Ostra(Italy) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Osimo, the top choice is Hotel Ristorante La Corte, a boutique gem nestled within the medieval old town. Housed in a 15th-century stone building, it blends authentic heritage architecture with modern comforts. Each room features handcrafted wooden furnishings and views of the Basilica di Santa Maria Assunta. The on-site restaurant offers Michelin-commended regional dishes like pasta alla chitarra with wild mushrooms and local pecorino cheese. Guests enjoy easy access to the Castello di Osimo, a well-preserved fortress perfect for history buffs and photography lovers.

The historic center of Osimo is the most convenient area for first-time visitors. Located just steps from the Piazza del Duomo and Palazzo Comunale, it offers walkable access to all major sights. Cobblestone streets flanked by Renaissance facades create a timeless ambiance, especially at dusk when the city lights glow softly. Most accommodations provide free parking and breakfast, and staying near the Porta Vecchia gate ensures proximity to local markets, artisan shops, and scenic trails into the surrounding hills.

Yes, B&B La Torre Antica stands out as a family-friendly retreat in Osimo. Housed in a restored 15th-century watchtower, it offers spacious family suites, a dedicated playroom, and complimentary cribs and high chairs. The hosts organize tailored activities such as visits to local pottery workshops or guided bike rides through the Valley of the Alto Nove. Nearby parks and an animal enclosure allow children to explore nature safely. Evening storytelling sessions in Italian and English add cultural immersion for young guests.

Osimo thrives with cultural vibrancy. Every Saturday, the Piazza del Duomo hosts "Notti nella Città Vecchia"—an open-air concert series featuring Baroque music and folk ensembles. In September, the Marche Food Festival brings over 30 stalls offering local delicacies like prosciutto di Fermo, black truffle pasta, and handmade bread. The Teatro Comunale stages opera and drama performances throughout the year, with pre-show tours revealing backstage secrets. Evenings often feature wine tastings and live poetry readings in intimate settings.

Visitors should try the handmade pottery workshop at Ceramica d'Arte, where you learn traditional wheel-throwing techniques to craft authentic Marche-style terracotta vessels. Another highlight is the "Old Town Walk & Tea Ceremony," led by elder locals who share family recipes and customs tied to seasonal festivals. Every late spring, the Festival of Flowers transforms Osimo into a floral wonderland, with tapestries and blossoms adorning every alleyway. Residents dress in 18th-century attire during the parade, preserving centuries-old traditions.

Surrounded by the Apennines, Osimo offers exceptional outdoor experiences. Hike the Montecassino Trail, winding through oak forests and wild lavender fields, ending with panoramic views of the valley and the Santa Maria Assunta Basilica. Summer sees visitors enjoying kayaking on Lago di Pietranera, a serene lake with picnic zones and fishing spots. In winter, ski at Carpegna Ski Resort, just 20 minutes away. Horseback riding tours through olive groves and vineyards provide a peaceful way to connect with the countryside.

Osimo’s cuisine centers on Marche region ingredients. Must-try dishes include pasta alla chitarra, hand-cut wide noodles served with wild mushroom ragù and fresh pecorino. Another local favorite is prosciutto di Fermo, paired with grilled figs and aged cheese. Try duck breast with wild berry sauce and creamy risotto made with foraged mushrooms. Many restaurants source ingredients daily from nearby farms. For hands-on experience, book a cooking class to learn how to cure ham and bake rustic black bread using traditional methods.

While Osimo is small, it’s well-connected. Trains run from Ancona and Urbino to Osimo Railway Station, taking about 45 minutes. There’s no bus system within the city, but walking covers all main attractions. Electric bike rentals are widely available—around €10/day. For trips to mountain areas, local shuttle buses operate seasonally, or you can book a private taxi. Renting a compact car is recommended due to narrow streets. The nearest airport is Ancona Falconara Airport (AOI), approximately one hour away by car.

The Castello di Osimo’s arched corridors and tiered courtyards make for stunning shots, especially during golden hour when sunlight bathes the ancient stones. The Piazza del Duomo fountain surrounded by century-old plane trees offers a classic composition—ideal for morning or evening photography. Don’t miss the carved stone reliefs at Porta Vecchia, which create striking silhouettes under backlight. Inside the Santa Maria Assunta Basilica, the stained-glass windows and frescoes glow dramatically in sunlight, creating a dreamlike atmosphere perfect for artistic shots.

The Festa della Madonna Assunta in June is Osimo’s grandest celebration, featuring a procession of locals in traditional attire, street markets selling crafts and antiques, and religious ceremonies at the basilica. In December, the Christmas Lights Festival illuminates the entire town, with a giant tree in the square and nightly choir performances. The Harvest Festival in spring invites guests to step on grapes, taste new wine, and join in joyful rural festivities—perfect for experiencing authentic local culture.