Tuscany in 10 Days

After arriving in Florence, your private driver will meet you at the airport and transfer you to the historic center to begin your time in Tuscany. Once checked into your hotel, head out together for a relaxed first afternoon exploring Florence on foot.

Walk through areas around Florence Cathedral, Piazza della Signoria, and Ponte Vecchio while passing wine bars, cafés, artisan shops, and smaller side streets throughout the center. Florence is compact and easy to explore on foot, making it a good place to ease into the trip after your arrival flight.

The evening includes dinner and wine in one of Florence’s historic neighborhoods before returning to your accommodation.

Spend the morning exploring Florence’s Renaissance landmarks with your private guide, beginning at the Accademia Gallery to see Michelangelo’s David before continuing toward the Uffizi Gallery.

Between the main sightseeing stops, spend time walking through Florence with your guide, passing churches, piazzas, local cafés, and smaller streets throughout the historic center while learning more about the families and artists who shaped the city over the centuries.

Later in the afternoon, head through Florence’s Central Market to see local produce, fresh pasta, meats, cheeses, and wine stalls before continuing into the Oltrarno neighborhood, where artisan workshops, small wine bars, and quieter streets give a different feel from the busier areas around the cathedral.

Your private driver and guide will collect you from Florence this morning before taking the countryside roads into Chianti. The journey passes vineyards, olive farms, small stone villages, and winding roads through the Tuscan hills before reaching Greve in Chianti. 

Spend time exploring Greve’s central square and local wine shops before continuing to Panzano, where smaller family-run wineries and countryside estates sit among the vineyards.

Throughout the afternoon, visit local wineries for tastings of Chianti Classico wines paired with regional cheeses, olive oils, and cured meats before arriving at your countryside hotel for the evening.

Your private driver will take you south toward Siena this morning through some of Tuscany’s best countryside scenery.

After arriving in Siena, head into the historic center with your guide to explore Piazza del Campo, Siena Cathedral, and the network of steep medieval streets that run through the city. Spend time walking between local cafés, smaller piazzas, wine shops, and historic buildings while taking in a very different side of Tuscany from Florence. 

Later in the afternoon, continue through smaller countryside villages and vineyard roads with stops for lunch, local cafés, and panoramic viewpoints before returning to your accommodation.

Leave Chianti behind and continue deeper into Southern Tuscany toward Val d’Orcia with your private driver. The scenery gradually changes into the wide open landscapes the region is known for, with rolling hills, cypress-lined roads, vineyards, and stone farmhouses spread across the countryside.

Begin in Pienza, where smaller streets, cheese shops, cafés, and panoramic terraces overlook the surrounding valley. After time in the town, continue onward to Montalcino, home of Brunello wine.

The afternoon includes a winery visit and tasting paired with a traditional Tuscan lunch before continuing through the surrounding countryside toward your accommodation.

Your private driver and guide will take you through more of Val d’Orcia today, beginning in Montepulciano, where steep streets lead uphill past wine cellars, churches, cafés, and local food shops.

After exploring the town, continue to Bagno Vignoni, one of Tuscany’s best-known thermal spa villages. The village is built around historic thermal waters that have been used since Roman times.

The afternoon includes time at a thermal spa surrounded by the Tuscan countryside before returning through Val d’Orcia’s scenic roads and vineyard landscapes later in the day.

On day 7, you’ll leave your accommodation in Val d’Orcia for the scenic journey northwest through Tuscany.

The first stop is San Gimignano, where medieval towers rise above the surrounding countryside. Spend time exploring the historic center, local wine shops, artisan stores, and smaller streets running through the hill town.

Later in the afternoon, continue onward to Volterra, where stone streets, Roman ruins, and local alabaster workshops give the town a completely different atmosphere from the busier Tuscan destinations earlier in the trip.

Meet your private driver and guide this morning and leave for Lucca and Pisa. The drive takes you across the Tuscan countryside, passing small towns, farmland, vineyards, and local villages.

Begin in Lucca, where Renaissance walls surround the historic center. Walk through quieter streets, local cafés, churches, and piazzas before spending time along sections of the city walls overlooking the rooftops below.

Later in the day, continue to Pisa, where you’ll visit Piazza dei Miracoli, including the Leaning Tower, cathedral, and baptistery, before returning toward Florence in the evening.

Return to Florence this morning for your final full day in Tuscany. Begin with time exploring some of Florence’s smaller neighborhoods and local food stores with your guide before joining a Tuscan cooking experience later in the day.

During the class, prepare traditional Tuscan dishes using fresh local ingredients before sitting down to enjoy the meal alongside regional wines.

The final evening is left for a relaxed dinner and one last evening exploring Florence before returning to your hotel.