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Val d'orcia and Positano itinerary help

Hi everyone!

My fiance and are in the beginning stages of planning our 13 day honeymoon in Italy (last week of May, first week of June 2019). Neither of us have ever been to Italy and obviously there are so many different itinerary options. We would like to experience both northern and southern Italy, for the contrast of food and scenery. We tend to enjoy smaller towns and hope to spend more time outside of the major cities. Any input would be appreciated. Here are some specific questions we would like your input on:

  1. Where do we stay in the Val D'Orcia region? It seems like Montepulciano is great, but we hope to stay in a villa/ farmhouse so that we can walk into town. This seems more likely in Pienza.

  2. We will have a rental car during out stay in Val d'orcia. Should we return it outside of Siena? The only day trip we might do is to Chianti or San Gig... so I am sure we could pay for an excursion instead.

  3. Is this too much? If so, what would you omit?

May 27: Arrive in Rome around 10 am. Train to Naples. Private Car to Positano (Arrive around 2pm)

May 28: Positano

May 29: Positano

May 30: Positano

May 31: Positano → Naples → Rome

June 1: Rome

June 2: Rome

June 3: Rome→ Val D'Orica (3 hours)

June 4:Val D'Orcia

June 5: Val D'Orci

June 6: Siena

June 7: Siena

June 8: Siena

June 9: Siena to Florence Airport

Posted by
52 posts

Congratulations! You will love Italy! If you had a week in Val D' Orcia, I would definitely stay at Cretaiole outside of Pienza. Personally, after seeing the Val D'Orcia for the first time two years ago, we will always spend at least a week there.

Cretaiole is booked for our Sept. trip so we are staying at Agriturismo Il Casalino near Pienza. You will probably want the car in the area because the roads are curvy and there is not a shoulder to walk on. This is not a small area, has long country roads, and as romantic as it sounds, walking to Pienza probably is not a good idea. Check with the place you stay to see if they have loaner bikes. We did see several bikers. We loved driving to all the villages and towns in the area, especially Montepulciano, Montalcino, San Quircio d'Orcia, Montefollonico, & Castelmuzzio
After a few days in Rome, we picked up our rental at the Termini station then drove to Val D' Orcia. It was only a few hours.