Land at Rimini and collect checked luggage; regional airport/rail connections are compact but allow ~20–30 minutes to clear arrivals and reach the rental car desk.
Collect your rental car and drive straight inland to Pennabilli to avoid a late stay in Rimini; the scenic drive takes about 1h15–1h30 along winding country roads—drive carefully after dark.
Arrive and check in to your Pennabilli lodging; confirm arrival instructions in advance if arriving late and ask about restaurant recommendations or reservations.
Enjoy Romagna-Appennino cuisine in Pennabilli — small local trattorie serve regional pastas, grilled meats and local wines and typically serve dinner until ~10:30–11:00pm; reservations recommended for late arrivals.
Have a hotel breakfast with espresso, pastries and fruit; most accommodations serve breakfast around 7:30–9:30am, giving you energy for morning exploration.
Scenic drive into the Casentino/Apennine area toward the Franciscan sanctuary; expect roughly 1h15–1h45 depending on roads and a short photo stop en route.
Arrive at the sanctuary area and take a short walk to the rim and viewpoints before lunch; trails and viewpoints are open daylight hours—wear comfortable shoes.
Eat a hearty Tuscan-Appennine lunch (mushroom dishes, pappardelle, local game) at a nearby trattoria; most places serve lunch from 12:00–14:30—check opening hours and reserve if possible.
Explore the Franciscan sanctuary perched on a dramatic cliff—visit the church, chapels and small museum; typical visiting hours are about 8:00am–6:30pm but verify seasonally.
Stroll the adjacent woodland trails around La Verna for quiet panoramas and serene spots linked to St. Francis—trails vary in length, choose a short 30–60 minute walk.
Dine on regional specialties (chestnuts, mushrooms, game and Tuscan wines); most mountain restaurants serve dinner from ~7:00–9:30pm—book ahead where possible.
Stroll the atmospheric Piazza Grande and visit the Cathedral (Duomo di Arezzo); many attractions open from mid-morning—this is a great time for photos and lighter crowds.
Try Tuscan dishes such as crostini, ribollita or pappardelle al cinghiale at a local trattoria—lunch service typically runs 12:00–14:30, so plan for a relaxed meal.
See the famous frescoes (including works by Piero della Francesca) and nearby museums; check current opening times as cultural sites often close in the early afternoon or late afternoon on certain days.
Depart Arezzo and head north to Cesena (approx. 2h–2h30m); expect to arrive early evening—use this drive to enjoy changing landscapes from Tuscany to Romagna.
Tour the UNESCO-listed Biblioteca Malatestiana, a Renaissance library and Cesena highlight; typical opening hours begin mid-morning (around 9:00–9:30), so arriving early is recommended—verify current hours online.
Explore the Rocca and enjoy panoramic views over Cesena and the Romagna plain; check the fortress’s opening hours as they can vary seasonally, generally mid-morning to late afternoon.
Pick up luggage, finish last-minute purchases and ensure travel documents are in order; allow extra time for any unexpected delays before the drive to Rimini Airport.
If time allows, enjoy a relaxed coffee or a final short walk in Cesena’s main square—cafés are open through the afternoon and provide a pleasant pause.
Depart Cesena for Rimini Airport (approx. 40–50 minutes). For an 8:00pm flight aim to arrive by about 6:00–6:30pm to allow sufficient time for check-in and security.
Check in and clear security at Rimini Airport; regional airports are efficient but allow time for baggage drop and boarding procedures—verify luggage restrictions beforehand.