A Tuscany Luxury Villa Tour Tour with Hill Towns, Castles,
Vineyards and Olive Groves.
October 15th - 30th, 2025

Pre Tour: October 14th. Arrive into Florence Peretola International and use the day to get rested up at our accommodation near the airport before the tour starts the following morning.

 

Day 1 - October 15th - After leaving the Florence Airport behind our first stop today will be 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. 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 further into the Tuscan countryside and then get settled into our accommodation before dinner. Welcoming Dinner and Overnight near Cortona. (B,L,D)

 

Day 2 - 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 Cortona. (B,D)

 

Day 3 - 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 to Assisi, the home of St. Francis. With the plains spreading picturesquely below and Monte Subasio rearing steep and wooded above, the mere sight of Assisi in the rosy glow of dusk is enough, but we will explore Assisi for a while anyway before we stop for Dinner. Overnight near Cortona. (B,L,D)

 

Day 4 - Today will be spent in and around our Villa and the estate after a Late Brunch. 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. This prestigious Italian villa in which modern accessories blend with original recycled materials and local architectural features confers warmth and typical Tuscan atmosphere to the rooms. Antique furniture, precious tapestries, elegant windows and doors, original chandeliers and accessories, painted ceilings and splendid terracotta-tiled floors dress the more than 1000 Square Meters of the villa. The completely fenced-in park that surrounds the Villa is planted with grass with a large variety of centuries-old plants and trees, pots of lemon trees around the villa and a lush row of oleander bushes that border the paved drive leading to the main entrance. 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. In the late afternoon we will gather for a Wine and Antipasto Lunch. You will then have more time to enjoy the estate and the house before we go into Cortona for you to find some dinner on your own and explore the city further. Overnight near Cortona. (B,L)

 

Day 5 - 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 have Lunch in Asciano before some time to wander and explore this delightful town with its Travertine Sidewalks as there is numerous Travertine Caves in this area. This afternoon we visit my favorite hill town of Serre di Rapolano, a characteristic small hilltop village surrounded by walls on the border of Crete Senesi to the south of Siena. We will also explore Foiano della Chiana before returning home for dinner. Dinner and Overnight near Cortona. (B,L,D)

 

Day 6 - 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. You will be able to find dinner on your own this evening in Cortona. Overnight near Cortona. (B,L)

 

Day 7 - This morning we make our way to 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 just down the hill to Sinalunga for Lunch. After lunch we visit Fattoria Cantagallo Winery in the heart of the Tuscan countryside with views of the famous Cortona, an old Etruscan town. The farm is lead by Edoardo Capecchi, a young winemaker, helped by his parents, his brother Tiziano and his sister, Stefania, that deal with management of the farm and with the growing of some farm typical product such as olives, barley, sunflowers, corn and wheat. Dinner and Overnight near Cortona. (B,L,D

 

Day 8 - This morning we make our north to our home near Florence with a few stops along the way. Our first stop of the day is 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. After lunch we make our way 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. Then it is just a short drive to our new home. Dinner and Overnight near Florence. (B,L,D)

 

Day 9 - 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. Dinner and Overnight near Florence. (B,D)

 

Day 10 - 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 Florence. (B,L)

 

Day 11 - Today will be a relaxing day in and around our Villa. This 16th century Villa that has been in the same family for 5 generations sits in extensive secluded grounds that features walking paths across roses and olive groves, from which their excellent Extra Virgin Olive Oil is produced every year. Perfectly kept at all times, the park offers multiple seating areas for al fresco dining and it is ideal for outdoor summer banquets. The Villa´s pool area is completely fenced and features a full set of sun loungers, deckchairs and umbrellas, as well as a changing room. The strategical position of the property nestled on the hills tight above Florence, allows us to both comfortably reach the city centre and at the same time enjoy the benefits of the Tuscan countryside with its plentiful options for rest and complete privacy. We will gather in mid afternoon for an Afternoon Tea with an Italian Flair! You will have more time to lounge in the house, take a swim in the pool or just enjoy the surrounds of this beautiful estate before finding some dinner on your own. Overnight near Florence. (B,L)

 

Day 12 - Today we have our winery tour in the Chianti Region of Tuscany withe Brolio Castle and Barone Ricasoli, the oldest winery in Italy! The guided tour will take us through the history by visiting the 12th century castle gardens, the Family’s Private Chapel and Unique Museum. After this visit to the past, we will visit the ultra modern wine-making facilities and finish the tour with a special wine tasting in a private room. We will Lunch at Osteria del Castello while at Brolio Castle. We will have their 5 Course Luncheon pared with wines from the estate. 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. We will return home before dinner. Overnight near Florence. (B,L,D)

 

Day 13 - This morning we make our way to Pisa and the Leaning Tower of Pisa. Most people come to Pisa for the Tower, but this is a lovely university town where the Piazza dei Miracoli, or Square of Miracles, where the tower, the cathedral and baptistery form the city's main attraction. The city is also home to more than 20 other historic churches, several medieval palaces and various bridges across the River Arno. After taking some time on your own to explore and find lunch on your own we are off to Lucca, located on a plain at the foot of the Apuan Alps and is less than half an hour from the coast of Versilia. Lucca is one of the most loved cities in all of Tuscany, and a must stop location. Most of the attractions in Lucca surround its ancient history: from the traces of the Roman Amphiteater that can be seen in the shape of the Piazza dell'Anfiteatro to the archeological remains under the 12th century Church of Saints Giovanni and Reparata to the various towers and villas from the 12th to 16th centuries. We will have a guided tour to take in all of these treasures and then stop for dinner on the way home. Overnight near Florence. (B,D)

 

Day 14 - 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! We then return home for dinner. Dinner and Overnight near Florence. (B,L,D)

 

Day 15 - October 30th - This morning we return to the Florence Peretola Airport for the journey home.