Small group tours for women who love to travel
Day 1: Monday - Welcome to Cortona
Upon arrival at Terontola railway station, you will be met and transported in a luxury minivan the short distance to our base in the town of Cortona. On our way from Terontola, we get our first sight of Cortona, red terra-cotta roofed buildings nestled on the hillside in front of us. At Cortona, you will be checked into your luxurious Tuscan style hotel which will be home for the duration of the tour.
Cortona received a great deal of attention and fame following the publication of Frances Mayes’ bestselling novel ‘Under a Tuscan Sun’ and the movie of the same name in which Diane Lane portrays Mayes’ relocation to Tuscany and her restoration of the beautiful villa, ‘Bramasole’, just on the edge of Cortona.
The town is filled with beautiful time-worn stone buildings dating back as far as the 13th century housing museums, galleries, artists’ studios, restaurants, b&b’s, boutiques, handbag and shoe stores with narrow cobblestone laneways winding between them. Cortona also has a wonderful selection of restaurants many of which we will be visiting for our evening meals, and not to be missed are the mouthwatering gelato shops.
After time to freshen up and settle in, you’ll be invited to meet the other guests over a glass of the local vino, a cheese platter and a short briefing session. We will then start exploring the local area by taking a short drive to the edge of town for a quick look at Frances Mayes’ Bramasole and then up to the top of the hill to the magnificent fort that towers over Cortona, offering panoramic views far out over the Tuscan countryside.
Upon return to our hotel there will be time to relax and refresh before our first night welcome dinner.
Day 2: Tuesday - Cortona
On our first full day of the tour we take the opportunity to more thoroughly explore our surroundings in Cortona at a leisurely pace. The village centre is filled with art galleries, boutiques, shoe and handbag stores, leather artisans, and gelato shops. The town square is always humming with activity and the cafes and restaurants have a great view of the passing parade.
Today we will visit sites of historical significance; visually spectacular and spiritually refreshing. The beautiful Santa Maria della Grazie was a challenge to engineers to build a place of worship at this site of miraculous healings and now sits as a landmark on the hill below Cortona. Also on the outskirts of the town is Santa Maria Nuova, another beautiful example of the gothic architecture in the area, and amidst a beautiful hillside setting we visit the tranquil Franciscan monastery Eremo Francescano La Celle, one of the most peaceful and spiritual places in all of Italy.
We will then head back into the heart of the old town for a visit to the acclaimed MAEC Etruscan Museum before taking a relaxed lunch at a special restaurant we know of.
Following lunch with the group you will have time to explore the old town of Cortona by yourself to visit the sites, museums and galleries or to do a spot of shopping at the boutiques as you please.
After a day spent exploring Cortona, we will gather again as a group to dine at an intimate little restaurant just down from the main piazza where we’ll enjoy fine Tuscan food and swap shopping stories.
Day 3: Wednesday - Assisi - Basilica Tour
Today, we head further afield, taking a drive to Assisi, which is situated in the neighbouring region of Umbria, Italy’s ‘Green Heart’. Umbria is located in the very centre of Italy, not having any coastline but containing within its borders the splendid waters of Lake Trasimeno in the northwest of the region. The typical Umbrian landscape spreads out before us in waves of agricultural fields patchworked over the rolling hills with rows of slender, tapering cypress trees defining the roads through the region.
Assisi is of course famous as the home of Saint Francis, patron saint of Italy, and recognition of this can be seen throughout the city including the magnificent 13th century Papal Basilica of San Francesco d'Assisi located at one end of the city on the hillside of Monte Subasio overlooking the panorama of the Umbrian valley.
Upon arrival at Assisi we will familiarise ourselves with the layout of the city, taking in the sights of the Cathedral of San Rufino (13th century) where Saint Francis was baptised and the Ancient Roman ‘Tempio di Minerva’ that now houses the Santa Maria sopra Minerva, built in the 16th century as we walk through the piazzas to the Basilica San Francesco d’Assisi. At the basilica we will take part in an audio tour to guide us through the magnificent rooms and frescoes of one of the most visited religious sites in all Italy.
Following our visit to the basilica we will have lunch in one of Assisi’s finest restaurants offering Umbrian style cuisine in a beautiful setting with transparent floors looking into an Etruscan archaeological site.
After our lunch we’ll take some free time to explore the city where the streets are filled with small shops selling all sorts of delicacies and wine shops offering up many of the local vintages as well as plenty of opportunities for clothing, trinkets and of course, religious souvenirs.
At the end of the day we head back to Cortona where refreshments will be waiting for us. Later in the evening, we’ll get together for a light dinner and an early night for a well earned rest.
Day 4: Thursday - Montepulciano and Pienza
Travelling south from Cortona through the rolling vineyards we visit the mediaeval hilltop town of Montepulciano, famous for it's wines and its history. Stopping first just outside the city at the high renaissance chiesa of San Biagio di Montepulciano before driving up the hill to enter the old part of the city near the Fortezza Medicea di Montepulciano.
Montepulciano was originally an Etruscan settlement and during the Middle Ages was fought over by Siena and Florence until finally coming under the banner of Florence permanently in 1404. This history has left the town with a fascinating mix of gothic and renaissance architecture. The history of wine in Montepulciano dates back just as far with Etruscan pottery showing traces of the culture.
The main piazza at the top of Montepulciano is Piazza Grande and this charming square is lined with restaurants, cafes and specialty shops where we will have time to explore and sample some of the local product before stepping down through an entryway below Palazzo Ricci to find ourselves in an underground wine cellar that has been awarded the title of ‘Most Beautiful Wine Cellar in the World’ where many thousands of hectolitres of Vino Nobile are stored for aging and where we will be taken on an informative tour of the cellar complete with wine tastings to be followed by a light lunch in the ‘cantina’.
After lunch we will have time to explore some of the shops and sights of Montepulciano before traveling the short distance to Pienza , another hilltop town famous for pecorino sheep cheese and spectacular views where we will wander through the picturesque streets of this beautiful village taking time to investigate the local shops, giving us the opportunity to sample some of Southern Tuscany’s traditional products, including Pecorino di Pienza and Extra Virgin Olive Oil.
Following our visit to Pienza we head back to Cortona once again for a short rest and a chance to freshen up before dinner in a wonderfully friendly atmosphere at one of our favourite local restaurants.
Day 5: Friday - San Gimignano
On Friday morning our first destination is the delightfully authentic medieval town of Monteriggioniwhere it is possible to walk along the fortified walls that surround the village offering spectacular panoramic views. We will also visit the small museum in the village that contains displays of medieval weaponry where you can actually try on some armour!
We then continue our journey to San Gimignano, ‘city of the beautiful towers’, the UNESCO World Heritage listed medieval city famous for the lofty towers built by competing wool merchants to display their status and wealth. Our first stop will be for lunch on the terrace of one of San Gimignano’s best restaurants where you will have the opportunity to sample the renowned Vernaccia di San Gimignano wine. After lunch we will explore this rich and vibrant city.
San Gimignano thrived during medieval times, becoming a trading centre due in part to its location along the Via Francigena. Entering the walled city is like taking a journey back to the 13th century with many buildings well preserved from that time; 14 of an original 72 towers still survive today. The market square in San Gimignano is a bustling cultural centre lined with cafés and street entertainers. We will have the opportunity to visit the Palazzo Comunale which houses some beautiful frescoes: "Virgin and Child" by Lippo Memmi and frescoes inspired by chivalry and courtly pursuits by Azzo di Masetto illustrating medieval lifestyle.
For those who are feeling energetic and adventurous an uphill walk to the Rocca di Monte Staffoli, where the ruins of a fort now contain a museum, you will be rewarded with breathtaking views over the city.
Following our day at San Gimignano we will enjoy the special treat of being invited into the home of one of Cortona’s larger than life characters for a home cooked Tuscan style meal and a few laughs to round out the day.
Day 6: Saturday - Arezzo - Market Day
Today is all about the markets, and just a short distance from Cortona, the vibrant city of Arezzo, famous for frescoes by Renaissance artist, Piero della Francesca, holds a colourful market every Saturday selling local produce as well as all manner of manufactured goods and textiles and the food vendors have so many treats and sweets that it’s almost impossible to choose.
Arezzo is also home to many fine boutiques and fashion stores interspersed with historical buildings, towers and churches. It is where we discover such treasures as La Favola Mia Arezzo, a textile and gift store that creates the most amazingly beautiful artworks out of linen, conveniently located halfway up the hill to the Duomo and only a couple of blocks from the medieval abbey, Badia delle Sante Flora e Lucilla that dates back to 1278 but was rebuilt in the 16th century to the design of Giorgio Vasari and houses works by Segna di Bonaventura, Bartolomeo della Gatta and Andrea Pozzo.
Of course, after a busy morning at the markets, we will enjoy lunch in a quiet atmosphere not far from these fabulous sights.
After lunch we will still have time to explore some more of the city before heading home to Cortona where you will have time to relax or wander through the town before preparing for another special dinner treat at a gorgeous villa not far from Cortona.
Day 7: Sunday - Perugia
Today we head back into Umbria, visiting the capital, Perugia. This compact hilltop city dates back to the 6th century BC and is rich with history and culture with many well preserved archaeological sites including the city gate and walls.
For a special dose of culture we visit the Galleria Nazionale dell'Umbria, one of the richest and most diverse collections in Italy, containing a comprehensive and complete collection of Umbrian art with sections dedicated to textiles, ceramics, jewellery and ancient graphics, including various masterpieces from the Middle Ages and Renaissance, with works by Arnolfo di Cambio, Nicola and Giovanni Pisano, Duccio di Buoninsegna, Gentile da Fabriano, Beato Angelico, Benozzo Gozzoli and Piero della Francesca.
Perugia is also a university city with lots of modern culture and life intermingling with medieval heritage.
We’ll take our lunch in a restaurant located in one of the oldest palazzos of Perugia that now houses a beautiful four star hotel.
Following our lunch we’ll have free time to explore some more of the city or visit some of the beautiful boutiques and fascinating shops before journeying home where we can prepare for another special surprise evening.
Day 8: Monday - Chianti Wine Tour Day
The area around Chianti is synonymous with the famous red wine in squat bottles with straw baskets and produces many great wines. Today we visit the wine region of Chianti to taste a few of the local wines and take in the picture perfect scenery of the gently rolling hills covered in vineyards, stopping for lunch in one of the estates.
Wine has been cultivated in the Chianti region since the time of the Etruscans when experimenting with grafting and hybrid varieties produced some very popular wines. The region was officially demarcated as the Chianti wine zone by Cosimo Medici lll early in the 18th century, and the Chianti DOC title was created in 1967 and in 1984 was further promoted to the highest Italian wine classification, DOCG. Today the zone produces in excess of 750,000 hL of wine per year.
The commune of Castellnuovo Berardenga in the southeast of the Chianti region dates back to the 16th century however there are numerous archaeological sites nearby dating back to Etruscan times. Just 5 km up the road from Castelnuovo Berardenga is the quaint village of San Gusme where we will visit after lunch for a stroll through the streets of this very pretty little village.
When we’re all suitably mellow from our day in Chianti, we will travel back home to Cortona where we’ll have time to relax before heading down the hill to another beautiful villa for dinner.
Day 9: Tuesday - Siena Guided Tour / Shopping
Today we travel west to Siena. Located at the very heart of Central Tuscany, Siena is a vibrant city filled with history and culture where the landscape has remained identifiable for hundreds of years. Formerly a long time adversary of Florence during medieval times, the hilltop city of Siena has a proud tradition of independence and today we’ll be shown around by a local guide who will educate us on some of the city’s background and take us to some of the historic sights. Siena, like Florence has a great deal to see compressed into a small area which makes it possible to visit many of the attractions on foot.
Some of the world famous sites of Siena we visit include the masterpiece of Gothic - Romanesque architecture, the Duomo built in the 13th century to be ‘the greatest monument to Christianity’, home of the famous Piccolomini Library and bearing work created by artists such as Pisano, Donatello, della Quercia, Michelangelo, and Bernini. Not to be missed is the spectacular Piazza del Campo, which has been the heart of Sienese lifestyle since the late 13th century, and where the famous Palio horse race is still held on two special days each year, Movie lovers will recognise the piazza from the recent James Bond thriller, ‘Quantum of Solace’ as well as many other movies such as ‘Letters to Juliet’.
Upon arrival at Siena we will meet up with our guide who will show us around the city and take us for a visit to the famous Duomo.
After our morning tour, we have a lovely restaurant selected close to the Piazza del Campo where we can rest and refuel before continuing our exploration of Siena in free time. Following a full day’s exploration of Siena we will return to our hotel in Cortona to freshen up or explore the local area before gathering at yet another of our favourite restaurants for dinner.
Day 10: Wednesday - Avignonesi Winery, Le Capezzine
Today we take a short ride towards Montepulciano, stopping near the village of Valiano at the renowned Avignonesi Winery where we’ll enrol in a very special cooking class conducted by the Avignonesi chef. Immerse yourself in the world of Tuscan cuisine and learn about their wines through the cuisine of this area. Learn how to make typical savoury dishes such as “pici” (handmade pasta, Montepulciano style), Tuscan “sugo all'aglione” (tomato garlic sauce), pecorino flan with swiss chard puree, “torta della nonna” or many other dishes. Enjoy a glass of wine while you're cooking!
In conjunction with our cooking class we will take part in a winery tour and tasting and the winemaker’s lunch where we will pair complimentary wines with our Tuscan cuisine on the restaurant terrace overlooking the vineyard.
Later that afternoon we’ll have another opportunity to pay a final visit to the boutiques in Cortona for some last minute souvenirs or perhaps an extra Italian leather bag before freshening up at the hotel for dinner.
Day 11: Thursday - Castiglione del Largo & Lake Trasimeno
Our final day’s excursion takes us on the short trip to the shores of Lake Trasimeno and the village of Castiglione del Lago, where the remains of a fort overlook the waters of the lake and the beautiful village it protected. From Castiglione del Lago we take a ferry ride across Lake Trasimeno to Isola Maggiore, the second largest island in the lake, taking time to explore the small village and wander along the scenic pathways to several beautiful historic buildings. Isola Maggiore is only a small island but well worth the visit to experience the unique feel of this community.
We will return to the mainland for lunch in Castiglione del Lago at a beautifully renovated hotel where we can enjoy our meal with a backdrop of stunning views over Umbria.
Following lunch, we will take a tour of the village and the ruins of the fort and the museum before once again returning to Cortona to finish packing or just relax prior to our farewell dinner that forms part of a weekly event in Cortona to showcase the local food and wines in a festival atmosphere.
Day 12: Friday - Departure Day
All good things must come to an end and today we must check out of our hotel in Cortona at 10:00 am and return to Terontola railway station to catch your train back to Rome, Florence or Milan to continue your adventures until next time.