Tuscany Walk: Montepulciano to Siena

What to Expect

Accommodation

Accommodation is in charming 3-star hotels, B&Bs and agriturismi*. Some of the places chosen have a swimming pool. All rooms have en-suite facilities. All places have been carefully hand-picked by us, and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Meals

Breakfast is included every day. Throughout the trip, there are plenty of opportunities to taste both the great local food and a wide range of the region’s prestigious wines.

Itinerary

Day 1: Arrival Montepulciano
Day 2: Montepulciano to Pienza | 15 km
Day 3: Pienza to Bagno Vignoni | 12 km
Day 4: Bagno Vignoni to Sant’Antimo/Montalcino | 14 km
Day 5: Montalcino to Buonconvento | 18 km
Day 6: Monte Oliveto Maggiore Monastery Walk | 14 km
Day 7: Monteroni d’Arbia to Arbia/Siena | 10 km
Day 8: Departure

Difficulty & terrain

The route is relatively easy, with ups and downs typical of Tuscany’s rolling hills. A good level of fitness is required for enjoying the walks to the maximum (read more about difficulty grades). The itinerary is mostly on paths and gravel roads (strade bianche), even if you find some sections on asphalted roads. Some walks are long but can be optionally shortened using local transport or private transfers. We strongly advise you to follow only marked trails and never try to shorten the path through the unknown and unmarked terrain. We will provide you with detailed road notes and maps, and you can call our 24/7 local assistance phone number anytime.

When to go

You can start your holiday every day between the beginning of April and the end of October. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August (If you’d like to catch the famous Palio di Siena, you will have to travel in July or August, however). In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.

Included

7 nights in charming B&Bs, small hotels and agriturismi.

7 breakfasts.

Luggage transfer on all walking days (only 1 piece per person up to 15 kg; there is a supplement for each additional bag).

Transfer from Castelnuovo dell’Abate to Montalcino (Day 4 at 16:00 h).

Transfer from Buonconvento to Monte Oliveto Maggiore Abbey (Day 6).

Transfer from Buonconvento to Monteroni d’Arbia (Day 7).

Holiday information pack including GPS-checked and regularly updated route notes and maps (digital copy sent by email and a hard copy delivered at the first hotel).

24/7 phone support by our local office/representative.

Excluded

Airfare and connecting land transfers

Lunches and dinners, drinks and snacks

Travel insurance

Personal expenses

Local tourist tax & entry fees (payable on the spot)

Any items not specifically mentioned as ‘Included’ in the programme

Options, extras & supplements

Supplement applies to members of a group who require a single room / single use of a double room. This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms). Extra nights. Private transfer from Arbia to Siena on Day 7. If you arrive by car in Montepulciano, we will book Hotel San Biagio (or similar) with a parking lot – please advise at the time of booking.