Reader Recommendations: Where to Go in Tuscany?

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I don’t believe in bucket lists, but I do keep a running list of the top 5 destinations I want to go to. Later this year I’ll finally be crossing off one of the top two! At last, I’m going to Tuscany! (The other top pick is Greece, and I’m gonna hold off on that for awhile)

The question is, where in Tuscany should I go? Unfortunately, I’m only going to have 2 1/2 days and I’m trying to figure out which province to focus my time on. I love beautiful scenery, fantastic food, and amazing wine tastings. I know only the basics of Italian wine, so looking forward to learning more about any/all varietals.

Would welcome recommendations!

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Living for the little (and big things) that make life so fun, especially mistake deals and crazy last minute weekend mileage runs across the world. www.twitter.com/klatravel


  1. Chris

    July 7, 2015 at 3:49 pm

    Was there two years ago with my wife. We stayed near Greve in Chianti and it was fabulous. We stayed at an old farmhouse/vineyard which was converted to a BnB and the staff and food was excellent. I think it was about a 15 or 20 min drive into Greve. Here is the link: http://www.rignana.it/property/fattoria-di-rignana/?lang=en

  2. Frank G

    July 7, 2015 at 3:57 pm

    A little outside of Tuscany, in Umbria, is the city of Assisi, home to St. Francis -great churches to see, small scale and easy to walk there, and after 5pm, the tourists are mainly gone and it’s locals – really nice. Just there last week.
    Also, in Tuscany itself, the little town of Cortona, featured in the book ‘Under the Tuscan Sun’, is also a great place to visit.

  3. Paul Feagan

    July 7, 2015 at 4:07 pm

    So many picturesque places, but I thought that Viareggio was stunning, considering it isn’t especially a place on the usual lists. I wrote about a good restaurant there plus included a picture of the harbour on my bugadvisor.com blog – shortlink here http://wp.me/p2BxLS-eu or just search for Viareggio

  4. James

    July 7, 2015 at 4:25 pm

    Just got back from Italy and went to Venice, Florence, Rome, and ORVIETO. Without a doubt, ORVIETO was the highlife of the trip for me. It’s technically in Umbria but only an hour train ride from Rome and probably not much further from Florence. It is a peaceful, hilltop town town with great dining, shopping and gelato and view to die for. Just my $.02

  5. Anne Woodyard (@MusicandMarkets)

    July 7, 2015 at 5:56 pm

    Agree with James about Orvieto – such a gem! But if you just have a few days in Tuscany, we’d recommend the southern part – Pienza, Montepulciano, and don’t miss a meal at La Porta in tiny Monticchiello! These are don’t-miss spots on both our winter and summer Music and Markets Italy tours and our guests always LOVE this area, which to us is the most beautiful of Tuscany (we’ll be back with our latest guests in a couple of weeks!). If you’re there on a Wednesday, visit the gardens of La Foce – just gorgeous!!

  6. Steve Thurman

    July 8, 2015 at 3:27 am

    Go on up to Lake Como. I stayed at Villa Vittorio in Laglio. Take a boat ride over to Bellagio one day. The next day drive up to Sighignola for the incredible vistas. Then drive back down to Menaggio for an espresso and gelato.

  7. auprog

    July 17, 2015 at 8:24 am

    If you like great italian food and wine you must go in the Val d’orcia where you can visit beautiful small towns like Montalcino (home of brunello and rosso), Pienza (home of famous Pienza cheese, very delicoius!) and Montepulciano (home of Nobile) and many others really close to each other and very beatiful. You can even make a short winery tour if you have enough time. It’s really worth!

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