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  • Writer's pictureTara

Tara's Tuscan Tips

“It’s market time in Cortona. The piazza is an ongoing party, and everyone's invited. Cliches converge at this navel of the world. You almost want to laugh, but you can’t help feeling these Italians know more about having fun than we do. . . “

~ Under the Tuscan Sun

I’ve dreamt of visiting Tuscany, the land of endless flowing wine, ever since watching Under the Tuscan Sun. I didn't buy a villa like the main character in the movie, but I did fall in love with the countryside. Sophia Loren said it best, "I'd rather eat pasta and drink wine than be a size 0." My family ate and drank our way through Tuscany (really Italy), it's the only way to travel.


Take a ride with me through Tuscany as I share tips from my trip . . .

Day 5:

  • We took a private car to the train station in Naples. Today was a 5 hour travel day. Napoli Centrale → Firenze SMN - Santa Maria Novella (3h) on the Italo Bullet Train.

  • Once we arrived in Florence, we took a taxi to the rental car company.

  • Note - renting a car in Europe is so difficult if you need an automatic vehicle. Even though we booked an automatic, they told us they didn’t have them and gave us a stick shift. We spent two hours searching for an available automatic, which in Europe is double the price! Thankfully, a random Italian rental company had 1 more automatic SUV for us to start our official Italian Road Trip!


We checked into Relais della Rovere. It’s a 30 room villa tucked away in the Tuscan countryside in the medieval village of Colle Val d'Elsa, 20 minutes from Siena. It was a perfect resting spot in a centralized area, 30 minutes to an hour from all the villages and places we wanted to see.

Other Lodging Options:

Day 6:

  • Casual day of exploring picturesque towns.

  • We discovered Montalcino - Montalcino is a small hilltop village known around the world for the production of two very famous wines: Rosso di Montalcino (Montalcino red) and Brunello di Montalcino, both made in the area.

  • We tasted wine, dined on cheese and salami and got wonderfully lost in Montalicino’s narrow alleys. The streets there are beautiful.

Streets of Montalcino
  • We continued to drive through Val d’Orcia - stopping for numerous pictures before arriving at the Rosewood hotel.

Dinner was at Oseria La Canonica at the Rosewood/Castiglion Del Bosco, located in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia, Rosewood Castiglion del Bosco is set within a 5,000-acre, 800-year-old Italian estate. The property has stunning views. Highly recommend a sunset dinner on the shaded patio.

Day 7:

Today was a day we will never forget. We scheduled brunch and massages at Borgo Santo Pietro, a 5 star luxury hotel and spa concept with a ‘farm to plate’ philosophy on a 300-acre estate. It’s ranked on Conde Nast Traveler’s Gold List for 2020. Situated in the heart of Tuscany, Relais Borgo Santo Pietro was once a healing stopover for medieval pilgrims.

As we drove down the private dirt road lined with Italian cypress trees we were warmly welcomed to the 800 year-old luxury farmhouse hotel. Flowers are freshly picked and arranged from the garden daily at this 20 room boutique hotel. The estate has market gardens, nut fields, herb gardens, vineyards, forests, pigs and chickens and honey bees. Each day the farmers collect milk from Borgo’s sheep, which is then transformed into artisan cheese and yogurt at the on-site dairy. The animals and vineyard supply the ingredients for its Michelin-starred restaurant.

Our brunch was at La Trattoria sull’Albero (meaning treehouse). It is designed around a large spreading oak tree with rustic interiors overlooking the fields and forests of the Valle Serena. Guests can enjoy a drink either inside by the cozy fire or outside by the large wooden bar or the shady courtyard that overlooks the infinity pool. With their open-plan kitchen you can watch the pizzaiolo make and twirl your pizza from scratch.

One of my mom's happiest days of her life :)

La Trattoria sull’Albero

It’s difficult to pick what we liked most from our meal - from the charcuterie spread with cheeses made onsite from the ingredients sourced from the onsite garden - everything was so fresh and made with love and attention to detail. After lunch we walked through the gardens to the spa - “Every day is a ritual which ensures a total five sense immersion of health and well-being for the mind, the body and the spirit."

Following our massages we visited the formal gardens, water gardens and culinary gardens. “The sound of flowing water is ever present at Borgo Santo Pietro. Whether it’s the bubbling streams, the ducks bobbing in the lake, the splashing of the fountains in the formal gardens, or the trickle of a waterway – the fresh sound of water keeps you cool on the warmest day while soothing the senses and inspiring you to wander further in your exploration of Borgo Santo Pietro’s extensive gardens.”

We spent all day in what felt like a heavenly escape. Our mom was brought to tears from the beauty of the property. Now just a memory, we are so grateful for the experience and highly recommend this property to friends and family.

We ended our day in Siena eating pizza at the Piazza del Campo, the famous medieval square, a central place for locals and tourists to come together to dine and dance.

Day 8:

  • We contemplated visiting Florence (if we had more time we would have), but today we wanted to casually roam the streets of other rustic Tuscan villages.

  • We drove to San Gimignano, the epitome of a small walled medieval hill town. Shopped, ate our daily gelato and listened to local musicians before ending our day in Volterra where I wish I remembered the name of the restaurant, but I had the best lasagna ever! For wine lovers or history buffs, Tuscany is the perfect Italian getaway.

San Gimignano


More Suggested Towns to Visit:

What I may love most about Italy is the slow pace of life. I think we need to slow down, not live too quickly. We've lost the magic or the ability to wonder because we are always so plugged in. It's difficult to remember days, but moments - we remember moments and there are many moments we will never forget from our Italian adventure.

Hope you enjoyed Tara’s Tuscan Tips - stay tuned for the final leg of our journey to the Dolomites!

If you haven't already - check out my Amalfi Adventures post

* All Pictures taken by Marc Scarioni

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