Tuscany Highlights

10 days from $3,590 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.
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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
    • Tour - Shared - San Gimignano, Siena, Monteriggioni & Chianti (with Snack & Wine Tasting) (11hrs) - Coach/Guide
  • 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 - 1/2 Day Wine Tour (3 hrs) (max 7pax) - Vehicle/Guide/Driver
  • 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 - Private - 1/2 Day Olive Oil of the Florentine Hills (with tasting) (5 hrs) - Vehicle/Guide/Driver(0)
    • 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

Driving south from Florence and crossing the beautiful Chianti hills you will arrive at San Gimignano, a picturesque, fascinating Medieval jewel (declared a World heritage Site by UNESCO), famous for its white wine, the world renowned Vernaccia, and its skyscrapers. The visit is free for independent sightseeing: you will have time to wind your way through the narrow streets and admire the relaxing rolling landscape. Continue to Siena, the medieval town with the suggestive Piazza del Campo, famous for the Palio horse race and its splendid examples of Gothic civic architecture. Here stands the magnificent Palazzo Pubblico with its Torre del Mangia. Then you will continue in the direction of the Duomo, one of the most beautiful Italian Gothic Cathedrals in Italy. After leaving Siena, drive to Monteriggioni, the medieval hilltop gem with its walls still intact, where you can relive the atmosphere of olden times, and enjoy a well-earned ice cream (April-Oct only). After, move into the Chianti area with its picture-postcard landscapes. You have the chance to taste the best Chianti red wine in a rustic wine estate along with homemade snacks, with a tour of the wine cellars and sampling of wines, oil, and balsamic vinegar.

Includes Cathedral entrance, ice cream tasting (in high season), wine estate tour + tastings.

Accommodation: L`orologio Hotel (4*)
Siena
Siena

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

You will be picked up for your small group tour at your hotel in Montepulciano to explore two vineyards in the area. Learn about how wine is produced from start to finish, by taking a walk amongst the vineyards, and visiting the inside of the wineries. Enjoy a wine tasting (not included) in one of the wine cellars at the end of your tour. This tour includes pick up and drop off at your hotel in Montepulciano, transportation, and English speaking guide.

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

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

Enjoy a private guided tour Impruneta and the Florentine hills to discover the art of olive oil making. Olive trees are an ever-present part of the Tuscan landscape, some trees being 300 years old, and have silently following the history of mankind. This excuriosn takes you the heart of the Tuscan oil kingdom- the hills around Impruneta, San Casciano, and Tavarnelle. To begin your tour, you will arrive in Impruneta for a guided tour of the main square and handmade terracotta factory. To this day, these enormous terracotta jars still store the olive oil that is made in this region. You will make a visit to the Torre Rossa farm for a tasting, visit their oil cellar, and an opportunity to see the terracotta jars in use. Afterwards you will head to La Querce farm and enjoy an olive oil tasting before returning to Siena. This tour includes private transportation, guide, and olive oil tasting at the two farms visited.

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*)
Terracotta Jar in Impruneta
Terracotta Jar in Impruneta
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.
  • Molly P. — June 22, 2016 — Europe

    Our family loved our week in Iceland. I am 70 and our youngest is 9. Each activity was well suited for the whole group. We changed one event and Kensington Tours immediately helped us cancel one and sign up for a new adventure. When I had questions they helped me out. Their professionalism, kindness, and attentiveness made our trip a complete success. Thank you!

  • Tammy M. — June 22, 2016 — Europe

    Jessica Clements was a tremendous help as my husband and I planned our pre-cruise visit to Athens and the Peloponnese. Many thanks for all your efforts. We enjoyed our tours very much. Our guides, Niki Stavrakaki and Andronikos Sakatos, were phenomenal. Our drivers, Makias and Demetrios, were very professional and delightful gentlemen. We had a great time exploring many of the ancient sites we've dreamed of seeing for years.

  • Caroline W. — June 22, 2016 — Europe

    Transfers were seamless and activities were great. Overall, we are very impressed with Kensington!

  • Beth N. — June 15, 2016 — Europe

    Everything exceeded our expectations!!! Our guides were amazing. Our hotels were wonderful. I wouldn't change anything about our trip! Thanks for your help!

  • Dalia D. — June 15, 2016 — Europe

    I am so glad that I used Kensington Tours to help me plan my trip to Italy. Ingryd was an excellent agent - she understood exactly what was important to my family and every aspect of our trip from Rome to Florence to Venice was well planned and enjoyable, with no hiccups. We made changes to our schedule when in Italy and the local agents were very responsive and quickly adapted our plans to work better for us. We loved the personal attention we got on our private guided tours and felt we learned a lot from knowledgeable guides that were personable and very informative.

  • Barbara K. — June 08, 2016 — Europe

    Another fabulous trip! John O'Connell was so congenial and knowledgeable. I feel like he has become a new friend. We had a great time with him and he made some excellent recommendations for small changes in our itinerary. He was so attentive and caring with my mother too! A really sweet man. Sean Finnigan in Dublin was a bundle of energy - took us to the museum to see the gold exhibit which we knew nothing about - so glad he did! Bought my sister and I a postcard of the Book of Kells alphabet as a remembrance - so kind! It was a trip we will never forget!!

  • Samuel T. — June 08, 2016 — Europe

    Wonderful preparation! Great time and great planning. Definitely use them again in the future.

  • Elliot S. — June 08, 2016 — Europe

    The accommodations and guides were great and everyone we were supposed to meet were courteous and knowledgeable.

  • Gale S. — June 08, 2016 — Europe

    Wonderfully planned! Everything was amazing. The high quality guides and tours were well worth the money, bypassing lines, personal attention and highly knowledgeable. The accommodations exceeded our expectations. Can't wait for our next trip!

  • Judith F. — June 08, 2016 — Europe

    Our trip to St. Petersburg was superlative. The hotel was beautiful, great location. Our guide was lovely; enthusiastic, full of knowledge, personable, helpful, and caring.

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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