Join us for a magical week as we travel to Montalcino, Italy, tucked into the breathtaking southwestern corner of Tuscany, where the unhurried pace of life in a medieval village will leave you refreshed, reawakened and reinvigorated.

We’ll enjoy spending our days just outside the walled village at the exceptional Borgo Canalicchio di Sopra Wine Relais, a beautiful property set among vineyards on one of Brunello di Montalcino’s historic, most renowned estates. We’ll take several day trips and explore the exceptional Tuscany region, including visits to the area’s top wine producers. Come experience the breathtaking vistas across the Val d’Orcia and dip your toes in the healing waters of the Tuscan countryside. Sample fresh pressed olive oil. Take a private cooking class or two. Hunt for truffles in the nearby hills and dine at our favorite restaurants off the beaten path.

Join us for this magical week of ‘la dolce vita’!

The group is limited to 10 participants.


Sample itinerary, our itineraries change with the season!

Day 1: Arrival

We will meet you at Rome airport and travel to Montalcino by private transport, at which time you can get acquainted with your fellow travelers over a welcome aperitif. After a bit of time to relax, we’ll visit the village and then enjoy our first wine tasting and dinner at cozy Grappolo Blu, a trattoria just off the main piazza.

Day 2: Getting to know Montalcino

The day begins with breakfast and then on to a fun trek across the vineyard and up the hill toward Montalcino. You will have free time to wander the village before a scrumptious lunch at Le Logge di Piazza, situated near the main piazza. Afterwards, we’ll go on a historical walking tour through the cobblestone streets of Montalcino before heading back to the Borgo for a bit of rest prior to dinner. We will then head to Sant’Angelo in Colle for the sunset and a delicious meal paired with spectacular wines at Trattoria il Leccio, one of the highest rated restaurants in the hilltop village of Sant'Angelo in Colle, near Montalcino.

Day 3: Free time in the village and an evening in Chianti

After breakfast at the Borgo, we will get to spend the morning in the village. Whether you choose to shop or just sit and watch village life go by, morning will be at a leisurely pace. In the afternoon, we will set out for the Chianti region where we’ll stop at Fontodi Vineyard for a tasting of the region's Chianti wines.  We will then stop to see the butcher shop of Dario Checchini, the famous butcher in the hills of Chianti. Dinner will be at a local restaurant in Chianti before we head back to our Borgo. 

Day 4: Cooking in the village

On this morning of our fourth day, we have a special treat as we will have a cooking class with the women of Quartiere Pianello in the village.  After class, we will walk to a local gelateria for a class on making creamy Italian gelato.

We’ll then head back to the Borgo for a rest prior to dinner. Dinner will kick off with a special candlelight wine tasting in the medieval fortress at the village, followed by a delectable meal at Drogheria Franci, featuring old vintages of Brunello wine.

Day 5: Hot springs and pecorino

Today we’ll spend the day touring the countryside around Montalcino.  After breakfast, we will travel to visit the spectacular village of Bagno Vignoni where one can take a dip in the hot springs. After a late lunch, we will visit to the village of Pienza and spend time at a local farm to see how the famed Pecorino is made.  Dinner will be in the picturesque village. 

Day 6: Local 'yard-to-table' cooking class and a tranquil Abbey

Today we will spend a delightful morning cooking with the friendly team at Locanda Demetra, who grow much of the food they use in their restaurant. After dining on the fruits of our  morning labor, we will visit the spectacular Abbey of Sant' Antimo in a nearby valley.  We will continue around the valley and visit one of our favorite Brunello vineyards, Ciacci Piccolomini, before returning to the Borgo. 

Dinner will be at the Borgo. Michele and Deb will be hosting a special poolside dinner where we can cook together and enjoy the spectacular beauty of our special home for the week.

Day 7: Truffle hunting and our farewell dinner

For our final day together, bring your walking shoes, for today as we are off to hunt truffles in the nearby village of San Giovanni d’Asso! Follow along as the truffle-sniffing dogs work their magic and find these prized possessions in the earth. From there, we’ll head to lunch at nearby Osteria delle Crete where we get to treat our palates with a taste of those incredible truffles.

After returning to the Borgo, we will head to the spectacular Boccon di Vino just outside the walls of the village for our Grand Finale Wine Dinner.

Day 8: Departure

Today we must bid each other farewell as we head home or to other parts of Italy.  Transfer will be provided to Rome to catch your flights to your next destination.

This itinerary is subject to change without notice, but we will make sure it is just as great!