to Rome and meet up with our daughter.

                        Again, thanks for all the suggestions.

                        2 Replies
                        1. re: SueFH

                          I love the food in Florence, but I find it to be one of the hardest cities to drive in or around in Italy. We often stay in Siena or Montalcino. We enjoyed a stay in Arezzo also. I believe the Montalcino, Pienza, Montepulciano area is too far for a day trip from Florence