How To Enjoy The Perfect Workation in Tuscany: Wine, Wellness and WiFi

A “workation” allows you to live, work, study and play – all in one place.
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This post was produced in partnership with Essenza Escapes.

The pandemic has changed a lot of things though it only seemed to embolden my sense of wanderlust. After far too many months cooped up indoors, I found myself craving an escape and the promise of spring had me daydreaming about spending days languishing in a Tuscan villa, sipping wine while gazing out onto the countryside. I longed for wide open spaces, the sunshine on my skin and most of all the chance to explore Italy again – to relish each forkful of pasta, to marvel at the beauty of its small towns and to swoon while cruising down its scenic country roads. And with the rise in remote work, I was curious to explore a new work-life balance on a workation.

A workation is a hybrid model that allows you to live, work, study and play – all in one place. If it sounds too good to be true, it isn’t. Luxury travel companies like Essenza Escapes are paving the way for this new reality and making it easier than ever to travel – or relocate – to Italy for an extended period of time. Essenza aims to connect travelers with the essence of Italy through a curated portfolio of luxury villa rentals, boutique hotels and unique, immersive experiences based around your interests. “We believe that our lives are enriched when we pursue our passions,” explains Margherita Piliero, the founder of Essenza. “So we designed our company to support guests who want to live the life of their dreams in Italy.”

In addition to designing wellness holidays, active retreats and cultural tours through Italy, Essenza promotes workations in the Bel Paese. And Italy is the perfect base for this new reality. Not only is it one of the most alluring countries in the world, it is well-positioned for both US and European time zones making it easy to arrange meetings and find time to work in between museum visits, wine tastings and afternoons by the pool.

By curating work-friendly accommodation with high speed internet, providing temporary gym and spa memberships, introducing you to international schools and providing access to specialist tax advisors, Essenza takes the heavy lifting out of traveling, or moving abroad. “Why be tied to an office when you can work, play and educate the family from a stunning Italian property?” asks Margherita. I can’t help but agree.

The biggest perk of a workation is the chance to immerse yourself in a destination for longer than a typical vacation. That’s why instead of spending a weekend in Chianti, I spent two weeks enjoying the countryside which consisted of dialing into work meetings from under a shady pergola, shopping for spring vegetables at the local farmer’s market and practicing yoga every morning to the sound of chirping birds. My Tuscan workation was all about wine, wellness and WiFi – and I’d highly recommend it to anyone with a flexible schedule and an adventurous spirit.

I was a guest of Villa Le Pratola, a stunning 400-year-old Tuscan villa set on a sweeping private estate in the heart of Chianti. Originally a historic farmhouse, the property was thoughtfully restored to represent a beautiful balance of traditional Tuscan fixtures – like high ceilings with wooden beams – with contemporary decor, modern furnishings and wide open spaces. I loved the floor-length windows, stone courtyard filled with lemon trees and the serene, panoramic swimming pool. There’s nothing but nature in sight and my stay at Le Pratola was a real respite to relax, recharge and daydream about all the possibilities available to us in a brave new post-pandemic world.

With a full-time house manager and a tight-knit local community, Le Pratola offers guests everything from pizza night in the wood fire oven to in-villa cooking classes, daily buffet breakfast and sommelier recommendations. The 600m2 property features 5 bedrooms and sleeps 10 guests so it’s a great place for a retreat or family reunion, though it’s also a supremely comfortable place for a workation. The villa has all the office supplies you need (like a large Mac desktop, high-speed internet, printer & scanner and personal gym) along with plenty of entertainment, like a billiard table, foosball and Netflix subscription. The family room doubles as a great yoga studio, though you’ll likely want to do your warrior poses out by the heated infinity pool.

There’s plenty to keep your nourished and entertained at Le Pratola but you’ll want to pay a visit to some of the region’s prettiest towns and legendary wineries while you’re in Tuscany. With preferred partners all over Italy, Margherita and her team arranged the following experiences for us during our workation and each one was truly memorable.

A farm tour at Podere Le Ripi in Montalcino

A biodynamic oasis right outside Montalcino, Podere le Ripi is not only a winery that produces an excellent Brunello. It is a dynamic, restorative place that champions harmony and celebrates Tuscany’s unique biodiversity through its holistic approach. The winery has a garden with dozens of farm animals to enhance its soil sustainability and even plants crops according to the lunar calendar. The innovative winery is built according to the Fibonacci sequence and is home to a Pantheon of Wine. Families with kids will enjoy the Tuscan Garden Experience with introduces you to Podere le Ripi’s farm animals before touring the vineyards and tasting the estate’s excellent wines.

A taste of contemporary art in Chianti

Art and wine go together like pasta and pomodoro – they just naturally complement each other. A short drive from Villa Le Pratola lies the Chianti Sculpture Park, which features a permanent exhibit of contemporary sculptures by artists from around the world. Opened in 2004, the park invites artists to create site-specific works that are integrated with nature. Lose yourself in a glass labyrinth by Jeff Saward of the UK, and admire multicolored cow cut-outs by Vincent Leow of Singapore. Nearby, Castello di Ama is one of Chianti’s most renowned wineries for producing L’Apparita, the region’s first 100% Merlot. The estate is home to works by international superstars including like Michelangelo Pistoletto, Anish Kapoor and Daniel Buren.

A dinner amongst the vines at Querceto di Castellina

With its dramatic vineyards and feminine flair, Querceto di Castellina is surely one of Chianti’s most Instagrammable wineries. A short drive from the charming village of Castellina (which is incidentally home to the excellent Gelateria di Castellina), Querceto di Castellina is an organic, family-owned estate that is in its third generation. Run by Jacopo Di Battista and his American wife Mary Shea, the winery produces single-varietal Sangiovese and Merlot vintages, along with a delicious Viognier blend with Roussanne named “Livia” (I have to admit, I’m a little partial to this one!). Querceto di Castellina also hosts the dreamiest al fresco dinner parties at a long-table in its vineyard each summer. With quaint, curated details, this winery is especially suited to female travelers and would be great for a bachelorette party or bridal shower.

A visit to a cheese haven at Podere Il Casale

The beautiful hilltop town of Pienza is known for producing some of Italy’s best pecorino cheese so you can’t miss a visit to Podere Il Casale. This organic farm and garden is run by Sandra and Ulisse, a Swiss couple who worked with indie labels in Zurich before they decided to relocate to Italy and begin a new life in the Tuscan countryside in the 1990s. Podere Il Casale is home to over 70 goats and dozens of sheep which produce over 40 types of raw milk cheeses, including taleggio, feta, pecorino, cream cheese and flavored varieties with chili pepper, truffles and grape must. The panoramic restaurant is a beautiful place for a leisurely lunch – the menu changes seasonally but in late spring, we loved the lasagna layered with Swiss chard, artichoke, asparagus and fresh ricotta.

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