Drive your car along Tuscany’s countless wine trails. There are more than 20 "Strade del Vino" connecting estates, restaurants and accomodation facilities located where the best Italian DOC and DOCG wines are made. Although wine is the main link between the areas covered by the itineraries, these zones are also renowned for their extra virgin olive oil and fresh farm produce. 

Find out about some of them here:
Lunigiana:
Candia hills and Lunigiana wine trail
Lucca:
Lucca and Montecarlo wine trail
Pisa:
Pisa hills wine trail
Prato:
Carmignano wine trail
Pistoia:
Montalbano hills wine and olive oil trail
Chianti:
Chianti Classico wine trail
Maremma:
Maremma hills wine trail  
Arezzo:
Wine trail of Arezzo
Cortona wine and food trails
Montepulciano:
Vino Nobile di Montepulciano wine trail
San Gimignano:
Vernaccia di San Gimignano wine trail  
Val D'Orcia:
Orcia wine trail
Etruscan coast:
Etruscan coast wine trail
Florence:
Useful info on http://www.florencewine.it

For the more adventurous of you, there are also wine bike tours led by a biker oenologist that allow you to experience aspects that you don’t usually get to see when taking more comfortable means of transport. Check this link: 
http://tuscanywinebike.com/
More wine and bike tours:
http://www.vinaio.com/bike-and-wine

Take a private wine tour or wine and food tour and travel around the most famous vineyards, experience wine and food pairing in restaurants and cellars, and learn the history of Tuscan wines through the centuries. Here are some private tours:
http://www.tuscany-cooking-class.com/wine-tours http://tasteflorence.com/

Tuscany is full of luxurious castles surrounded by vineyards. Many of them are family-owned vineyard estates that offer wine and local cuisine tastings, many accommodation options and wine tours.

Tuscany is famous for hosting stunning modern wineries created by famous world-renowned architects. Book a tour around one of the many amazing designer cellars.

Shows, tastings, seminars, there are several wine events all year round. Among the most important dates, don't miss:
- In Greve in Chianti, Chianti Classico Expo and Terre di Toscana in Lido di Camaiore.

Don't forget that September is also the wine month and there are several historic grape festivals celebrating the “vendemmia”, or annual wine harvest.