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Itinerary Advice for May 2023 Trip

My friend and I are going to Italy from May 18 to June 2 (14 nights). We don't usually plan a trip like this with such short notice, but the opportunity presented itself. We are flying in and out of Rome. I have booked lodging in the first three destinations:

Rome 3 nights
Florence 3 nights
Gaiole en Chianti - agriturismo/4 nights (near Siena)

We will pick up a rental car at the airport in Florence for the drive to Gaiole en Chianti. The drive is just a little over an hour. My dilemma is where to go from there. We have four more nights we haven't planned for yet. Does anyone have any suggestions? I have not been to the Abruzzo region. Which towns in that region would you recommend? Depending on where we decide to go will determine if we keep the car or drop it off before leaving Gaiole en Chianti.

While we love museums, history, tours, etc., I think for these last four days, we just want a place to wander, relax and explore - no museum tickets or strict schedules. Thank you much for your input! Everyone on this site is so helpful.

Posted by
11802 posts

Umbria is a good choice. Base yourselves in Assisi or Perugia or another agriturismo. Lots of nice day trips in the countryside to Spello, Spoleto, wineries, etc., and not too far from Rome, where you should spend your last night before the flight.

Posted by
11616 posts

Since you will already be staying in Gaiole you should use your short time visit the Chianti towns and villages that stretch from Siena to Florence along SSS 222, the historic Chiantigiana. Then move to Pienza and explore Montalcino and Montepulciano.
Or head into Umbria using Spello as a base. Keep your car to take drives through the Umbrian countryside and vineyards.

Posted by
7240 posts

We are flying in and out of Rome.

Tp avoid the split stay/1 nighter in Rome (you need to be there night before departure flight) put all your Rome nights at end. As it is you only have 2 full days plus your jet lagged arrival half day.

Have you been to Rome?