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Welcome to Italy! Upon arrival into Rome Airport, you will be greeted by your private driver and transferred to your accommodation in the city to check in.
Rome, the Eternal City. Capital of the western empire from 201 BC to 476 AD it has been one of the most influential civilizations in western culture. It's the famed city of the Roman Empire and home to the Seven Hills, La Dolce Vita, the Vatican City and Three Coins in the Fountain. Rome has an immensely rich historical heritage and cosmopolitan atmosphere, making it one of Europe's and the worlds most visited and beautiful capitals.
After breakfast and checking out this morning, you will be greeted by your private driver-guide and depart to your hotel in Umbria, an approximately 2.5hour drive, making stops at Narni and Spoleto along the way.
Ever-changing, untouched landscapes in the green of winding valleys make Umbria a region that will never fail to amaze. This region comprises mainly hills, mountains, hollows and plains and extends along the Tiber’s central basin. The Umbrians are very proud of their unique and delicious cuisine. Let’s begin with truffles, one of only two places in Italy they grow, they can be found on almost any menu and no one who comes to visit misses the opportunity to taste. Wild boar makes for some of the fine charcuterie and the Umbrians are the very best at its preparation. Historically one of the richest parts of Italy dating to the pre roman culture of the Etruscans through to the 14th century, home of St Francis of Assisi.
Continue after the visit and stop in the magical city of Orvieto whose mysteries are still being discovered as archaeologists plumb its fifty-meter deep wells, many dug in antiquity using techniques we have yet to understand. First rising to prominence with the pre-Roman Etruscans, this city still proudly carries forth the Etruscan emphasis of friendship, feasts and good wine. Enjoy a visit of the city including the Orvieto Cathedral and its magnificent Signorelli frescoes. Stroll through the charming pedestrian-only streets visiting a few of the artisan boutiques selling items such as fine hand-painted pottery and woodwork for which Orvieto is justly famous.
Later this afternoon after a day of sightseeing and exploration your guide will take you to your accommodation for check in.
After breakfast you will be greeted by your guide in the morning and set out for a full day of sightseeing and finest Umbrian wines tasting.
We will start with a visit of the old walled town of Spello, sitting on Mount Subasio, commanding a lovely view of the plains below and Villa dei Mosaici an exceptional archaeological treasure for reconstructing the ancient history of the city. Unique in its kind, the archaeological site dating back to the imperial age still preserves refined mosaics and traces of frescoes and stuccoes.
The journey continues to Montefalco and Assisi, one of the most beautiful villages in Italy.
Assisi represents a unique example of continuity of a city-sanctuary within its environmental setting from its Umbrian-Roman and medieval origins to the present, represented in the cultural landscape, the religious ensembles, systems of communication, and traditional land-use.
At the end of the visit you will be welcomes for a wine tasting in a wine cellar. We will enjoy the Umbrian traditional lunch from seasonal truffle dishes to silky pastas discovering the Italian region's culinary delights and the finest Umbrian wine to compliment its rich flavors.
At the end of the day, your guide will return you to your hotel.
Enjoy a day at leisure to explore at your own pace. Or simply relax and make use of the facilities at your accommodation, from spa and massage experiences to a day full of adventure and truffle hunting, cooking class or hiking in leisure.
Besides the natural beauty and the nature trails available in the area, it offers a culinary tradition full of genuine and typical products. Norcia is a culinary paradise, rich and sophisticated. Make sure to stop in at the Delicatessens to sample regional specialties like Umbrian cured meats, dried pasta, and Umbrian chocolates.
Find your seats in an atmospheric restaurant in the village and enjoy included traditional Umbrian lunch. Typical dishes include a charcuterie cold cuts and cheeses with Cannara onion jam, truffle gnocchi with old-fashioned sauce and panna cotta with quince compote – all enjoyed while sipping Umbrian wine!
Your guide will meet you at your accommodation this morning for an exciting day of enroute touring in one of the most historic wine growing regions in Italy, Chianti Classico.
Throughout the day explore one of the many beautiful Tuscan villages such Radda in Chianti or Castellina in Chianti. We will continue exploring the heart of the area through the history of its charming medieval towns followed by with private visits to a great vineyards. This small wine-region produces perhaps one of the best-known and appreciated wines in Italy, Chianti Classico DOCG, comprised of 80% of Sangiovese, and 20% other various varietals such as native grapes Canaiolo and Colorino. Chianti Classico stretches between Florence and Siena and includes 14 different municipalities.
One of the producers we will consider for todays tasting include:
• Buondonno - This farm is in the Chianti hills, surrounded by woods, vineyards and olive groves. It covers approximately 20 hectares, of which 8 are vineyards and 4 are olive groves.
• Podere La Piaggia - Located in the heart of Chianti, La Piaggia is a small family business farm and has the oldest vines in the area of Chianti Classico, dating back to around 1920!
• Caparsa - Produces an organic Chianti Classico wine called Doccio a Matteo, the wine is considered an essential food for life. The cellar of Caparsa is more than 400 years old and, pending availability, you may be able to taste the famous wines of Caparsa with Paolo Ciamferoni, owner and winemaker.
• Castello della Paneretta - Situated on the western slopes of the dominating hills of the Elsa valley, looking towards San Gimignano. Ancient records date back to wine production since 1596 and with 22 hectares of vineyards, only Sangiovese and Canaiolo Nero grape varieties are grown.
Later this afternoon you will arrive to your accommodation for check in.
This morning your guide will meet you at your accommodation for another day of town and wine touring in the Chianti Region.
You will visit the quaint medieval village of San Gimignano. San Gimignano is the epitome of a Tuscan hill town with its skyline of medieval towers. Wander through picture perfect cobbled streets and climb one of the many towers for a panoramic vista of the surrounding countryside. Called one of the most romantic towns in the world and we will see why!
Continuing on from yesterdays discovery of the Sangiovese grape, you will be welcomed again to some of our preferred producers to deepen your knowledge and gain a deeper appreciation for this style of wine. You may be welcomed to some of the producers not visited yesterday, or perhaps one of the following producers for a curated visit and premium tasting:
• Losi Querciavalle - The Losi, an ancient family of Chianti winemakers, has been producing wine for five generations. They are small wine producers who search for the quality through their daily commitment and their secrets of ancient roots. A few miles from Siena, in the southernmost hills of the Chianti, the Losi wine estate is blessed by a privileged position, both for its excellent sun exposure, and for the richness of its land.
• Castello di Brolio - The impressive Castello di Brolio dominates the southern Chianti Classico countryside and has done so for over ten centuries. Located on top of an isolated hill near Gaiole in Chianti, the castle has Lombardic origins and has been property of the Ricasoli family since 1141. We will have our lunch during one the visit, getting acquainted with Tuscany through the region's top culinary experience paired with the finest Chianti Classico.
Later this afternoon your guide will deliver you to your accommodation.
Enjoy a day at leisure. We can provide suggestions to make the most of your day or set out and explore at your own pace. Indulge in a peaceful day today at the property exploring the surrounding vineyards and olive groves, activities may include hiking, tennis, yoga class or spa visit.
Or set out to discover the nearby charming villages and find endless things to do in Siena, Italy, and the surrounding hill towns. Autumn is just as magical thanks to olive and grape harvests. Hunt for truffles and mushrooms and uncover the region’s history. If you are feeling adventurous, discover the White Roads that branch in the area and make the ideal setting for strolls by foot or bicycle or master your culinary skills in cooking class.
This morning meet your guide at your accommodation and depart the drive to Montalcino and Pienza.
Montalcino is one of the most famous Tuscan hilltop towns and is located 40 km South of Siena. The rigorous outline of the 14th century fortress overlooks the Orcia valley and as we may learn
from many documents, the territory is well-known for its excellent wine from time immemorial: of course we are talking about the extraordinary Brunello di Montalcino!
The Brunello di Montalcino was awarded the first Denominazione di Origine Controllata e Garantita (DOCG) designation and today is one of Italy's best-known and most expensive wines.
Start first at a boutique Brunello producer for a guided visit with expert of the cellars, followed by a wine tasting of the various blends.
We will stop for a visit at a winery such as Altesin or similar. Altesino has become a reference point for the entire territory. The introduction of the "Cru" (Montosoli) concept in 1975, the first experiments with barriques in '79, the production in '77 of the first Grappa di Fattoria under the consultancy of the master distiller Gioacchino Nannoni and the first printed for Brunello 1985 are some of the positive contributions putting Montalcino on the world map.
During your visits you will become familiar with the history and origins of Brunello di Montalcino
and other wines. You will see where their wonderful vineyards are located, visit the cellar, and also discover high quality oenological practices. Continue tasting and appreciate their refinement and elegance, surrounded by beauty.
We will enjoy lunch in the heart of the countryside at local trattoria and bask in the aromas of the dishes being artfully created.
Your day will include a visit of Pienza where the best Pecorino cheese is made. Pienza is a rare example of Renaissance town design. Often described as the "ideal city" or the "utopian city", it represents a model of ideal living, based on the concept of a town able to satisfy the needs of a peaceful and hardworking populace. Pienza's location in the centre of the Val d'Orcia.
Afterwards, time permitting, a stop can be made at one of the areas famous abbeys such as the Abbey of Sant’Antimo, known for the Gregorian Chants at Mass. Your driver guide will return you to your accommodation to spend the evening at your leisure.
This morning after your breakfast and check out of the hotel, you will be greeted by your private driver-guide and depart towards Rome, an approximately 2.5hour scenic drive through Grosseto charming town of Porto Ercole.
This area of Italy is rich in Etruscan history and we will make a few stops along the way to visit town like Pitigliano, a very charming hilltown built atop a rock. Further down toward Rome we will continue through picturesque Tarquinia and Cerviteri, more Etruscan sites.
After the visit and lunch along the way, continue on the road to your bespoke accommodation in Ladospoli. Hotel La Posta Vecchia is a member of The Leading Hotel of the World. It was once the residence of Jean Paul Getty whose collection of antique furniture remain part of what is now a 19 room luxury hotel complete with every comfort and amenity. This 17th century jewel is one of the most prestigious hotels in Italy. This elegant renaissance villa is a perfect place to unwind after long days of travels and immerse in a true Italian world of comfort, chic and elegance.
Your driver will meet you at your accommodation and bring you to Rome airport for your onward flight. Buon Viaggio!
Hassler Roma is a legendary, luxury five star hotel in Rome’s City Center located at the top of the Spanish Steps. The hotel is renowned as a setting for unforgettable memories with its panoramic terraces with breathtaking views of Rome. Hassler is a residence and a luxurious sanctuary meticulously created to give the most memorable experiences of the Eternal City. Each of the rooms and suites are uniquely designed and carefully decorated with antiques and art masterpieces. Situated in the heart of Rome's historic city center, it is close to all the famous monuments and landmarks such as the Pantheon, St. Peter’s Basilica, the Coliseum, Villa Borghese gardens and the elegant Trevi Fountain.
Set in a restored 16th-century palace in the Parco Nazionale dei Monti Sibillini, the cozy and charming Palazzo Seneca overlooks the rooftops of the historic town centre of Norcia. This elegant hotel is a minute's walk from the Museo della Castellina. Some rooms are decorated with wrought iron canopies, as of old, while others have wooden headboards carved by the expert hands of the Umbrian artisans or ‘Cardinal’ chairs, the same used in the Vatican for meetings among cardinals, strictly made by Umbrian artisans. Class and elegance characterize all the bathrooms of the rooms, made with ecru marble.
An old Tuscan hamlet nestled in the hills of Chianti Classico. Siena, Montalcino, and the enchanted lunar landscape of the creti senesi are all nearby. The property is surrounded by woods, olive groves, and vineyards that have been cultivated for centuries. It has been the only Mansion Relais & Chateaux in Chianti Classico since 1992. The 5-Star Relais & Chateaux Borgo San Felice are in perfect harmony with the enchanted surrounding countryside and are defined by traditional Tuscan elegance. Here, you will experience refined modernity perfectly mixed with centuries-old charm.
La Posta Vecchia Hotel is built on the site of an ancient villa in Palo Laziale, just outside of Rome. A blend of new and old, the hotel boasts an exclusive 18th century décor, breathtaking panoramic views of the Tyrrhenian Sea and immaculately manicured grounds. All rooms and suites are spacious and uniquely decorated with Renaissance furnishings, paintings and antique tapestries. Ideal for those who love hotels with rich in history, and charm, combined with all the modern comforts and family-style service
Hassler Roma is a legendary, luxury five star hotel in Rome’s City Center located at the top of the Spanish Steps. The hotel is renowned as a setting for unforgettable memories with its panoramic terraces with breathtaking views of Rome. Hassler is a residence and a luxurious sanctuary meticulously created to give the most memorable experiences of the Eternal City. Each of the rooms and suites are uniquely designed and carefully decorated with antiques and art masterpieces. Situated in the heart of Rome's historic city center, it is close to all the famous monuments and landmarks such as the Pantheon, St. Peter’s Basilica, the Coliseum, Villa Borghese gardens and the elegant Trevi Fountain.
Set in a restored 16th-century palace in the Parco Nazionale dei Monti Sibillini, the cozy and charming Palazzo Seneca overlooks the rooftops of the historic town centre of Norcia. This elegant hotel is a minute's walk from the Museo della Castellina. Some rooms are decorated with wrought iron canopies, as of old, while others have wooden headboards carved by the expert hands of the Umbrian artisans or ‘Cardinal’ chairs, the same used in the Vatican for meetings among cardinals, strictly made by Umbrian artisans. Class and elegance characterize all the bathrooms of the rooms, made with ecru marble.
An old Tuscan hamlet nestled in the hills of Chianti Classico. Siena, Montalcino, and the enchanted lunar landscape of the creti senesi are all nearby. The property is surrounded by woods, olive groves, and vineyards that have been cultivated for centuries. It has been the only Mansion Relais & Chateaux in Chianti Classico since 1992. The 5-Star Relais & Chateaux Borgo San Felice are in perfect harmony with the enchanted surrounding countryside and are defined by traditional Tuscan elegance. Here, you will experience refined modernity perfectly mixed with centuries-old charm.
La Posta Vecchia Hotel is built on the site of an ancient villa in Palo Laziale, just outside of Rome. A blend of new and old, the hotel boasts an exclusive 18th century décor, breathtaking panoramic views of the Tyrrhenian Sea and immaculately manicured grounds. All rooms and suites are spacious and uniquely decorated with Renaissance furnishings, paintings and antique tapestries. Ideal for those who love hotels with rich in history, and charm, combined with all the modern comforts and family-style service
Bespoke organization of the trip
Bilingual guide with expert regional knowledge
Regional restaurant recommendations
Accommodation as per the daily summary
Meals as per the daily summary
All transfers on private basis as per the daily summary
All tours on private basis as per the daily summary (unless otherwise stated)
Wine tasting fees
International and domestic airfares
Any entrance tickets not mentioned in the itinerary
All meals and beverages not included in the daily summary
Dinner restaurant reservations (available for a supplement)
Gratuity (at your discretion)
Travel insurance
Items of a personal nature
Rental vehicle hire (if applicable)
Paolo is the founder and director of Into the Vineyard, and has dedicated himself to create unforgettable wine-focused experiences. He is passionate about understanding the traveler's needs and building upon them to create personalized trips.
He has a deep connection to his Italian heritage, stemming from his parents' immigrations and numerous trips to Italy. Paolo has over 15 years of experience as a destination travel guide, leading cycling and walking trips in 18 countries around the world. He is fluent in five languages, a testament to his dedication to traveling and understanding different cultures.
Paolo's love for sports, including sailing, water polo, and cycling keep him youthful along with spending time with his family of four.
Valeria is new to the team, but not new to the world of travel. Canadian in essence, Ukrainian by birth, she has a true wanderlust spirit, passion and curiosity for vines and dines around the world, one continent at a time.
After completing her studies in Tourism and Hospitality in Canada, Valeria worked in luxury hotels and resorts from Hawaii to Latin America, Europe and the Caribbean. Now she calls Vancouver home, sharing an active lifestyle between hiking, yoga and sailing.
Prior to joining the team, Valeria worked in luxury lifestyle management, benchmarking bespoke concierge service and granting access to the inaccessible. She loves designing unique travel experiences powered by art, wine and culture, wellness, adventure and connection, where strangers become friends and friends become family. Valeria’s favorite saying is Annie, amori, e bicchieri di vino – non si contano mai – “Years, lovers, and glasses of wine should never be counted.” Salud!
