After living here for many years and trying out all the recommendations from locals, here are my most favorite spots (bars, restaurants, & gelato shops). Most restaurants in Tuscany require a reservation especially in high season as they fill up quickly but the bars and gelato shops you can just hop into.
Taverna di San Giuseppe - Very popular as this restaurant has won many accolades but what makes it unique is the menu and its own wine cellar. While they stay true to Tuscan cuisine, you will see more different items on the menu and they have a fabulous wine list.
Salefino Vino e Cucina - An Italian local recommended this place and it does not disappoint. If you are looking for something other than pasta and pizza, this is the place for you. The small menu will have a mix of seafood, meat and vegetarian and or you can do a tasting menu chosen by the chef.
Osteria Cice - Great place for lunch or dinner and closed on Mondays. Every dish is delicious so you cannot go wrong. The menu slants more towards traditional Tuscan with some slightly different pasta dish offerings.
Quarto Bistrot - Looking for an upscale, more modern take on Tuscan cuisine then this is your place. Tucked into a corner and a little off the beaten path. Loved by locals. Not open on Mondays.
Sosta di Violente - Offering a more traditional atmosphere this place offers some Italian home-cooked dishes done right from pici al ragu, bistecca alla Fiorentina, to Pappa al pomodoro . Don't miss the mozzarelline fritte con marmellata for dessert.
Quattro Venti - Great wines, great presentation, and comfortable atmosphere. This place is slightly more upscale than other Osterias but offers some great dinner options like risotto, polenta, beef tartare, carpaccio, veal tongue, and more.
Vineria Tirabuscio Siena - This is a great lunch option spot (or place for aperitivo) but you must arrive before the crowds as it is a tiny (yet cozy) establishment. It's menu is mostly crostone (small flatbread) with various toppings and a seasonal chalkboard menu. You can also find natural wines or orange wines here as well.
Trefilari Wine Bar - Fills up fast for aperitivo but it has a great wine menu so its a must do
Best artisan gelaterias goes to the following:
Golosi di Gelato Siena - offers a very different flavor menu (e.g. blueberry sage or crema di nonna)
La vecchia Latteria - more traditional flavors but you can tell this gelato is not commercially made and shipped in. Made on site with care from locals.
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