Downtown Monteloro

Three brothers ran the local restaurant in Monteloro, called da Orlando, named after the most vivacious of the three. The ristorante occupies the entire “downtown” with a surprising quasi-Art Deco interior behind the traditional Tuscan facade. The site boasts a delightful valley view from the vine-covered dining terrace in the back. We had many meals in that favorite local haunt during the years while finishing our place on the hill. Orlando, being the most talkative of the three brothers, often stood by our table telling us jokes, stories and neighborhood gossip as he deemed necessary. He was so engaging and funny, it always felt like we should pay extra for the live entertainment.

As the years passed and the brothers grew older, they finally decided it was time to throw in the “dish-towel,” so to speak. Il Pensione, retirement called to them one day and so they all went into retirement en-mass. We smile to ourselves, imagining the same “group think” that started their shared life’s work so many years ago. It was sad, however, to see a favorite restaurant and a family tradition suddenly disappear, but you know how the saying goes, “When one door closes, another opens.”

Relic of the Past

The Ristorante Orlando sign still hangs above the door. But now, on the glass entrance are some new 2 inch high, delicately scripted letters, La Riffa. Andrea and his wife Concetta have replaced the old Orlando restaurant with their dream. They have lots of energy and offer a menu of delightful Tuscan dishes. And while they are busy establishing the “new” restaurant, just upstairs, over the dining room is Orlando and and his wife Daniella’s apartment. You might say that even though Orlando has retired, he still watches over the operation.

Chestnuts and Vin Santo

So, last night toward the end of our meal, we found ourselves in the dining room with only one other couple. The logs were still glowing in the corner fireplace a few meters away. Suddenly, Concetta passed our table, carrying a special pan and a brown paper bag full of something. “È la ora per castagne! Time for chestnuts!” We watched as she tossed several handfulls into the pan and began shaking/swirling them over the fire. Next, Andrea arrived from the kitchen declaring that Vin Santo, wine of the saints was the perfect complement to chestnuts. Everyone cheerfully agreed, making it an official party.

Brochure of Artisan Mosaics

We all sat around the fire for another hour eating roasted chestnuts and drinking multiple rounds of vin’ santo as our dinner companions engaged in fascinating conversation. We learned that Renzo and Gabriella work together in Florence in their laboratorio, studio with their son, Leonardo, and daughter Catia. Renzo leads the artigiani, artisans workshop, where they craft stone mosaics in the famous Florentine tradition. He invited us to visit so we could see first-hand how the craft continues. Of course, we said YES!

After about 3 hours, at around 23 (11 o’clock), we all got up from the typical wood and wicker chairs, exchanged multiple ciaos and threw in some grazies, and headed for the car. Before starting the engine, we sat in the quiet reflective lamplight for just a few moments. The contrast of  the illuminated “da Orlando” sign hanging over the “la Riffa” script was striking.

Looking Back – We See What We Want to See

As we drove away into the moody Tuscan countryside, under the twinkling night sky, something caught my attention in the rear-view mirror. It may have been my imagination, but I thought I spotted Orlando at the window above the door. Then the silhouette receded and the lights went out, signaling that another day in Monteloro had, once again, come to a peaceful close—all was right with the world.



  1. My Mum lives in Tuscany and I received a letter from her where she wrote about Montelore and the only restaurant of the village. I googled it up and I came across your blog. How wonderful! Whenever we are going on holidays to Italy again, we will definitely have lunch here. Do you know by the way Trattoria La Casa del Prosciutto in Ponte a Vicchio. Only open for lunch and booking is essential. Also lovely…
    Wishing you a wonderful time in La Bella Italia.

    With greetings from Cape Town, Carolina


    1. Dear Carolina,
      How nice to hear from you about your connection to the restaurant in Monteloro. As mentioned in the story, it’s now called La Riffa, although local signs in the area still direct people to da Orlando. As for Trattoria la Casa del Prosciutto, it’s in Torre di Buiano, only 5 minutes from us, and is one of our favorite places. Good news . . . their hours have expanded since you were here.
      Buon appetito!
      Cheryl and Em


      1. Dear Cheryl and Em,
        Thank you for your quick response! But my trattoria La Casa del Prosciutto is in Vicchio in the Mugello
        I will definitely tell my Mum about your Casa del Prosciutto as she always tours on her pink motorino through Tuscany and likes to explore new things.
        Grazie mille!


  2. Hello we are the new family running the “Ristorante da Orlando”
    we writIng to give you a quick update on the restaurant status. We always make Tuscan cuisine with traditional dishes, and we decided to keep the original restaurant name as we wanted to honour the big work made from Orlando and his family through the years.
    Orlando and his brothers are all fine as well as their wives, as you know they are living upstair so we can deal with them daily, they are like part of our family, it seems to have six aunts and uncles always near and ready to help with their huge experience.
    if you come to Italy we would like to have you in our restaurant and Orlando will surely meet you with pleasure.


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