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Special Day Trip in Umbria for Anniversary… help!

We are staying for a week with friends at a villa between Arezzo and Perugia at the end of September and will have a car. I have most of the week’s itinerary planned but am stumped on one special day… our 28th wedding anniversary …and would appreciate some suggestions. We enjoy cute villages with good food and local shops. For reference, my husband “has seen enough museums and churches” and isn’t much of a wine drinker.

Here is my draft itinerary:
Sat. Arrive
Sun Drive Val d’ Orcia, visit Pienza, Montalcino and Montepulciano
Mon. Arezzo
Tues Gubbio
Wed. Perugia
Thurs Orvieto
FRIDAY. ????
Sat Leave

Once we leave we will spend another week, visiting Barga, Lucca and finally Rome.

Posted by
294 posts

We loved Spello and it's not too far for you to drive there - no big sights, just a pretty little town with narrow winding streets and steep lanes filled with charming houses and views. There are a number of good local restaurants too. Plus easy parking just outside the town walls. In fact we stayed there for 4 days and loved every minute.

Posted by
1244 posts

I second Spello. We went as we were driving to Orvieto and wish we could have stayed there. Very cute town.

Posted by
3961 posts

Another vote for Spello! We spent 2 nights while on a culinary tour. Wonderful! Our tour started in Florence and ended in Rome. We hit most all the places you’ve highlighted in your draft. In addition we visited CT, Rapolano Terme, Orvieto, Lucca, San Gimignano, Volterra, Siena, Cortona, Lake Trasimeno, Assisi, Todi, & Civita di Bagnoregio.

We were supposed to go to Deruta, but our guide said we were going to “her home” in Gubbio instead. It ended up to be the highlight of our tour!! We were pleasantly surprised when we arrived that she said she was a Countess & had inherited the Noble Floor of the Palace. Gubbio is a charming medieval town, Roman ruins, Aquaduct and not touristy!

We were celebrating our Wedding Anniversary and when we were in Montepulciano we stopped at Bottega del Rame Coppersmith. Several of us purchased items and shipped them home.

Yes, the food along the way was wonderful. Many cooking classes and demonstrations on our tour. Good memories. Enjoy your planning!

Posted by
11647 posts

We spent two weeks in beautiful Spello and highly it! There are many excellent restaurants there.

Posted by
2106 posts

When we stayed in Perugia, we enjoyed our day in Spoleto.

Posted by
30 posts

Thanks for your replies! Both Spello and Spoleto look like great destinations.

In doing further research I’m wondering if my Val d’ Orcia day is too ambitious. Thoughts?

It looks like the drive in Val d’ Orcia, Pienza, Montepulciano, Montalcino is more than a day and then there are a couple of other cute towns nearby…. Montecchielio and San Quirico d’Orcia.

Should I plan a second day to visit this are?

Posted by
2329 posts

Yes, if you can. We enjoyed every one of the towns you mentioned.