Tuscany: Art Cities & Wine Country

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
  • Custom Quote

Delve into Tuscany’s gilded heritage through its venerated artistic, historic and viticultural delights. Feel the Tuscan region’s fabled allure come to life as you luxuriate in every ruby sip and sun-drenched vista.

Sample Itinerary

Day 1

Your robust exploration of Tuscany will take you through the region’s most famed art cities and lush wine country, beginning in Florence. Be greeted at Florence Peretola Airport by your private chauffeur and travel to your historic luxury accommodation in the heart of Florence. After check-in, spend free time relaxing or begin exploring the city's picturesque streets at your leisure. In the evening dine at an elegant eatery noted for its historic ambiance and Central Italian cuisine.

Day 2

The art and architecture of the Renaissance will be brought to life as you discover the era’s finest treasures within the famed salons of the Galleria Uffizi and the Galleria Dell’Accademia, with the help of a local art expert. Stop for a lunch of typical Tuscan fare at a charming eatery near Ponte Vecchio. Afterward, visit a workshop dating back to the Renaissance to learn about the artisan traditions for sculpting wood and semi-precious stones, as well as woven tapestries. End the day with a visit to the vibrant Oltrarno district, best known for its community of artisans and their unique boutiques.

Day 3

Begin the day with a chef-led cooking class of authentic Tuscan recipes at a gourmet culinary school, before dining on your delectable creations for lunch. In the afternoon, embark on a private boat tour down the River Arno before experiencing the wonder of the 16th century Boboli Gardens with your own private guide.

Day 4

Following check-out, your chauffeur will transport you to the heart of Chianti wine country, where you will begin the day with an exclusive wine tasting at the renowned Ruffino family estate. Afterward, visit the shop of the noted butcher Dario Cecchini to dine on his artisanally crafted salumi and fine cuts of Tuscan meat paired with local wine. In the afternoon check-in to your splendid 18th century villa turned wine country retreat in the hills of Montepulciano.

Day 5

Spend the morning exploring the UNESCO world heritage city of Siena with an insider’s perspective. Your local expert will guide you on a private walking tour of the city to experience such signature sites as the iconic Piazza Del Campo, Siena's breathtaking 12th century cathedral, and its historic contrade neighborhoods. Next, set-off by chauffeur for an organic farm to savor an al fresco lunch highlighting the estate's renowned production of extra virgin olive oil and San Gimignano DOCG white wine. In the afternoon travel to the UNESCO designated center of San Gimignano to learn about the unique history of its medieval towers while taking in scenic vistas of the surrounding landscape, during a private walking tour.

Day 6

Embark on a day of wine tasting through the vineyards of Montalcino and Montepulciano. Visit some of the area's most revered boutique wine producers while sampling local gourmet specialties to accompany the region’s signature vintages. In the evening, spend free time in the picturesque hilltop town of Pienza before dining on classic Tuscan specialties at a traditional trattoria located in the historic heart of the city.

Day 7

After breakfast depart Montepulciano by chauffeur for your return flight or the next leg of your adventure.

Experiences We Recommend

  • Visit to workshops dating back to the Renaissance to learn artisanal craftsmanship of wood sculpture, semi-precious stone sculpting and tapestries
  • Private boat tour along the river Arno in Florence
  • Privately guided art tour of Galleria Uffizi and the Galleria Dell’Accademia with no-line access
  • Private cooking class with gourmet chef in modern design culinary space
  • Visit of the Oltrarno artisan district
  • Guided walking tour of the Boboli Gardens and Pitti Palace
  • Guided architecture and interior design tour of private noble palaces
  • Visit to exclusive perfume shop dating back to the 17th century
  • Private winery visits with premium tastings in Chianti Classico wine country
  • Cooking class of seasonal Sienese cuisine at esteemed winery
  • Invite only visit to contrada of Siena to learn about Palio horse racing tradition


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Italy Encounters begins at:

  • $850-$1,000/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Janet M.

    Cultural & Culinary Escape to Tuscany and Liguria
    "It is with pleasure, that I write about the 12 day tour of Toscana and Liguria that CountryBred handcrafted for our family. On very short notice of about 9 weeks, and with little to go on"
  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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