A few summers ago, my husband went wine tasting in Tuscany with our good friend Hans.  A “mancation” they called it.  Not your typical definition of the word but if you know my husband and Hans, wine tasting in Italy fits.  It seemed like a harmless idea at the time – he had more vacation than I did – but as the pictures and stories rolled in of stunning wineries, gourmet lunches, panoramic views and cozy bed and breakfasts, with Hans, I was unbearably jealous.  As a result, when we planned our own family holiday in Tuscany last year, it couldn’t be anything less than epic.  It was even better.

What made this trip particularly special was our eight month old daughter.  Our first family holiday adventure, just the three of us.

We landed in Rome in the wee hours of the morning and spent what was left of the night at a little hotel just outside the city.  After breakfast it was a two and a half hour drive straight to Montalcino, Siena for lunch at Poggio Antico, one of the highest altitude producers of Brunello and a favourite from my husband’s last visit.  Lunch was served at a lovely table in the terraced garden overlooking the vineyards and olive groves below.  We parked the stroller next to our table and ordered a bottle of 2008 Brunello di Montalcino. As I savoured my first sip of Italian wine in Italy, I thought that no glass of wine had ever tasted better.

I had recently started supplementing our daughter’s bottles with pureed baby food.  Inspired by our Italian location I had purchased a bag of Ella’s Kitchen Vroom Vroom Veggie Lasagna and proudly presented it to her for lunch.  She spit it out.  Fair enough.  Who would want to eat lumpy pureed lasagna in a bag when Mommy and Daddy are dining on crispy Cinta Senese suckling pig with rosemary-flower honey.  She did, however, enjoy the afternoon wine tour and tasting of Poggio Antico’s collection and even insisted we buy a double magnum of the 2008 Brunello to bring home with us.

By late afternoon we were in a holiday state of mind and headed to Siena House for a few days, another favourite from the mancation. Siena House is a unique cross between a bed and breakfast, a luxury boutique hotel and the grand home of a generous friend.  A quiet Tuscan house situated between Cortona and Pienza, its hilltop location and gardens offer sweeping views of the rolling green fields and organic farms that sprawl in all directions.

Malvin, who owns the house with his wife Amanda, showed us around the grounds pointing out the saltwater pool and their own impressive organic vegetable garden, olive grove and fruit trees.  We approached a beautiful fig tree and he expertly picked two plump, fresh figs from the tree.  “A fig is ready to be picked when it has turned slightly yellow and feels soft to the touch”, he explained as he handed them to us.  I may have picked a few more.

Siena House Tuscany

We arrived late in the afternoon without any real dinner plans so Malvin kindly offered us some goodies from his fridge. A simple plate of pecorino, prosciutto and fresh tomatoes from the garden coupled with a cold bottle of Prosecco and some brownies for dessert.  Perfect.  We sat outside and watched the Italian sun set. Coming from summertime in Dubai where everything is shades of brown, my daughter was captivated by the beautiful green setting.  Me too.

In contrast to the old Tuscan stone and clay exterior of the house, the interior was chic and contemporary.  Big, airy windows filled the house with light.  White walls were covered with colourful modern art created by Malvin’s talented wife Amanda.  Designer furniture and lighting.  Luxe bathrooms.  A second floor lounge and fireplace.  What used to be a cattle stall has attentively been turned into a bright, open kitchen centred by two giant stainless steel islands. The open living space beyond has floor lighting, a bar, and a collection of pin ball machines for rainy days.  With only four guest rooms the house offered both a private and a social setting.  The three of us stayed comfortably in the “Cortona” superior double room and would stay there again in a heartbeat.

Malvin knew how to put the “breakfast” in Bed and Breakfast. Frothy cappuccinos, fresh squeezed orange and grapefruit juice, cut fruit, a selection of locally produced cured meats and cheese (think caponata crusted with fennel and soft, fresh pecorino) and daily baked goods made with love by Malvin – muffins, tarts, breads and homemade jam.  Each day’s breakfast was a mini vacation in and of itself, leisurely enjoyed at a table in the morning sunshine.  Our baby girl napped beside us in the fresh Italian air and distant church bells rang beyond the Cyprus trees in the neighbouring town of Sinalingula. Bellissimo!

For lunch the next day we drove to Boccon Di Vino where the food was as pretty as the view.  I ordered handmade gnocchi with Sienese black truffles.  My husband unconsciously swirled a rich, red Brunello in his glass, as he explained how Brunello di Montalcino, the only Tuscan red wine that is not a blend, is made from Sangiovese grapes and in his humble opinion, is the only wine one should drink in Tuscany.  (Now imagine him doing this in a really terrible Italian accent.)  My daughter wasn’t listening. Mesmerized by his real Italian accent, she flirted with the waiter and watched the clouds drift by.  Time actually slowed down.

Boccon Di Vino

When we eventually dragged ourselves from the table, the rest of the afternoon was spent sightseeing in one of the many little towns scattered throughout the Tuscan hills.  In a vain attempt to work off our heavy lunch, we walked up and down hilly streets, dear daughter asleep in a baby carrier attached to my husband’s chest.  Then we stopped by Altesino winery where we tasted a few few more wines and bought some fresh olive oil.  Be warned – It is difficult to go back to store-bought olive oil after consuming fresh olive oil from an Italian vineyard.

By sunset we were comfortably seated in lounge chairs at Siena House with a bottle of Poggio Antico and stayed there until dusk when my daughter tired of crawling around in the grass and fell asleep. With an eight month old in tow we weren’t interested in fancy dinners on this trip so we went to a little pizzeria nearby called “Sorry I’m Late”. Painted bright shades of purple, pink and green and decorated with random images from the Ice Age movies, it was surprisingly busy for such an odd little place.  The pizza was good though – I have yet to find bad pizza in Italy – and we ate it hungrily.

In my usual style, we had arrived in Italy without much of an agenda besides the hotels my husband had booked.  Having traveled extensively around the region, Malvin was pleased to share the places he loved. One of his best suggestions and now filed among our favourite memories, was a casual lunch at Podere Canapaccia.

That afternoon, we pulled into the driveway and immediately thought we were in the wrong place.  The yellow villa on the hilltop was faded, mismatched lawn chairs were strewn haphazardly in the yard and a man on his phone glanced at us quickly, uninterested in our arrival.  Surely this wasn’t the place that Malvin had recommended.

We were considering leaving when a tall man with dark curly hair rushed outside to greet us.  “Welcome to Podere Canapaccia”, he said in a welcoming Italian accent.  “My name is Simone.”

Podere Canapaccia

Moments later we were seated under a tree overlooking the Val D’Orcia.  Three hours later we were still there. Charming stories, bottomless glasses of red wine, delicious homemade “pici”, Brunello di Montalcino tasted straight from the barrels of Simone’s cellar and the “world’s best tiramisu”.  Afterwards, Simone joined us at the table with a bottle of grappa and more stories about the history of Podere Canapaccia.  As we returned to Siena House, our daughter sound asleep in the back seat we wondered whether Simone and his family sold more wine than they drank or drank more wine than they sold.  I didn’t come to any conclusions.

For dinner on our last night at Siena House we dined in the Summer Kitchen, an adorable little kitchen at the edge of the property near the garden.  A converted pig sty, the kitchen has been remodelled for guests to prepare their own meals in private.  It is stocked with the basics (salt, pepper, olive oil) and the fridge is full of local wine and cold Italian beer free of charge.  We picked up some bread and cheese at a little shop during our travels that day and upon our return, meandered through the garden with a basket.

Fresh tomatoes, basil and a selection of other fresh vegetables became a deliciously simple dinner of spaghetti and bruschetta.  Hours passed. Dusk fell. Our daughter fell asleep in a warm corner of the kitchen and a bottle of red wine from Podere Canapaccia slowly disappeared into our wine glasses.  Pleasantly tipsy from the wine and fresh air, we pondered agenda ideas for the rest of our stay in Italy.  While no final decisions were made, we unanimously agreed that more vineyards, Italian food and another luxurious country house would be in our future.

The next morning we devoured a final gourmet breakfast, promised Malvin we would return again one day soon and drove towards the little Tuscan village of Pienza.