This original shore excursion from the Port of Livorno will introduce you to the hidden treasures of one of Tuscany’s lesser-known cities; as well as its beautiful province where some of the best wines in Italy are produced.

Livorno, an original town

Start the day with a drive looking at Livorno, the city founded by the Florentine Medici family in the late 16th century to support its flourishing port. Discover the old Venezia quarter with its quiet canals, intriguing churches and sturdy buildings once the homes of wealthy merchants from all over Europe. Take a look at Livorno’s two impressive fortresses, also the work of the Medici. The drive beside the churches that belonged to the Dutch, Greek, Armenian and British communities of the 16th-19th centuries; then the impressive modern Synagogue that replaced the original one which served what was once one of the most important Jewish communities in Italy. Also well worth a visit is Livorno’s indoor food market, one of the largest in Europe, boasting a vast array of fresh produce.

Next head along Livorno’s attractive seafront, past the huge terrace overlooking the sea known as the Terrazza Mascagni, through the elegant quarters of Ardenza and Antignano driving us to the hill of the Sanctuary of Montenero – a fascinating church and monastery – and some stunning views over Livorno.

Bolgheri wine region

Now head south along the rocky Romito coastline and on to the wine-producing area of Bolgheri (about 50 minutes). The charming village, located about eight kilometres inland from the Tuscan coast, has fewer than 200 inhabitants. However, some of Italy’s most celebrated vineyards lie just west of the village which has made Bolgheri a popular destination for wine lovers.

Sassicaia historical origins

The wines of the area became famous after Marquis Incisa started growing Cabernet Sauvignon grapes on his estate; that area had previously only been known for rustic Sangiovese and Trebbiano wines. As a result, he produced the very successful Sassicaia wine; it has since gained international fame and have led to other winemakers in the same area following his example of using French grape varieties in their wines.

Your first stop will be at one of the prestigious Bolgheri wineries previously reserved; the tour of the cellars and a tasting of the wines (the exact winery will depend on availability at the time of booking). Later, you can enjoy a Tuscan lunch in the pretty medieval village of Bolgheri. After lunch, visit another of the area’s wine makers and then pay a visit to medieval Castagneto Carducci; the borgo was named after the famous Italian poet, Giosue Carducci. This hilltop village culminates in the castle belonging to Count Gherardesca; this noble family has owned the land here for many centuries and still lives here today. It is a peaceful little place where time seems to have stood still, offering a unique opportunity to see life in a real Italian village.

It takes about an hour to drive back to Livorno from Castagneto Carducci.