Imagine an intimate vacation in a luxurious villa in the elegant countryside of Tuscany, Italy, immersed in artistic legacy, drinking fine wines and enjoying the good company of your family and friends.

Kensington has carefully selected 25+ properties in order to meet requirements of the highest quality standards. Choose the abode that best suits your needs from various farmhouses, cottages, manors, estates and palaces ranging in size, style, splendour and location. Ideal for family holidays of all sizes, groups, reunions, weddings and other celebrations, these picturesque properties are an elegant and intelligent alternative to staying in hotels.

Customize your vacation property with the amenities and services that your party requires for their ultimate getaway. At your wish Kensington can organize guides, chauffeurs, maids, childcare, chefs, masseuses and other staff to tend to your every want.

For those of you who want to experience the sights, sounds and smells of this gorgeous region Kensington provides private guided day trips and excursions custom designed just for you. Explore Rome, Florence or Siena or discover the region’s renowned vineyards, hilltop towns, colourful festivals, celebrated cuisine in the care of our experienced local guides.

You and your companions will lose yourselves in the breathtaking landscape, history and culture that inspired artistic legends like Michelangelo, Botticelli, Dante and Donatello. When it’s time to go, no traveler will want to leave this blissful region but your memories of time spent in Tuscany will last forever.
Villa rentals are based on a weekly rental, starting on a Saturday and typically include linens, towels, & kitchen equipment as well as a cleaning service (frequency varies depending on villa). Villa rentals tend to book up well in advance, so early booking is advised!

Smile - for what worries can you possibly have when everything is looked after seamlessly for you from start to finish... Bravo!

The Tuscan city of Siena is one of the most lovely in Italy. Though abundant with Renaissance palazzi, churches and museums, the city is compact by any standards. The focal point of the town is the Piazza del Campo. Surrounded by elegant public buildings, it's the perfect starting point for seeing the city's myriad attractions. Nearby, the cathedral sits in its own square, the elaborate façade just a teaser for the grandiose interior. When you need a rest from pacing the streets, you'll find plenty of restaurants serving delicious Tuscan fare and numerous pavement cafés where you could spend hours sipping cappuccinos and watching the world go by.

A welcome package with your itinerary, vouchers, a city map, train tickets (if relevant) and any other touristic information that we deem you may find useful will be waiting for you upon your arrival at your first hotel on your trip.

Enjoy a private transfer from Florence airport to Siena by private vehicle and driver.

Choose from a selection of premium villas in Tuscany. Our portfolio of villas are chosen for their high standards, exclusivity criteria, and quality. Extra care is taken to ensure that all properties are located in key areas with access to a wide range services and facilities, including sightseeing opportunities, gourmet and healthy dining, as well as sport and other leisure activities. Whether you want to rent a residence in a medieval hamlet or a private villa in the heart of the Chianti wine region, we will ensure that you have the property best suited to your needs. Amenities vary from villa to villa but typically include such things as satellite TV, dial-up Internet, stereo/CD, alarm system, safe, screens, ceiling fans in all bedrooms, dishwasher, washing machine, reserved parking, private swimming pool and/or tennis court on estate, and a private garden. Villas typically range from 2 to 6 bedrooms.

Overnight at Premium Villa (2 bedroomed).

Overnight at Custom Hotel.

Consider spending a half day on a private walking tour with a local guide. Discover the most unusual and unforgettable aspects of Siena, including the Cathedral Crypt. See the city's monuments and hidden alleyways, which all give a true insight into Sienese Life. The tour would take in the Campo Square, following the pilgrims, wayfarers, artists, merchants and saint's and the traces they left behind in courtyards, fine old churches and forgotten frescoes, including the 13th century frescoes in the Cathedral Crypt. Please speak to your Sales Advisor if you would like to include this in your itinerary.

Choose from a selection of premium villas in Tuscany. Our portfolio of villas are chosen for their high standards, exclusivity criteria, and quality. Extra care is taken to ensure that all properties are located in key areas with access to a wide range services and facilities, including sightseeing opportunities, gourmet and healthy dining, as well as sport and other leisure activities. Whether you want to rent a residence in a medieval hamlet or a private villa in the heart of the Chianti wine region, we will ensure that you have the property best suited to your needs. Amenities vary from villa to villa but typically include such things as satellite TV, dial-up Internet, stereo/CD, alarm system, safe, screens, ceiling fans in all bedrooms, dishwasher, washing machine, reserved parking, private swimming pool and/or tennis court on estate, and a private garden. Villas typically range from 2 to 6 bedrooms.

Overnight at Premium Villa (2 bedroomed).

An option for today would be to enjoy a 5 hour private tour focusing on two hilltop jewels of wine: Brunello di Montalcino and Vino Nobile di Montepulciano. The Brunello, a rich, robust pure Sangiovese, is one of the handfuls of DOCG wines hunted by wine collectors for its depth of flavor and potential to age for decades. In nearby Montepulciano, the Vino Nobile has been praised by popes and princes alike for centuries for its elegance and "noble" structure. The tour would start in the first of the two wineries. Before the tasting, you would enjoy a tour of the entire vineyard including a stroll through the vines continuing on to the cellar where you would be shown the various stages of wine production - fermentation, maturation and aging. The wine tasting is usually accompanied by typical Tuscan dishes and guided by the owners/winemakers. The second winery, although still adhering to the strict guidelines imposed by the region, always differs from the first in its style and methods of production, allowing you to experience and to compare the contrasting characteristics of the two wineries that reflect the strategy and the personality of the wine makers. (Includes a visit with wine tasting and lunch in a Top Quality winery in Montalcino, and a visit and wine tasting in a quality winery in Montepulciano). Please speak to your Sales Advisor if you would like to add this tour to your itinerary.

Overnight at Premium Villa (2 bedroomed).

Explore the area of Siena at leisure. Visit the local shops and market for fresh produce and wine. Fill your arms with fresh bread, household goods, flowers, fresh fruit, and vegetables before returning to your accommodation. Siena is filled with one of a kind boutiques and shops at every corner, but you'll want to stroll along three main pedestrian streets for sure: Via di Citta, Banchi di Sopra and Via Dei Montanini. Styles range from trendy to classic. You'll find a gelateria, pizza shop or bar between every few shops , so you can stop for gelato breaks between browsing. Simply window shopping in Siena can be enjoyable, indeed, the locals can often be seen strolling along the main streets, admiring the window displays and designs.

Overnight at Premium Villa (2 bedroomed).

An option today would be top have the services of a chauffeur driven vehicle and English speaking driver at your disposal for the day (8 hrs and max. of 100 km). There are many places of interest to visit in the area including Florence and it's wonderful Uffizi gallery and Academia as well as it's many bridges and squares, the town of Perugia, known for it's chocolate, Assisi, with it's interesting architecture and pleasant cityscape, Arezzo with it's sloping main square and pedestrianised shopping street and all of the hilltop towns in Chianti. You can arrange what you would like to do in advance and let your Sales Advisor know, or simply let your driver know on the day as to what you would like to do. Please let your Sales Advisor know if you would like to add this service to your itinerary.

Overnight at Premium Villa (2 bedroomed).

Enjoy the comforts of your Villa today. Relax by the pool side (if relevant) or hike in the local hills. Have a private chef prepare for a beautiful dinner looking out at the Tuscan Hills (not included) and leave the cleaning up to the hired staff. Relax while you read a good book and enjoy a glass of local wine under the Tuscan sun.

Overnight at Premium Villa (2 bedroomed).

Consider spending a full day on a shared tour  giving you the opportunity of discovering San Gimigamo, a tiny city that has remained intact through the centuries. The city is situated on top of a hill and is famous for its numerous towers, frescos and other art treasures. Take the opportunity to explore the city and there is some free time for lunch (not included). Continue on through the countryside of Chianti, known all over the world for its wine and its countryside of unequalled beauty. Woods with vines and olive trees, romanesque churches, farmhouses, villas and castles of rare beauty are to be found. This tour includes a visit to a place of particular historic and artistic interest in an old village, and to one of the most renowned castle farms with a snack and tasting of its prestigious wines. Please speak to your Sales Advisor if you would like to add this tour to your itinerary.

Overnight at Premium Villa (2 bedroomed).

Even among Italy's finest cities, Florence is something special, rising from the beautiful landscape of Tuscany as a living piece of history. Everywhere you turn you'll see works by Michelangelo, Donatello, Brunelleschi and any number of Masters of Italy's Golden Age. It is in the museums and galleries of the city that most of Florence's treasures are concentrated. The piazzas are full of fashionable boutiques and ever more fashionable people, and the café is still central to the Florentine social life. In the evening the city lights up and its squares and streets are thronged with visitors and locals taking their "passeggiata" as the denizens of the city have done for thousands of years.

Airport transfer with private vehicle and English speaking driver. (Extra surcharge will be applied if after 8pm or before 7am).

Kensington Tours donates a portion of proceeds to our charitable initiative www.kensingtoncares.com which supports education-based initiatives in disadvantaged communities.

Depart from International Airport. End of itinerary.

Overnight at Depart (Int`l Airport) (standard).