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The best area to stay in Penna San Giovanni is within the historic hilltop town itself, particularly around the central Piazza XX Settembre.This area is the heart of Penna San Giovanni, characterised by its ancient stone buildings, narrow cobbled lanes, and panoramic views of the surrounding Marche countryside. The Piazza XX Settembre is a natural gathering spot, often hosting local events, and is home to the town's main church and a few small, traditional shops and eateries. Staying here offers direct access to the town's history and a truly local experience.For couples seeking a romantic and peaceful retreat, staying within the old town is ideal. You'll enjoy quiet evenings, stunning sunsets from your accommodation, and the convenience of strolling to local trattorias for dinner. The intimate scale of the town means everything is just a short walk away, superb for relaxed exploration.Families might also find the old town suitable if they appreciate a calm environment and the chance to experience authentic Italian village life. Children can enjoy the freedom of walking the pedestrian-friendly streets and exploring the historic nooks.

The best time to visit Penna San Giovanni is during the spring (April to June) and autumn (September to October) months, when the weather is pleasant and the Marche region truly shines.Spring brings mild temperatures and the landscape is lush and green, with wildflowers blooming across the hills. It's a wonderful time for exploring the local area on foot or by bicycle, enjoying the natural beauty without the heat of summer. You'll find local markets starting to become more active, offering fresh seasonal produce.Autumn offers comfortably cool weather, superb for exploring the historic towns and enjoying the region's culinary delights. This season is particularly good for food enthusiasts, as it coincides with grape harvests and truffle hunting season.