City Explorers: SienaAn in-depth two-week European City Stay in Tuscany

Your Travel Itinerary

Days 1-2 — U.S., Tuscany, Italy
Depart the U.S. and arrive in Tuscany the following day. The drive from Florence to Siena features views of the quintessential Tuscan landscape. Our local hosts will welcome you and give a brief orientation to the city during a festive reception and dinner at a local trattoria this evening. (D)

Day 3 — Neighborhoods of Siena
Get into the spirit of Siena with an in-depth walking tour through the medieval heart of town, including a visit to the incomparable Duomo, a distinctive cathedral known for its white and black striated design. The historic center of Siena is small enough that within a few days of navigating the different neighborhoods, you’ll begin to recognize familiar faces and even acquaintances as you stroll about the city. At lunch, an informal language chat introduces you to basic terms. Enjoy the afternoon to explore on your own. (B,L)

Day 4 — Gothic and Renaissance Art and Piazza del Campo
Brush up on your art history at Siena’s most famous art museum, the Pinacoteca. Then stroll down cobbled streets to the Palazzo Pubblico, an exquisite example of Gothic Tuscan architecture that towers over the Piazza del Campo. With a free afternoon, check out another museum or linger over an espresso in the Campo. (B)

Day 5 — Local Markets and Modern Italy
Take part in daily life at an outdoor market, where local residents come for fresh fruit and vegetables, meats, cheese, oil, and olives—and try out your language skills under the reassuring support of your resident director. Then visit the idyllic Orto dei Pecci, a garden-park oasis for the Sienese, located in the midst of town. Following an afternoon at leisure, meet with a group of local residents for a lively discussion on modern Italy. (B)

Day 6 — The Palio Horserace Culture
The Palio horserace—known as the wildest horserace in the world—is at the core of Siena’s identity. This afternoon you’ll become a temporary member of one of Siena’s 17 contrade, or districts, each with its own mascot, stable, museum, and strong rivalries. Visit a contrada museum as a personal guest, watch flag-throwers as they practice, learn the insider’s meanings of the mascots and costumes, and then dine in the contrada with members of the community. (B,D)

Day 7 — San Gimignano: Walking and Painting
Enjoy the essence of the Middle Ages in beautifully preserved San Gimignano, the “town of towers,” where 14 medieval towers still stand tall above the houses. Take the day to explore this small town at leisure. And for those who have ever dreamed of sitting in a piazza in front of an easel, painting a medieval tower or a relaxed café scene, we’ll provide all the supplies (or you can bring your own favorites brushes and paints). In the evening, enjoy an aperitivo and tasting at Siena's most famous café, Nannini, makers of spiced Tuscan pastries since the 1800s. (B)

Day 8 — Chianti: Countryside Biking or Walking and Wine Tasting
What better way to see the Tuscan countryside than along the back roads, biking or walking past rows of cypress and umbrella pines? Following your walk or bicycle ride, enjoy a traditional picnic lunch and leisurely wine tasting at a Chianti winery. This evening, enjoy a lively discussion on the highlights of Italian cinema and the international impact of Italian films. (B,L)

Day 9 — Everything Under the (Tuscan) Sun
Today is yours to explore Tuscany at your leisure. Enjoy a day poking around Siena and enjoy the unrushed feeling of being in a familiar place. Or, design a more ambitious day with the guidance of your resident expert as you set out to see the museums of Florence, take another bike ride in the countryside, or visit a nearby town. (B)

Day 10 — Pienza: A Culinary Adventure
Pienza is a beautifully preserved Renaissance market town and a center of pecorino cheese making. During a full-day trip here, you’ll see time-honored methods for creating world-famous cheeses and wines and try some samples. Then join renowned gourmet cookbook author Pamela Sheldon Johns for a private, hands-on cooking class and lunch. Bring the day to a peaceful close at the secluded abbey of Sant’ Antimo as you listen to Gregorian chants sung by resident monks. (B,L)

Day 11 — Medieval Siena and an Afternoon to Paint or Walk
Spend a mellow day in Siena. Take the morning easy or join in a discussion of medieval politics to learn about the powerful Guelph and Ghibelline factions, whose rivalries shaped the region. In the afternoon, enjoy another chance to paint or a guided walk in the countryside. This evening, after dinner on your own, meet for a gelato sampling at a neighborhood gelateria, then grab a cone of your favorite flavors for a group stroll, soaking in the atmosphere of Siena’s most beautiful squares after dark. (B)

Day 12 — Gardens and Literature in Tuscany and Family Dinner
The family home of writer Iris Origo, Villa La Foce, features Renaissance gardens that were re-envisioned by the designer of Florence’s renowned Villa I Tatti. The result, which you tour today, is a realm of perfect harmony between the villas, the garden, and the natural surroundings. (Frances Mayes’ bestseller Under the Tuscan Sun was written nearby.) This evening, join a Sienese family for dinner as their special guest for a unique and intimate look at Italian culture. (B,D)

Day 13 — Siena: A Final Day
Join our local historian for a talk on the history of banking and trade in Siena. Your discussion continues with a special visit to the Monte dei Paschi Bank, the oldest bank in the world, with an art collection dating from the 1400s. The afternoon is at leisure to return to your favorite sites or café, or choose to participate in a group activity with new-found friends. Enjoy a festive dinner as we say arrivederci to Siena and Tuscany—not “goodbye,” but rather “until we meet again.” (B,D)

Day 14 — Return to the U.S.
Depart for your return flight to the U.S. (B)