Livorno

After a drive north to the medieval city of Lucca, much of it alongside a lovely natural park, you will be guided through the remarkably preserved city center and cathedral. Atop the walls that encircle Lucca are parks, gardens and a tree-lined promenade. You will see the Church of San Frediano with a Byzantine mosaic on its façade, the elliptic Roman amphitheater and the Church of San Michele. Then you will explore the gardens of Palazzo Pfanner, attributed to the genius of architect Filippo Juvarra.

Tuscany’s powerful ruling family, the Medici, built Livorno’s waterways in the 17th century so that goods could be transported more easily from ships in the bustling harbor to merchants’ homes and storehouses in town. Barges have since been replaced by pleasure craft along these canals, offering unique perspective on Livorno’s picturesque historic center. This tour combines evening sightseeing by boat with a tasting of Italian sweet wines.

On the indescribably beautiful Etruscan Coast, discover what put Bolgheri and Castagneto Carducci on the wine map, beginning in 1974 when a local vintage bested French Bordeaux in international competition. Tour the organically farmed vineyards and cellars of Le Macchiole, where the local chef will demonstrate pasta-making techniques and serve a four-course lunch paired perfectly with wines from the estate. Enjoy some leisure time in the village of Bolgheri before heading to Tenuta Argentiera for another tour and tasting.