How do people decide where to stay in the tuscan countryside? There are so many choices and options, and they all look so amazing. My husband and I are looking for somewhere in the countryside, but in a good position to visit the Chianti region, Siena, Volterra, and Montepulciano... We are also looking for somewhere that does dinners, or that has restaurants near by... and ideally is under 150 euro a night. Any suggestions???
Of the three I believe Siena is the only one that is technically in Chianti, if that helps. Also Siena is best at night which may work out well for you if you spend your days out in the countryside. You will miss the bus crowds during the day.
A lot depends on how you are travelling--by train or car. Since we drove, we stayed outside of San Gimignano to visit that hilltown & Volterra. Then we stayed outside of Pienza for Montepulciano. Then we stayed 10km outside of Siena in the countryside to visit that general area. We generally stay for two nights. We like to stay in different areas to enjoy a variety of experiences.
We just got back from Tuscany. We stayed at La Bruciata agriturismo. It is near Montipulciano. It was excellent and we could get dinner at this agriturismo. The dinner was truly fantastic and most of the items were grown right there on the farm including the delicious wine. The owners were great and very helpful. Breakfasts were also very nice.
We have a car rented... would you highly recommend any of the places that you stayed at?
FWIW here is the strategy we used for our last trip. I had previously visited Florence so we concentrated on the hilltowns. I, too, had a terrible time deciding which towns. Siena - 3 nights, 2 full days; 1/2 day seeing Siena highlights; 1 day tour with Tours By Roberto into the Chianti Region; Rented car for 2nd full day to Volterra and Monteriggioni. Could have hit San Gimignano that day but chose to return to Siena as the weather was turning to rain. Next day drove to Montalcino via Lauretan Road, Asciano, Monte Oliveto Maggiore, Buonconvento. Lovely! Montalcino - 3 nights, 2 full days; One day hike to Sant'Antimo and touring Montalcino; one day driving to Montepulciano and Pienza. Moved on to Orvieto for 2 nights via a scenic drive around Monte Centona that led is to 3 more tiny and scenic hilltowns. This turned out to be a great overview of Tuscany for us. We do not like driving endlessly, so kept the car trips purposefully short. Just one idea. We are going to Umbria later this year and using a whole different strategy: one town for 6 nights, no car, train and bus daytrips. We'll see how that works!
As to where to stay:
Siena: Antica Residenza Cicogna, B&B. Fabulous! They had a parking spot for 10 euros per night extra. We only needed that for one night. Montalcino: Palazzina Cesira. Elegant, fully restored 13th century palazzo. Right near the square, super quiet. Orvieto: B&B Ripa Medici. Right above the wall, quiet end of town, beautiful view.
We stayed at Agriturismo Marciano in Siena. It is out of town, but close. They are a winery and also make olive oil. They serve fabulous optional dinners (not every night) to their guests. The food was the best we had in our 3 weeks in Italy. It was my favorite place to stay. Check them out on Trip Advisor for reviews. We paid 85 euros per night last September, so it is well under your budget.