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The historic center is compact and best explored on foot. A popular self-guided route starts at Piazza del Popolo, continues to Piazza Arringo to see the Cathedral of Sant'Emidio and Baptistery, and then explores the Roman remains like the Ponte Romano. Many visitors enjoy simply wandering through the charming alleyways to discover hidden gems and admire the travertine architecture.

The historic center is generally flat, making it suitable for most walkers. However, as an ancient city, some streets and squares feature uneven surfaces, cobblestones, and occasional gentle inclines. Comfortable footwear is highly recommended to navigate these historical paths.

While the city itself is a visual feast, the confluence of the Tronto and Castellano rivers provides picturesque natural boundaries. For architectural viewpoints, the medieval towers offer glimpses of the city's skyline, and the open spaces of Piazza del Popolo and Piazza Arringo provide grand perspectives of the surrounding historic buildings.

The Historic Center is well-connected by public transport. The Ascoli Piceno railway station serves the town and is the terminus of the San Benedetto del Tronto–Ascoli Piceno railway. From the station, local buses or a short walk can take you directly into the historic center.

Ascoli Piceno is generally welcoming to dogs, especially in outdoor public spaces. Many cafes with outdoor seating may allow well-behaved dogs. However, it's always best to check with individual establishments before entering. Keep dogs on a leash and be mindful of local regulations regarding pet waste.

The historic center boasts numerous options. For a classic experience, visit Caffè Meletti in Piazza del Popolo, famous for its Art Nouveau ambiance and anisette liqueur. You'll find many other cafes and trattorias around Piazza del Popolo and Piazza Arringo, perfect for enjoying an aperitif or tasting local specialties like olive all'ascolana.

To comfortably explore the main squares, significant churches, and Roman remnants, visitors should allocate at least half a day to a full day. This allows time for leisurely strolls, enjoying a meal or aperitif, and perhaps visiting one of the museums like the Civic Art Gallery. A more in-depth exploration could easily fill two days.

While the historic center is charming year-round, spring (April-May) and early autumn (September-October) offer pleasant weather and fewer crowds than the peak summer months. If you wish to experience the vibrant Quintana jousting tournament, plan your visit for the first Sunday of August, though this will be a very busy period.

Due to its ancient origins and historical preservation, the Historic Center of Ascoli Piceno presents challenges for wheelchair accessibility. Many streets are cobbled and uneven, and some older buildings may lack ramps or elevators. While main squares like Piazza del Popolo are generally flat, navigating the narrower alleyways and some attractions might be difficult.

Beyond the famous squares, seek out the Church of Saints Vincenzo and Anastasio with its unique facade, or the Ponte Solestà, a well-preserved Roman bridge. Exploring the quieter side streets can reveal charming courtyards, smaller medieval towers, and local artisan shops that offer a glimpse into daily life away from the main tourist paths.

For a comfortable day trip, bring comfortable walking shoes for the cobbled streets. Depending on the season, a light jacket or umbrella might be useful. Don't forget a camera to capture the stunning travertine architecture, and perhaps a small bag for any local delicacies or souvenirs you might pick up.