Nestled up in the mountains outside Gaiole along an undulating strada bianca (white road) is the tiny borgo of Casa al Vento. While the Gioffreda family runs a very nice country resort here (including a spa experience of bathing in wine), I recommend a visit to taste the natural wines produced by Francesco.
Casa al Vento is a classic example of artisan wine making with a focus on boiolgico production and respect for the natural environment. The wines are produced in a modern style, often finished in small French barrique while still respecting local Chianti Classico traditions.
Francesco produces a simple, quaffable red called Gaiole (red wine, 60% Sangiovese + 40% Merlot, €10) that tends to be very fresh and aromatic -- perfect as a house red to go with pizza and pasta. For white lovers, Casa al Vento also releases a simple white wine called Chardò (white wine, Chardonnay + Sauvignon Blanc, €10) that's nice for summer sipping with antipasti and fish dishes. Both Gaiole and Chardò are meant to be drunk young, ideally in the year after production.
More interesting is their entry-level Chianti Classico Aria (red wine, Sangiovese, €12), a classic Chianti Classico wine with some reasonable structure and plenty of dark fruits like cherry and blackberry on the nose and palate. Aria spends 12 months in French barrique, and another 6 in the bottle.
Their more complex wine is the Chianti Classico Foho Riserva (red wine, 90% Sangiovese + 10% Merlot, €19), a structured red with intense fruit, spices and a touch of smokiness from time (18 months) in toasted French oak. In some years, Foho is a bit more austere and could benefit from some time resting, but it's well worth tasting it young to get a feel for the house winemaking style.
Casa al Vento will graciously welcome you into their cantina for tasting or a tour. Strictly speaking, you don't need a reservation, but I always recommend giving them a heads-up that you're coming. Just e-mail or call them (or have your hotel call them for you).