Luxurious Tuscany

8 days from $5,336 per person*
  • Explore the towns and countryside of Tuscany with private driver.
  • Enjoy a local Tuscan farmhouse visit for lunch and wine tasting.
  • Visit Michaelangelo’s David with private guide.
  • Gain complimentary access to the Ferragamo Museum.
  • Featuring expertly selected hotels.
Request a Quote

Luxuriate in the charms of Tuscany as you travel first class through the jewel-toned landscapes of a region known for impeccable cuisine and a rich cultural heritage.

Immerse yourself in sensual pleasures on this exclusive journey through the wonders of Tuscany. With your private expert guide and driver, tour hidden historic sites, narrow streets lined with quaint cafes and boutique shops, Renaissance palaces and glorious landscapes of wheat fields and olive groves. From a private Florentine residence of a refined art collector, to a magnificent country Estate nestled among rolling hills, to a highly individual luxury hotel located in the heart of the beautiful Rome, enjoy exclusive accommodations that will pamper your mind and body.

Shop in Via dei Tornabuoni, Florence's Fifth Avenue where you'll find everyone from Armani, Gucci, Versace, and Coveri. Sit down to an unforgettable meal at the Borgo San Jacopo Restaurant as an exclusive guest of Chef Beatrice Segoni. Enjoy a walking tour through Florence and visit the Ponte Vecchio, the famous Piazza della Signoria, and the Accademia Gallery where you’ll view Michelangelo's David. Tour the Chianti region and visit Le Capezzine Estate for a tour of the ancient stone wine cellar. Elsewhere on your journey, why not consider a game of tennis or bocce, horseback riding, a round of golf, or simply spend the day at the spa being pampered; after taking in all of that history, you deserve it! La Dolce Vita exists, we can help you experience it. ... Show More »

Enjoy a personalized vacation that best suits your needs, developed by one of our experienced destination experts. Relax during your trip with our 24/7 support and expert local guidance. « Show Less

Day
Activities Hotel & Meals
Hotel & Meals
  • Day 1 Florence
    Florence
    • Transfer - Private - Airport with Meet & Greet - Vehicle/Assistant/Driver(2)
    • Hotel Lungarno - Optional Meal/cocktails in sumptuous surroundings
    • Self-Guided - Shopping
  • Day 2 Florence
    Florence
    • Private - 1/2 Day Walking Tour with Accademia Gallery (3 hrs) - Guide(10)
    • Hotel Lungarno - Complimentay access to Ferragamo Museum for guests
  • Day 3 Florence
    Florence
    • Private - San Gimignano & Siena (with Local Farmhouse Lunch & Wine Tasting) (8 hrs) - Vehicle/Local Guide/Driver(2)
  • Day 4 Florence to Montalcino
    Florence to Montalcino
    • Florence - Montalcino [1 hr 45 mins ] - Vehicle/Driver (2)
    • Castiglion del Bosco - Dining options
  • Day 5 Montalcino
    Montalcino
    • Private - Pienza & Montepulciano (8 hrs) - Vehicle/Local Guide/Driver(2)
  • Day 6 Montalcino
    Montalcino
    • Castiglion del Bosco - Optional Activities on the Estate
  • Day 7 Montalcino to Rome
    Montalcino to Rome
    • Montalcino - Rome [with walking tour of Orvieto en route] - Vehicle/Local Guide/Driver(2)
  • Day 8 Rome
    Rome
    • Transfer - Private - Airport (Fiumicino/Ciampino) - Vehicle/Driver (2)
We can customize this private tour just for you. Any element can be tailored – activities, length, hotels and destinations.
Call us at 1 888 903-2001 or request a quote.
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Day 1: Florence

For your added comfort, you will have Meet & Greet assistance upon your arrival, which will be waiting for you outside the customs. Your representative will help to co-ordinate meeting up with your private chauffeur at the airport and accompany you to your accommodation.

Discover the richness and creativity of Tuscan and Italian cuisine in the exclusive and inviting setting of the Hotel Lungarno overlooking the Arno. Resident chef Beatrice Segoni invites you to sample her delightful interpretations over lunch or dinner in the unforgettable Borgo San Jacopo Restaurant gourmet restaurant  in the heart of the elegant Hotel. The Picteau Bar in the lounge of the luxury hotel is the perfect place to enjoy a coffee or a cocktail surrounded by original art by Picasso and Cocteau, while the beautiful terrace of the Sky Bar on top of the medieval Consorti tower, seems just one step away from heaven and the famous sights of Florence.

From posh designer brands like Armani, Gucci, Versace and Ferragamo to locally created hand-crafts, souvenirs, quality leathers and traditional clothing, the city of Florence is a never-ending dream for shopping enthusiasts. For those searching for ancient relics and traditional crafted antiques, Via Maggio is the street for you. The shops and merchants on this street boast numerous "Objects d'Art" and furnishings that are sure to create an atmosphere straight out of the 16th century.  Via del Tornabuoni is considered Florence's 5th Avenue, featuring shops lined with best quality leather products, elegantly expensive shoes, and modernly stylish clothing boutiques.  It is here where you'll find all the “big brand names” products as well as the posh, and potentially upcoming Italian styles.  Besides the traditional shops, Florence also boast some of Italy's best open-air markets including the centralized Market of San Lorenzo, the New Market located under the 16th century Loggia del Porcellino, and the Flea Market at the Piazza Santa Croce. 

Accommodation: Lungarno Hotel (4.5*)

The magnificent Hotel Lungarno is conveniently located in Florence, just a stone’s throw away from the Ponte Vecchio. Imagine the most wonderful rooms and luxury suites, softened by beautiful light and surrounded by the reflections of the Arno River and the inspirational atmosphere of the medieval quarters of Florence. This luxurious accommodation was included as one of Travel & Leisure’s 500 Best Hotels, as selected by their readers.  The great chef Beatrice Segoni invites you to sample her delightful interpretations over a lunch or dinner in the unforgettable Borgo San Jacopo Restaurant. The Picteau Bar in the lounge of this luxury hotel is the perfect place to enjoy a coffee or a cocktail among original art by Picasso and Cocteau.

Michelangelo's Statue of David
Michelangelo's Statue of David
Lungarno Hotel (4.5*)
Lungarno Hotel (4.5*)

Day 2: Florence

Enjoy a half day walking tour with your private English-speaking guide. You will be met at your hotel, and proceed on foot to view the top sights in Florence. This personalized tour will give you a local insight into the real history and hidden gems the city has to offer. You'll visit the Ponte Vecchio, the famous Piazza della Signoria, the elegant palaces and fashionable shops, the charming narrow medieval streets and the impressive Cathedral Square with Brunelleschi's imposing dome will all be concentrated in a pleasant slowly paced tour.  After exploring the city, you will proceed with your guide to the Accademia Gallery where you will have the chance to view Michelangelo's David. Completed in 1504 after four years' work, this stunning statue attracts millions of art lovers from around the globe each year. Your entrance tickets (included in the cost of the tour) are pre-booked so you can bypass the line.

Overnight guests at the Hotel Lungarno receive complimentary access to the Ferragamo museum in Florence - an artistic centerpoint in Florence. The museum’s footwear collection documents the entire span of Salvatore Ferragamo’s career, from his return to Italy in 1927 to 1960 the year he died. It highlights his technical and artistic skills which, through his color choices, the creativity of the designs and use of innovative materials made a fundamental contribution to the growth and establishment of "Made in Italy". Some of the items reveal Salvatore Ferragamo’s relationships with artists of his day, such as the futurist painter, Lucio Venna who created some advertising sketches and the famous Ferragamo footwear label. Others document his continuous quest for the perfect fit and the invention of special constructions and materials, from the famous cork wedge patented in 1936 and immediately imitated all over the world, to the raffia or cellophane vamps, and candy-wrapper paper used during World War II. In addition, there are the shoes that are famous because they were made for Hollywood stars such as Marilyn Monroe, Greta Garbo and Audrey Hepburn. This museum truly gives an insight into a century of history told by footwear. The items on display are periodically selected from the over 10,000 models in the museum’s archives and featured in biennial exhibitions that present different themes through Ferragamo shoes.
The Collection is also enriched by footwear production after the death of Salvatore Ferragamo, down to the present day. Every year, in fact, a number of models suitably representative of the season are entered in the Salvatore Ferragamo Archives which the museum draws on for its exhibitions. 

Accommodation: Lungarno Hotel (4.5*)
Salvatore Ferragamo Museum
Salvatore Ferragamo Museum
City of Florence
City of Florence

Day 3: Florence

You will be met at the hotel by your private driver for a panoramic drive for approximate 1.25 hours to San Gimignano recently the landmark for the highly successful movie Under the Tuscan Sun. Explore this beautiful town independently, viewing the "Manhattan of Tuscany" skyline, bristling with a large number of towers dating back to the 11th and 13th centuries. Enjoy a typical local meal in a nearby farmhouse before continuing to Siena an hour away. Upon arrival in Siena, you will meet your English speaking guide to begin your guided walk to explore Siena, amazingly rich in masterpieces of art and rising above three hills, you will walk to the Piazza del Campo, the square where the world famous folkloric event called Palio Horse Racing takes place twice a year during the summer. Discover this fan-shaped, gently sloping square lined with marvelous buildings like the City Hall, erected in the 13th century, and the Torre del Mangia bell tower, rising 102 meters high. The Sansedoni Palace and the Gaiai Fountain are also close by. You also get to see the exterior views of the gothic-style Duomo of Siena dating back to the 12th century and the Battistero, both adorned with a variety of frescoes, sculptures and painting masterpieces created by some of Italy’s most famous artists. Some free time will later be provided before returning to your hotel. Wine tasting and lunch at Local Farmhouse in San Gimignano, and Duomo is included.

Accommodation: Lungarno Hotel (4.5*)
San Gimignano
San Gimignano

Day 4: Florence - Montalcino

Take a private transfer with vehicle and driver to Montalcino. The drive will take approximately 1 hour and 45 minutes.

There are two restaurants and a cozy bar at the Castiglion del Bosco property which showcase the talented chefs' seasonal and regional cuisine using the finest local ingredients, complemented by an extensive list of Castiglion del Bosco and regional wines. The traditional Osteria offers a casual ambience for an informal lunch or dinner, while the fine dining restaurant, Ristorante Campo Del Drago, presents an elegant setting for a sumptuous Tuscan dining experience.

Accommodation: Rosewood Castiglion del Bosco (5*)

Rosewood Castiglion del Bosco is set within one of the oldest and best-preserved estates in Italy and is located in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia. Castiglion del Bosco is an 800-year-old estate comprising the ruins of a castle, a medieval church, and the Borgo, a village that was once an important farming and social hub. The Borgo now forms the heart of the resort and suites are housed within its buildings. The resort also offers villas which have been created from restored farmhouses with antique furniture, artisanal pieces and modern comforts. Rosewood Castiglion del Bosco also offers a cooking school, a carefully curated store, an organic kitchen garden, a spa, an infinity pool and fitness center. Guests can choose to dine at two restaurants – the more rustic Osteria La Canonica or the understated Ristorante Campo del Drago which offers classic Tuscan and Italian cooking. The property is also a historic winery and the fifth largest producer of Brunello di Montalcino. The estate’s breathtaking 18-hole golf course was designed by the legendary winner of the British Open, Tom Weiskopf. This prestigious course set within a UNESCO World Heritage Site offers an unparalleled playing experience in Italy's only private golf club.

Montalcino
Montalcino
Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco

Day 5: Montalcino

Enjoy a scenic drive through the Tuscan countryside in the company of your chauffeur for approximately 45 minutes to get to Pienza, a very charming little town which dates back to the 15th Century. Your private local guide will be waiting for you in Pienza to commence your walking tour around the narrow streets and show you around. You will visit the typical “botteghe” (small stores) where you can find and taste all sorts of Pecorino cheese (with pepper, truffle, nuts, etc). Pienza also offers nice artisan stores which sell handmade leather items. Some free time will be provided before heading off to Montepulciano which is 30 minute drive away. Montepulciano is a beautiful medieval town built on a hilltop with an “S” shape and surrounded by very well preserved city walls. Discover on your own its hidden narrow streets with many shops where you can also find beautiful handmade ceramics and reach the main square “Piazza Grande” with the imposing Town Hall Palace. After about three hours of free time during which you may also want to enjoy a typical Tuscan lunch accompanied by the amazing Vino Nobile di Montepulciano red wine (not included), your driver will transfer you back to your hotel which will take approximately an hour.

Accommodation: Rosewood Castiglion del Bosco (5*)
Montepulciano
Montepulciano

Day 6: Montalcino

Castiglion del Bosco is well set up for activities on the estate. In and around the Borgo, one can take advantage of a state-of the-art fitness center, a soccer pitch, and tennis and bocce (Tuscan bowls) courts. The Estate also features miles of picturesque hiking and biking trails that hug spectacular ridges and meander past streams, waterfalls and hidden historic sites. Handsome Maremma horses, used by traditional Tuscan herdsmen, are also an option if a horseriding trek is of interest and treks are taken through a network of riding trails extending to the far-reaching corners of the property.

Immersed in the heart of the Val d'Orcia Artistic, Natural and Cultural Park, Castiglion del Bosco Golf Club centres on a spectacular eighteen-hole course designed by the legendary Tom Weiskopf. Golf enthusiasts will certainly be pleased with the course.

Spa lovers will be truly content with the offerings at the Care Suite Spa by Daniela Steiner which is a serene oasis that specializes in unique therapies based on organic ingredients from the Estate. Entrust yourself to the caring hands of the in-house team, who will pamper you with a complete range of exquisite beauty, spa and wellness treatments. Alternatively, relax by the heated infinity pool or enjoy a wine tasting on the propertry if you haven't already - Castiglion del Bosco is among the first five Brunello wine producers!

The extensive Gardens are a magnificent amenity in their own right, and encompass a radiant Tuscan palette for all seasons, including flower-decked terraces, rustic olive groves, manicured fruit orchards and sprawling Sangiovese vineyards. The splendid vegetable garden, designed by the Vatican's garden landscaper, is home to more than 180 varieties of vegetables, fruits and aromatic herbs grown exclusively for La Canonica's restaurants and Culinary Academy.

Accommodation: Rosewood Castiglion del Bosco (5*)
Castiglion del Bosco Pool
Castiglion del Bosco Pool

Day 7: Montalcino - Rome

Depart Castiglion del Bosco today by private driven vehicle and after approximately 2 hrs 30 minutes you'll arrive at Orvieto, an important Etruscan town built around the 6th Century BC, situated in the Southern part of Umbria region. Meet your private local guide and enjoy an approximately 2 hr walking tour through Orvieto’s narrow streets. Admire the magnificent cathedral with the famous Rosone window situated right on top of the main entrance, and at the end of the tour, you'll have some free time for a nice lunch (not included) before heading to Rome. Inclusions: return cable cart, entrance fee to Underground Orvieto and Cathedral.

Accommodation: Bernini Bristol (5*)

Dating from the 1800's, The Hotel Bernini Bristol, overlooking the splendid Piazza Barberini at one end of Via Veneto, the street of the Dolce Vita, is a museum within that most amazing of all museums: the city of Rome. The hotel offers the glamour of a bygone era along with the most modern amenities. Its ample salons are enchanting with their period furnishings and tapestries, and its rooms are marked by a refined atmosphere and comfortable elegance. The delectable gourmet cuisine at Giuda ballerino and the terrace with its amazing views are sure to please. A cutting edge gym, Jacuzzi, Turkish bath, sauna and relaxing massages all create a blissful oasis for guests to enjoy.

Please note that under Roman law, hotels now charge a small amount per traveller per day as a “tourist tax”, which needs to be paid locally through your hotel in Rome. Amounts may vary, but currently the cost is 4EUR per person for 3* hotels, 6EUR for 4* hotels and 7EUR for 5* hotels. The charges will be added to your bill upon check out and are non-negotiable.

Piazza Navona
Piazza Navona
Hotel Bernini Bristol
Hotel Bernini Bristol

Day 8: Rome

Enjoy a private airport transfer in Rome (Fiumicino/Ciampino) with a private vehicle and driver.  Please note drivers may or may not speak English, as their sole responsibility is to transfer clients from one location to another.  If you would like to have the presence of an English speaking assistant or guide for your transfer, this can be pre-arranged upon request and would be subject to an additional supplement.

Accommodation:
We can customize this private tour just for you. Any element can be tailored – activities, length, hotels and destinations.
Call us at 1 888 903-2001 or request a quote.

Trip Terms & Conditions

  • Your deposit is due immediately on booking (30% of program price, minimum $350). The balance is due 90 days prior to departure.
  • Cancellations of confirmed bookings 90 days or more prior to departure will receive full refund minus a $350 (per person) administrative fee and any non-refundable paid fees (e.g. non-refundable airfare, cruise or hotel deposits). 60-89 days will be subject to loss of 30% of program price. 30-59 days will be subject to loss of 50% of program price. 29 days or less will be subject to loss of 100% of program price.
  • Tour quotes do not include airfare to/from the trip start point unless noted on the itinerary
  • Cost increases in currency exchange, government fees, taxes, surcharges or hotel/lodge tariff increases between quote date and start date are payable by the client.
  • Availability cannot be guaranteed until booked. We will exercise best efforts to book hotels per the itinerary, however, in busy seasons and with client bookings made within 90 days of tour date we may be forced to offer substitutes.
  • Payment of the program price constitutes your acceptance of the terms and conditions set out at www.kensingtontours.com/terms-and-conditions
  • Living Standards and practices at destination may differ from those in North America with respect to provisions of utilities, services and accommodation.

Lungarno Hotel (4.5*): Florence

The magnificent Hotel Lungarno is conveniently located in Florence, just a stone’s throw away from the Ponte Vecchio. Imagine the most wonderful rooms and luxury suites, softened by beautiful light and surrounded by the reflections of the Arno River and the inspirational atmosphere of the medieval quarters of Florence. This luxurious accommodation was included as one of Travel & Leisure’s 500 Best Hotels, as selected by their readers.  The great chef Beatrice Segoni invites you to sample her delightful interpretations over a lunch or dinner in the unforgettable Borgo San Jacopo Restaurant. The Picteau Bar in the lounge of this luxury hotel is the perfect place to enjoy a coffee or a cocktail among original art by Picasso and Cocteau.

Lungarno Hotel (4.5*)
Lungarno Hotel (4.5*)
Lungarno Hotel Lobby
Lungarno Hotel Lobby

Rosewood Castiglion del Bosco (5*): Montalcino

Rosewood Castiglion del Bosco is set within one of the oldest and best-preserved estates in Italy and is located in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia. Castiglion del Bosco is an 800-year-old estate comprising the ruins of a castle, a medieval church, and the Borgo, a village that was once an important farming and social hub. The Borgo now forms the heart of the resort and suites are housed within its buildings. The resort also offers villas which have been created from restored farmhouses with antique furniture, artisanal pieces and modern comforts. Rosewood Castiglion del Bosco also offers a cooking school, a carefully curated store, an organic kitchen garden, a spa, an infinity pool and fitness center. Guests can choose to dine at two restaurants – the more rustic Osteria La Canonica or the understated Ristorante Campo del Drago which offers classic Tuscan and Italian cooking. The property is also a historic winery and the fifth largest producer of Brunello di Montalcino. The estate’s breathtaking 18-hole golf course was designed by the legendary winner of the British Open, Tom Weiskopf. This prestigious course set within a UNESCO World Heritage Site offers an unparalleled playing experience in Italy's only private golf club.

Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
Barriccaia Cellar
Barriccaia Cellar

Bernini Bristol (5*): Rome

Dating from the 1800's, The Hotel Bernini Bristol, overlooking the splendid Piazza Barberini at one end of Via Veneto, the street of the Dolce Vita, is a museum within that most amazing of all museums: the city of Rome. The hotel offers the glamour of a bygone era along with the most modern amenities. Its ample salons are enchanting with their period furnishings and tapestries, and its rooms are marked by a refined atmosphere and comfortable elegance. The delectable gourmet cuisine at Giuda ballerino and the terrace with its amazing views are sure to please. A cutting edge gym, Jacuzzi, Turkish bath, sauna and relaxing massages all create a blissful oasis for guests to enjoy.

Please note that under Roman law, hotels now charge a small amount per traveller per day as a “tourist tax”, which needs to be paid locally through your hotel in Rome. Amounts may vary, but currently the cost is 4EUR per person for 3* hotels, 6EUR for 4* hotels and 7EUR for 5* hotels. The charges will be added to your bill upon check out and are non-negotiable.

Hotel Bernini Bristol
Hotel Bernini Bristol
Spa
Spa
We can customize this private tour just for you. Any element can be tailored – activities, length, hotels and destinations.
Call us at 1 888 903-2001 or request a quote.
We can customize this private tour just for you. Any element can be tailored – activities, length, hotels and destinations.
Call us at 1 888 903-2001 or request a quote.
  • Vanessa Oquendo — April 21, 2014 — Europe

    Melissa Field was extremely helpful! She was courteous, professional, knowledgeable, and friendly! She kept me updated on the status of everything and provided timely correspondence. She took ownership for any problems I had and remedied them. I had the most amazing time of my life in Iceland and Paris! I would not have experienced everything without the help of Kensington Tours.

  • Marilynn Weaver — April 21, 2014 — Europe

    All of our guides were beyond fabulous! Our time in Dublin was much too short, would have loved to stay there at least one more full day. Would recommend extending this package to 15 days for any future visits. The train to Edinburgh was super! Beautiful scenery and great steak pies!

  • Ann Saxon — November 06, 2013 — Europe

    Our trip was fantastic!!! I cannot say enough good things. Lianne worked with our exact dates and time frame beautifully.Our drivers were prompt and friendly. The private guides were so knowledgeable. We left with an appreciation of the history, the culture, and the beauty of Andulasia. We were very pleased and will certainly recommend your company to friends and family.

  • Coby Scherr — November 05, 2013 — Europe

    Everyone involved in our Portugal trip made it terrific. Exactly as advertised. Every event on time and most pleasant. Guides were well-informed, courteous and friendly. Really made for a great journey every time. Each hotel was clean, upgraded and staffed with knowledgeable and friendly folks. Breakfasts were complete -- almost too much to eat. It will always be a wonderful memory thanks to Kensington Tours.

  • Couples Dellinger & Hubbell — November 06, 2013 — Europe

    We've been raving to everyone about the food, the friendliness of the people and the amazing history and sites in Turkey. Yes, we want to go back.

  • John Edstrom — October 22, 2013 — Europe

    Overall, our tour in Spain was very enjoyable, and well planned and executed. Our private tour of the Alhambra was excellent. Virginia, tour guide for royal palace ruins outside of Cordoba, was also excellent. In Seville, we went to the Flamenco Show/dinner, and the Flamenco was outstanding!

  • Kevin Wilshere — October 19, 2013 — Europe

    Great trip to Spain! Thanks again for all your help, Lianne. The destinations, hotels, guides and everything were all top notch.

  • Chery Westlund — November 07, 2013 — Europe

    My husband and I took a 3 week vacation to southern Europe and North Africa and had a great time. All the guides were very knowledgeable and bent over backwards to accommodate us. The arrangements made by Kensington went off without a hitch. This is our second trip with Kensington (we went to Peru in 2009) and we will certainly book with them again.

  • Randy Gramlich — October 07, 2013 — Europe

    Thank you for your follow up, we both loved our time in Croatia. It’s really a beautiful place, especially the coast. Your choice of hotels was great. It was an incredible view from the Bellevue hotel in Dubrovnik and the Vestibule in Split was in the best possible location. We were able to relax in our room listening to the wonderful singers in the courtyard and its central location made it so easy to walk anywhere we wanted to see with ease.

  • Jay Steffan — September 24, 2013 — Europe

    We just returned from a 10 day trip to Paris and Normandy. We spent three nights in Paris and then enjoyed a seven night cruise on the Seine to Normandy with AMA Waterways. The time in Paris was well spent and has piqued our interest to return for a more thorough visit. Guide Wafaa Lankey was superb in our visit to Versailles. The Seine cruise was relaxing and beautiful. So many wonderful little towns and we wished we had more time in each one to explore and enjoy.

    We traveled to Croatia and Slovenia using Kensington earlier this year which was a fantastic trip.

We can customize this private tour just for you. Any element can be tailored – activities, length, hotels and destinations.
Call us at 1 888 903-2001 or request a quote.

* USD per person, double occupancy. Custom designed personal tour. Prices subject to change.

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