Tuscany Highlights

10 days from $5,100 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. 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
    • Transfer - Private - Airport with Meet & Greet - Vehicle/Assistant/Driver
    • Italy - Welcome Package (1 pack)
  • 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 - Pisa, Lucca & Viareggio Tour (Max 8 pax) (11 hrs) - Vehicle/Driver-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
  • Day 5 Montepulciano
    Montepulciano
    • Tour - Shared - Tuscan Gourmet Tour (6 hrs) (max 7pax) - Vehicle/Guide/Driver
  • Day 6 Montepulciano
    Montepulciano
    • At Leisure
  • Day 7 Montepulciano to Siena
    Montepulciano to Siena
    • Montepulciano - Siena [1 hr 15 mins] - Vehicle/Driver(2)
    • Tour - Private - 1/2 Day Walking Tour (3 hrs) - Guide
    Breakfast
  • Day 8 Siena
    Siena
    • At Leisure
    • Tour - Private - 1/2 Day Wine Tasting & Dinner (6 hrs) - Vehicle/Guide/Driver
    Breakfast
  • Day 9 Siena
    Siena
    • Tour - Private - Tour - Private - 1/2 Day Siena (6 hrs) - Vehicle/Local Guide/Driver
    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.

Tuscany Highlights Tours 2017 - 2018 -  Michelangelo's Statue of David
Michelangelo's Statue of David
Tuscany Highlights Tours 2017 - 2018 -   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*)
Tuscany Highlights Tours 2017 - 2018 -  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 2017 - 2018 -

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*)

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 2017 - 2018 -  Montepulciano
Montepulciano
Tuscany Highlights Tours 2017 - 2018 -  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 2017 - 2018 -  Cheese & Meat Platter
Cheese & Meat Platter

Day 6: Montepulciano

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

Accommodation: Villa Cicolina (4*)

Day 7: Montepulciano - Siena

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

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 2017 - 2018 -  Siena
Siena
Tuscany Highlights Tours 2017 - 2018 -  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 2017 - 2018 -  Montalcino
Montalcino

Day 9: Siena

You will be met at the hotel by your private driver for a 45 minute panoramic drive to Siena where you will meet with your private local guide to begin a 2 hour guided walk. You will explore Siena city which is 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 built in the 13th century and the Torre del Mangia which is a bell tower rising at 102 meters high. The Sansedoni Palace and the Gaia Fountain are also close by where you will stop. You also get to see the gothic-style Duomo of Siena, which is a stunning medieval cathedral 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. Upon completion of the walking tour, your guide will leave you so that you can enjoy some free time (approximately 2.5 hrs) before driving back towards your hotel. Entrance fee to Siena, Duomo and crypt included.

Accommodation: Athena (4*)
Tuscany Highlights Tours 2017 - 2018 -  Siena
Siena
Tuscany Highlights Tours 2017 - 2018 -  Siena
Siena

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 2017 - 2018 -   L'orologio Hotel
L'orologio Hotel
Tuscany Highlights Tours 2017 - 2018 -  Restaurant with View
Restaurant with View

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 2017 - 2018 -  Villa Cicolina
Villa Cicolina
Tuscany Highlights Tours 2017 - 2018 -  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 2017 - 2018 -  Hotel Athena
Hotel Athena
Tuscany Highlights Tours 2017 - 2018 -  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.
  • Chuck B — November 09, 2017 — Europe

    Everything was perfect. The scheduling of drivers, trains and guides was perfect. Hotel accommodations (rooms) were the best at each hotel. Superb. Kensington Tours out did themselves.

  • Curtis M — October 25, 2017 — Europe

    Our trip experience was excellent. We are very likely to use Kensington again to plan our next trip to destinations that are new to us.

  • Betty Berke — November 09, 2017 — Europe

    Our trip was well organized and paced. Guides and drivers were all knowledgeable and friendly. Trip agent was also quite helpful.

  • Cynthia B — November 09, 2017 — Europe

    Amazing attention to detail and personalizing the experience for each of us. The tours provided Historical information specific to each of our interests.

  • Alyssa B — November 09, 2017 — Europe

    Thank you so much for helping make our honeymoon amazing! You guys made the process of planning and travel stress-free. We will never forget all the amazing experiences we had.

  • Lowell A — November 09, 2017 — Europe

    We totally appreciate the quality of the guides, knowledge, expertise, history of family and relationship, attention to detail. I especially appreciate the personal touch.

  • Kimberly M — September 15, 2017 — Europe

    Fiona was fabulous and planned a dream vacation for us from start to finish. Our guides and tours were all very personable, knowledgeable, and comfortable. Our drivers were very punctual and professional. Our itinerary and tickets kept us knowing exactly where and when we needed to be somewhere. The weather, food and hotels were amazing. We truly had our dream vacation and now need a beach vacation to recuperate from the fast paced vacation we just returned from! Would recommend your agency to anyone! Thank You!

  • James M — November 09, 2017 — Europe

    The information exchange in planning the tour went very well. The tour information and itinerary provided for the trip was the best and most complete for any tour we have taken. All drivers and tour guides were available at the exact minute scheduled. The guide in Athens, particularly, was excellent and answered all of our many questions as well as being very in tune to our needs. We had several questions for local staff and they responded immediately. In addition, we recommend the Hotel Kouros in Mykonos to anyone. A beautiful well maintained hotel with an excellent staff on all levels.

  • Elizabeth N — November 09, 2017 — Europe

    Our guide was very knowledgeable and accommodating. I appreciated the flexibility in catering to elderly travelers. We got so much more out of the trip with a private driver and guide. Worth the money. A memorable success!

  • Ronald C — November 07, 2017 — Europe

    Emma Winter, did an amazing job of trying to match the activities we were looking for. The whole process of arranging and completing our travel plans was seamless and hassle free. I'm definitely looking forward to working with Emma and Kensington Tours for our next excursion.

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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