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A Spring Adventure in Tuscany with Hill Towns, Castles, Vineyards and Olive Groves.

April 8th - 23rd, 2026

Two weeks through the beautiful Tuscany region of Italy visiting hill towns, castles, vineyards and olive groves. The colors in April are amazing! The fields turn yellow and green and the sunflowers abound with the olive groves greening up. With spring in the air, the day time temperatures are becoming quite pleasant making this the perfect time of year to explore this beautiful region of Italy!
We will visit Montalcino, a distinct hill town hill town famous for its Brunello di Montalcino wine. Another lovely hill town is Montepulciano, renowned for its pork, cheese, "pici" pasta, lentils, and honey and it is known world wide for its wine. We will also visit Siena which is the embodiment of a medieval city and a UNESCO World Heritage Site. We will also spend a day in the Province of Perugia, Umbria’s largest province with Perugia at the heart of it. The city lies on a hill 1,640 feet 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. We will also visit the amazing cities of Arezzo, Cortona, San Gimignano probably the most famous of the walled Medieval hill towns of Tuscany and where you can get some of the best gelato you will ever taste! My favorite is the white chocolate pistachio.
We will also spend a day in Florence seeing The David as well as a climb to the top of the Duomo which gives the most amazing views of the city. Florence is so alive with culture, beauty and history that we will make a full day of it. We will also visit Pisa to see the Leaning Tower of Pisa. Vinci, which is the birthplace of Leonardo da Vinci and Volterra, the home to Alabaster! We will visit the

city of Siena, built around the Piazza del Campo, Greve in Chianti, Lucca and several Castles and have 3 very different cooking classes.

$9995 per person. 2 Singles and 3 Doubles available.

$1595 per person single supplement.

$1000 deposit to book your tour.

 

 

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Day 1 - April 8th - This morning we meet at our Florence Airport Accommodation and leave Florence behind as make our way 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. To better explore the city we will have a Flavors of Lucca Food Tour. To live like a local is to eat like a local so will be shown how to drink and dine like they do in Lucca, with a dash of history thrown in along the way. We then 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, we make our way to our home in Volterra to get settled in before a Welcoming Dinner. Dinner and Overnight Volterra. (B,L,D)

Day 2 - April 9th - This morning we make our way to 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 as 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. After you find some lunch on your own we will visit the home Leonardo was born in. We stop for lunch in Pontedera before we make our way back 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. You will have some time to explore Volterra before we have a Sunset Tour of the city we will take some time to enjoy all the delights of this medieval walled hill town. Dinner on your own in Volterra this evening. Overnight Volterra. (B,L,D)

Day 3 - April 10th - This morning we make our way to Siena with a stop in 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. We will have a tour of the town and its towers, for which it is known. The patrician families who controlled the town built around 72 tower-houses (some as high as 50 m) as symbols of their wealth and power. Although only 14 have survived, San Gimignano has retained its feudal atmosphere and appearance. 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 will experience both saffron and wine with our lunch stop before continuing on 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. Dinner and Overnight Siena. (B,L,D)

Day 4 - April 11th - This morning we will learn to cook traditional Italian dishes during a Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, our professional chef Francesco who will leads us through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. We will learn how to prepare a full Tuscan menu of 5 recipes from starter to dessert including  fresh hand made pasta which may include pici, tagliatelle, ravioli and gnocchi, with related condiments. The best part of the day will be eating our creations accompanied by some great wine! Then the rest of the afternoon and evening is free in Siena. You may want to visit the Palazzo Pubblico where you can climb up the over 500 steps will reward you with a wonderful view of Siena and its surroundings. The Museum here offers some of the greatest of Sienese paintings. The Sala del Concistoro houses one of Domenico Beccafumi's best works, ceiling frescoes of allegories on the virtues of Siena's medieval government. But it is the Sala del Mappamondo and the Sale della Pace that hold the palaces's highlights: Simone Martini's huge Maestà and Equestrian Portrait of Guidoriccio da Fogliano and Ambrogio Lorenzetti's Allegories of Good and Bad Government, once considered the most important cycle of secular paintings of the Middle Ages. There is so much to do and see here that you will be captivated all afternoon. Overnight Siena. (B,L)

Day 5 - April 12th - This morning 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. Then 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. In ancient times, the village of Serre was famous for its Grancia, an old-style fortified farm/granary, which belonged to the Hospital of Santa Maria della Scala in Siena. It was part of many properties the hospital owned in the territory around Siena, you can see it by the emblem of the stairs above the door tells the importance of this institution. Today, this 13th century building hosts a museum that documents the history of the ancient fortified granaries (le Grance) belonging to the Hospital of Santa Maria della Scala and the ancient working process of producing wine and olive oil. This afternoon we visit Lucignano known as the Pearl of the Val di Chiana where you can find some lunch before we explore this small village with 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. We then make our way to Montepulciano to check into our accommodation before dinner. Dinner Overnight near Montepulciano. (B,D)

Day 6 - April 13th - As we are in the Heart of Tuscany it would only make sense to spend our day visiting hill towns most associated with wine and doing some wine tasting! The two 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. Brunello di Montalcino is considered one of the greatest wines of the World. Brunello is only produced in the vineyards surrounding the hill town of Montalcino. We will have a wine paired lunch here before making our way 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. Montalcino and Montepulciano are great rivals in the wine market. Montepulciano wine is a typically red wine crafted from the grape variety of the same name, though it also makes excellent rosé. It is most frequently associated with Montepulciano d’Abruzzo, which is grown in Abruzzo, in east-central Italy. We then return to our accommodation to get rested up before we gather for dinner. Dinner and Overnight near Montepulciano. (B,L,D)

Day 7 - April 14th - This morning on our way to Perugia we make our way to Fattoria Bistecca for another 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 recipes. The adventure will end at our beautiful table while we are enjoying the meal we have created. The we must depart, and continue on our way to Perugia with a stop at Passignano sul Trasimeno, a town in the Province of Perugia, in the Italian region of Umbria. The town's oldest quarter is preserved intact as a fortified village enclosed within the circuit of medieval walls. The gates and towers of the walls have survived, including the tower known as the Torre di Ponente, which still bears the Commune's coat of arms. The Rocca, or fortress, sits prominently on the highest point in town. We will also stop in the nearby delightful little village of Castel Rigone, with gorgeous views of Lake Trasimeno. We then get checked into our accommodation before dinner. Dinner and Overnight Perugia.  (B,L,D)

Day 8 - April 15th - This morning we spend in the beautiful city of  Perugia. 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 still intact for several miles, dating back to the Middle Ages. They are 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'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 our accommodation to get checked in before dinner. The historic centre of Umbria's capital is a true 14th-century village, one of the most beautiful and beloved in Italy. It boasts a very intense city life thanks to the two historic universities – the University of Perugia founded in 1308 and the University for Foreigners, the oldest of its kind in Italy. We then make our way to Arezza to get checked into our accommodation before dinner. Dinner and Overnight Arezzo. (B,L,D)

Day 9 - April 16th - As we are about half way through the tour, the entire day will be spent at your leisure in Arezzo, a rural centre of Etruscan origin. Its handsome Medieval square is one of the city’s main attractions, used in the Oscar winning film “Life is Beautiful”. It is far from the well-trodden tourist trail in Italy, which makes it the perfect place to spend the day exploring. It’s as well known for its art as it is for its shopping, with clothes, home-wear, jewellery and antique stores, all jostling for space along the narrow streets. The local cuisine with fresh products from the nearby Valdichiana and Casentino Valley has a following of its own. The Piazza Grande is a great place to relax and have lunch, without the crowds that usually fill the squares of tourist destinations. The famous loggia, which once hosted artisan stalls, is now home to trattorias and coffee shops. A walk in the streets around Piazza Grande reveals picturesque corners, old botteghe and Medieval buildings like the Palazzo Pretorio, its façade covered in coats of arms. The Palazzo dei Priori in via Libertà near the Cathedral is a splendid example of civic Gothic architecture. Enjoy your day and get rested up for the rest of the tour. Overnight Arezzo. (B)

Day 10 - April 17th - This morning we visit Cortona, a small charming town in the Val di Chiana enclosed by stone walls dating back to Etruscan and Roman times. Its dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno.We will explore this lovely hill town where we will have a guided tour that takes into the heart of Cortona with the Piazza della Repubblica and the Palazzo Comunale or town hall building overlooking the square. Various small shops on the main streets offer local handmade items and gastronomical products. Great red wines are made in the area and the wine bars offer a wide selection. The city is small but offers many interesting places to visit, among these the Diocesan Museum, and the MAEC (The Etruscan Academy Museum of the City of Cortona), where it is possible to see many artifacts found in the Eruscan archeological sites in the area. You should not miss a visit to the beautiful Santa Margherita Sanctuary, patron of the city, and to the Girifalco Fortress. After some exploration on your own we have lunch before returning 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. This tour is one of our very favourite things to do in Italy. We love Arezzo, we love our guide and the whole experience is full of wonderful treasures, insights and conversations. Dinner and Overnight Arezzo. (B,L,D)

Day 11 - April 18th - We make our way toward Greve in Chianti this morning with a few stops along the way including Castellina in Chianti, a pretty village in the Sienese Chianti area, set in the hills straddling the Val d'Elsa, Val di Pesa and the Arbia river valley. The heart of the village is the ancient Rocca designed in the second half of the 15th century by Giuliano da Sangallo. At the crossroads leading to the Rocca is the church of San Salvatore in neo-Romanesque style, rebuilt after the destruction of the last World War. It is impossible to pass through Castellina and not stop for a tasting in the numerous wine shops in the village and appreciate the art of pork butchery with cured meats and flavours to be discovered. Then we head just a few miles up the road to Castello Vicchiomaggio located at the top of a hill overlooking the valley of Greve in Chianti. The Castle is known for its vineyards where owners John and Paola Matta dedicate their lives to preserving this centuries-old tradition. We will have lunch  in one of the castle’s Renaissance dining rooms and then enjoy a guided tour of the vineyards, the historical cellars and the Castle’s Italian Gardens. Following our tour you can stand in the middle of the garden and enjoy breath-taking views over the hills of Greve and the Chianti vineyards. We then get settled into our accommodation before dinner. Dinner and Overnight Greve in Chianti. (B,L,D)

Day 12 - April 19th - Today we have a wonderful winery tour in the Chianti Region of Tuscany with Brolio Castle and Barone Ricasoli, the oldest winery in Italy! The guided tour will take us through the history of the castle 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 enjoying 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 this family 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. This wonderful family operation will charm you in every way and you won't want to leave, but you will want to explore Montefioralle itself. This is one of the smallest hill towns in Tuscany, but loaded with so much charm that it will immediately captivate you. Overnight Greve in Chianti. (B,L)

Day 13 - April 20th - 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 tasting, attend the cooking school and then eat our creations! After lunch 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 Greve in Chianti. (B,L,D)

Day 14 - April 21st - This morning we spend some time in Greve whose history is connected to the beautiful town of Montefioralle located above the town and Greve'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. We then make our way toward the capitol of Tuscany, Florence with a stop at Castello Verrazzano. The Castle sits in the heart of the Chianti Classico area, between Florence and Siena. Initially the Castle was an Etruscan then a Roman settlement and it has remained within its boundaries for over 1000 years. There is a great tradition of winemaking here and the “vineyards situated in Verrazzano” are mentioned in a manuscript which dates back to 1150 and is preserved at the Abbey of Passignano. We will have a guided tour to the Renaissance Gardens of the Castle and to the historical aging Cellars built directly into the hill below it. After a walk in the lush gardens of the Castle we will cross the secrets of the underground cellars until we reach the warmth of the Hosteria where a complete lunch with a traditional menu of the Tuscan countryside combined with the most prestigious wines from their cellar will wait upon arrival. We then continue on to Florence to get checked into our accommodation. Overnight Florence.

 

Day 15 - April 22nd - 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 our Farewell Dinner in the city, a walk across the Ponte Vecchio at sunset is a must do! And then we prepare to say goodbye to Florence and our Tuscany Adventure. Farewell Dinner and Overnight Florence. (B,L,D)

Day 16 - April 23rd - This morning we return to Florence Peretola Airport.

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