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Spain
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Ostuni, Puglia
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Lezzeno, Lago di Como .
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Tuscany. Arezzo would be a good choice.
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I would go for the lakes, we went for Lake Garda as accommodation was a little cheaper.
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Want food, wine, light walking, pool, where should I go?
Yeah Tuscany. Rent a villa with a pool. See Florence and Sienna.
The lakes are great, got married there, it's mountainous though so the walking is rarely 'light' unless pottering around a small town. It's touristic, too, but in a fairly good way.
Personally I like Naples and the coast there is amaze, but it's all a bit full on.
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Assuming you're cycling or driving
Start in Florence for a day or two then head down towards Siena, stop in Greve in Chianti or Radda in Chianti for a few days then a day in Siena and back to Florence.
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I'd recommend the north rather than Tuscany/Umbria as the latter is still swamped with tourists in September. You can rarely go wrong for food and wine anywhere in Italy. An interesting itinerary could be a few days in Verona (good food and wine, lots of interesting places to see), a few days on Lake Garda (use the boat to get around, have lunch in places like Salo) and then a few days in Bologna which claims (like a lot of Italian towns and cities) to be the food capital of Italy (it has a better claim than most).
There are loads of places to choose from in that area too - Treviso, Vicenza, Padua, Mantua, Bergamo, you can't really go wrong.
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@rogan
Italians, italy lovers and travellers alike.
7 or 8 nights in italy, likely mid-late September, want 2 or 3 places, never been to italy before, no interest in rome or venice.
Want food, wine, light walking, pool, where should I go?