The Tuscany Month countdown to the release of the totally redesigned 2010 Lonely Planet Tuscany & Umbria is nearing its end. I’ve been saving the best for last, including my carefully considered list of the best hotels in Tuscany (and pensions and agriturismi).

As always, the caveats are: this list is merely the product of my personal opinions about the hotels in Tuscany and is not endorsed by Lonely Planet. I have not slept in all of these places, usually for financial reasons, but I’ve thoroughly toured them all, usually more than once, and on the strength of having seen about a squillion properties in my travel writing career, I’m pretty confident I’ve got this list nailed. I have not accounted for Florence and northwest Tuscany in this list, as this is not my research area. All prices listed were accurate as of spring/summer 2009.

Speaking of ‘financial reasons’, you’ll notice that several of the places on the list are decidedly aimed for special occasions and lottery winners. I have nothing to say in my defense. Oh-wow moments and historic surroundings rarely come cheap, especially in Tuscany.

In no particular order, I present the best hotels in Tuscany!

Agriturismo La Cerreta (outside Sassetta)
Località Pian delle Vigne; per person per night with half board €55-65
You get a definite hippie vibe here, even before you see the owner’s impressive hair. Once he starts chatting about his 20 years in the business of engineering a “self-sufficient, biodynamic, harmonic project” (all in Italian, so bring your favorite translator), you start to understand that this farmhouse is more about providing a simple, gastronomically authentic Tuscan lifestyle tutorial rather than the run-of-the-mill tourist services – though they can do that too. They raise cinta senese (indigenous Tuscan pig), Maremma cows, and the rare Livornese chicken, among others. Cooking instruction, guided hiking/biking, farm activities and even photography are arranged onsite. Horse tours are nearby and a brand new, three-pool thermal spa was near completion when I last visited. Wwoofing stays are available.

Borgo Stomennano (outside Monteriggioni)
Room sleeping four people €900-1000 per week (including internet and swimming pool)
A sprawling unforgettable property 2km outside Monteriggioni. This historic collection of farmhouses dating from the 1600s has been converted into apartments, furnished and decorated with an amazing collection of heirlooms dating back hundreds of years – children under 14 are not permitted due to the delicate nature of these items. Though geared for large groups (six to 32 people) and events, couples are welcome during select periods. You can self-cater or request full board. Special touches include an infinity pool, welcome bottles of wine (with personalized labels!) and a private trail from the property, through undulating fields, leading to Monteriggioni.

Antica Residenza Cicogna (Siena)
Via dei Termini 67; singles €70-75, doubles €90, triples €130 (including breakfast, air-con and wi-fi)
Springless beds, soundproof windows (priceless with the way sound carries on the streets of Siena), ornate frescoes, wi-fi and antique furniture make this central option justifiably popular. With a mere five rooms and two suites, class exudes from prominent elements such as the four-poster bed, elaborate, thick-framed mirrors and the breakfast space (enormous buffet style). Reception has limited core hours (8am to 1pm), so arrange your arrival in advance. Parking is €18.

Palazzo Brandano (Pretoio)
Via di Valgelata 18; singles €150, doubles €225 (including breakfast, air-con, wi-fi and PC access)
Within the hilltop, 12th-century walls of peaceful, wedding cake-shaped Pretoio, the four-star Brandano is practically an attraction on its own. Rooms are sumptuous, wood-beamed affairs with frescos, classic furniture, plush beds, wi-fi, sensational views, and Jacuzzis. They have an impressive onsite restaurant, with a chef that’s available for cooking classes.

Hotel Leon Bianco (San Gimignano)
Piazza della Cisterna 13; singles €65-80, doubles €80-135, triples €110-135 (including breakfast, air-con, wifi- and PC internet access)
Among the seemingly limitless number of hotels in Tuscany, this one stands out. When you take into account super expensive San Gim, it’s really a great value. The hotel, occupying a 14th-century mansion, faces the historic central square. It’s smoothly run and friendly, with a ground-floor abundance of plants, a pretty inner courtyard, a breakfast patio, billiard table and fitness room. Wi-fi (extra charge) is available in common spaces, though I was able to hop onto someone’s unsecured hub from my room.

Agriturismo San Lorenzo (outside Volterra)
Doubles €90; apartments (without breakfast) €95-110 (pool, internet available)
This is probably my favorite all-around agriturismo in all of Tuscany. Just 3km outside Volterra on the road to Siena, sits this giddying fusion of sustainable tourism, countryside vistas, modern conveniences and wonderful food (dinner per person is a very reasonable €28). The mountain spring-fed biological swimming pool, complete with frogs and salamanders, fronts the converted farmhouse, circa the 1400s. Rooms are ‘farmhouse chic’, individually decorated and colorful with modern kitchens and bathrooms. Walking, biking, horseback riding and hands-on, seasonal olive-oil production (October-November) are immediately available, as are cooking classes (€90 per person) with meals served in the 12th-century Franciscan chapel. Whether you consider it a curse or blessing, some mobile-phone services don’t work out here. They sell their own olive oil too!

Hotelito Lupaia (outside Pienza)
Doubles €240 (breakfast, swimming pool included)
Full disclosure: I was sent here for a magazine assignment and was comped for a three night stay. Just north of Pienza, this farm dates from 1237. Each room has been uniquely and meticulously designed by the family matriarch, a 30 year veteran of fashion and interior design. The main house, containing a sitting room, dining room and open kitchen, is similarly bedecked with restored and agreeably weathered furniture. The progressive use of medieval space, doing as little as possible and sigh-inducing countryside views punctuate stays here, which are only interrupted by alluring eating options in nearby Pienza, Montepulciano, Montichiello and Montefollonico.

La Frateria di Padre Eligio (outside Cetona)
Via di San Francesco; singles €140-160, doubles €220-240 (including breakfast)
This is probably the most historic, best-value sleeping option among hotels in Tuscany. Up a signed lane (‘Mondox la Frateria Conv S Francesco’) 1km from Cetona on the road to Sarteano, this is a former convent dating from 1212. It’s been painstakingly restored and converted into an unforgettable, seven-room hotel and gourmet restaurant (meals without wine are a steep €110 per person), where you can expect a lavish eight-course dining experience, 90% of which is made from local products.

La Corte Del Re (Arezzo)
Via Borgunto 5; singles €60-75, doubles €70-90 (including air-con and internet)
A collection of six apartments, centimeters from Arezzo’s Piazza Grande, harmoniously blending contemporary design into elements of the historic building. The Pietro Aretino Suite has an ultra-modern bathroom that bleeds right into an Etruscan wall. Some apartments have kitchenettes and views of the square. There’s a three night minimum stay.

Hotel San Michele (Cortona)
Via Guelfa 15; doubles €79-220 (including breakfast, air-con and wi-fi)
This is Cortona’s finest hotel, which is surprising when you take into account their frequent discounted room rates. The property is primarily Renaissance, but with elements dating from the 12th century and modifications over subsequent centuries, it’s like a little history of Cortona in stone. Rooms are airy, spacious and exquisitely furnished. Unfortunately, for every week there are €79 rooms, there are two weeks with €200 rooms, so plan carefully. If you’re driving, parking will cost €20. Wi-fi costs €3 per hour.

L’Andana (outside Castiglione della Pescaia)
Doubles €500 (including breakfast, pool, internet, wi-fi and parking)
That’s right, rooms are €500 per night. When you coast down the gated, kilometer-long, tree-lined dirt track flanked by vineyards, olive trees and 50 sq km of rolling hills and rock up to this once summer abode of Duke Leopold, you’ll know why. Opened in 2004 and designed with the help of French three-star Michelin chef Alain Ducasse, this 16th-century property is not only one of the finest hotels in Tuscany, but also the last hotel you’ll ever want to stay in, because your taste in hotels will be ruined forever. And you can bet your tongue that the onsite Trattoria Toscana (open for dinner only from Tuesday to Sunday) won’t disappoint. Avail yourself of the indoor and outdoor swimming pools, spa with signature treatments, tennis court, 18-hole golf course, lobby wi-fi and the largest showers in Tuscany – maybe Europe.