One of my favourite writers, Leif Pettersen has listed the best and worst things about Tuscany:
I took it right from his blog:

Best drive: In Central Tuscany the stretch between Abbazia di Monte Oliveto Maggiore and Asciano is by far the one where I wished I was the passenger in the car and not the driver. In Southern Tuscany, the bit between Albinia and Magliano in Toscana gets awfully pretty for the last 10 km. On the Coast, the back road connecting Sassetta and Suvereto is hailed by a local cycling journalist as being one of the best in all of Italy for biking and motorcycling, to which I agree whole-heartedly.
Worst drive: Anywhere within the Livorno city limits.
Best parking: Cortona. Close to the historic city center and free.
Worst parking: It’s a tie between Livorno and Arezzo.
Best view from a hotel room: I’m giving it to the same place as last time, the Albergo Guastini in Pitigliano. Specifically, rooms six and 18, among others. There’s just no equal.
Best Hostel: Sadly, the best hostel in my territory is in one of the least noteworthy areas. I’m talking La Cocciara in tiny, ho-hum Cetona. The hostel is large, clean, safe, friendly and has great beds, but apart from some fine dining in town and the inviting climb on Monte Cetona, there’s really not much to keep you in the area.
Best hotel room (budget): Santa Margherita in Cortona. Run by sweet, obliging nuns and just completed a total renovation, including new beds, fresh paint, and sparkling bathrooms. Honorable mention goes to Pensione Weekend in Porto Santo Stefano, on the Monte Argentario peninsula.
Best hotel room (mid-range): Antica Residenza Cicogna in Siena. Springless beds, soundproof windows, ornate frescoes, free wi-fi, antique furniture, huge buffet breakfast and a great location. What’s not to love?
Best hotel room (high-end): La Frateria di Padre Eligio, also near ho-hum Cetona. It’s a gorgeous former convent dating from 1212, lovingly restored and converted into an unforgettable seven-room hotel and gourmet restaurant.
Worst hotel room: I’ll name the worst service, which was hands-down the disastrously pretentious Hotel Vogue in Arezzo. I didn’t stay there, but my time in reception was probably the most frustrating, customer service-starved 10 minutes of the entire trip. They started out cagy and difficult and then, even after I relented and identified myself, they refused to give me prices, refused to let me see a room and refused to smile (or look away from his computer screen in one clerk’s case). Kiss all your Lonely Planet business goodbye!
Worst city for overall accommodations: Overall, Livorno has the worst price-to-value accommodation options in Tuscany. This is unfortunate, as they don’t exactly have the strongest visitor appeal, unless eating at endless exceptional seafood restaurants is enough to snare long-stay visitors. I imagine their biggest tourism hotel customer base are those people arriving late or departing early on ferries, so we’re talking one overnight max, whereas if they lowered prices a bit, people might be inclined to stay longer, giving them more money and less work turning over the rooms. Capice?
Best wine: Once again, Vernaccia di San Gimignano. Though I’d be remiss in my duties if I didn’t mention the incredible, relatively discounted prices one can get if they shop carefully in Montalcino for very decent bottles of the coveted Burnello.
Most over-rated wine: It was amazing, don’t get me wrong, but I’d have a hard time finding the money to regularly indulge in the Super Tuscan Sassicaia, made in Bolgheri, for €20 per 10cc pour.
Best plate of pasta: It was the buckwheat lasagna au gratin with pheasant and fennel seeds on a base of creamed garlic and squash. This complex miracle of gastronomic wizardry was served at Antica Osteria da Divo in Siena. I’ve gotta give two honorable mentions (that I actually ate): the first was the Spinach ravioli with walnut and radicchio sauce, served at Ristorante Don Beta in Volterra. The other was the Chianina beef and tarragon ravioli with porcini mushrooms and cherry tomatoes, a tiny but nonetheless amazing dish I had at Sobborgo in Cetona (there’s that town again).
Best meal: I’m giving this one to Ristorante Don Beta in Volterra. I ate there twice and although the service on the second visit was wooden at best, the food standard was with either superior or beyond both times. Also, as my companion pointed out, the place was full of locals, which you don’t often find at higher end restaurants in tourist towns.
Best budget meal: This one was easy, Cantina Senese in Livorno. Excellent seafood at prices dock workers will pay.
Worst meal: I’ll just say how disappointed I was that the formerly great and relatively affordable restaurants that sit on the northeast edge of Piazza Grande in Arezzo have started to charge 10-15% service charges on top of the coperto, which is just unnecessarily greedy and opportunistic. They still have wonderful meals, but staring at not one, but two compulsory tips on the bill irritates a special place in my soul.
Best gelato: Gelateria di Piazza in San Gimignano, who I named in 2007, is still doing great work, but I was very impressed with newcomer Visola del Gusto in Volterra, whose signature flavor redefines the word ‘creamy’.
Best town: Portoferraio, on the island of Elba. It’s got fun streets, interesting Napoleonic history and too many good restaurants to fit into the space that I was allotted to write about them in the book. Just avoid it in June/July/August or you’ll have difficulty enjoying most if not all of these perks. Also, the accommodation situation could use improvement. Entrepreneurs, get going.
Best big city: As in 2007, it’s Siena. There’s nothing like it.
Best beach: Passable beaches are on the coast, like just south of Livorno or the less objectionable profiteering beach towns like Castiglioncello, but the island of Elba still takes honors. If you don’t like rubbing oiled-up elbows with strangers, head for the southeast corner of the island. There’s a bunch of places that take a little effort to reach, meaning they’re pretty roomy, even in high season.
Best monastery: Again this is a toughie, but I found myself more impressed this time around by Abbazia di Monte Oliveto Maggiore near Asciano. The fresco cycles by Luca Signorelli and Il Sodoma are just amazing.
Best agriturismo: I was introduced to a new winner this year that takes the title, La Cerreta, outside of Sassetta. They’ve been at it for over 20 years, engineering a ’self-sufficient, biodynamic, harmonic project’, a mindset and lifestyle that will cause all but the most die-hard city lover to re-think their lives. They aim for a simple, gastronomically authentic Tuscan lifestyle. They raise cinta senese (indigenous Tuscan pig), Maremma cows, and the rare Livornese chicken, among others and welcome WWOOFers for short and long-term stays. When I visited they were close to finishing their brand new, three-pool spa, using a thermal spring that they’d discovered late last year.