This swathe of Tuscany has a landscape to fall in love with. Rugged Chianti’s bumpy backroads reveal a timeless terrain traced with cypress avenues and criss-crossing vines. In vineyards innovative and ancient you’ll hear people talking of wine having a soul; taste it and see if you agree.
There is far more to this green corner of Tuscany than Italy's iconic Leaning Tower. Usually hurtled through en route to Florence and Siena's grand-slam queue-for-hours sights, this is the place to take your foot off the accelerator and go slow – on foot, by bicycle or car.
Central Coast & Elba
Despite landscapes dreams are made of, much of this part of Tuscany is free from well-known destinations and feels far away from the tourist trails. Here you can revel in the hustle of port-city Livorno, where a gritty harbour borders enchanting canals and restaurants overflowing with fish.
In Siena the architecture soars, and could well lift your soul. Effectively a giant, open-air museum to the Gothic, its spiritual and secular medieval monuments still sit in harmony, many filled with collections of Sienese art. Add vibrant streets where every third door (literally) opens into a restaurant, enoteca or deli, and you’re in for a very fine time indeed.
The eastern edge of Tuscany is beloved by film directors who've immortalised its landscape and medieval hilltop towns in several critically acclaimed and visually splendid films. Yet the region remains refreshingly bereft of tourist crowds and offers uncrowded trails for those savvy enough to explore here.
Once a maritime power to rival Genoa and Venice, Pisa now draws its fame from an architectural project gone terribly wrong. But the world-famous Leaning Tower is just one of many noteworthy sights in this compelling city. Education has fuelled the local economy since the 1400s, and students from across Italy compete for places in its elite university.
Despite being barely a blip on many visitors’ radars, Southern Tuscany is really a region for the Italy connoisseur. Here you'll encounter the intensely atmospheric Città del Tufa, a trio of still-inhabited hill towns that have been sculpted from volcanic rock since Etruscan times.
Tuscany's second-largest city is a quintessential port town. Though first impressions are rarely kind, this is a 'real' city that really does grow on you. Its seafood is the best on the Tyrrhenian coast, its shabby historic quarter threaded with Venetian-style canals is übercool, and pebbly beaches stretch south from the town's elegant belle époque seafront.
A local legend says that when Venus rose from the waves seven precious stones fell from her tiara, creating seven islands off the Tuscan coast. These little-known gems range from tiny uninhabited Gorgona, just 2.23 sq km in size, to the biggest and busiest island, 224-sq-km Elba (Isola d'Elba), best known as the place where Napoleon (poor thing) was exiled.
Arezzo may not be a Tuscan centrefold, but those parts of its historic centre that survived merciless WWII bombings are as compelling as any destination in the region – the city's central square is as beautiful as it appears in Roberto Benigni's classic film La vita è bella (Life is Beautiful).
As you crest the nearby hills, the 14 towers of this walled town rise up like a medieval Manhattan. Originally an Etruscan village, the settlement was named after the bishop of Modena, San Gimignano, who is said to have saved the city from Attila the Hun. It became a comune (local government) in 1199, prospering in part because of its location on the Via Francigena.
The Alta (Upper) Maremma starts south of Livorno and continues down to Grosseto, incorporating Massa Marittima and the surrounding Colline Metallifere (metal-producing hills) that are now part of Unesco's European Geopark Network. It also covers inland territory including the hill towns south of the Crete Senesi and the mountainous terrain surrounding Monte Amiata.
Napoleon would think twice about fleeing Elba today. Dramatically more congested than when the emperor was charitably dumped here in 1814 (he did manage to engineer an escape within a year), the island is an ever-glorious paradise of beach-laced coves, vineyards, azure waters, hairpin-bend motoring, a 1018m mountain (Monte Capanne) and mind-bending views.