Siena & Chianti
Your day begins as your private English-speaking driver greets you directly dockside at the Port of Livorno in a premium luxury vehicle. Setting off across the rolling, cypress-lined hills of central Tuscany, you will journey inland to the remarkably preserved medieval city of Siena.
Arriving in Siena, spend your morning stepping into a living Gothic masterpiece. Head into the shell-shaped Piazza del Campo, universally recognized as one of Europe's greatest medieval squares. Paved with herringbone red brick, this gentle slope is dominated by the soaring Torre del Mangia and the Palazzo Pubblico, and serves as the historic arena for the exhilarating Palio delle Contrade—the legendary bareback horse race run twice every summer between the city's ancient neighborhood districts. Stroll along winding, stone-flagged lanes up to Piazza del Duomo to admire the breathtaking Siena Cathedral (Duomo di Santa Maria Assunta). Marvel at its striking black-and-white striped marble facade, intricate carved pulpit by Nicola Pisano, and world-famous inlaid marble mosaic floors crafted by master artists over several centuries.
When midday arrives, you enjoy complete flexibility for lunch. Choose to linger in Siena to dine at a historic trattoria—savoring authentic regional specialties such as handmade pici pasta with wild boar ragù, cinta senese cured meats, and traditional spiced panforte—or set off straight away into the countryside to dine at a rustic vineyard estate.
In the afternoon, your driver guides you into the heart of Italy’s most prestigious wine region: Chianti. Driving along scenic country roads framed by rolling Sangiovese vineyards, ancient stone hamlets, and silvery olive groves, you will immerse yourself in this legendary winemaking terroir. Arrive at a hand-selected boutique winery to explore the historic barrel aging cellars, discover the strict traditions behind Chianti Classico DOCG production, and enjoy an exclusive guided tasting flight of refined red wines paired with artisan pecorino cheeses and estate-pressed extra virgin olive oil. Following an enriching day pairing medieval pageantry, world-class art, and Tuscan viticulture, sit back and unwind on a smooth, punctual return drive to the Port of Livorno, arriving comfortably ahead of your cruise ship’s departure.
