Luxurious Tuscany

8 days from $5,536 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.
  • Stay in exclusive five-star properties.
Request a Quote

Travel first class through the heart and soul of Italy on this opulent Tuscan voyage. With a personal guide and chauffer, you’ll discover the finest Renaissance masterpieces, ornate palaces and sumptuous cuisine.

Tuscany's sun-soaked vineyards, sparkling coastline and postcard-perfect towns have captured the imaginations of travelers for centuries. With your private expert guide and driver, tour Renaissance palaces, hidden historic sites, narrow streets lined with quaint cafes and boutique shops, and glorious landscapes of wheat fields and olive groves. Tour the spectacular vineyards in the Chianti region and savor the refined fruits of a centuries-old wine-making tradition. From a private Florentine residence of a refined art collector, to a magnificent country Estate nestled among rolling hills you’ll unwind in exclusive accommodations that pamper your mind and body.

Choose from optional activities like tennis or bocce, horseback riding, golf, or simply spending the day at the spa being pampered. 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 More »

Day
Activities Hotel & Meals
Hotel & Meals
  • Day 1 Florence
    Florence
    • Transfer - Private - Airport with Meet & Greet - Vehicle/Assistant/Driver(2)
    • Italy - Welcome Package(2)
  • Day 2 Florence
    Florence
    • Tour - Private - 1/2 Day Walking Tour with Accademia Gallery (3 hrs) - Guide(10)
  • 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
    • Tour - 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)
    Breakfast
  • 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.
Kensington Advantage
Personalized itinerary with private guide & driver. Award winning value.
  • Personalized itinerary that fits like a glove
  • Full attention of your own private guide & driver
  • In-country offices for 24/7 peace of mind
  • Multi-award winning
  • 30,000 delighted clients

With the inside track on the new, the old, the off-the-beaten track and the out-of-this-world, you won't find a more knowledgeable team of destination specialists.

Meet Our Experts
Curators of extraordinary experiences, you won't find a more skillful team.
30,000 Delighted Customers
"Kensington, you've done it again...perfection!"

Don't take our word for it.
Here's what our clients say.

"Fabulous trip. Every aspect from the planning to execution was excellent."

Newsletter Subscription
Have our hand picked trips, news & specials delivered to you.
Thank you for signing up!

Your details have been received and processed successfully.

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.

A welcome package with 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.

Accommodation: Bernini Palace (5*)

The Hotel Bernini Palace is situated in the heart of Florence behind the famed Piazza della Signoria and the Uffizi Gallery.  Built within the confines of a 15th century structure, the property features an outstanding blend of sumptuous modern furnishings and magnificent antiques throughout. Guests will surely enjoy just how spacious and elegant each of the rooms at the Hotel Bernini Palace truly are, amongst the many modern fittings and conveniences made available. Guests can be sure that dining at the hotel’s restaurant, Ristorante La Chiostrina, is an exceptional experience. The menu offers a range of exquisite options including innovative regional dishes, classic Italian options, and popular westernized items. Relax and enjoy a cocktail or local wine at the Lounge Bar, often accompanied by delicious appetizers. In the morning, classical products of Italian and continental tradition wait for you inside the magnificent Sala Parlamento, enriched by marvelous frescoed ceilings. The property’s dynamic location allows guests to enjoy various Florentine "trattorie" within walking range from the hotel.

Michelangelo's Statue of David
Michelangelo's Statue of David
Bernini Palace
Bernini Palace

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.

Accommodation: Bernini Palace (5*)
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: Bernini Palace (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: Portrait Roma (5*)

Delight in the ‘Dolce Vita’ at the breathtaking Portrait Roma in Rome in the heart of Via Condotti, a stone throw away from the Spanish Steps. Reflecting the splendor and the luxury of Rome of the 50’s and dedicating each suite to a grand personality, Michele Bönan, the elegant Florentine architect, gives tribute to the extra ordinary style of Salvatore Ferragamo. The magical feeling of these luxury suites in Rome resembles the divine spirit of a fashion studio or film set and is carried on in the splendid bedrooms comprised of the finest materials, the bathrooms of superb beauty, the delightful living rooms, and the comfort of the hidden kitchen area. A magnificent terrace on the top floor offers the most spectacular views over Rome and the Trinità dei Monti. Indulge in this delightful one of a kind setting and experience Roman hospitality at its finest during a sumptuous breakfast in the beautiful morning lights, a moment of quiet reading in the afternoon, or a cocktail and a private dinner.

Piazza Navona
Piazza Navona
Portrait Roma
Portrait Roma

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.

Bernini Palace (5*): Florence

The Hotel Bernini Palace is situated in the heart of Florence behind the famed Piazza della Signoria and the Uffizi Gallery.  Built within the confines of a 15th century structure, the property features an outstanding blend of sumptuous modern furnishings and magnificent antiques throughout. Guests will surely enjoy just how spacious and elegant each of the rooms at the Hotel Bernini Palace truly are, amongst the many modern fittings and conveniences made available. Guests can be sure that dining at the hotel’s restaurant, Ristorante La Chiostrina, is an exceptional experience. The menu offers a range of exquisite options including innovative regional dishes, classic Italian options, and popular westernized items. Relax and enjoy a cocktail or local wine at the Lounge Bar, often accompanied by delicious appetizers. In the morning, classical products of Italian and continental tradition wait for you inside the magnificent Sala Parlamento, enriched by marvelous frescoed ceilings. The property’s dynamic location allows guests to enjoy various Florentine "trattorie" within walking range from the hotel.

Bernini Palace
Bernini Palace
Hotel Bernini Palace
Hotel Bernini Palace

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

Portrait Roma (5*): Rome

Delight in the ‘Dolce Vita’ at the breathtaking Portrait Roma in Rome in the heart of Via Condotti, a stone throw away from the Spanish Steps. Reflecting the splendor and the luxury of Rome of the 50’s and dedicating each suite to a grand personality, Michele Bönan, the elegant Florentine architect, gives tribute to the extra ordinary style of Salvatore Ferragamo. The magical feeling of these luxury suites in Rome resembles the divine spirit of a fashion studio or film set and is carried on in the splendid bedrooms comprised of the finest materials, the bathrooms of superb beauty, the delightful living rooms, and the comfort of the hidden kitchen area. A magnificent terrace on the top floor offers the most spectacular views over Rome and the Trinità dei Monti. Indulge in this delightful one of a kind setting and experience Roman hospitality at its finest during a sumptuous breakfast in the beautiful morning lights, a moment of quiet reading in the afternoon, or a cocktail and a private dinner.

Portrait Roma
Portrait Roma
Portrait Roma
Portrait Roma
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.
  • Nancy L. — May 25, 2016 — Europe

    Thank you very much for all of your efforts. We had a wonderful trip to France. This was our third trip with Kensington. Once again it was perfect. The guides, hotels, drivers, suggestions, everything was lovely. It was rewarding to be able to plan the trip together. Thank you for your flexibility and expertise.

  • William C. — May 19, 2016 — Europe

    We had a great time. Loved Amboise and Le Choisel and the chateau tour. Thanks

  • Betty H. — May 19, 2016 — Europe

    Once again Kensington did a magnificent job for us. They planned the tour around just what we wanted to see. The guides were very knowledgeable. The drivers were always on the dot and excellent as well.

  • Connie P. — May 19, 2016 — Europe

    The sunset cruise on the island of Santorini was fabulous!

  • Elijah S. — May 19, 2016 — Europe

    Once again, Kensington Tours did not disappoint. Our accommodations in Greece were marvelous, the private vehicles were comfortable, and the selected itineraries were well planned. What truly made our vacation memorable were the tour guides. Everyone was professional, courteous, friendly, and possessed an impressive knowledge of history and culture. Our guides added a new level of appreciation and depth to our travels through Greece. We're already planning a repeat visit. Highest possible recommendation and bravo!

  • Andrea H. — May 19, 2016 — Europe

    We really enjoyed our experience. Our guides were fantastic in each place we went and the hotels were also superb. Great experience.

  • Glen G. — May 19, 2016 — Europe

    Theresa planned a wonderful trip for us. The additional stopovers in Bratislava and Cesky Krumlov were fantastic. Guides were exceptional and really made the travel day worthwhile. All hotels were excellent. Well located within easy walking distance of prime city tourist areas, excellent breakfasts, very clean and comfortable. All of our guides were good - feel Monica in Vienna was exceptional - she really knew her stuff and was a wealth of knowledge.

  • Catherine B. — May 19, 2016 — Europe

    Andreia and Jose, our driver, were very professional. Andreia was knowledgeable, spoke very good English, and was very understanding and very helpful. Jose was an excellent driver. The car was very clean and very comfortable. We enjoyed and appreciated the personal attention and the tours provided at our own pace.

  • David J. — May 19, 2016 — Europe

    The hotels were 3 star and in the center of the most interesting parts of the cities - just as I prefer. Guide Ion Dima was 5 star and a pleasure to be touring with.

  • Connie S. — May 18, 2016 — Europe

    Both my guides were extraordinary in their knowledge, rapport and professionalism.

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.

Kensington Tours is committed to protecting your privacy and ensuring you have a positive experience on our website. You can read our complete Privacy Policy here. You can Contact Us here.

National Geographic Traveler : 50 Tours of a Lifetime 2014 Travel + Leisure : World's Best Award 2014 Family National Geographic Traveler : 50 Tours of a Lifetime