Weekend in Tuscany: ideas for 2 days among villages and flavours

A weekend in Tuscany - Saturday and Sunday, or even Friday evening to Sunday - is one of the most satisfying short trips you can take from anywhere in Italy or Europe. You arrive, breathe different air, eat well, see something beautiful. And you return rested.

This guide proposes four different weekend formats, depending on what you are looking for.

A weekend in Tuscany is not just any weekend. It is different air, real food, something beautiful to look at. It is the kind of trip from which you return rested - not exhausted.

Weekend in Tuscany: how to choose your theme

The first thing to decide is the “tone” of the weekend. Tuscany offers very different experiences:

• Cultural: villages, museums, churches
• Food and wine: wineries, markets, restaurants
• Relaxation: thermal baths, spas, slow walks
• Adventure: trekking, cycling, nature

Each theme has its own logistics, its own rhythms, its own destinations. Choosing one main theme and building the weekend around it gives better results than a “a little of everything” approach.

Cultural weekend: Siena + San Gimignano

Saturday:

• Arrive in Poggibonsi in the late afternoon or evening
• Dinner at Ristorante Alcide or a local trattoria
• Evening walk in the centre of Poggibonsi

Sunday morning:

• San Gimignano (15 minutes by car): the Collegiata, the towers, Gelateria Dondoli if it is open
• Lunch in San Gimignano

Sunday afternoon:

• Siena (30 minutes): Piazza del Campo in the late afternoon, when the light is most beautiful
• Return home

This weekend is ideal for first-time visitors wanting to “taste” medieval Tuscany.

Food and wine weekend: Chianti + wineries

Saturday morning:

• Arrive in Poggibonsi
• Head into Chianti (15 minutes): Castellina in Chianti, explore on foot

Saturday afternoon:

• Visit a winery with advance booking: Chianti Classico tasting
• Dinner at the winery’s agriturismo or in Radda in Chianti

Sunday morning:

• Local market or visit to Macelleria Cecchini in Panzano
• Lunch in Chianti

Sunday afternoon:

• Greve in Chianti: Enoteca Falorni to buy bottles
• Return home

This weekend is for wine and Tuscan cuisine lovers.

Relaxation weekend: thermal baths + Val d’Orcia

Saturday:

• Arrive in Poggibonsi
• Afternoon: head to Bagno Vignoni (1 hour): thermal pools or free baths
• Dinner in Bagno Vignoni or San Quirico d’Orcia
• Return to Poggibonsi for the night (or stay overnight in the area)

Sunday:

• Morning: Pienza (12 km from Bagno Vignoni) - the piazza, the Duomo, Pecorino cheese
• Lunch in Pienza
• Afternoon: return towards Poggibonsi with a stop in Montalcino or Siena

This weekend is for couples seeking a slow pace and unhurried beauty.

Adventure weekend: trekking + villages

Saturday morning:

• Set off from Poggibonsi on foot: the Via Francigena section towards San Gimignano (12 km, 3 hours)
• Arrive in San Gimignano: quick visit, lunch

Saturday afternoon:

• Bus back to Poggibonsi, or walk towards Colle Val d’Elsa (part of the route)

Sunday:

• Excursion in Chianti: circular route from Castellina (15-20 km, 4-5 hours)
• Stop at a winery mid-route

This weekend is for those who love walking and do not want to spend all their time in a car.

How to reach Poggibonsi for the weekend

From Florence: 55 minutes by train, or 40 minutes by car on the A1 motorway. From Bologna: 2 hours by train (with one change) or 1h30 by car. From Rome: 3 hours by train (with a change at Chiusi) or 3 hours by car. From Milan: 3 hours by train (with a change in Florence) or 3h30 by car.

The train is particularly convenient from Florence and northern Italian cities.

Hotel Alcide for the weekend: availability and prices

Hotel Alcide offers rooms for every type of weekend - couples, families, groups of friends. Direct booking on the official website guarantees the best available rate.

Spring and autumn weekends tend to fill up early, especially those around the Palio di Siena (July and August) and the harvest season (September). Advance booking is recommended.