Fine Wines of Val d'Orcia & Maremma

  • Sample Itinerary
  • Experiences
  • Pricing
  • Featured Hotels
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Embark on a viticultural adventure as you taste your way through Southern Tuscany’s finest wine-making appellations from Chianti Classico to Maremma, and experience the fine wines, exceptional producers and gastronomic flavors of this unique region.

Sample Itinerary

Day 1

Begin your trip by arriving at Florence Peretola Airport where you will be greeted by your private chauffeur and transported to your luxury five-star boutique hotel nestled in the heart of Chianti Classico wine country. Enjoy a free day to settle-in and relax after your journey, then in the evening, enjoy an elegant dinner of seasonal Tuscan cuisine paired with estate produced wines.

Day 2

Whisk away for a day of wine tasting through Tuscany’s Chianti Classico wine appellation. Begin the day with a visit to one of the area’s most esteemed producers of Chianti Classico and Super Tuscan vintages where you’ll enjoy a private tour of the estate followed by an exclusive tasting. Next, you will travel by chauffeur to the castle estate of one of the finest winemaking dynasties in Italy. Said to be the oldest winery in Italy, the estate dates back to the 11th century and the family has for centuries played an integral role in the development of the Chianti Classico wine appellation, while producing their own exceptional wines since the 19th century. Upon arrival you will partake in a private visit of the estate cellars before enjoying a special tasting of the producer’s finest Super Tuscan and Chianti Classico Riserva wines in the historic dining room of the estate’s 12th century castle. After your tasting has concluded you will savor a lunch of local Tuscan cuisine at the estate’s osteria. After lunch concludes, your chauffeur will transport you back to your hotel for a free evening.

Day 3

Depart Tuscany’s Chianti Classico wine country by chauffeur for the breathtaking landscapes of Southern Tuscany’s Val d’Orcia where you will arrive in the famed wine town of Montepulciano. Enjoy a privately guided tour of Montepulciano before stopping for lunch at a quaint enoteca where you’ll sample typical dishes from the province paired with local wines. Depart Montepulciano by chauffeur for check-in to your 18th century villa turned luxury accommodation. After check-in, enjoy an afternoon cooking class where you’ll learn how to prepare regional specialties before sitting down to enjoy the dishes you’ve created paired with wines from the Montepulciano appellation.

Day 4

Depart for a chauffeured day of wine and cheese tasting throughout Val D’Orcia, starting with a visit and seated tasting at one of the region’s most prolific producers of Brunello di Montalcino. After your seated tasting, savor a lunch of classic dishes from Montalcino paired with Brunello wines while taking in stunning views of Val D’Orcia. After lunch travel to Pienza for some free time to explore the town, then in the afternoon be transported to the countryside for a visit to the farm of a local Pecorino di Pienza cheese producer where you’ll learn about the traditional cheese-making techniques of the region while sampling artisanal cheeses along with other special delicacies.

Day 5

Depart Val d’Orcia for Southern Tuscany’s wine producing appellation of the Maremma, famed for its exceptional wines and rolling hillsides lined by cypress tress to the sea. Arrive at your five-star luxury wine country resort, L’Andana, owned by world class entrepreneurs, hoteliers and winemakers, the Moretti family. Upon arrival, check-in to the hotel, a former Medici villa, before enjoying free time to explore the estate’s breathtaking grounds, which include a historic chapel, lovely gardens, an outdoor swimming pool, tennis courts, golf driving range and wine cellar. In the afternoon, enjoy either an exclusive Gourmand Spa package at L’Andana’s ESPA Spa or partake in a hands-on cooking class of classic Tuscan recipes followed by a delectable meal of your creations.

Day 6

Set-off by chauffeur for the coastal wine production zone of Bolgheri, one of Tuscany's most revered appellations, to sample the region's fine Super Tuscans. Start the day at a famed producer of Bolgheri superiore wines for a visit of the estate’s vineyards and cantina before enjoying a three flight tasting of the winery's best Bolgheri reserves, accompanied by bruschette, salumi, and regional cheeses. Next, depart for famed Maremma producer Petra, celebrated for their exceptional wines and the architectural splendor of their Mario Botta designed winery. Partake in a very exclusive private winery tour and five-wine vertical tasting of historic estate vintages, followed by a farm to table lunch highlighting seasonal flavors.

Day 7

Whisk away by chauffeur to the medieval town of Scansano, the epicenter of Morellino di Scansano wine production, where you will enjoy a privately guided visit of the town and learn more about its history and fabled wine producing heritage. Following your tour, depart Scansano by chauffeur for a wine tasting at renowned Fattoria Le Pupile, the winery of Elisabetta Gippetto, known as the “queen of Morellino.” During your visit you will enjoy an exclusive 8 wine tasting followed by an aperitivo lunch in the estate’s vineyards. After your tour and tasting, depart for the nearby hilltop village of Pitigliano for a privately guided visit of its historic center, known as “the little Jerusalem” for the presence of its Jewish community throughout the centuries. Originally an Etruscan settlement, the vestiges of its medieval, Renaissance and Jewish past can be observed in Pitigliano’s architecture, original city walls and 16th century synagogue.

Day 8

Depart Maremma wine country for Florence Peretola airport for your return flight home or to continue on to the next leg of your trip.

Experiences We Recommend

  • Private winery visit with tasting of DOCG Chianti Classico in historic castle
  • Typical bistecca Fiorentina lunch at gourmet butcher shop
  • Cooking class with Michelin-starred chef in Chianti Wine Country
  • Visit to historic Vin Santo aging room in Montepulciano with seated tasting
  • Expert led Montalcino winery tour with premium Brunello di Montalcino tasting
  • Cheese making demonstration and tasting at traditional Pecorino di Pienza cheese farm
  • Private winery tours in Bolgheri and Maremma with seated tasting of Super Tuscans
  • Architecture meets wine experience at Mario Botta designed winery
  • 7-flight tasting and vineyard walk at premium small batch Morellino di Scansano producer
  • Guided historical walking tour of Pitigliano, known as the "Little Jerusalem" of Southern Tuscany


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

  • Lorena M.

    Tuscan Vineyards to Ligurian Coast
    This trip was absolutely astonishing and was above what we expected, but yet nothing less knowing the caliber of ownership of CountryBred!
  • Frances & Thomas K.

    Gourmet Switzerland: Lavaux to Luzern
    We can't say enough about our trip at every level. The first class accommodations; the wonderful food and wine experiences; the regional ambassadors; and most importantly, the intricate trip details that were so well planned and executed throughout our stay.
  • Jessica & Len G.

    Southern Italy From Amalfi to Puglia
    This is our second trip we have taken with CountryBred and the attention to detail and the caring on every level is quite extraordinary. We love the company and the quality of everything they touch: the hotels, the level and selection of restaurants, the guides and drivers. We rate everything as "exceptional" because truly it is!

Crafting the Experience

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

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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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