Eileen Holland: From Boston’s North End to a “Secret” Paradise in Umbria

In 2009, Eileen Holland and her husband Lorenzo de Monaco discovered a ‘secret spot’ (La Segreta) in the heart of Italy. They purchased land, moved to Umbria with their children, and began a new journey together. Today, the La Segreta brand includes villa rentals (wait until you see this gorgeous property), organic hand-blended red wine (Pottarello wine), and a line of cold-pressed organic extra virgin olive oil.

The inspiration behind Eileen Holland’s love of Italy

RCG: Hi Eileen! Thank you so much for being here! I’m fascinated to learn more about what brought you here. Can you tell me your story?

Eileen: I was raised in The Berkshires as the youngest of 6 children. As a young adult, I followed my passion for the Classics and Art History over to Italy, where I worked at The Peggy Guggenheim Museum in Venice. I eventually returned to New England and settled in Boston’s North End with my husband.

Collazzone – Eileen’s town in Umbria

In 2010 we packed up house and kids and headed back to Italy; Umbria, to be exact. We restored a beautiful old farmhouse on our property for weekly rentals, planted grapes, made wines and extra virgin olive oil…and spent many afternoons on soccer and rugby pitches with our three kids in a tiny Italian town. New England is still home, and we get back every summer and again for a quick visit at Christmas. 

Wisteria and wine, La Segreta terrace

RCG: What has been the most useful advice you’ve received?  

Eileen: Don’t always be making lists; get out and do it. 

Eileen Holland and her husband Lorenzo de Monaco at the grill

RCG: What are you most proud of?

Eileen: Family. Both the family I grew up with in The Berkshires, and my family here and now.

On how close female relationships, near and far, play such an important role in who she is today

RCG: Is there an example you can share of how another woman has lifted you up?  

Eileen: Oh, I can’t name only one! From my mum, my sister, and my sister-in-law, to my high school BOFAs, college roomies, and all the smart, capable women I know in Boston. Even from far away, they’ll always listen, talk through ideas and encourage me – whether it be for work or with raising kids. When I am homesick, I have friends who send me postcards and jelly beans…. and that makes all the difference! 

Two cantina dogs at Agri Segretum

RCG: What is a small and simple daily ritual that brings you joy?  

Eileen: Coffee very first thing every morning with my husband and sitting around a table at lunch every day with my family. All schools finish here at lunchtime so that no matter what our morning is like, we are all together around a table at 1:00 for at least an hour. 

RCG: Name a quality that you admire about yourself?  

Eileen: Determination 

On how the natural beauty of her land brings Eileen Holland happiness every day

Women in the vineyard at Agri Segretum

RCG: What activity do you do makes you feel most connected to your inner beauty?  

Eileen: Hiking up our dirt road. Last spring, when all of Italy was on a strict lockdown, people could not leave their homes besides trips to the grocery store or pharmacy.  So, almost every afternoon, I would, with my two white Maremma sheepdogs in tow, hike up and out of our dirt road.

We had no idea our isolation would last this long. I relished every season: the smell of log fires burning in the homes in the village and fog around the hills in the winter, white plum blossoms and wild asparagus in the woods during the spring, and the intense green fields of grain and rows of sunflowers in the summer. Come rain or shine, I get out into the hills almost every afternoon. I always, always return home with a smile. 

La Segreta Terrace

RCG: If you were wearing your rose-colored glasses, what place would you most want to be to revel in its awe and beauty?  

Eileen: Right here in Umbria. On our farm.  (https://lasegreta.com) 

Below are some items that can be purchased from Eileen Holland’s La Segreta property:

Olive oil sourced at Agri Segretum

Pottarello wine, from Agri Segretum

Follow Eileen Holland and her incredible journey at La Segreta on Instagram.

RCG: Thank you so much for sharing your story, and for giving us all a peek into your life in Umbria. I, for one, can tell you that visiting La Segreta is now at the very top of my bucket list.