Highlights
- Snap a silly photo with the famous Leaning Tower of Pisa
- Learn family recipes at a cooking class near San Gimignano
- Join a guided tasting at the Tuscan Wine School in Siena
- Drive across one of the most beautiful areas of Italy, the Val D'Orcia
- End the trip at a luxurious spa resort with thermal springs and treatments
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Pisa, Self-Guided Visit | Pisa |
| Day 2 | Drive to San Gimignano, Tuscan Cooking Class | San Gimignano |
| Day 3 | Tuscan Countryside Bike Tour | San Gimignano |
| Day 4 | Drive to Montalcino via Siena & Tuscan Wine School Tasting | Montalcino |
| Day 5 | Hot-Air Balloon, Brunello Wine Tasting & Cooking Class in a Tuscan Castle | Montalcino |
| Day 6 | Truffle Hunt & Brunello Cooking Class | Montalcino |
| Day 7 | Val D'Orcia Wine Tour | Montalcino |
| Day 8 | Drive to Terme di Saturnia, Afternoon at Thermal Springs Resort | Saturnia |
| Day 9 | Free Time at Terme di Saturnia, Wine Tasting & Tuscan Dinner | Saturnia |
| Day 10 | Drive to Pisa, Depart |
Detailed Itinerary
Day 1: Arrive in Pisa, Self-Guided Visit
Ciao, and welcome to Italy! You've landed in Pisa, the city famous for the Leaning Tower that needs no introduction. On arrival, collect a rental car and make the short drive to your accommodation to drop off your bags. The rest of today is yours to explore this small city and its iconic monuments. Start your explorations at the Plaza of Miracles, the square where you'll see the famous tower alongside the Pisa Cathedral, the 12th-century Baptistery, and the Monumental Cemetery. This is your chance to take a silly photo with the tower!
Afterward, head into the historic center, where you'll find the curious Pisa Botanical Gardens and find places frequented only by locals and students. It's your first day in Tuscany, a destination famous for its olive oil, wines, and delicious food, so seek out a trattoria or wine bar and make yourself comfortable. In Pisa, you might also like to try torta coi bischeri, a delicious cake made with pine nuts.
Day 2: Drive to San Gimignano, Tuscan Cooking Class
After breakfast, 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 from 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 3: Tuscan Countryside Bike Tour
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 your destination, where a local cycling guide is waiting for you with your own two wheels. You'll cycle a leisurely 16 miles (26 km) through some magnificent Tuscan scenery, with the chance to visit local churches and small medieval villages as you go.
Partway through the day, you'll visit a local winery to taste the region's famous red wines, and at some point, you'll pause for a traditional Tuscan meal at an authentic local spot. As a private cycling tour, the day can be adapted to your level and enthusiasm for biking! After, return to San Gimignano for the evening.
Day 4: Drive to Montalcino via Siena & Tuscan Wine School Tasting
This morning starts in 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 Piazza del Campo, a main square 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.
Chat with a local specialist who can help organize your trip.
Day 5: 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 6: Truffle Hunt & Brunello Cooking Class
This morning you'll join a local truffle hunter and watch their specially trained dog sniff out precious black truffles in the woods. As you wander, you'll learn to identify different species of trees and the ideal habitat for truffle growth. Then, you'll return to the estate building with the delicious bounty and sit down for a truffle tasting and wine pairing.
In the afternoon, you'll switch to Castello Tricerchi, a boutique winery where you'll enter the kitchen. Under the guidance of a local chef, you'll learn all about Tuscan cuisine and produce a multicourse feast with the finest local produce and ingredients. When the meal is ready, venture out to the panoramic terrace to enjoy your meal paired with spectacular Tuscan wines, including the region's famous DOCG Brunello di Montalcino, made right at the castle.
Day 7: Val D'Orcia Wine Tour
Enjoy a relaxed breakfast this morning, then leave the car keys behind as a private driver helps you explore one of the most beautiful areas of Italy: the Val D'Orcia. The drive from Montalcino to Montepulciano via Pienza is considered one of the most amazing routes in Italy, and you'll soon understand why. Start in Montalcino, where you'll taste Brunello di Montalcino, a top-quality wine that has made this village famous across the world, and enjoy a fresh and seasonal Tuscan lunch.
After, hit the road, passing glorious hills covered with vineyards, olive groves, cypress, beech and chestnut trees, and medieval villages. The second stop is Pienza, the Renaissance jewel of the Val d'Orcia, filled with 15th-century architecture. Wander into the Cathedral and shop for antiques and pecorino cheese. Use your free time for a romantic walk down Via del Bacio, where you'll enjoy a magnificent view. The final stop is a special winery in Montepulciano, where you'll taste the Vino Nobile of Montepulciano and have time to wander the town's alleyways.
Day 8: 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 that have been 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 9: Free Time at Terme di Saturnia, Wine Tasting & Tuscan Dinner
Enjoy another slow start to the day. This morning is yours to explore the Tuscan countryside at your pace. At your luxurious resort, you can go hiking through the property's landscape of rolling green hills and cypress trees, or pick up speed on horseback or a bicycle. Or, stay close to the resort, booking yourself a morning spa treatment or joining the on-site cooking class.
Later, you'll join a private tour of an organic vineyard with a member of the estate's family. Step through the vines while learning all about how each wine is produced and the various characteristics, then continue the wine experience with an exclusive tasting of four wines. After, you'll sit down to try the estate's extra virgin olive oils and enjoy an authentic four-course Tuscan-style meal featuring family recipes passed down for generations. After, return to your resort for your final night in Tuscany.
Day 10: 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!
More Great Italy Itineraries
Looking for more inspiration for your trip to Italy? Check out these other Italy itineraries, explore different ways to spend 10 days in Italy on your honeymoon, or discover the best time to visit Italy.
Map
