Livorno

On this wonderful experience for foodies, your day begins with a journey to Forcoli to reach the estate of the Savini family, whose business has been linked to Tuscan truffles since the 1920s. Handing this passion down over generations, they follow a cycle each season from gathering, selecting and cleaning truffles to product creation, packaging and sale. You will meet the Savini staff, who will teach you to spot the prestigious underground delicacy, and then you will enter the Tuscan woods to begin the hunt, assisted by the dedicated and adorable Savini hunting dogs.

This excursion unveils Siena, famous for its cuisine, art, museums and the medieval cityscape cast in warm brown bricks that gave the color its name. Near the hub of Piazza del Campo, one of the few structures of a different hue is the black and white marbled Duomo. Tour this marvelous Romanesque and Gothic cathedral and its Piccolomini Library, renowned for the Pinturicchio frescos covering the ceiling and walls and for its hand-illuminated manuscripts.

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 Barges have since been replaced by pleasure craft along these canals, offering unique perspective on Livorno’s picturesque historic center.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.