Highlights
- Join a special cooking class with views of San Gimignano's medieval towers
- Learn to taste local wines at the prestigious Tuscan Wine School
- Float over the Tuscan countryside in a hot-air balloon
- Soak in thermal springs with a two-night stay at a 5-star spa resort
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Pisa, Self-Guided San Gimignano Tour, Tuscan Cooking Class | San Gimignano |
| Day 2 | Truffle Hunt & Lunch, Chianti Cellars Visit | San Gimignano |
| Day 3 | Drive to Montalcino via Siena & Tuscan Wine School Tasting | Montalcino |
| Day 4 | Hot-Air Balloon, Brunello Wine Tasting & Cooking Class in a Tuscan Castle | Montalcino |
| Day 5 | Drive to Terme di Saturnia, Afternoon at Thermal Springs Resort | Saturnia |
| Day 6 | Traditional Tuscan Lunch at Organic Farm, Free Time at Terme di Saturnia | Saturnia |
| Day 7 | Drive to Pisa, Depart |
Detailed Itinerary
Day 1: Arrive in Pisa, Self-Guided San Gimignano Tour, Tuscan Cooking Class
Ciao, and welcome to Italy! You've landed in Pisa, the city famous for its leaning tower. On arrival, collect a rental car, zip over to snap a picture with the iconic landmark, and then drive 80 minutes to San Gimignano. This charming hill town is encircled by 13 medieval towers—both architectural marvels and symbols of power and wealth. Prominent merchant families constructed these towering structures to show off their riches, creating a medieval skyline like no other. Settle into your hotel, then use your free time to explore the UNESCO World Heritage Site and grab lunch at a trattoria.
Later this afternoon you'll roll up your sleeves and learn a handful of traditional Tuscan recipes in a local family kitchen. The fun starts with a traditional dessert of your choice, then you'll prepare the pasta from scratch, either pici or ricotta gnocchi, which will be paired with a sauce made from seasonal vegetables. Then, it's time to prepare a Tuscan bruschetta. When it's time to eat, venture out to the garden to enjoy the meal with views of San Gimignano's medieval skyline. You'll also taste the family's organic wines and extra virgin oils.
Day 2: Truffle Hunt & Lunch, Chianti Cellars Visit
This morning you'll venture into the Chianti countryside, enjoying views of hilltop towns, charming villages, ancient castles, olive groves, and vineyards along the way. Soon you'll reach the Tenuta Torciano truffle ground for today's thrilling hunt. Join a local truffle hunter and watch the dog sniff out precious black and white truffles in the woods. You'll learn to identify different species of trees and the ideal habitat for truffle growth, then return to the estate for a traditional lunch with salami, cheeses, bruschetta, lasagna, and more—enriched with truffles and Tuscan wines produced on the estate.
Day 3: Drive to Montalcino via Siena & Tuscan Wine School Tasting
Chat with a local specialist who can help organize your trip.
This morning you'll head to Siena, an easy one-hour drive along rural Tuscan roads. Siena is considered an open-air museum of medieval monuments, museums, palaces, and churches. Park outside the pedestrian-only city center, and venture into the UNESCO World Heritage Site. Use your time to explore the main square, the Piazza del Campo, which is dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Find a local trattoria for lunch and try pici, a rustic homemade spaghetti, with pork or wild boar ragù.
Day 4: Hot-Air Balloon, Brunello Wine Tasting & Cooking Class in a Tuscan Castle
Beyond delicious food and wine, one of the best things about Tuscany is the spectacular landscape—and today you'll see it from above with a scenic hot-air balloon flight. Rise before dawn and climb into the balloon basket, ready to float gently above the undulating Tuscan plains, watching olive groves, rolling vineyards, and medieval hilltop villages float by below you. After your bird's-eye view of the countryside, return to Earth and seek breakfast at a local café or pastry shop.
After, you'll drop into a well-preserved 13th-century castle for a Brunello wine tasting, cooking class, and classic Tuscan lunch. Follow a sommelier around the vineyard, learning about the landscape and methods of wine production. Then, join an exclusive cooking class to learn traditional techniques and time-honored Tuscan recipes. Finally, sit down to savor the simplicity of farm-to-table cooking and enjoy the fruits of your labor. Your three-course lunch will be paired with local Montalcino wines, aged in the castle's underground cellars.
Day 5: Drive to Terme di Saturnia, Afternoon at Thermal Springs Resort
Sleep in this morning and enjoy a slow morning in Montalcino, a gem of history and art in the hills of the Val d'Orcia. Discover the city's old medieval layout and its 1361-built citadel, then drive just over an hour south to Terme di Saturnia, a 5-star spa resort with a scenic GEO-Certified championship golf course. The estate covers 300 acres (120 ha) of Tuscan countryside, allowing you to truly leave the busy world behind and relax in the picturesque landscape.
You're staying at a spa resort, so use the rest of today to indulge in the thermal waters, in use since Roman times. Experience rejuvenating spa treatments, and lock in a day spa program with outdoor thermal pools, hydro-massages, a Roman bath with sauna, a Turkish bath, whirlpools, and vascular paths. Later in the day, reserve a table poolside at the resort's 1919 restaurant for a romantic meal under the stars.
Day 6: Traditional Tuscan Lunch at Organic Farm, Free Time at Terme di Saturnia
Enjoy another slow start to the day—or squeeze in another spa treatment—ahead of today's traditional Tuscan lunch. Today you'll travel to a nearby organic farm for a special four-course meal on a terrace with views of the Tuscan countryside and hills. Giacomo will share the history of the family's ancient farmhouse, and tell you about their food philosophy and sustainable systems as you sit beneath a centuries-old holm oak. Enjoy an aperitif of local wine and a traditional Tuscan appetizer of local salumi.
Then Giacomo, a skilled chef and expert sommelier, will present a seasonal pasta dish and a seasonal main that make the most of the produce grown at the organic farm. He'll explain the ingredients and pair each with a high-quality local wine. Finally, your long lunch in the countryside concludes with dessert. After, return to the resort and spend the remainder of the day enjoying the thermal pools and spa.
Day 7: Drive to Pisa, Depart
It's the final morning of your romantic vacation in Italy. After breakfast, make the three-hour return drive to Pisa for your departing flight home or onward. Make sure you leave enough time to refuel and return the rental car. Safe travels!
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