Discovering the True Essence of Tuscany
Private & Customized Tours of Italy for the Sophisticated Traveler

4 days
4 nights

Winter in Tuscany

The off-season in Tuscany is a special time. The casual daily rhythms slow down, the crowds have left, village life returns to its natural pace. Gone is that bright sun that drenches Tuscany in extraordinary colors in summer...but winter has its own mystical shades evoking nostalgia of long-ago times, painting the landscapes and cityscapes in a surreal light that can enchant the soul. This is the time to discover the real Tuscany and to admire and appreciate Tuscans in their true nature. Sitting by the hearth of a blazing fire, enjoying a hearty traditional stew with a glass of red...perhaps within the walls of an ancient town dating back a thousand years or with a stunning view over the region's eternally green hills... This is the magic of WINTER IN TUSCANY. It is another kind of Tuscany, an undiscovered Tuscany, waiting to be explored.

HIGHLIGHTS OF THE DEAL - 4 days / 4 nights

- Private luxury vehicle service for all ground transportation with English-speaking driver.
- Explorations of the area around Siena and the spectacular Val d'Orcia region.
- Visits to ancient villages and hamlets such as Montalcino, Pienza, Montepulciano and Monteriggioni among others.
- Private walking tour of the city of Siena with a certified and licensed guide.
- Visit and tastings at a local winery producing the prestigious Brunello di Montalcino.
- Visit to see the production process, lunch & tasting at an organic cheese farm specializing in sheep and goat cheese.
- Visit to a historical abbey along the traditional pilgrimage route from Canterbury to Rome.
- Visit to an ancient Roman bath town with a dip in the area's hot spring pools.
- Gourmet cooking class with a local chef.
- Hearty homecooked meals, cozy fires and plenty of wine to warm up with!


PRICE PER PERSON (including taxes and fees)

Prices are per person, based on a booking of:
2 people: ¤1910 / 3 people: ¤1500 / 4 people: ¤1410 / 5 people: ¤1290 / 6 people: ¤1160 / 7 people: ¤1070 /

Please note that accomodations are NOT INCLUDED in the above prices. We work together with you to choose the best kind of accomodations according to your tastes, needs and budget. Please contact us for ideas and proposals!

For larger groups, please contact us for a price quote.
Please note that any request to customize the itinerary may incur additional costs.


All ground transportation in luxury Mercedes (or equivalent) full-optional vehicle with helpful English-speaking driver.
Daily Italian-style continental breakfasts
Private walking tour of Siena with certified and licensed guide
Guided tour and tastings at a local winery
Organic cheese farm tour with lunch and tastings
Gourmet cooking class with local chef
Entrance to spa pools (beauty and body treatments available at additional cost)
Visits to various picturesque medieval villages and towns
Lunch reservations for Days 1 and 4, all dinner reservations (meals not included)
Booking services for city and countryside accomodations (accomodation costs not included)*
Local taxes & fees

Please check our Accomodations page for info on our offerings in charming B&Bs, prestigious luxury hotels and exclusive, lovingly-restored country estates amidst picturesque Tuscan hills.

Please note the private car service for the above itinerary is for up to 8 hours a day. You may choose to extend the service for any day but this may incur additional costs.


Travel insurance
Entrance fees to museums, exhibitions, monuments and historic sites not mentioned in itinerary
Personal expenses
Anything not expressly mentioned above

Terms and Conditions


Full itinerary for our Winter in Tuscany 4 days / 4 nights

This is designed as a private tour and not a generic group tour so that you may customize it as you wish to suit your interests, needs and budget. Please see our ideas for other activities.
  • DAY 1

    - Morning arrival in Florence airport or train station.
    - Your private driver will pick you up and transfer you to your countryside accomodations.
    - Enjoy a scenic drive to to Montalcino, a marvelous hilltop village famous for its prestigious Brunello wines.
    - After exploring the town, stop by a local winery that produces Brunello for a tour of the estate.
    - Enjoy a delightful lunch prepared with local produce paired with tastings of the estate's wines.
    - In the afternoon visit a mystical ancient abbey located on the Via Francigena, the famous pilgrimage path leading from Canterbury to Rome. If the timing is right, you may witness the inspiring Gregorian chants performed by the abbey's friars several times a day.
    - Return to your country accomodation for a hearty dinner prepared with seasonal produce.
  • DAY 2

    -After breakfast your driver will pick you up and take you to the picturesque town of Pienza, renown for its many varieties of pecorino cheese (made with sheep's milk). Enjoy a leisurely stroll through this quaint medieval village, down its pecorino-scented streets.
    - Visit a local organic cheese farm perched on a hill with a spectacular view of the entire valley. Tour the farm, learn of the cheese-making process and enjoy a lovely lunch made with fresh local products including tastings of their cheeses, accompanied by the farm's own wine.
    - Spend the afternoon visiting another nearby hamlet before heading to Montepulciano.
    - Stroll down ancient cobblestone streets, visit artisan shops and the town's famous underground wine cellars.
    - Return to your country accomodation for a hearty dinner prepared with seasonal produce.
  • DAY 3

    - Start off the day with a fun and lively gourmet cooking class with our local chef. You will be guided through the preparation of a variety of traditional Italian recipes using local seasonal produce. Learn the fundamentals of Italian food philosophy and the basics behind its culinary tradition.
    - At the end of the lesson you will sit down and enjoy the multi-course meal you have just prepared with plenty of local wine to go with it.
    - After lunch visit an ancient Roman bath town whose warm therapeutic waters have been used to cure minor ailments for centuries.
    - Dedicate the afternoon to absolute relaxation while indulging in the area's private spa pools.
    - Return to your country accomodation for a hearty dinner prepared with seasonal produce.
  • DAY 4

    - Take the morning to visit the tiny fortress town of Monteriggioni.
    - Lunch in Monteriggioni or in Siena, depending on time.
    - Spend the afternoon in Siena, one of the most charming cities of Italy. Enjoy a guided private tour of the city, discover its history and the stories and legends behind the many facets of life in this medieval town.
    - Afterwards spend the afternoon freely roaming the winding cobblestone streets at your own pace, exploring its sites, shopping in the many specialty boutiques or simply people-watching at an outdoor café.
    - Dinner in one of Siena's wonderful local trattorias will bring a close to an incredible week.
  • DAY 5

    - After breakfast, your driver will accompany you to the Florence airport or train station.
    - Departure.
    - Arrivederci!