Food & Wine Trails Of Cortona, Montepulciano, Valdorcia, Pienza
Our Romance in the Vineyard program is specially designed for couples who are eager to discover the art, countryside and cuisine of Italy, and offers entertaining, hands-on cooking classes, visits to artisan markets, trips to some of the most important romantic Tuscan towns, and of course, ample opportunity to sample Tuscany’s heartwarming cuisine and world famous wines. Terenzio, your charming Italian host, wine maker and owner of the Villa, created this special program for couples in mind the common thought of food & wine in good company.
Team up with Terenzio and Chefs Maria & Luca for a tour that will take you to Valdorcia, Pienza, Montalcino, Cortona and Bagno Vignoni, emerge you in the world of super Tuscan wines and help you discover the roots and traditions of a cuisine steeped in history. Here you will participate in small group activities with people who share your own interests for food and wine and the good things in life: a leisurely lunch by a lake, wine tasting sessions, unforgettable trips though timeless Tuscan landscapes and a morning spent rejuvenating body and soul at the area’s famous thermal baths.
Tuscan food is simple, hearty and best enjoyed with a glass of local wine of Montepulciano. Along with Maria and Luca you will discover the area’s best loved dishes and develop a new appreciation for quality ingredients, such as lardo di colonnata, local Chianina beef from which come the delicious Fiorentina steaks, game of all types, boar, Tuscan pastas like Pici, another cornerstone of Tuscan cuisine. And of course, the fundamental role of food in Italian culture, and its power to soothe, heal, nourish and unite.
Cooking Classes
Classes are held at the property in the Tuscan kitchen with Chef Luca in Montepulciano and with Chef Maria at Villa Ortaglia and last approximately three hours. The entire menu changes daily according to Maria’s inspiration and the availability of seasonal local ingredients. During each class you will create a full course feast featuring antipasto, primo, secondo and dolce. Regional appetizers include dishes like crostini toscani, assorted bruschetta appetizers made with unsalted Tuscan bread slices seasoned with fresh tomatoes and herbs, or fegatini (liver pâté), regional cold cuts including capocollo, prosciutto, pancetta and salumi. First courses cover delicious handmade pastas such as pici with an aglione sauce, and the world famous ribollita soup made with beans, vegetables and served with crostini (delicious!).
For seconds you can expect meat of some type, bistecca fiorentina, wild boar, duck or a platter of scottiglia, the traditional main course of southern Tuscany which includes rabbit, chicken, veal, pork, pigeon, lamb and turkey. Or learn how to make Maria’s signature pollo con olive, chicken sautéed with local olives of Grosetto (olives that are cured in brine and marinated with grated orange zest, fennel and a little garlic) for a unique Tuscan flavor. And then dolce! Maria’s desserts are her specialty. She will show you how to make traditional cakes and biscotti like the world famous tiramisu and cantucci (hard biscotti, traditionally dipped in Vin Santo, a unique dessert made in Tuscany). Another time-honored cake is the stracciata alla fiorentina, a sweet pizza made for the religious feast of Carnevale. The traditional pannello con l’uva is a sweet bread made with fresh grapes and usually served during the time of the harvest. And at the end of each class, participants sit back to enjoy eat the fruits of their labor at dinner, and toast with local Tuscan table wine. So why not join us in Tuscany for this fabulous new singles experience!
Tuscany
Tuscany has been charming visitors for centuries with its rolling hills, medieval villages, charming farmhouses enclosed by cypress trees, country markets bursting with artisan produce, and its simple, delicious cuisine which is firmly rooted in history. The villa is located close to the nearby towns of Montepulciano, the jewel of artistic and architectural treasures, Pienza, the town of Pope Pio II Piccolomini, and Chiusi, a most important and powerful Etruscan town. Also nearby is Montalcino, with its great fortress and the vineyards that produce the world famous Brunello di Montalcino. And not to be missed is Orvieto, Arezzo, Cortona, Siena, San Gimignano, Perugia, Assisi, Gubbio, and Firenze.
Accommodation
The villa is a beautiful farmhouse that was built in the 17th century and has recently been restored. The renovations, while keeping the original character, transformed the farmhouse into a five-star luxury accommodation. Each suite is decorated with exquisite antiques, maintaining the traditional feel of old-world charm in the heart of Tuscany.
Ortaglia Relais is privately owned by Terenzio, and cared for by his son Nicola and the family. After several years in the hospitality industry and wine making business, the Biscardo family created exclusive programs with Lauren at Cooking Vacations. Lauren’s long-term friendship with Nicola ripened the idea for hands-on cooking classes that explore the regional cuisine of Tuscany while staying at the gorgeous Villa Ortaglia. The property is surrounded with the family’s vineyards, vegetable gardens, Tuscan sunflowers and a private swimming pool. The ancient town of Montepulciano can be seen in the distance.
Each suite has been named after the eight districts of Montepulciano, created by the City Stature in 1337. They are San Donato, Voltaia, Poggiolo, Talosa and Gracciamo. All of the bedrooms have been furnished with great attention to functionality and elegance. Interior decorators have carefully selected the colors, paired the cloths and blended the various antique pieces with simple Tuscan handicrafts. The rooms are magical and each one has a private bathroom. In the three suites, guests can enjoy a tonic Jacuzzi sipping a glass of the best Spumante Classico. All the rooms are equipped with TV, refrigerator and telephone.
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Villa Ortaglia
Much to wine lovers’ delight, the Villa Ortaglia estate boasts a well-furnished wine cellar where you will discover thousands of different Italian wines, including the property’s own production. The underground wine cellar in the farmhouse, which keeps it well protected from light, vibrations and changes of temperature, guarantees that the selection of wines are kept in perfect condition. Not only that, but Nicola, who is a member of the ONAV (National Organization of Wine Tasters), of the AIS (Italian Association of Sommeliers) and of the Society of Wine Educators, can escort you during this trip through guided tastings: together you will explore the secrets of Tuscany.
Itinerary: 7 days, 6 nights
Day 1 (Monday): Arrival & Welcome Dinner In Montepulciano
• Pick up at the Chiusi-Chianciano train station.
• Arrival at Ortaglia before 4pm, check-in, relax.
• Welcome aperitivo on the terrace facing the estate’s Vino Nobile di Montepulciano vineyards
• 8pm Welcome Tuscan BBQ Dinner a traditional Tuscan dinner with wines chosen by Terenzio.
Day 2 (Tuesday): Tour of Val d’Orcia
• Breakfast is served.
• 10am: Tour of Valdorcia, a UNESCO World Heritage Site, with lunch in the medieval town of Sant’Angelo in Colle, where Luca, chef-owner of a local and authentic osteria, will delight palates with his specialties, but also with the world famous Rosso and Brunello di Montalcino.
• Visit Pienza, the town of the Pope Pius II, and San Quirico d’Orcia, a little town with 12th century walls and a beautiful Romanesque-Gothic “Collegiata Church. And Montalcino, the hillside town with enclosed walls and fortress from the 13th century, home to Brunello wine and the stunning abbey, the ‘Abazzia di Sant’Antimo’, which has preserved its solitude in the depths of a delightful landscape with olive and cypress trees.
• Continue to Monte Amiata, the tallest mountain volcano in Tuscany (5.650 ft) with its lower slopes covered with lush grass, cypress, vineyards and olive trees; and Bagno Vignoni, the oldest hot spring famous since Roman times. From the springs you can see the ruins of the Spa-for the treatment of arthritis and rheumatism. You will visit Parco Naturale di Lucciolabella, with the most famous country road of Tuscany; and Monticchiello, the medieval village from where you can enjoy a superb view of Val d’Orcia.
• Late afternoon, return to Villa Ortaglia and relax by the pool, walk the rolling vineyards, or sit back in the library room with a great glass of Terenzio’s vino.
• Dinner at our hand-selected restaurant in Montepulciano.
Day 3 (Wednesday): Cooking Class 1, Cortona & Lake Trasimeno
• Breakfast is served
• 10am: Set out for a tour of the beautiful town Cortona, made famous by the bestseller “Under the Tuscan Sun.” Ancient stone paths lead you to churches, quaint shops selling linen, Tuscan olive oil, hand-painted ceramics and wine.
• Lunch at Terenzio’s favorite trattoria by Lake Trasimeno.
• Return to Ortaglia where you can relax.
• 5pm: Aprons on and get ready for Cooking Class 1 where you’ll create a delicious full menu Tuscan dinner under Maria’s expert tutelage. Dinner follows and includes the foods prepared in class paired with Terenzio’s wines.
Day 4 (Thursday): Market visit
• Breakfast is served
• Morning: Visit the local market, a lively open-air affair bustling with stalls and sellers, where you will select and buy artisan made food, vegetables and fruits to bring home for lunch. Relax by the pool.
• Early afternoon free.
• At 6,30pm Terenzio will drive you to Radicofani, the fortress-town of Ghino di Tacco the Italian Robin Hood, where you will enjoy beautiful landscapes but also some of the dishes prepared by talented Giuseppina and Natalina, the chef-owners of this hidden jewel restaurant, another of Terenzio’s favorites.
• On the way home we will stop briefly to admire millions of stars high above in the deep blue sky of the Valdorcia.
Day 5 (Friday): Trekking Tour of Montepulciano, Cooking Class 2
• Breakfast is served
• After breakfast, you will go for a walking tour of Montepulciano, where you can admire the town’s many beautiful palaces and churches.
• Stop off at the Cantina, Tenezio’s hot-pick, for a wine tasting.
• Lunch in town.
• Return to Villa Ortaglia and relax by the pool.
• 5pm: Into the kitchen for Cooking class 2, to create a delicious Tuscan antipasto, pasta, secondo and dolce. Dinner follows and includes the foods prepared in class paired with Terenzio’s wines.
Day 6 (Saturday): Thermal Spa
• Breakfast is served.
• After breakfast, Terenzio will drive you for the wonderful experience of the Terme Sensoriali. The three hour itinerary starts with a walk on river pebbles and continues with sensual showers with oils, lights and colors and thermal pools with internal and external water massages, including a salt-water pool, and much more. The atmosphere of the pool with its underwater music is magical. Then there are traditional and Etruscan saunas, the Turkish bath, to be alternated with cold steam or ice crash. After water and fire, along the itinerary, we meet air and ether: in aromatherapy rooms you can choose between an energizing or relaxing treatment, in the chakra chromotherapy and music therapy room you are enveloped by music and colors. Finally there is a relaxation area, where you can rest, read and drink herb teas specially chosen to heighten the sensorial experience. The earth element is at the lower level, in the melmarium, where guests can choose from various types of mud to treat their body: relaxing, purifying or energizing. The skin eliminates toxins and you feel regenerated, ready for the Pyramid. Built on the model of the Cheope pyramid, this is an energy collector which according to various theories, helps cure insomnia, anxiety and other similar ailments. Don’t forget your bathing suit!
• After your thermal treatments, take a stroll on your own to the main piazza of Chianciano, window shopping at the elegant shops, and grab a seat for a pannini or a creamy gelato in Piazza Italia. Terenzio will pick you up when you are ready and will drive you back to Villa Ortaglia.
• At 7,30pm, everyone heads out for dinner at the Osteria where you’re faced with the challenge of eating a delicious three pound Fiorentina steak. Terenzio helps you order the full course dinner and wine.
• Return to Villa Ortaglia for an after dinner drink by the pool and make a wish to come back soon while watching falling stars in the beautiful sky of Ortaglia.
Day 7 (Sunday): Departure
• Breakfast.
• Check-out and transfer to Chiusi train station.
*This schedule may vary due to weather, feast days, market days, openings and closings of vineyards, etc. If you happen to have a specific private activity in mind, please let us know so we can check your final itinerary.
Program Includes:
- 7 days, 6 nights accommodations, based on double occupancy.
- Daily breakfast.
- Transportation to and from the Chiusi-Chianciano train station. (Arrival before 4pm on arrival day.)
- Welcome aperitivo.
- BBQ dinner at Ortaglia, wine included.
- Tour of Val d’Orcia with lunch in Sant’Angelo in Colle, wine included.
- Dinner in Terenzio’s favorite restaurant in Montepulciano, wine included.
- Visit to the weekly open market in Montepulciano.
- Light lunch at Ortaglia, wine included.
- Drive to Radicofani and dinner, wine included.
- Two cooking classes followed by dinner, wine included.
- Walking Tour of Montepulciano with lunch in town, wine included.
- Wine tasting at the Cantina Wine Cellar in Montepulciano.
- Tour of Cortona and Lake Trasimeno with lunch in Terenzio’s favorite local trattoria, wine included.
- Terme Sensoriali in Chianciano, including transportation.
- Dinner at Osteria in Montepulciano, wine included.
- Transportation to the dinners and to the Tour of Montepulciano
Program Prices
$3,095 per person, based on double occupancy in Deluxe Double room. All taxes and Italian VAT included.
$500 per person, supplement for Junior Suite.
$700 per person, supplement for Superior Suite.
Program includes all lunches and dinners except lunch on Day 6 (based on minimum 4 in the group).



















