At a glance
- Civita di Bagnoregio is a village atop a tuff hill, reached on foot via a footbridge after you park. Check the current entry and parking arrangements first. On day 1 from Rome, visit Civita and then head to accommodation near Pienza or Montepulciano before dark.
- It’s best to stay at the same place near either Pienza or Montepulciano for both nights. Choose Pienza for scenery and quiet evenings, or Montepulciano for wine tasting and evening strolls through the historic center. Changing accommodation every day can let check-ins and luggage take over your schedule.
- Start day 2 with a walk through Pienza’s historic center. The historic center of Pienza is a UNESCO World Heritage Site, and Val d’Orcia is a separate UNESCO cultural landscape. Rather than just stopping for photos, walk around the piazza and cathedral before heading out on the country roads in the afternoon.
- Don’t search for cypress scenery by entering only “Val d’Orcia” on the map. Save specific destinations, such as SP 88 near Monticchiello and the Vitaleta Chapel. Vitaleta is about a 1 km walk after you park. Don’t stop along the road for better light; park in a designated spot and walk.
- Set aside time for Montepulciano on day 3. Book either a winery tour or a tasting at the Enoliteca in the Fortezza, and decide in advance who will drive without drinking. Montepulciano is in the neighboring Valdichiana Senese area, outside the UNESCO-listed Val d’Orcia, but it makes a good final wine-town stop on a scenic trip.
Head north from Rome, splitting scenery and wine across 3 days
The route goes from Lazio in the south to Tuscany in the north. On day 1, visit ① → ② → your accommodation; on day 2, visit ③ → ④; and on day 3, visit ⑤ before returning to Rome. Stay at the same place for both nights.
See the travel guidance for each stop below.
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Rome Day 1 departure · Return on day 3
Decide where and when to pick up and return your rental car first. If you’re starting from Florence or Siena, or have only 2 days, skip Civita and focus on Val d’Orcia.
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Civita Day 1 · Lazio
After parking, walk across the footbridge and back. Make this your only sightseeing stop today, then head to accommodation near Pienza or Montepulciano.
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Pienza Day 2 morning · Historic center
Leave the car in a parking lot outside the ZTL and walk around the piazza and cathedral. Choose one place near Pienza or Montepulciano as your base for both nights so you don’t have to repack.
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Val d’Orcia scenic roads Day 2 afternoon · Two stops
Combine SP 88 near Monticchiello with Vitaleta. The map groups these two destinations together. Vitaleta is about a 1 km walk from the parking area, so leave plenty of time to get there.
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Montepulciano Day 3 · Wine or a walk
Book just one wine tasting, then return to Rome. The driver should not drink. If everyone wants to taste, book a tasting for the previous day at a venue from which you can walk back to your accommodation, or arrange round-trip transportation in advance.
Day by day
Suggested itinerary
See each day's route, highlights, background and stay together in one place.
Pick up your car in Rome and drive to the Civita parking area. After seeing the footbridge and village, make just one more drive to accommodation near Pienza or Montepulciano. Don’t add a Val d’Orcia viewpoint to this day.
Walk through Pienza’s historic center in the morning, then visit SP 88 and the area around Vitaleta in the afternoon. Return to your accommodation before sunset. If it rains or the roads are difficult, skip unpaved roads and spend more time in Pienza.
In the morning, confirm where to park near the historic center, then visit just one booked wine tasting. The person driving back to Rome should not drink. If everyone wants to taste, move the tasting to the previous day and arrange a walk or booked ride back to your accommodation. Spend this day walking around Montepulciano before returning to Rome.
Places and meals
A village perched on tuff cliffs, reached by crossing a footbridge.
Google MapsSee the heart of a planned Renaissance town around Piazza Pio II and the cathedral.
Google MapsA spot for the winding road and cypress scenery along SP 88.
Google MapsA chapel reached on foot along an unpaved road after parking.
Google MapsA hill town where you can combine a historic-center walk with Vino Nobile tasting.
Google MapsHow to fit it in
This itinerary assumes a 2-night, 3-day trip starting with a rental car in Rome. Civita di Bagnoregio is in the region of Lazio, not Tuscany. It can make a good first-day stop if you’re starting from Rome or Orvieto. If you’re starting from Florence or Siena, or have only 2 days, skip Civita and focus on Val d’Orcia instead.
Reality check
A car is convenient for connecting Civita with Val d’Orcia’s smaller roads. However, don’t follow your navigation into a historic center right up to the door of your destination. Before booking, ask your accommodation for the exact parking location, whether you can enter the ZTL, and whether they need to register your license plate. Save a route to the public parking lot first.
Allow half a day for the footbridge round trip and a visit to Civita. Set aside 2–3 hours for Pienza’s historic center and 1–2 hours for Vitaleta, including parking and the walk. Book day 3’s tasting only after allowing enough time to drive back to Rome and return the car. If you move the tasting to the previous day, make it your last sightseeing stop that evening.
Entry and parking at Civita, accommodation, rental cars, fuel, and wine tastings vary by travel date and booking conditions. In particular, don’t assume tastings are free; check the price, included wines, and cancellation terms on the booking page.
On country roads, signs and pedestrians can be hard to see after dark. Don’t stop in the road to take photos; walk from a designated parking area. Don’t drive after a tasting. Even if a place is near your accommodation, arrange a sober driver or booked transportation if you need a car to get there.
If plans change
Skip Civita. For a 1-night, 2-day trip, stay near either Pienza or Montepulciano and limit your route to the two towns and one scenic-road stop. If you can spend 2 nights and 3 days, stay at the same place both nights and give Val d’Orcia an extra day.
Instead of visiting the cypress-lined roads, visit Pienza’s historic center and move your indoor tasting reservation in Montepulciano to an earlier time. If road conditions are poor, skip unpaved roads.
Small tip
Civita requires a round trip across a footbridge after you park, so it’s hard to treat as a quick stop along the way. After visiting Civita on day 1, head straight to your accommodation. Split Pienza and Montepulciano across the next 2 days to leave time for walking and meals.
Final check before departure
- First decide whether to visit Civita on day 1 or skip it if you’re starting from Florence or Siena.
- First consider staying near either Pienza or Montepulciano for both nights, and ask about the ZTL, parking location, and license plate registration.
- Save the parking areas and walking distances around Vitaleta and Monticchiello so you arrive before sunset.
- Before booking a winery or Enoliteca tasting, decide on the time, cost, cancellation terms, and who will drive afterward.
Information checked on September 13, 2026. Civita’s entry and parking hours, roads and ZTLs in Tuscany, accommodation, and winery tastings vary by season and booking. Check the latest information from each operator before you leave.
Information checked: 2026-09-13