San Casciano in Val di Pesa


Photo of San Casciano in Val di Pesa

About San Casciano in Val di Pesa

A gorgeous walled medieval town dripping in history, San Casciano is the perfect destination for lovers of history. Surrounded by countless vineyards, olive groves and the northern Chianti hills that seem to stretch on forever into a sunswept blue horizon, she is filled with pretty little churches, museums, galleries and the remnants of the old walls. A bustling place awash in art and viticulture, she is a sparkling symbol of what Italy means to the rest of the world, a place stylishly strewn with the past, rich in local festivals and fabulous wine. Our collection of the best places to stay in San Casciano Val di Pesa provide the perfect properties from which to explore the area.

The town and its surroundings have been inhabited for many thousands of years, the famous "Archer's Tomb" up a hill nearby is an Etruscan burial place. The Etruscans were a great civilisation in Northern Italy before the Romans chipped away at their influence and power.

During the height of Roman power, San Casciano was an important market town - owing to her position on the Roman crossroads - and this prominence remained into the medieval era, with her location between Florence and Siena. Eventually she became a border town of Florence, an important military outpost, and walls were built in the early 14th century. During Napoleon's invasion, much of the town was abandoned - including the convent where the Musuem of Sacred Art now stands - and when WWII marched along, the town was decimated, but quickly and lovingly restored by the locals.

Now it bustles with life. There are lots of cafes, boutique shops, gelato parlours and restaurants, particularly in the town centre. All round the year there are festivals, from the medieval carnival in Spring and the wine-tasting in May to the rock 'n' roll festival in June and the olive oil tasting in November.

What Not to miss

  • Santa Maria del Prato: a beautiful little church with a Gothic facade just inside the city gate. It is filled with religious iconography and artwork.
  • Torre del Chianti: a newly-built 33 meter water tower that doubles up as an art gallery. If you climb to the top, it boasts panoramic views of the Florentine mountains, Chianti hills and, on clear blue-sky days, you can even see the sea and the hamlets littered about Siena.
  • The ancient city walls: ideal for a long, leisurely stroll, many parts of the medieval walls are painted with modern artworks.
  • The Archer's Tomb: discovered in 1978, it is an Etruscan tomb from the 7th century BCE. A few miles outside of town, the walk is simply beautiful, strolling through vineyards and olive groves to get there. The original slab depicting the archer lies in the Museum of Sacred Arts.
  • The Museum of Sacred Art: formerly a convent housing the nuns that fled Napoleon's armies, it was built in the 13th century and holds many wonderful works of art and sculpture.

Ideal for soaking up Italian history and culture, this beautiful little town boasts many sights and smells to delight the tastebuds and the best places to stay in Santa Casciano Val di Pesa provide a great starting point for exploring the town.

The best places to stay in San Casciano Val di Pesa

On a budget

  • Villa I Barronci: with 21 rooms, a wellness centre and an outdoor pool, this property is great value for money. Set in the idyllic countryside, it has a fresh contemporary feel whilst remaining in keeping with its rustic traditions.

Luxury living

  • Villa Mangiacane: a 5* luxury villa wih 27 room and suites, that runs food and wine tastings. Just outside Florence, it has a pool, spa and fantastic views of the vineyards below.

Countryside escape

  • Villa Il Poggiale: with 24 rooms, fragrant gardens, beautiful views of the Tuscan countryside and an outdoor pool. It also offers cooking classes. Spend time walking through the endless gorgeous meadows and vineyards surrounding her.

For an apartment or villa

  • Our partner Booking.com has a wide range of villas and apartments if you'd prefer a self catering option.

Travel information

  • The nearest airport is Florence International Airport.
  • If you want to rent a car, contact our partner Rentalcars.
  • The best time to go is in the sunkissed summer months, between June and August, when the temperature peaks around 32 degrees celcius.

Still not sure?


Monthly Weather in San Casciano in Val di Pesa

Best Hotels in San Casciano in Val di Pesa

  • Castello di Bibbioni San Casciano in Val di Pesa 13 rooms from €95

    Country Escape  -  A rustic farmhouse set in the gorgeous Chianti hills.
    Swimming Pool  -  Outdoor pool.
    Views  -  Great views from hotel
    Full of character
    Swimming PoolGardenPet friendlyDisabled accessViewsParking

    A traditional Tuscan castle with gorgeous views of the Chianti region. Farmhouse-style apartments with high beamed ceilings, delightfully uneven white-washed walls and cast iron beds. An impressively proportioned infinity pool and bikes to potter around the surrounding countryside. Rural bliss. See More

    Check Availability
  • Salvadonica San Casciano in Val di Pesa 19 rooms from €149

    Families  -  The generously proportioned family room with 2 adjoined ensuites, make this a comfortable choice for those travelling with kids
    Country Escape  -  A classic Tuscan stay hidden in the rolling Chianti hills, where life is slow and focused on good food and wine
    Cooking classes  -  Learn to cook traditional dishes with the resident chef
    Tennis  -  Play a game on the property's all-weather outdoor court
    Air conditioningTennisRestaurantSwimming PoolGardenParking

    A delightful farmhouse hotel amongst vineyards. Contemporary rooms and suites have rustic features; wrought-iron beds, frescoed walls, and exposed wooden beam ceilings. Pool, boules green, olive tree garden, tennis court and massages available. Excellent Tuscan cuisine. Romantic and very relaxing. See More

    Check Availability
  • Villa Il Poggiale San Casciano in Val di Pesa (Tuscany) 24 rooms from €153

    Great walks  -  Spend some time walking through the enchanting Tuscan countryside, explore the surrounding meadows, hills and vineyards.
    Cooking classes  -  Cooking classes can be arranged from the on-site chefs, learn to whip up your favourite dishes from the menu.
    Swimming Pool  -  Outdoor swimming pool fringed with hydrangea and jasmine.
    Views  -  Wonderful views of the rolling countryside.
    Air conditioningSpaRestaurantSwimming PoolGardenPet friendlyViewsParking
    Recommended by  -  Fodors, Sawdays

    Sun kissed Tuscan villa with fragrant gardens and wonderful views. Intimate and elegant bedrooms filled with paintings, antiques and fine linens. Fantastically well stocked wine cellar and local cuisine served in the shaded garden. Heavenly. See More

    Check Availability
  • Villa I Barronci San Casciano in Val di Pesa 21 rooms from €174

    Total relaxation  -  A tranquil base set in the rolling hills of Tuscany within its own private park and complete with a wellness centre.
    Value chic  -  A luxurious property offered at very reasonabe rates.
    Sights nearby  -  Located just 15km from Florence there's plenty to see from the Uffizi Gallery to the Duomo.
    Swimming Pool  -  Outdoor pool
    Air conditioningSpaRestaurantSwimming PoolGardenViewsParkingNo pets

    An ancient property set in picturesque parkland just outside of the historic city of Florence. Interiors are fresh and contemporary yet the building keeps its original features. The best rooms feature characterful mezzanines. Complete with a fabulous pool and wellness centre. See More

    Check Availability
  • Villa Mangiacane San Casciano in Val di Pesa (San Casciano In Val di Pesa Firenze) 27 rooms from €299

    Romantic Break  -  With in room baths, private dining and many acitivities couples would enjoy this property is perfect for a romantic break.
    Romantic  -  Superbly romantic bedrooms, decoration, and location.
    Views  -  Stunning valley views.
    5* Luxury  -  Very high service standards.
    Air conditioningSpaRestaurantSwimming PoolGardenViews
    Recommended by  -  Kiwi Collection, Small Luxury Hotels

    A Five Star luxury villa just outside Florence. Romantic bedrooms and suites, a pampering spa, fantastic food and wine tasting. Guest rooms have four poster beds, fireplaces, mezzanine levels, big bath tubs and a butler service. Stunning views over vineyards below. Ideal for couples or honeymooners. See More

    Check Availability