Tuscany Highlights

10 days from $5,160 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. Marvel at the slanted structure of the Leaning Tower of Pisa, stroll the streets of medieval Montepulciano and Siena, and taste the fine wines of the world-renowned Chianti region. 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
    • Private Transfer - Airport with Meet & Greet - Vehicle/Assistant/Driver
    • Italy - Welcome Package
  • Day 2 Florence
    Florence
    • Private Tour - 1/2 Day Walking Tour with Accademia Gallery (3 hrs) - Guide
    • Optional: Dinner at Boccanegra
  • Day 3 Florence
    Florence
    • Small Group Tour - Pisa, Lucca & Viareggio Tour (11 hrs) - Vehicle/Driver-Guide
  • Day 4 Florence to Montepulciano
    Florence to Montepulciano
    • Private Transfer - Florence - Montepulciano [1 hr 20 min] - Vehicle/Driver
    • Private Tour - 1/2 Day Walking Tour - Guide
  • Day 5 Montepulciano
    Montepulciano
    • Small Group Tour - Tuscan Gourmet Tour (6 hrs) - Vehicle/Guide/Driver
  • Day 6 Montepulciano
    Montepulciano
    • Small Group Tour - Historic Cellar Tour (with Wine Tasting, 2 hrs) - Guide/Small Group
  • Day 7 Montepulciano to Siena
    Montepulciano to Siena
    • Private Transfer - Montepulciano - Siena [1 hr 15 min] - Vehicle/Driver
    • Private Tour - 1/2 Day Walking Tour (3 hrs) - Guide
    Breakfast
  • Day 8 Siena
    Siena
    • At Leisure
    • Private Tour - 1/2 Day Wine Tasting & Dinner (6 hrs) - Vehicle/Guide/Driver
    Breakfast
  • Day 9 Siena
    Siena
    • Private Tour - San Gimignano & Cooking Class (with Dinner) (6.5 hrs) - Vehicle/Local Guide/Driver
    Breakfast
  • Day 10 Siena
    Siena
    • Private Transfer - Siena - Florence [1 hr 15 mins] - Vehicle/Driver
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

Meet your private English-speaking assistant outside of airport customs. Waiting with a sign with your name on it, they will direct you to your awaiting private transfer, and accompany you to your hotel for check-in.

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.

Tuscany Highlights Tours 2018 - 2019 -  Michelangelo's Statue of David
Michelangelo's Statue of David
Tuscany Highlights Tours 2018 - 2019 -   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.

Optional (Not Included):
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. 

Accommodation: L`orologio Hotel (4*)
Tuscany Highlights Tours 2018 - 2019 -  City of Florence
City of Florence

Day 3: Florence

Enjoy a small group (min. 4 people/max. 8 people) excursion to Pisa, Lucca and Viareggio. Dive into a "sea of beauty," and experience emotional discovery of fascinating art masterpieces, while embracing the relaxing sights and sounds of these splendid Italian cities. Your journey begins in the city of Lucca. You will explore its beautiful city walls, while taking in the wonderful views over roofs and alleys. From here, you move towards the seaside town of Viareggio, famous for its glamorous beaches. Your trip travels further inward towards the city of Pisa, one of the world’s most famous cities. After visiting the Piazza dei Miracoli, home of the "Leaning Tower," you will return to Florence in the early evening. Included in this tour is a pick up and drop off at the hotel (for those staying in hotels in the city centre), transport in luxury minivan, and a qualified English speaking driver.

Accommodation: L`orologio Hotel (4*)
Tuscany Highlights Tours 2018 - 2019 -  Piazza dei Miracoli
Piazza dei Miracoli

Day 4: Florence - Montepulciano

Meet your private driver and vehicle for a transfer to Montepulciano. Approximate travel time is 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*)

Villa Cicolina is an enchanting hideaway that was once a home to a noble family of Montepulciano. Secret gardens, romantic characteristics and sun-kissed hues floor every corner of this charming villa. 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 travertine infinity pool, and Jacuzzi.

Tuscany Highlights Tours 2018 - 2019 -  Montepulciano
Montepulciano
Tuscany Highlights Tours 2018 - 2019 -  Villa Cicolina
Villa Cicolina

Day 5: Montepulciano

Today you will be picked up at your hotel for your small group tour, to discover the gourmet food and beverage products of the region. The day will be dedicated to food and wine enthusiasts, as you wander around the Val di Chiana and the Val d'Orcia. Here you will get the opportunity to participate in various tastings, such as cheese, extra virgin olive oil, and typical cured meats sourced from the area. Next, you will taste handmade pasta, and enjoy a visit to a wine cellar with a tasting of Vino Nobile di Montepulciano. This tour includes: transportation with pick up and drop off at your hotel, guide, and tastings.

Accommodation: Villa Cicolina (4*)
Tuscany Highlights Tours 2018 - 2019 -  Cheese & Meat Platter
Cheese & Meat Platter

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*)
Tuscany Highlights Tours 2018 - 2019 -  Montepulciano Cellar
Montepulciano Cellar

Day 7: Montepulciano - Siena

Meet your private driver and vehicle for a transfer to Siena. Approximate travel time is 1 hour and 15 minutes.

Enjoy a half day walking tour with your private local guide. You will be met at your hotel and proceed on foot to view the top sights. Discover the most unusual and unforgettable aspects of Siena, including the Cathedral Crypt. See the city's monuments and hidden alleyways, which all give a true insight into Sienese Life. The tour starts from the Campo Square, following the pilgrims, wayfarers, artists, merchants and saint's and the traces they left behind in courtyards, fine old churches and forgotten frescoes. The tour will end with the 13th century frescoes in the Cathedral Crypt.

Accommodation: Athena (4*)

Surrounded by great ancient walls and breathtaking panoramic views of Tuscany lies Hotel Athena. Located in the heart of Siena, Duomo and Piazza del Campo are just walking distance away. The Hotel Athena provides rooms fitted with all the comforts you require for a 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.

Tuscany Highlights Tours 2018 - 2019 -  Siena
Siena
Tuscany Highlights Tours 2018 - 2019 -  Hotel Athena
Hotel Athena

Day 8: Siena

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

Enjoy a private tour with wine tasting and dinner today in the beautiful Tuscan countryside. Depart from hotel by private vehicle, driver and English speaking guide for a guided visit to the winery Setriolo and wine tasting. Continue with a guided walking along the ancient walls in Radda in Chianti followed by dinner at Restaurant Le Panzanelle. After the tour concludes you will return to your hotel in Siena.

Accommodation: Athena (4*)
Tuscany Highlights Tours 2018 - 2019 -  Montalcino
Montalcino

Day 9: Siena

Enjoy a private tour with a local English speaking Guide in the ancient town of San Gimignano. Tour the town with your own private vehicle at your disposal.  You will arrive at a Tuscan winery - Pietraserena and enjoy a guided visit with wine tasting.  Under the direction of an English speaking chef, you will start to work on a Tuscan menu.  Once finished, enjoy the dinner you have created with a glass of wine from the winery.  At the end of your meal, you will be returned back to your hotel. 

Accommodation: Athena (4*)
Tuscany Highlights Tours 2018 - 2019 -  San Gimignano
San Gimignano

Day 10: Siena

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

Accommodation: Depart (Int`l Airport) (standard)

Depart from International Airport. End of itinerary.

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.

Tuscany Highlights Tours 2018 - 2019 -   L'orologio Hotel
L'orologio Hotel
Tuscany Highlights Tours 2018 - 2019 -  Rooftop Views
Rooftop Views

Villa Cicolina (4*): Montepulciano

Villa Cicolina is an enchanting hideaway that was once a home to a noble family of Montepulciano. Secret gardens, romantic characteristics and sun-kissed hues floor every corner of this charming villa. 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 travertine infinity pool, and Jacuzzi.

Tuscany Highlights Tours 2018 - 2019 -  Villa Cicolina
Villa Cicolina
Tuscany Highlights Tours 2018 - 2019 -  Outdoor Lounge
Outdoor Lounge

Athena (4*): Siena

Surrounded by great ancient walls and breathtaking panoramic views of Tuscany lies Hotel Athena. Located in the heart of Siena, Duomo and Piazza del Campo are just walking distance away. The Hotel Athena provides rooms fitted with all the comforts you require for a 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.

Tuscany Highlights Tours 2018 - 2019 -  Hotel Athena
Hotel Athena
Tuscany Highlights Tours 2018 - 2019 -  Reception
Reception

Depart (Int`l Airport) (standard): Global Location

Depart from International Airport. End of itinerary.

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.
  • Gary C. — April 21, 2018 — Europe

    Two international experiences with Kensington and was thrilled with both!

  • Jo W. — April 15, 2018 — Europe

    We had a wonderful trip. Everything was on schedule as planned. Everyone we dealt with was friendly, polite and knowledgeable.

  • John C. — April 07, 2018 — Europe

    Our consultant Adam, provided excellent service and developed a thorough trip plan. This was our second trip with Kensington. Accommodations, guides and drivers were top notch. Thank you Kensington!

  • Bryce F. — April 03, 2018 — Europe

    My wife and I had an amazing trip! Our consultant arranged a customized honeymoon that fir my wife and my interests perfectly. Our guides were knowledgeable and patient. We coudln't have asked for a better experience. Top Notch!

  • Colin W. — March 08, 2018 — Europe

    Incredible trip, absolutely seamless. We loved every moment. From the planning to guides, drivers, accommodations, beautiful destinations.

  • Elaine P. — March 03, 2018 — Europe

    Our family had a wonderful trip to Iceland. It was perfect in every way! Cant wait to plan our next adventure with Kensington!

  • Erin R — December 21, 2017 — Europe

    Absolutely amazing trip to Ireland and the U.K! Our accommodations, tours, guides and all travel details were absolutely perfect. We had no problems, but if we did, Kensington would have been there to help in any way.

  • LaTisha S. — January 16, 2018 — Europe

    We had a wonderful time! The quality of the guides and service were top notch. We loved having the shared tours but with very small groups. Thank you for planning such a great experience.

  • Alfred N — May 08, 2018 — Europe

    Once again, another marvelous Kensington journey. Our advisor Ola was a joy to work with!

  • Rochelle Yedlin — October 06, 2017 — Europe

    We greatly enjoyed dealing with Kensington, from pre-trip planning, through the experience itself. Our advisor, Julienne Bourgeois was very helpful and responsive. All the arrangements went off without a hitch. We like all our drivers and guides and the trip was well balanced, exciting, easy and fun. All the accommodations were wonderful. It was a memorable 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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