Collect your pre-booked rental car at the airport or station; confirm your supplier's evening desk hours ahead of arrival to avoid delays. This is the start of your inland drive to Pennabilli.
Scenic drive northwest into the Apennine foothills (SS258/SP roads); expect about 1h–1h20 depending on traffic and exact route — be cautious on narrow stretches after dark.
Settle into a centrally located B&B or small hotel in the medieval town; notify your host of late arrival if needed so they can hold keys or arrange reception.
Dine at a family-run trattoria offering regional Marche/Romagna dishes (handmade pasta, seasonal mushrooms or game); many small-town restaurants are open until ~22:00–22:30, so call ahead to confirm.
Enjoy a short post-dinner walk to the town's viewpoint or illuminated towers for peaceful night panoramas over the Marecchia valley; public viewpoints are accessible anytime.
Grab a quick Italian breakfast at a local bar to fuel the mountain drive; many bars open from ~7:00. If you prefer, arrange a packed snack with your B&B.
Explore the Franciscan sanctuary complex, chapels (including the Stigmata chapel) and surrounding forest paths — the sanctuary grounds are typically open in daytime (often from early morning to early evening), but check current opening and guided-tour times before you go.
Enjoy hearty mountain cuisine—polenta, porcini-based dishes or local game—at a nearby rifugio or rustic trattoria; many serve lunch from ~12:00 to 14:30, and portions are generous after hiking.
Take a peaceful walk on marked trails around the sanctuary, visit smaller hermitages and viewpoints overlooking the Casentino forest; trails are open year-round but check seasonal signage for closures.
Check into a nearby convent guesthouse, mountain hotel or agriturismo — staying close to the sanctuary allows evening quiet and early access for sunrise or low-light photography; confirm check-in times in advance.
Dine at your guesthouse or a nearby restaurant offering regional Tuscan-Appennine dishes—expect simple, hearty fare and local wines; many establishments in mountain areas close earlier (around 21:00–22:00), so reserve or arrive early.
If the sanctuary permits evening access to external grounds, take a quiet walk beneath the stars — check sanctuary notices for any restricted hours or services that might limit access.
Enjoy a relaxed breakfast at your accommodation or nearby café—this is a good chance for a packed snack if you plan a longer driving day; confirm breakfast service hours with your host (often 7:30–9:30).
Drive southwest into Tuscany toward Arezzo; the journey typically takes about 1h–1h20 on scenic, sometimes curvy regional roads — aim to arrive mid-morning to enjoy the town with fewer crowds.
Stroll the striking Piazza Grande, browse antiques (if it’s an antiques market day) and visit the Duomo and Church of San Francesco for Piero della Francesca frescoes — check cathedral and museum opening times (often mid-morning to late afternoon) and any timed-entry requirements.
Savor Tuscan dishes such as ribollita, pappardelle with wild boar or other regional specialties at a well-reviewed trattoria; lunch service typically runs from ~12:00–14:30—reservations recommended at popular spots.
Check into your hotel in Cesena's center so you can walk to major sights (library, piazza, fortress); confirm late check-in if your arrival is after typical desk hours.
Tour the UNESCO-listed Biblioteca Malatestiana, a rare intact medieval public library — opening hours often include mid-afternoon slots but vary seasonally, so verify times and book guided visits if required.
Stroll the lively Piazza del Popolo, visit the Rocca fortress and riverside areas for photos and local atmosphere; museum/fortress hours typically run into early evening, but check closing times before arrival.
Enjoy Romagna cuisine—fresh piadina, seafood or meat specialties—at a central trattoria or a recommended local eatery; dinner service usually begins ~19:00, and reservations are advised on busy nights.
Return to your hotel in Cesena for overnight; use this time to pack or confirm onward travel plans such as returning to Rimini or continuing elsewhere the next day.