tuscany28 | Scottish Dream Tours

An Amazing Spring Time Ramble through the Tuscan Countryside visiting hill towns, castles, vineyards and olive groves with cooking classes and wine tasting.

April 14th - 30th, 2028

Our first week will be spent in Cortona where take complete advantage of all that this beautiful region of Tuscany has to offer. 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. We will also visit the amazing cities of Arezzo and Cortona. We will have dinners at our hotel along with one night out to an Osteria, one night our to a Pizzaria and one night on your own.

We will visit San Gimignano and Sienna on the way to our home near Florence for the second week. We will explore hill towns, villages, castles, wineries and olive oil refiners and of course take in many wonderful places to eat. We will visit Castello Di Sonnino and also Castello Di Poppiano home of the Guicciardini family since the year 1200. We will 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. We will also spend a day visiting Pisa to see the Leaning Tower of Pisa. Along the way we will visit the small village of Vinci, which is the birthplace of Leonardo da Vinci. We will spend time in the Chianti Region with wine tasting and visit the Chianti towns of Panzano, Greve in Chianti and Montefioralle. We will also spend a day visiting the amazing town of Volterra, the home to Alabaster! We will have dinners at our hotel along with one night out to a lovely restaurant and one night out to a Trattorio and then one night on your own.

$11,995 per person.

$1795 Single Supplement. Can be avoided if you book a single room.

$1000 deposit to book your spot.

Please do not sign up for a tour until you have thoroughly read

our Terms and Conditions in regards to mobility, luggage,

cancellation etc.

Day 1 - We will meet this morning at our Rome Leonardo da Vinci Airport accommodation and start our journey to Cortona. Our first stop will be at the Catacombe di Priscilla for a Guided Tour. Rome is splendid, but Underground Rome preserves unique wonders in the world, such as the Catacombs of Priscilla: a true 'city of the dead' excavated between the end of the second and fifth centuries, located on the Via Salaria. The first and oldest level of the Catacombs of Priscilla is a fascinating labyrinth of irregular galleries where you can admire frescoes, inspired by the stories of the Old or New Testament, expressing faith in salvation and resurrection. Next we stop at Orvieto, a stunning medieval hilltop town in the Umbria region of Italy, famous for its dramatic volcanic tufa cliffs and striking architecture. We will have lunch here and then do some exploring. A visit here will reward you with a delightful, perfectly preserved, and virtually traffic-free world highlighted by a colorful-inside-and-out cathedral and some of Italy's best wine. We then continue on to Cortono to get checked into our accommodation before a Welcoming Dinner. Dinner and Overnight 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. If time permits we will stop to explore a new hilltop village we have not been to, Montefollonico before arriving in 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 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 Cortona. (B,L,D)

Day 4 - Today will be spent on your own in the Etruscan town of Cortona, not far from “Villa Bramasole” where the movie “Under the Tuscan Sun” was filmed. Cortona is a small charming town in the Val di Chiana enclosed by stone walls dating back to Etruscan and Roman times. 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. The steep cobblestone streets lead both up and down from the main square and have sweeping views of the Val di Chiana valley and Lake Trasimeno. Wonderful exploring includes the Fortress of Girifalco, a 16th-century Medici fort at the peak of the town offering panoramic valley views and Basilica of Santa Margherita, a scenic sanctuary dedicated to the town's patron saint. Overnight Cortona. (B)

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 - Today we will have a cooking class at Fattoria Bistecca with our friend Ilaria. The kitchen we are cooking in was priginally where the Chianini cattle lived in the past. 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 and use fresh vegetable products from Mama Paola's garden. We will cook either panzanella, ribollita, pappa al pomodoro or zucchini flowers and also learn to make a dessert like tiramisù, cantucci toscana (almond biscuits), zuppa Inglese. The adventure will end at our beautiful table while we are enjoying the meal we have created. Next we join another friend of ours in 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 make our way back home. Overnight 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 you find some lunch on your own 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,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 hotel in Impruneta, a historic Tuscan town located about 10 miles south of Florence. Famous as the world capital of handmade terracotta and a gateway to the Chianti wine region, it features rolling olive groves, local wine traditions, and the central Piazza Buondelmonti. Artisan kilns here have shaped local clay for centuries. Even the iconic red tiles on Florence’s Duomo came from Impruneta. It is also the birthplace of Peposo all'Imprunetina, a rich, slow-cooked beef and red wine stew originally made by tile kiln workers. The jewel of Piazza Buondelmonti is the church, a major Marian shrine that has drawn so many pilgrims over the centuries: the Basilica di Santa Maria all’ Impruneta. The exact site has been used for devotion since Etruscan times, in all probability, but the basilica was first consecrated as a pieve, a parish church, in 1060 (the crypt and bell tower date from this period). Explore to your hearts content and if you did not get your fill of Florence, you can easily get there by bus. Overnight near Florence. (B)

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 join a cooking class at Castello di Oliveto. One of the tradition of Castello di Oliveto is their Cooking Class where the kitchens are transformed into a real school where you can learn how to prepare a traditional Italian menu, from the typical Tuscan appetizers to the most delicious desserts. The course is a wonderful opportunity to understand the secret of real Tuscan meat sauce and to prepare amazing pasta like ravioli or pici with tomato. The we will move on to the main course like vegetables stuffed with beef or cacciatora chicken and then finish the lesson with cantuccini or a dessert chosen by us. Finally we will have the opportunity to visit the Castle, enjoy and relax with what we have prepared during the course. This is one of our favorite things to do in Tuscany and you will love it. On our way home we stop in Tavarnelle Val di Pesa nestled in the Chianti hills about half-way between Florence and Siena. It was a historic crossroads and stop-over point on the main route between the two republics and the road that lead to Rome, and provided a point of hospitality for lodging, meals and stables for travelers in the Middle Ages and Renaissance periods. In fact its name derives from the word "taverna" - the type of inn that provided a variety of services to travelers. It is one of the few medieval villages without fortifications. Dinner and Overnight near Florence (B,L,D)

Day 15 - This morning 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. Dinner and Overnight Cortona. (B,L,D)

Day 16 - This morning we make our way back to the airport in Rome. Along the way we will stop at Monteriggioni, a medieval walled town in Tuscany, Italy, built by Siena between 1213 and 1219 as a defense against Florence and famous for its intact almost 2000 foot wall and 14 towers. From the top of this gentle hill near Siena, this splendid medieval village transports you into the distant past and a walk along the ramparts affords panoramic views of the spectacular Tuscan countryside. After thorough exploration we make our way to Grosetto where you can find some lunch on your own. Grosseto, the capital of the Province of Grosseto, is renowned for its rich history, stunning landscapes, and vibrant local culture. Our last stop before reaching our airport accommodation is Orbetello, a unique town in southern Tuscany that sits on a narrow strip of land right in the middle of a scenic lagoon. The area is famous for the iconic Spanish Windmill in the water, long sandy beaches on surrounding sandbars, and a nature reserve filled with pink flamingos. Once we are settled into our accommodation we will gather for our Farwell Dinner. Dinner and Overnight Leonardo di Vinci Airport. (B,D)

Day 17 - This morning we return to the Florence Peretola Airport for the journey home.