Tuscany Highlights

10 days from $3,130 per person*
  • Marvel at the slanted structure of the Leaning Tower of Pisa.
  • Sip wine in the Tuscany region on multiple wine tasting excursions.
  • Visit famous works of art at the Accademia Gallery in Florence.
  • Discover medieval Montepulciano and Siena with private guide.
  • Featuring expertly selected hotels.
Request a Quote

On this elegant private tour through the birthplace of the Renaissance, marvel at endless art and architectural gems in Florence, savor fine Chianti wines in sun-drenched Tuscan vineyards and wander through Italy’s most beautiful medieval towns.

Tuscany is a masterpiece equally blessed by the genius of man and nature, bursting with world-class artistic treasures, lyrical landscapes and epicurean pleasures. Regarded by many to be the heart and soul of Italy, its hidden alleyways and ancient cobblestoned streets trace a rich and orphic history. One visit to Florence, the beating heart of Tuscany, reveals an artistic and architectural tour de force. Take in the city’s world-renowned paintings, frescos and historic landmarks. Stroll the streets of medieval Montepulciano and spectacular Siena and taste the fine wines of the world-renowned Chianti region. Marvel at the slanted structure of the Leaning Tower of Pisa and visit the UNESCO World Heritage Site of medieval San Gimignano. Italy’s most culturally rich region will lift your spirit and capture your soul.

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 (1 pack) (2)
  • Day 2 Florence
    Florence
    • Tour - Private - 1/2 Day Walking Tour with Accademia Gallery (3 hrs) - Guide
    • Self-Guided - Dinner at Boccanegra
  • Day 3 Florence
    Florence
  • Day 4 Florence to Montepulciano
    Florence to Montepulciano
    • Florence - Montepulciano [1 hr 20 mins] - Vehicle/Driver(2)
    • Tour - Private - 1/2 Day Walking Tour - Guide(30)
  • Day 5 Montepulciano
    Montepulciano
    • At Leisure
  • Day 6 Montepulciano
    Montepulciano
    • Tour - Shared - Historic Cellar Tour (with Wine Tasting) (2 hrs) - Guide/Small Group
  • Day 7 Montepulciano to Siena
    Montepulciano to Siena
    • Montepulciano - Siena [1 hr 15 mins] - Vehicle/Driver (2)
    Breakfast
  • Day 8 Siena
    Siena
    • Tour - Private - 1/2 Day Walking Tour (2 hrs) - Guide(10)
    Breakfast
  • Day 9 Siena
    Siena
    • Tour - Shared - Chianti & San Gimignano (5 hrs) - Vehicle/Guide
    Breakfast
  • Day 10 Siena
    Siena
    • Siena - Florence [1 hr 15 mins] - 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.

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: L`orologio Hotel (4*)

The L'orologio Hotel is conveniently located in the heart of Florence, just a short stroll away from important monuments such as the Duomo, the Basilica of Santa Maria Novella, and the Medici Chapels. The concept of the L'orologio Hotel is inspired by prestigious international Haute Horlogerie (Fine Watchmaking) and in particular, by the world of collecting vintage watches. The interior design pays an extreme attention to detail, providing a bold sensory experience to guests.  Guestrooms are comfortable and full of character, and offer various cityscape views. Guests can dine at bar L’O for classic Italian cuisine in an warm and illuminating environment. Visit the fitness center for a workout during your stay, and the sauna to relax after a long day of sightseeing.

Michelangelo's Statue of David
Michelangelo's Statue of David
 L'orologio Hotel
L'orologio Hotel

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.

The venue for dinner is nestled in a cozy and comfortable corner in the heart of Florence. Here, you will be served delicious, savory dishes that pronounce the creativity of the chef during this romantic and unique evening outing. A selection of the finest wines and the strictest attention to detail make this restaurant of one the most pleasant in Florence. Dishes are prepared using only the best available foods of the season. Particular attention is devoted to the presentation of every dish and to the intriguing combinations of flavors and aromas. Meal not included, and paid locally.

Accommodation: L`orologio Hotel (4*)
City of Florence
City of Florence

Day 3: Florence

Accommodation: L`orologio Hotel (4*)

Day 4: Florence - Montepulciano

Enjoy a private transfer from Florence to Montepulciano. Your journey will take approximately 1 hour and 20 minutes.

Explore the medieval and Renaissance hill town, Montepulciano, as you enjoy a private, half- day walking tour. You will be met at your hotel and proceed on foot to view the top sights. You will be accompanied by a very knowledgeable, English-speaking local guide. This personalized tour will give you local insight into the real history and hidden gems. Be sure to bring along your camera in order to capture all of the wonderful sights!

Accommodation: Villa Cicolina (4*)

Until the end of the 19th century, Villa Cicolina was the country residence of a noble family of Montepulciano. This beautiful country house was built in the late sixteenth century, as the lovely decor proudly reflects. Guestrooms boast fantastic views of the Tuscan countryside, as well as onsite gardens and many olive groves. Wake up and start your day off with a rich breakfast buffet featuring delicious cheese and salami, as well as seasonal fruit and pastries. Each evening, enjoy a traditional Tuscan meal, prepared with only the finest seasonal ingredients. Relax with a glass of local wine while savoring your dinner outdoors, looking out at the gorgeous panoramic view. Escape to the peaceful gardens and be immersed between olive trees and flowers, or relax in the tavertine infinity pool, and Jacuzzi.

Montepulciano
Montepulciano
Villa Cicolina
Villa Cicolina

Day 5: Montepulciano

Enjoy time at leisure to explore at your own pace, or relax at your hotel.

Accommodation: Villa Cicolina (4*)

Day 6: Montepulciano

Montepulciano is a beautiful medieval town nestled in the Tuscan landscape which prides itself on a long history of tradition in winemaking. The thick underground network of ancient cellars dug into the rock have long housed the precious oak casks (barrels) with Vino Nobile, an iconic symbol of the deep ties that for centuries have existed between the city of Montepulciano and its wine. The tour includes a guided visit to the cellars with a final wine tasting of Rosso di Montepulciano DOC, Vino Nobile di Montepulciano DOCG.

Accommodation: Villa Cicolina (4*)
Montepulciano Cellar
Montepulciano Cellar

Day 7: Montepulciano - Siena

Take a private transfer with vehicle and driver to Siena. The drive will take approximately 1hr 15min.

Accommodation: Athena (4*)

Hotel Athena is located in the heart of the old town center inside Siena’s ancient city walls. Only 500 meters from the Duomo and Piazza del Campo, Hotel Athena is situated in a quiet and easily accessible area with a wonderful panoramic view of the surrounding countryside. The Hotel Athena provides rooms fitted with all the comforts you require for a perfectly relaxing stay. Visit Il Mangia Restaurant to savor deliciously prepared traditional Tuscan food, all featuring natural and organic ingredients.  Ideal for an appetizer at sunset, the San Marco Terrace Bar happily serves guests until late in the evening, featuring all kinds of drinks and snacks. Admire the breathtaking landscape of green hills and the ancient city walls of Siena from the panoramic terrace, a spacious yet intimate environment that is ideal for enjoying an appetizer at sunset or a drink in total relaxation.

Siena
Siena
Hotel Athena
Hotel Athena

Day 8: Siena

You will be met at your hotel to begin a 2 hour guided walk around Siena; a city masterfully perched atop three rising hills.  Your private guide will provide direction and insight during this exploratory tour.  Marvel during this guided walk at the many sites and highlights of the city including the Piazza del Campo; home to the twice annual, world famous folkloric event known as the Palio Horse Race.  This fan-shaped piazza features some truly marvelous buildings including the 13th century City Hall and the Torre del Mangia bell tower, rising over 100 meters high.  Some other monuments nearby to the square include the Sansedoni Palace and the Gaiai Fountain.  Admire the exterior gothic styling of the 12th century Duomo of Siena and the Battistero, both featuring a variety of painted frescoes and sculpted masterpieces created by some of Italy’s most renowned artists.  Upon completion of the guided portion of this tour, you are left to enjoy some individual leisure time before returning to accommodation on your own.  Entrance fees are included.

Accommodation: Athena (4*)
Cathedral in Siena
Cathedral in Siena

Day 9: Siena

The beautiful ruby color and the characteristic fragrance with hints of violet are the distinguishing marks of the identity of one of the most famous wines in the world: Chianti. You will taste this refined product at one of the best wine cellars of the area accompanying the wine with a selection of bruschetta’s, typical Tuscan salami, and sliced cold meats. You guide will lead you in the discovery of the marvellous unspoiled landscapes that have been cradling the Chianti vineyards for centuries. The sounds, fragrances and tastes of this land will steal your senses trough a unique experience to be discovered, tasted, and understood by visiting ancient churches, medieval castles, and little hamlets where the pace of life has remained unchanged over the course of time. Continue on to San Gimignano which is an example of medieval town. It has been declared a UNESCO World Heritage Site. This town is also famous for its wine, the Vernaccia di San Gimignano.(Includes: GT coach or minivan with air conditioning, expert multilingual escorts, guided tour Chianti, San Gimignano, guided tour of famous wine estate with wine tasting and sampling of bruschetta, sliced cold meats and salami.).  Please note that shared tours can have up to approx. 50 people (depending on the number of people that have signed up for the tour on the particular day, and are carried out in a number of languages). The group may be divided out into smaller groups so the tour is lead in one language or kept as one larger group (in which case the tour will be lead in various languages).

Accommodation: Athena (4*)
San Gimignano
San Gimignano

Day 10: Siena

Enjoy the transfer from Siena to Florence in a private chauffeured vehicle.

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.

L`orologio Hotel (4*): Florence

The L'orologio Hotel is conveniently located in the heart of Florence, just a short stroll away from important monuments such as the Duomo, the Basilica of Santa Maria Novella, and the Medici Chapels. The concept of the L'orologio Hotel is inspired by prestigious international Haute Horlogerie (Fine Watchmaking) and in particular, by the world of collecting vintage watches. The interior design pays an extreme attention to detail, providing a bold sensory experience to guests.  Guestrooms are comfortable and full of character, and offer various cityscape views. Guests can dine at bar L’O for classic Italian cuisine in an warm and illuminating environment. Visit the fitness center for a workout during your stay, and the sauna to relax after a long day of sightseeing.

 L'orologio Hotel
L'orologio Hotel
Lounge
Lounge

Villa Cicolina (4*): Montepulciano

Until the end of the 19th century, Villa Cicolina was the country residence of a noble family of Montepulciano. This beautiful country house was built in the late sixteenth century, as the lovely decor proudly reflects. Guestrooms boast fantastic views of the Tuscan countryside, as well as onsite gardens and many olive groves. Wake up and start your day off with a rich breakfast buffet featuring delicious cheese and salami, as well as seasonal fruit and pastries. Each evening, enjoy a traditional Tuscan meal, prepared with only the finest seasonal ingredients. Relax with a glass of local wine while savoring your dinner outdoors, looking out at the gorgeous panoramic view. Escape to the peaceful gardens and be immersed between olive trees and flowers, or relax in the tavertine infinity pool, and Jacuzzi.

Villa Cicolina
Villa Cicolina
Jacuzzi
Jacuzzi

Athena (4*): Siena

Hotel Athena is located in the heart of the old town center inside Siena’s ancient city walls. Only 500 meters from the Duomo and Piazza del Campo, Hotel Athena is situated in a quiet and easily accessible area with a wonderful panoramic view of the surrounding countryside. The Hotel Athena provides rooms fitted with all the comforts you require for a perfectly relaxing stay. Visit Il Mangia Restaurant to savor deliciously prepared traditional Tuscan food, all featuring natural and organic ingredients.  Ideal for an appetizer at sunset, the San Marco Terrace Bar happily serves guests until late in the evening, featuring all kinds of drinks and snacks. Admire the breathtaking landscape of green hills and the ancient city walls of Siena from the panoramic terrace, a spacious yet intimate environment that is ideal for enjoying an appetizer at sunset or a drink in total relaxation.

Hotel Athena
Hotel Athena
Reception
Reception
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.
  • Jessica A. — January 04, 2016 — Europe

    I had the most amazing trip of my life. Everything was completely seamless, I didn't have to worry about anything aside from making sure I captured every moment on film! Jessica Pretty was outstanding in helping me choose my activities, work within my price range, and I cannot thank her enough for recommending Cambodia - it was my favorite stop! We are using Kensington again this March for a return trip to Asia :)

  • 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.

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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