Long autumn weekends have become one of the most sought-after travel occasions for those who don’t want to wait for summer to take a break. Between October and November, central Italy offers still-mild days, the last stages of the grape harvest, truffle season, village festivals and a far more relaxed atmosphere than the peak season. Staying in a villa during this period means enjoying these moments with more space, more privacy and generally more flexible conditions than in July and August. In this article we select four Emma Villas properties between Tuscany and Umbria, designed for exactly this kind of long autumn weekends, together with practical guidance on what to check before booking.
What really matters for an off-season getaway
Planning a short stay outside the summer months requires attention to different variables than a classic July or August week. Before choosing your villa, it’s worth considering:
- Weather and microclimate: the hills of Tuscany and Umbria remain pleasant well into November, but night-time temperatures drop noticeably: check the indoor heating and whether a working fireplace is available.
- Swimming pool: most outdoor pools traditionally close on the first Saturday of October; only a few properties offer a heatable pool on request.
- Logistics and minimum stay: in low season the minimum number of nights required is often more flexible, an advantage for anyone planning a 3-4 night getaway.
- Privacy: fewer occupied villas in the same area mean a more intimate experience, with quieter villages and restaurants.
To make the most of your long autumn weekends, it’s worth starting from these four factors before checking the availability of individual properties.
Our villas for an off-season escape
The following selection was made directly among the Emma Villas properties, focusing on villas between southern Tuscany and the border with Umbria: an area particularly suited to an autumn getaway among villages, thermal baths, grape harvest and truffles.
SAN FRANCESCO 12 – Sleeps 12 (6 bedrooms, 7 bathrooms)
Surrounded by vineyards, olive groves and the woods of Monte Cetona, this farmhouse restored with terracotta floors and exposed beams is the ideal base for exploring Chiusi, Sarteano, Montepulciano and Pienza, and for day trips to Orvieto, Assisi, Perugia and Todi in Umbria. The thermal waters of San Casciano dei Bagni are just minutes away, perfect for completing a wellness-focused, slow-paced low-season weekend.
VILLA PUCCI 12 – Sleeps 12 (6 bedrooms, 6 bathrooms)
An old stone building restored in the Tuscan tradition, Villa Pucci sits in the Aretine Val di Chiana, about one kilometre from the hamlet of Alberoro and minutes from the medieval villages of Civitella della Chiana, Lucignano and Castiglion Fiorentino. The spacious living room with fireplace and the panoramic tower make it especially suited to cooler evenings, while the garden and pool remain a bonus on the still-mild days of early autumn.
NONNO FERNANDO 18+4 – Sleeps 18+4 (9 bedrooms, 11 bathrooms)
A stone farmhouse dating back to the early 1800s at the foot of Cortona, overlooking the Val di Chiana and Lake Trasimeno. The main house keeps a spacious living and dining room with fireplace, while the five annexes comfortably host large groups across two floors. It’s the natural choice for anyone planning an off-season escape with friends or extended family, perhaps around a dinner built on the autumn produce of the area.
Practical advice for every kind of traveller
Couples looking for long autumn weekends will find the thermal-baths-and-vineyards combination at San Francesco 12 the ideal value, with slow rhythms and few distractions. Families and larger groups can look to Nonno Fernando 18+4, whose five annexes make it easy to divide up the space while still sharing evenings by the fireplace. Remote workers wanting to extend their stay will appreciate the WiFi connection and quiet of Villa Pucci 12, equally suited to a short working break between calls and walks through the villages of the Val di Chiana.
What to check before booking
Before confirming one of your long autumn weekends, check these points with the Emma Villas booking office:
- Exact dates of any local events you plan to combine with your stay: these can change from what is published online, so always confirm them on the event’s official calendar before planning your trip.
- Pool heating and the actual opening period: many pools close on the first Saturday of October, unless otherwise stated on the property page.
- Indoor heating system and whether a working fireplace is available, particularly useful for November evenings.
- Minimum number of nights required for your chosen period, which can differ from summer in low season.
What to do nearby in October and November
Low season between Tuscany and Umbria coincides with some of the area’s most distinctive moments: the grape harvest in the cellars of Chianti and the Val di Chiana, white truffle hunting in the Sienese and Aretine countryside, and the village festivals that animate the towns on weekends. A short drive from the Cetona and Cortona area, Perugia hosts Eurochocolate, the international chocolate festival, whose 2026 edition is announced for 13–22 November: as with any event of this kind, the dates should be reconfirmed on the festival’s official website before planning the trip, since they may change. It is exactly these occasions, together with the autumn foliage across the hills, that make long autumn weekends a travel experience quite different from a classic summer holiday.
Frequently Asked Questions
When is the best time to plan a long weekend in autumn between Tuscany and Umbria? The weeks between mid-October and late November offer still-mild weather, the last of the grape harvest, truffle season and a calmer atmosphere than summer: the ideal moment for one of the classic long autumn weekends in a villa.
Do Emma Villas’ pools stay open in autumn? Most outdoor pools close on the first Saturday of October. Only a few properties, such as Villa San Giuseppe 12, offer the option to heat the pool on request for an extra fee: availability should always be confirmed at the time of booking.
What is the minimum number of nights to book a villa in low season? The minimum stay varies by property and by chosen period: in autumn it is often more flexible than in high season, but it should always be confirmed with the Emma Villas booking office before fixing the dates of your getaway.
Is it worth booking in advance for a getaway timed around events like Eurochocolate in Perugia? Yes. Around well-attended events such as Eurochocolate, villa availability in the area drops quickly: booking a few weeks ahead is the safest choice for anyone planning one of their long
