Il Paluffo is the ideal starting point for two unforgettable days in the heart of Tuscany. This 48-hour itinerary combines history, art, breathtaking views and authentic flavours, taking you through medieval villages where time seems to have stood still, centuries-old vineyards and restaurants that showcase local traditions. All destinations are less than forty minutes away by car, allowing you to explore without stress and return to Il Paluffo each evening. Prepare to slow down, savour every moment and discover the most authentic soul of Tuscany.

DAY 1

8:30 a.m. Breakfast at Paluffo

There is nothing better than a good breakfast to start the day off right. At Al Paluffo, we use only high-quality organic products sourced locally: wholemeal bread made from ancient grains, Tuscan salami, finocchiona and artisan Tuscan pecorino cheese, homemade cakes and pastries baked fresh every morning, honey and organic oil produced on our farm, and many other delicacies.

9:30 a.m. to 1:00 p.m. Certaldo Alto

The morning of the first day is dedicated to exploring Certaldo Alto, the ancient centre of Certaldo, which has retained its medieval charm intact. Perched on top of a hill, it is surrounded by a circle of well-preserved walls with historic gateways: Porta Alberti, Porta al Sole and Porta al Rivellino. The main attractions of Certaldo Alto are: the house of Giovanni Boccaccio, now converted into a museum; and the 13th-century Palazzo Pretorio, once the residence of the Alberti counts. Other places of interest include: the Church of Saints Thomas and Prospero, with Benozzo Gozzoli’s Tabernacle of the Executed; the Church of Saints James and Philip, where Boccaccio is buried; and the Museum of Sacred Art, housed in a 15th-century Augustinian convent.

1:00 p.m.-2:30 p.m. Lunch at L’Antica Fonte Restaurant

Located in the heart of Certaldo Alto, L’Antica Fonte is a restaurant offering traditional Tuscan cuisine using only the highest quality, fresh, seasonal ingredients. The house specialities? Pappardelle with game sauce and Florentine steak. In addition to the indoor dining room, there is also an outdoor terrace from which you can enjoy a magnificent view of the surrounding hills.

3:30 p.m. to 5:30 p.m. Guided tour of the Corzano and Paterno Farm

Located in San Casciano in Val di Pesa, Fattoria Corzano e Paterno brings together two properties that once belonged to the Niccolini and Machiavelli families. Here you can take a guided tour of the winery and dairy, with explanations of the production processes and various techniques. Followed by a tasting.

6:00 p.m. to 8:00 p.m. Walk in San Donato in Poggio

San Donato in Poggio (a hamlet in the municipality of Barberino Tavarnelle) is a small medieval village still almost entirely surrounded by imposing 13th-century walls, from which emerge the characteristic watchtower and its monumental entrances: Porta Fiorentina and Porta Senese. The central point is Piazza Malaspina, overlooked by Palazzo Malaspina, one of the most important architectural examples of the 16th century; the 15th-century Church of Santa Maria della Neve, with two beautiful paintings by an unknown artist inside; and Palazzo Pretorio. The rest of the village is a succession of alleys and narrow streets offering beautiful panoramic views.

8:00 p.m.-9:30 p.m. Dinner at La Locanda di Pietracupa Restaurant

The first day ends with dinner at La Locanda di Pietracupa restaurant. Located near the Sanctuary of the Madonna delle Grazie in Pietracupa, it offers Tuscan cuisine revisited with local and seasonal ingredients, in an elegant and welcoming setting. During the summer, you can enjoy the charming panoramic terrace overlooking the village of San Donato in Poggio.

DAY 2

8:30 a.m. Breakfast at Paluffo

The second day also begins with our typical Tuscan breakfast.

9:30 a.m. to 1:00 p.m. San Gimignano

The morning of the second day is dedicated to exploring San Gimignano. With its forest of towers dominating the rolling hills, it is one of the most iconic and recognisable destinations in all of Tuscany. The historic centre is built around Piazza del Duomo, which is overlooked by some of San Gimignano’s most important buildings: the Collegiate Basilica of Santa Maria Assunta, famous for its frescoes and in particular for the Chapel of Santa Fina; the Palazzo del Popolo, which houses the historic headquarters of the Civic Museums; and the Palazzo Vecchio del Podestà, distinguished by the Torre Rognosa. Another unmissable site is Piazza della Cisterna, which takes its name from the 13th-century cistern located in the centre. The square has a curious triangular shape and is surrounded by medieval palaces and towers, among which the Torre del Diavolo stands out, which according to legend was built by Satan himself.

1:00pm-2:30pm Lunch at Enoteca La Vecchia Nicchia

Located just a few steps from Piazza del Duomo, La Vecchia Nicchia is a small, cosy wine bar with a kitchen. Here you can enjoy bruschetta with typical Tuscan flavours, platters of high-quality local cold cuts and cheeses, accompanied by an excellent selection of over 200 wine labels.

3:30 p.m. to 7 p.m. Monteriggioni

After lunch, we continue on to Monteriggioni, one of Italy’s oldest and most recognisable villages. Perched on a hilltop, it is famous for its perfectly preserved walls, built in the 13th century by the Sienese to defend themselves from the Florentines. From the walkways along the walls, you can admire a splendid view stretching from the Chianti hills to the woods of the Montagnola. The heart of the village is the charming Piazza Roma. Surrounded by vegetable gardens and parks, it is paved with stones from the quarries of Rosia. Among the things to see are: the 13th-century Pieve di Santa Maria Assunta, which houses a valuable 17th-century painting of the Madonna del Rosario; and the Monteriggioni in Arme educational trail, which features faithful reproductions of medieval and Renaissance weapons and armour (some of which can even be worn).

8:00–9:30 p.m. Dinner at Trattoria del Pesce

The second day ends with dinner at Trattoria del Pesce al Bargino, just under ten kilometres from Paluffo. Here, the menu focuses on fish, crustaceans and molluscs served both raw and cooked according to Tuscan seafood traditions. The owners Fabrizio and Milena, or their children Gianni, Barbara and Filippo, will guide you in choosing your dishes and recommend the best options based on your tastes and the catch of the day.

In just two days, you can discover some of Tuscany’s most fascinating places, from Certaldo to San Gimignano, passing through Monteriggioni and the Chianti countryside. Paluffo, with its strategic location, organic breakfast and rooms nestled in the quiet hills, is the perfect base for a stay that combines culture, relaxation and taste.