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The best area to stay in San Filippo is directly within the historic village centre, particularly near the main square, Piazza San Filippo.This area is the heart of the village, characterised by its traditional stone buildings, narrow cobbled streets, and stunning views of the Tuscan countryside. Piazza San Filippo is a natural gathering spot, often hosting local markets and events, and it's surrounded by local eateries and artisan shops. The famed thermal baths, Terme San Filippo, are just a short walk or drive away.Couples seeking a romantic and authentic Tuscan experience will find the village centre perfect. You'll be able to enjoy leisurely strolls through charming streets, dine at intimate trattorias, and easily access the thermal springs for a relaxing day. The evenings offer a quiet, relaxed pace, ideal for unwinding together.For travellers looking for a more secluded and luxurious retreat, the areas immediately surrounding the village, often referred to as the "countryside estates," are an excellent choice. These properties typically offer more space, private pools, and expansive gardens, while still being a short drive from San Filippo's amenities.Families or groups of friends might prefer one of these countryside estates. They provide ample room for everyone, often with self-catering facilities, allowing for a more independent and private holiday.

The best times to visit San Filippo are during the spring (April to early June) and autumn (September to October) months. These periods offer pleasant weather, ideal for exploring the region, and allow you to avoid the peak summer crowds.Spring in San Filippo brings mild temperatures and the Tuscan countryside bursts into bloom, making it a beautiful time for scenic drives and outdoor activities. You'll find the vineyards and olive groves particularly picturesque. This season is great for couples looking for a romantic getaway, with opportunities for leisurely walks and wine tasting without the intense heat of summer.Autumn is another excellent choice, especially for those interested in culinary experiences. The weather remains comfortable, and it's harvest season for grapes and olives. Many local festivals celebrate these traditions, offering a chance to sample fresh produce and regional specialities.