Traveling to Tuscany and Umbria (only up to Day 3)

I am traveling to Tuscany and Umbria with my daughters and many friends.  My pictures of travel, food and stories will will follow soon with pictures.

Update:  I had the most amazing food/experience/friend/family trip to Italy in May.  After being home for 5 days – I am now prepared to write/share about my experiences.  I encourage everyone to visit a new place/country sometime in your life.  Chat with the locals, taste things you have never tasted before.

Day 1 (Saturday):  We left Chicago for Rome (via Madrid).  When we reach Rome, we will be meeting up with 2 friends and a driver who will whisk us off to our Villa in Passignano Sul Trasimeno, Italy.  We call it our Tuscany trip, but the villa actually sits in Umbria – just south of Tuscany.  We asked our driver (Simone) to stop at a grocery store on the way, so that we could pick up some essentials (bread, coffee, fruit and wine).  The name of the grocery was Penny market and reminded us of Aldi in the US (except it had a wonderful bakery as you entered the door and a killer meat department).  We were astounded by the inexpensive wine.  Before we began shopping, we gathered pizza, sandwiches and drinks to eat at the market.

We arrived at our Villa –   We have the most lovely view of Lake Trasimeno.

After getting our luggage to our rooms – we opened some wine, made a large platter of bread/cheese/olives – and went to bed by 9:00 (a LONG day).

Day 2 (Sunday):  3 more of our ‘villa-mates’ had arrived late Saturday evening.  Today is Santa Margarita day – who was born in 1220.  We had planned to visit Cortona today.  Cortona is a medieval town where new ruins were recently found.  We drove up winding roads to a monastery where Frances of Assisi lived after he left Assisi.


We also drove to Brama Soleil (the house depicted in ‘Under the Tuscan Sun’).  Our wonderful driver Luca Perrucchini made a lunch reservation for us at La Loggetta, where we dined on Cortona Syrah and wonderful pasta/fish dishes.


After lunch, we explored the town of Cortona – visiting an incredible Art Gallery, Il Pozzo.  We met with the owner who gave us a private tour and glasses of Prosecco to sip.  

We also visited a lovely Jewelry/Shoe Store – Del Brenna.  They have an incredible shop in a lower level that dates from 1300.  They house an olive press from 1625 within the store.  They also served us Prosecco, with a sprinkle of gold dust.  Sebastian and his wife Megan toured us through the store.

Megan is from Kansas and told us about how she and Sebastian met.  They now host wine tasting events on Thursday (we might have to look into this)  Two of our group decided that they MUST purchase the Del Brenna shoes – they are works of art.   Many of the group also bought rings & earrings.

Before we left Cortona, we stopped for a lovely balcony view.  We were told that during WWII, Cortona was never bombed and that the residents of the town could stand on the balcony and watch the war going on in the distance.

Later that day, our last two ‘villa-mates’ were due to arrive, so we stopped at the COOP grocery store for more staples.  We arrived back at the villa to the wonderful smell of a home-cooked dinner being prepared by a chef.  She served:

  • Sausage Bruschetta
  • Fried Zucchini Blossoms
  • Risotto w/ Saffron & Asparagus
  • Potatoes
  • Salad
  • Chicken w/olives & capers
  • Berries w/fresh whipped cream


Monday (Day 3):  We visited Sienna & San Gimignano today.  We first had a guided tour through Sienna by a wonderful guide who explained the different districts that make up the quaint town of Sienna.  This is my 4th trip to Italy, and I never forget this square.

We ate at Il Campo and enjoyed a wonderful setting and food.




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