A hilly, fertile region in central Italy, Tuscany was the home of the Etruscan civilization, and later the birthplace of the Renaissance. It’s known for its picturesque landscapes and charming, historic towns like Siena, Arezzo, Cortona, Lucca, San Gimignano, and Volterra. It’s also renowned for its bold red wines and fruity extra virgin olive oils. Tuscany’s capital, Florence, is a great art center whose well-preserved centro storico remains closely linked to its medieval past, in spite of year round tourist crowds. The region’s Tyrrhenian coast is famous for its white sand beaches and pine forests. Come August, Florentines depart en masse for spots such as Viareggio, Camaiore, Forte dei Marmi, and the island of Elba.
Saturday – Arrival
Meet your local contact at the villa. Familiarize yourself with the property, ask for restaurant recommendations, the closest grocery store, and whether there are any special events happening during your stay! Most stores will be closed on Sunday, so shop for any supplies you’ll need before Monday morning.
Sunday – Get Your Bearings
Sunday is a day of rest for most Italians, so relax at your villa. Head into town for a casual lunch at a trattoria; in the late afternoon, join the locals in la passeggiata, a leisurely stroll along the main street.
Monday – Hill Towns
Depending on your location in the region, visit a notable hill town such as San Gimignano, Volterra, Cortona, Montepulciano, or Montalcino. Spend all day in one spot or drive to another town after lunch. In the evening, return to your villa for a simple meal of pasta topped with chopped tomatoes, basil, garlic and a splash of extra virgin olive oil. Add a green salad and a bottle of local red.
Tuesday – Day Trip!
Spend the day in Florence, Siena, or Lucca. Visit museums, investigate churches, and shop for local crafts. Enjoy a leisurely lunch in the shade at an outdoor café or trattoria. Return home before dark so you can stop at a local rosticceria or tavola calda for delicious take-out.
Wednesday – Learn Something New
Sleep in; then eat breakfast Italian-style by visiting a bar and ordering un cappuccino e cornetto (a cappuccino and a croissant). Afterward, head to class! Cooking, painting, olive oil tasting, or perhaps a visit to a farmer’s market to practice your Italian – whatever your interest, take some time to learn something new. If you’re planning ahead, this is a great evening to have a chef come and prepare a gourmet Tuscan dinner for your entire group.
Thursday – More Hill Towns
Head out to a hill town you haven’t yet explored. Hand-painted ceramics, linens, and leather goods make great gifts and souvenirs. With dinner in mind, keep your eyes open for a salumeria, where you will find cured meats such as salami, prosciutto, and bresaola. Don’t forget the marinated artichokes and roasted eggplant!
Friday – Pool and Relaxation
Spend your last full day sunning by the pool, catching up on your travel journal, and reliving the week’s adventures with your companions. In the late afternoon, pack your bags and treat yourselves to dinner in a local restaurant.