Medieval Villages and Hidden Gems: Slow Excursions in Valdelsa
Discover the Authentic Soul of Tuscany: Short Itineraries Minutes Away from Our Farmhouse
If you wish to experience a more intimate and secluded Tuscany, beyond the famous art cities such as Florence, Siena, and Pisa – which you can visit comfortably thanks to our guide dedicated to major cultural destinations – the surroundings of Montaione offer a heritage of inestimable value. Staying at Piè di Costa Holiday Home means being at the center of an extraordinary territory, where enchanting villages like Certaldo, Vinci, Montespertoli, Monteriggioni, and San Miniato are just a few kilometers away, allowing you to enrich your holiday with never-banal daily discoveries.
Choosing these smaller centers means escaping the chaos of the most crowded tourist destinations, often stormed during the high season. Here, among the hills of Valdelsa and the Tuscan valleys, time seems to have stood still: you can stroll through medieval alleys, admire breathtaking views, and discover authentic local traditions, far from the flows of mass tourism. These are perfect destinations for those seeking pure beauty, the silence of the countryside, and that rustic charm that makes Tuscany a unique region in the world.
Thanks to their strategic proximity to our holiday home, these villages are the ideal destination for half-day excursions or relaxing trips of just a few hours. The ease of travel and the compact size of the historic centers make these visits particularly pleasant even for families with children, who can explore castles, towers, and ancient squares without the stress of long queues or long travel distances, then returning to enjoy the relaxation of our pool upon their return.
Discovering hidden Tuscany: itineraries through the villages of Valdelsa
If you are looking for a more intimate experience, away from the crowds and perfect for those traveling with children, the villages surrounding Montaione are true treasures ready to amaze you. Here are 4 itineraries designed to experience the slow pace of our land, all reachable within a few minutes' drive from Piè di Costa.
Day 1: Gambassi Terme and Castelfiorentino
Wellness and Sacred Art
Gambassi Terme
A village of ancient thermal origins located along the Via Francigena pilgrimage route. Gambassi Terme is famous for its healing waters, its Municipal Park, and the ancient tradition of glassmaking, which has deep roots in the area.
- Well-preserved historic center: a walk through the characteristic medieval streets typical of Tuscan villages.
- Municipal Park: a green oasis rich in exotic plants and rare species, perfect for relaxing in the shade of palms and magnolias.
- Pieve di Santa Maria a Chianni: a splendid example of Romanesque architecture.
- Thermal Waters: a regenerating experience thanks to the historic springs, known since antiquity for their beneficial properties.

Castelfiorentino
A lively hub in the heart of the Valdelsa, rich in unexpected art treasures. Castelfiorentino is the perfect place to combine a cultural stroll with a relaxing break in its public squares and historic cafés.
- BEGO Museum: dedicated to Benozzo Gozzoli, featuring interactive installations perfect for children.
- Teatro del Popolo: an architectural gem in the heart of the city.
- Church of Santa Verdiana: an important place of worship rich in history and artistic charm.
- Upper Historic Center: with its ancient alleys and authentic atmosphere.

Day 2: Certaldo Alto and Montespertoli
Among the fathers of Italian literature and the wine hills
Certaldo
Certaldo is a charming medieval village overlooking the Val d'Elsa. Famous as the birthplace of Giovanni Boccaccio, the town is distinguished by its typical terracotta houses that give it a warm, reddish hue, creating an atmosphere suspended in time.
- Palazzo Pretorio: the historic symbol of the village.
- Boccaccio House Museum: to retrace the life of the great writer.
- Church of SS. Tommaso e Prospero: featuring splendid frescoes by Benozzo Gozzoli.
- Funicular: for a panoramic ride up to the upper part of the village.
Kids love it!

Montespertoli
The heart of Chianti and a land of great wines, Montespertoli stands out for its well-tended agricultural landscape and gentle hills. It is the ideal place for those seeking the authenticity of the Tuscan rural world and tranquility far from the beaten paths.
- Vine and Wine Museum: to learn about the local winemaking tradition.
- Poppiano Castle: an ancient fortress that enchants both adults and children.
- Pieve di San Piero in Mercato: a Romanesque gem hosting the important Museum of Sacred Art.
- Village of Lucardo: a small fortified hamlet with a magical charm.

Day 3: San Miniato and Vinci
Truffles and the Genius of Leonardo
San Miniato
Perched on a hilltop, San Miniato is a village of rare beauty, famous worldwide for its prized white truffle. Its historic center, filled with noble palaces, preserves its medieval charm intact.
- Frederick II Tower: for a 360-degree panoramic view of the valley.
- Truffle hunting: an exciting and educational experience for children as well.
- Seminary Square: an architectural jewel that fascinates every visitor.

Vinci
Nestled on the slopes of Montalbano, Vinci is inextricably linked to the genius of Leonardo. The village retains an intact charm, where ancient medieval walls still surround the historic heart of the town, offering unique views of the surrounding countryside.
- Leonardo Museum: an extraordinary exhibition of machines conceived by Leonardo's genius.
Includes a path suitable for children. - Castle of the Guidi Counts: a historic stronghold overlooking the village.
- Leonardo's Birthplace: located in Anchiano, just a few minutes from the village of Vinci.

Day 4 (Half day): Colle di Val d'Elsa
At the origins of glass art in Tuscany
Colle di Val d'Elsa
Divided between the "Lower Town" and the striking "Upper Town" (the historic part), this city is universally known as the "City of Crystal". A village where art, craftsmanship, and history blend uniquely.
- Crystal Museum: a fascinating experience with transparencies and light effects.
- Sentierelsa Trail: a nature path along the Elsa River, among turquoise waterfalls, natural pools, and wooden bridges.
Perfect for families with children. - Walk through the medieval streets: full of arches and picturesque views.
- Sapìa Bastion: to admire the historic walls with a view of the Val d'Elsa.

FAQ on the best excursions to discover the small medieval villages near Piè di Costa
Which short excursions near Montaione do you recommend for families with children?
For a relaxing trip of just a few hours, the medieval villages of Valdelsa are the perfect choice. Only 15-30 minutes from Piè di Costa, you’ll find treasures like Certaldo Alto, accessible by a fun funicular, or Vinci, where children can discover the machines of Leonardo's genius. From the shaded parks in Gambassi Terme to "truffle hunting" in San Miniato, these small centers offer a magical, traffic-free atmosphere, ideal for exploring authentic Tuscany with little ones without long travel times.
Choose How to Experience Tuscany
What kind of holiday are you looking for? Discover experiences designed for every travel style.
If you are on holidays with children
Explore activities designed for families near Montaione: playgrounds, outdoor trails, swimming pools and creative workshops. The perfect holiday for both adults and kids!
Discover moreIf you want an active holiday
Hiking, cycling, trekking and outdoor sports await you at Piè di Costa and around Montaione. Experience Tuscany immersed in nature and rolling landscapes.
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Savor the authentic flavors of Tuscany in typical restaurants, local markets, and farm-to-table products. From Valdelsa wines to traditional recipes, every meal becomes a unique experience.
Discover moreIf you love art and culture
Explore medieval villages, museums and cultural itineraries around Montaione. Discover local events and stories that reveal the artistic and historical identity of the region.
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