Land at Rimini and pick up your rental car; allow 30–60 minutes for luggage and paperwork and check the rental desk closing time if your flight is late.
Enjoy fresh Adriatic seafood or classic Romagna dishes at a seafront trattoria — recommended example spots: a seafront seafood restaurant or an osteria on Viale Vespucci (many stay open until ~22:30); confirm hours and book if possible.
Scenic inland drive to Pennabilli (approx. 1h10–1h30). Roads are winding after leaving the coast—drive carefully at night and allow extra time for narrow stretches.
Arrive and check in at your hotel, B&B or guesthouse; many small properties have limited reception hours—confirm late arrival arrangements with your host in advance.
If awake, take a brief walk to a nearby viewpoint for night views of the valley, then rest—Pennabilli is peaceful after dark and a good place to recharge for the next day.
Grab espresso and a cornetto at a local bar or have breakfast at your accommodation — many bars open by 7:00–8:00, but confirm if you need an earlier start.
Explore the Franciscan sanctuary where St. Francis is said to have received the stigmata; outdoor areas are open year‑round and many chapels open around 9:00 — check museum/chapel hours seasonally.
Enjoy simple mountain dishes—soups, polenta, mushroom or game-based plates—at the refectory or a nearby rifugio; lunch service typically runs midday but hours can vary by season.
Drive southwest into Tuscany toward Arezzo (approx. 1h45–2h15 depending on route). Plan for some winding mountain stretches and toll-free regional roads.
Arrive in Arezzo, check into your hotel, then relax with a coffee on Piazza Grande while enjoying the square’s sloping medieval vistas — cafés are usually open mid‑afternoon.
Visit Arezzo's Duomo for stained glass and architecture if open (cathedral hours vary — often afternoon openings exist), or stroll the streets to orient yourself before dinner.
Dine at a classic Tuscan osteria — recommended example: Osteria del Teatro or a trattoria near Piazza Grande for pappardelle al cinghiale, bistecca or ribollita; many restaurants begin dinner service around 19:00–20:00 so reserve if possible.
Enjoy a relaxed evening walk through Arezzo’s lit streets or a gelato near the square, then overnight in central Arezzo for an easy start next morning.
Visit the Basilica to see Piero della Francesca’s famous fresco cycle; fresco access and ticketing can require reservation or have limited hours, so check and book ahead if possible.
Choose a short visit to Casa Vasari or the archaeological museum for insights into Arezzo’s art and history — confirm opening hours which can be limited to mid‑morning/afternoon windows.
Enjoy a quick but delicious lunch of piadina farcita or local Romagna dishes at a central piadineria or trattoria — most places serve lunch 12:00–14:30.
Visit the 15th‑century Biblioteca Malatestiana, a rare example of a preserved humanist library; check opening hours and guided tour times in advance as they can be limited.
Explore the Rocca fortress and nearby viewpoints for short walks and views over Cesena; parts of the fortress may have seasonally limited access, so verify opening times.
Wander Cesena’s medieval streets, browse local shops or markets if operating, and pause for an espresso or gelato before preparing to depart for Rimini.
Drive to Rimini Federico Fellini Airport or central Rimini (approx. 45–60 minutes). If you have an evening flight, aim to arrive at the airport 1.5–2.5 hours before departure to allow for car return and check‑in.
Return the rental car and complete airline check‑in and security — adjust timing to your specific flight; if you have time, enjoy one last aperitivo on the Rimini seafront.