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Holiday dates are November 10th - 25th. We will fly into Rome Fiumicino Airport. You will need to arrive on November 9th and we will stay at an airport hotel that night so that we can start on the morning of the 10th.

Our first week will be spent just outside of Greve in Chianti at Villa Di Nozzole.

Our second week will be spent just outside of Torrita di Sienna at Villa Monarca.

We will return to the Rome Fiumicino Airport on the 24th and you will fly out from there on the morning of the 25th.

Mario and I will be flying in a few days early and others have expressed an interest in also doing this. We have an add on that can be taken if you do fly in early.


On November 8th we will take an all day excursion to the Amalfi with a stop in Positano. This all day tour is by train and boat and is $280 per person with everything below included. We are happy to arrange for this adventure and of course will include an extra night accommodaion at your cost which is about $100 per person.

  • Get the most out of your full-day tour by taking a high speed train from Rome to Salerno. From there, you'll begin your exploration of the Amalfi Coast by sea.

  • Cruise the crystal-blue waters of the Amalfi Coast on three separate ferry rides. From the water, you'll be able to fully drink in the stunning vistas that draw countless visitors to this corner of Italy.

  • Enjoy free time in the picturesque town of Positano to shop, snack, stroll, or swim.

  • Taste homemade limoncello and watch a demonstration of how it's made at a peaceful lemon grove with spectacular views.

  • Relax and enjoy a perfect day on the Amalfi Coast. Your expert guide is on hand to answer any questions and to handle all logistics.

Itinerary Below


Day 1 - November 1oth. We will depart Rome Fiumicino Airport and make our way to our first Villa in Greve in Chianti. On the way we will stop at Anguillara Sabazia, a tumble of medieval houses, painted shutters gaping, scattered down the hillside like a handful of rolled dice. The town takes its name from the Roman villa that is buried somewhere beneath its erratically cobbled streets. Our next stop is Città della Pieve, a mini medieval masterpiece. We will have lunch first before doing some exploring. On a hill overlooking Lago Trasimeno and the Chiana Valley, the municipality of Città della Pieve has an exquisitely medieval structure, made entirely of high-quality local brick, made in the area since the Middle Ages. A free city since 1228, it was an ally of Siena in its struggles against the papacy and in constant conflict with Perugia. Today, it is delightful getting lost in its alleyways that open onto grandiose views of the mountains of Central Italy, from Amiata to Cetona, from the Sibillini to Subasio. Overnight Greve in Chianti.


Day 2 - November 11th - Today will be spent in and around Greve in Chianti, gateway to the famous Chianti region. Greve's history is connected to the beautiful Castle of Montefioralle located above the town and Greve was the castle's marketplace starting in the 13th century. This is one of the smallest hill towns in Tuscany, but loaded with so much charm that it will immediately captivate you. After exploring we make our way down the hill to Greve where the market still takes place here every Saturday in the Piazza Matteotti. We will wander this lovely market town where you will want to visit the Antica Macelleria Falorni, a Tuscan butcher shop that has been in the same spot since 1729, and the Bottega dell' Artigianato, a shop specialized in hand-woven baskets and products made in olive wood. Just a few miles up the road we find Panzano where will Stop for Lunch. After some time to look around, we will head to Volpaia, a small fortified village in referred to as a "castello" in Italian - Castello di Volpaia. Its main claim to historical fame is as the home town of the della Volpaia family of clock and instrument makers. Volpaia retains a great deal of its original architecture and has been attractively restored. Overnight near Greve in Chianti. (B,L,D)

Day 3 - November 12th - This morning we make our way to Volterra, considered to be Tuscany's most underrated hill town. Far fewer people visit here as compared to San Gimignano make it a delight to navigate. The Piazza dei Priori is one of the most impressive town squares in Tuscany and the 13th century Palazzo dei Priori, the oldest town hall in Tuscany. While here we will visit the Roman Theater, Forum, and Baths. Construction started on the Roman Theater in the 1st century BC and behind the theater are remains of Roman Baths dating from the 4th century AD. After our tour of the city we will take some time to enjoy all the delights of this medieval walled hill town and find some lunch. We will stop for you to find dinner before we return with a stop in the small village of Vinci, in the rolling landscape of vineyards and olive grove between Pistoia and Empoli. Leonardo da Vinci was born here in 1452 and lived here until 1469 when he left for Florence. While here we will visit the 13th century castle which now holds the Museo Leonardino. Here you can see numerous recreations of da Vinci's inventions such a bicycle, a car, a helicopter, a parachute and a tank and the drawings that inspired the wooden models, along with various pulleys and gears and other contraptions. We will stop for dinner on our way back home. Overnight near Greve in Chianti.


Day 4 - November 13th - Today will be spent at home in our beautiful Villa on the estate of the Folonari family, a renowned name in the Italian wine panorama and one of Tuscany’s most respected and successful wine making families. The villa is surrounded by 9220 acres of vineyards, 37 acres of olive groves and overlooks an extensive forest of century-old maritime pines. The garden is on different levels, and boasts a beautiful terracotta terrace overlooking the vineyards, a shaded area perfect for relaxing during the hot summer days, a private heated pool with beautiful views, an olive grove and a large lawn. The whole property extends over a total of 385 hectares (950 acres) of land. Spreading over a surface of more than 18,000 square feet, the villa offers its guests a unique blend of indoor and outdoor living, providing the perfect setting for either a family reunion, a group of friends travelling together, or an anniversary party… With its 9 wonderfully decorated bedrooms all with en-suite bathrooms and air conditioning, the villa offers the ultimate accommodation for your dream luxury holiday in Tuscany! We will gather in the afternoon for an antipasto and wine lunch followed by wine tasting on the estate. Overnight near Greve in Chianti.

Day 5 - November 14th - Today we will spend the day in the beautiful city of Florence, the Capitol of Tuscany. Our first stop will be the Accademia Gallery Museum to see "The David". We will take a tour of the Accademia which will cover not only Michelangelo – his life, torment and creative genius and his sculptures which include the David, his Unfinished Slaves and St. Matthew, but also works of art by great such as Botticelli, Ghirlandaio, Pontormo and other greats from the 13th to 16th centuries. After lunch we will take a tour of The Duomo, the religious heart of the city, through the tiny and narrow streets of the medieval quarters and we will see where artesans still work keeping ancient traditions alive. The Duomo or The Cattedrale di Santa Maria del Fiore stands tall over the city with its magnificent Renaissance dome designed by Filippo Brunelleschi. The cathedral is a vast Gothic structure built on the site of the 7th century Church of Santa Reparata, the remains of which can be seen in the crypt. After dinner in the city, a walk across the Ponte Vecchio at sunset is a must do! Overnight near Greve in Chianti.

Day 6 - November 15th - This morning we will take in a few castles with our first stop being Castello di Oliveto. Built in 1424 by the noble Dei Pucci family of Florence, the Castello di Oliveto is one of Tuscany's most beautiful historical residences. What's more, it provides the ideal setting for unforgettable, history-making events of our very own. One of the traditions of Castello di Oliveto is the “Cooking Class”. The kitchens are transformed into a real school where we will learn how to prepare a traditional Italian menu, from the typical Tuscan appetizers to the most delicious desserts. We will tour the castle, have wine tasing, attend the cooking school and then eat our creations!After eating and drinking until we are ready to burst, we make our way to another hill town to imbibe even more as after leaving Brolio behind we make our way back to Greve in Chianti and up the hill to the Montefioralle Winery. Along with the Wine Tasting, we will have a Tour of the Vineyards and the Small Winery, located right in the middle of their farm. The Sieni Family themselves will describe the special features of their Chianti Classico, Chianti Classico Riserva, IGT and Vin Santo, that they produce on their farm at the base of Montefioralle. Overnight near Greve in Chianti.

Day 7 - November 16th - This morning we will take in a few castles with our first stop being Montespertoli and Castello di Sonnino. We will discover this 14th century historic residence with a thrilling tour of the courtyard, the very heart of the Castle, and the thirteenth-century tower where we will visit the room where the ancient clock is still working and enjoy the breathtaking panoramic view over the surrounding valleys. We will find some lunch and then while we are in the area we will visit Castello Di Poppiano home of the Guicciardini Family since the year 1200. They are one of the most ancient Florentine Families who held a prominent position in the social , political and commercial life of Florence. Today they are more famous for their wine and olive oil. A tour of the castle will take in the Wine Making Cellar, the Underground Agin Cellar, the Olive Oil Mill, the Vinsanto Tower where the grapes are dried, The “Vinsantaia” inside the Main Tower, the Panoramic View from the Main Tower and of course the Wine Tasting! Overnight near Greve in Chianti.

Day 8 - November 17th -  This morning we make our south to our home near Montepulciano with a few stops along the way. Our first stop of the day is to San Gimignano, Tuscany's most famous walled hill town, famous for its medieval architecture and towers that rise above of all the surrounding buildings offering an impressive view of the city from the surrounding valley. San Gimignano offers visitors the chance to step back in time while enjoying its local products including saffron and its white wine, the Vernaccia di San Gimignano. We then make our way to Siena where we will take a Walking Tour of the City. Siena is one of the leading art cities in Tuscany and a place which has managed to preserve carefully its medieval character. Our walking tour will take in the Church of San Domenico, the magnificent palace of Monte dei Paschi Bank, founded in 1472 - the oldest bank in Europe, Piazza del Campo, the Chigi-Saracini Palace and finally the Duomo with its marble pavement made with a startling sequence of 56 marble panels. Then it is just a short drive to our new home. Overnight near Montepulciano. (B,L,D)

Day 9 - November 18th - As we are in the Heart of Tuscany it would only make sense to spend our day visited visiting hill towns and doing some wine tasting! Two of the most famous hill towns associated with wine are Montalcino and Montepulciano. Montalcino is a classic Fairytale Hilltop Town, set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection. This beautiful village is immersed in the breathtaking Val d'Orcia Natural Park, renowned all over the world for the production of its precious Brunello Red Wine. The historical center is dominated by the mighty and imposing fortress built in 1361 and the views from its ramparts are spectacular, stretching towards Monte Amiata, across the Crete to Siena, and across all of the Val d'Orcia. We will lunch here before continuing on to Montepulciano, a medieval town of rare beauty and full of elegant Renaissance palaces, ancient churches, charming square and hidden corners. It boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it. Dinner and Overnight near Montepulciano. (B,D)

Day 10 - November 19th - This morning we make our way to Arezzo for a Walking Tour that takes in the historic center and the Church of San Francesco with its frescos by Piero della Francesca, the Pieve Santa Maria Assunta, the Piazza Grande bordered by Vasari's Loggia, the Cathedral Church of San Donato, the Palazzo del Comune and the Church of San Domenico housing a Crucifix by Cimabue. We will take some time to further investigate Arezzo and all its antique and gold shops before we are off to tour the city of Cortona, a small charming town in the Val di Chiana enclosed by stone walls dating back to Etruscan and Roman times. We will have lunch before taking time to explore this lovely hill town. The heart of Cortona is Piazza della Repubblica, with the Palazzo Comunale or town hall building overlooking the square. Various small shops on the main streets of offer local handmade items and gastronomical products. Great red wines are made in the area and the wine bars offer a wide selection. Overnight near Montepuliano.


Day 11 - November 20th - The first part of the day will be spent in and around our lovely Villa and the estate. The Villa is a 17th century frescoed Italian Villa located at the foot of the Etruscan town of Cortona, not far from 'Villa Bramasole' where the movie “Under the Tuscan Sun” was filmed. The large gazebo surmounted by stone columns, located a few steps from the big swimming pool and from the many entrances to the villa, is furnished with marble tables and chairs for relaxing and dining al fresco, with the complicity of the silent garden embellished by the gentle setting of the Tuscan hills. This afternoon we will make our way to the lovely town of Foiano della Chiana for some exploration and then we will pick up some amazing pizza to take back to the Villa to have a Pizza and Wine Party. Foiano della Chiana is a settlement of Etruscan, and later, Roman origin. For a long period it was almost completely surrounded by water, and that led to the flooding of Valdichiana. In 1337 the village fell under the dominion of Florence and this led to the reconstruction of the city walls and towers. Overnight near Montepulciano.

Day 12 - November 21st - This morning we make our way to Fattoria Bistecca for a Cooking Class with Old Tuscan Recipes'. Ilaria and her family are recreating the recipes and passion of Great Grandmother Dinda and Aunt Anna. Starting with pasta: pici, tagliatelle, pappardelle, gnocchi then an appetizer which will change with the season. We are very lucky because we will get fresh vegetable products from Mama Paola's garden. We will cook panzanella, ribollita, pappa al pomodoro, zucchini flowers and more. The cooking class will include a dessert: tiramisù, cantucci toscana (almond biscuits), zuppa Inglese. The recipes are seasonal using fresh products and we can choose our favourite recipe. The adventure will end at our beautiful table while we are enjoying the meal we have created. We then visit Lucignano known as the Pearl of the Val di Chiana. This small village represents one of the more extraordinary examples of medieval urban planning for its system of elliptic rings arrived intact over the centuries. As we walk through the narrow streets, between houses of stone and brick, we reach the heart of the village where we find the Square of the Tribunal, which is overlooked by the Town Hall, the Church of St. Francis and the Collegiata. Inside the 13th century Town Hall building is the Museum, the keeper of Lucignano’s Treasures with works of art from the Tuscan Middle Ages and Renaissance. After a Tour of Lucignano we make our way back home. Overnight near Montepulciano.

Day 13 - November 22nd - This morning we are off to Perugia located in the centre of Italy. The Province of Perugia is Umbria’s largest province with Perugia at the heart of it. The city lies on a hill 1,640 ft above sea level, with the old town spreading all around it, and partly surrounded by Etruscan and Medieval Walls. There are two city walls with the external dating back to the Middle Ages, is still intact for several miles and is marked by several entrances, such as the Cassero di Porta Sant'Angelo. While here we will have a Taste of Perugia Tour. We will stroll through a maze of medieval streets as we taste and sip our way through the capital city of Umbria, Italy's "Green Heart" with over 7 tastings, bites & sips – with locally sourced foods and much more! We will enjoy Umbria's local food and wines, including handmade pasta, truffles, chocolates, cheeses and more as we walk in the footsteps of ancient Etruscans, Roman Emperors, Noble Families and Renaissance Painters. As Perugia is the European Capital of Chocolate, we may have to find some places to do some more sampling before we make our way back home. Overnight near Montepulciano.

Day 14 - November 23rd - Today we will explore the beautiful area of Crete Senesi in the eastern part of Siena countryside. This area, sometimes referred to as the Desert of Accona, is full of traces of ancient cultures, small medieval towns, local festivals and stunning landscapes. Our first stop will be the Abbey of Monte Oliveto Maggiore, situated in a beautiful position among a forest of cypresses and oaks. The Abbey was founded in 1313 by Sienese Bernardo Tolomei who retired in this isolated place, property of his family, after he converted to Benedictine order. We will then make our way to Asciano where we will find some lunch and wander and explore this delightful town with its Travertine Sidewalks. The whole town seems to be made from Travertine and it is no small surprise as there are numerous Travertine Caves in this area. Later this afternoon we will visit one our favorite small hill towns, Serre di Rapolano, a characteristic hilltop village surrounded by walls on the border of Crete Senesi to the south of Siena. We next make our way to Castiglion Fiorentino is a historical village in the province of Arezzo and overlooking the Val di Chiana. The town’s ancient origins date back to the Etruscans, who assiduously first inhabited it, and then to Roman times. Archaeological excavations in the village’s square have uncovered a sacred area dating back to the 5th century BC. The medieval city walls overlooked by the Cassero fortress are almost intact. Overnight near Montepulciano.

Day 15 - November 24th - We make our way back to Rome for the journey home. We will make a few stops along the way including Civita di Bagnoregio, a magical, surreal, fantastic place located on top of a tuff hill that can only be reached by crossing a narrow pedestrian bridge. From there you can enjoy one of the most stunning panoramic views of the whole Lazio region. Nick-named "the town that is dying", due to the constant erosion of the tuff rocks where it is placed, this citadel half-way between Orvieto and Lake Bolsena has Etruscan and Medieval origins. Suspended in time and space, Civita di Bagnoregio is beyond doubt one of the most beautiful and characteristic Italian villages. Then we visit Fiano Romano soaked in histroy and traditions. Fiano, like other towns in the area, has been inhabited since ancient times thanks to its strategic position near the Tiber river. The area was first a meeting point for ancient pre-Roman civilisations, then came under the control of first the Etruscans and then the Romans. The exceptional archaeological sites of 'Lucus Feroniae' and 'Villa dei Volusii' remain as evidence of this period. From 1300 and throughout the Renaissance, Fiano came under the rule of the Orsini family, to whom we owe the construction of the imposing castle, and then passed into the hands of other noble families, like the Sforza and Ludovisi. We then get settled into our accommodation at the Rome Airport. Overnight Rome Fiumicino Airport..


Day 16 - November 25th - Rome airport for your flight.

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