In The Florentine Chianti
If you really need to stay in a town -- for transport links, for example -- the Giovanni da Verrazzano, Piazza Matteotti 28, 50022 Greve in Chianti (www.ristoranteverrazzano.it; tel. 055-853-189), hotel-restaurant sits across from its namesake's statue on Greve's triangular piazza. Rooms are on the smallish side, but are pleasantly decorated in a simple Tuscan style. Those on the front overlook the piazza, while the back rooms have terraces with late-morning sun and a view over lichen-spotted roof tiles to the Chianti hills. Prices range from 90€ to 105€ for a double.
In the Sienese Chianti
Besides the choices below, the medieval Castello di Volpaia (www.volpaia.com; tel. 0577-738-066), recommended above for its wine, rents out apartments with kitchenettes and TVs and, in a few, working fireplaces in the stony buildings of its 13th-century village for 95€ to 150€ per night for two people (plus a sofa bed for children if required), or 180€ to 340€ per night for one that sleeps seven. Guests can take part in various programs, from self-guided hikes to cooking lessons and of course tastings. They also rent lovely villas (sleeping up to 8 or 11) with private gardens and pools with views (Saturday to Saturday rental only), and lease a casa colonica on a nearby hillock amid the estate's vineyards to a hotelier who operates it as an exquisite rustic-chic hotel, La Locanda (www.lalocanda.it; tel. 0577-738-832), with 220€ to 290€ double rooms. To stay in Radda itself, the best lodgings are at the Palazzo Leopoldo, Via Roma 33 (www.palazzoleopoldo.it; tel. 0577-735-605), where the ambience is traditional and the panoramic terrace will knock you out. Doubles range from 119€ to 226€.
Cheap Sleep -- The Ristoro a Lucarelli (www.lucarelli.info; tel. 0577-733-538) in the town of the same name midway between Panzano and Radda, offers clean, simple bed-and-breakfast singles for 50€ per night and doubles for 60€. It's no frills, but a neat throwback to the days when weary travelers spent the night at a room above the tavern. The trattoria downstairs is closed on Friday.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.