Tuscany: Art Cities and Wine Country

Tuscany: Art Cities and Wine Country

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.

Tuscany: Art Cities and Wine Country

Sample 7-Day Private Tour Itinerary

Florence, Chianti Wine Country, Montepulciano, Siena, San Gimignano, Montalcino, Pienza


Day 1

Ponte Vecchio

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 the airport by your private chauffeur and be transported to your five-star luxury 16th century palace in the historic heart of Florence. Relax and enjoy your hotel’s sunlit courtyard or meander the surrounding picturesque streets and open air eateries in preparation for tomorrow’s full day of activity. In the evening dine at an elegant eatery noted for its historic ambiance and Central Italian cuisine.

Day 2

private_custom_luxury_tours_tuscany_countrybredThe 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 local’s only eatery near Ponte Vecchio. Afterward, visit the Florentine neighborhood of Oltrarno, best known for its abundant community of artisans and their unique workshops and boutiques.

Day 3

Spend the day experiencing the wonder of the Pitti Palace and Boboli Gardens with your own private guide before savoring regional dishes like Bistecca Fiorentina and Ribollita bean soup at one of Florence’s most coveted trattorias. Enjoy a free evening to explore the city at your leisure.

Day 4

tuscany_gourmet_food_tour_countrybredDepart Florence for the heart of Chianti wine country, where you will begin your day with an exclusive wine tasting at the renowned Ruffino family estate. Afterwards visit the shop of the noted butcher Dario Cecchini and dine on his artisanally crafted salumi and fine cuts of Tuscan meat paired with local wine. In the afternoon depart for your luxury Montepulciano country retreat restored to its original splendor as an exquisite 18th century aristocratic summer home. In the early evening partake in an exclusive cooking class, where you will learn how to prepare quintessential Tuscan fare before savoring your creations for dinner.

Day 5

siena_private_tour_countrybredSpend the day exploring the UNESCO world heritage site of Siena. Enjoy an insider’s perspective of the city with a privately guided walking tour of Siena’s contrade neighborhoods and its breathtaking 12th century cathedral with a local expert. Set-off via private chauffeur for the countryside surrounding San Gimignano for a rustic lunch in an organic farmhouse renowned for producing its own oil and wine. In the afternoon make your way to the walled city center of San Gimignano for an unique look at its tower houses dating back to the 14th century while taking in beautiful vistas of the surrounding countryside before returning to Montepulciano.

Day 6

monteriggioni_custom_tours_tuscany_countrybredEmbark on a day of wine tasting through the vineyards of Montalcino and Montepulciano. Visit some of the area’s best boutique wine producers and while sampling the regions wild boar salumi to accompany the region’s signature vintages. In the evening, enjoy some free time in the charming town of Pienza before dining on classic Tuscan specialties at a traditional trattoria located in the historical heart of the city.

Day 7

Depart Montepulciano for your return flight home or the next leg of your trip.

-As part of our Enriched Booking process your customized itinerary will be designed with the assistance of a CountryBred specialist.
-This trip can be specifically tailored for organizations, associations and corporate incentives.


The recommended tour length for this sample itinerary is 7 days/6 nights with pricing options beginning at $4,875/person based on double occupancy. Please note that the “Share Bred With Friends” preferred pricing program will be applied to travel parties of four or more.

The final price of your custom trip 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.

Included in this sample CountryBred Encounter are:

  • 6 Nights at CountryBred approved, luxury boutique accommodations
  • Deluxe and/or Superior room stays
  • Private luxury chauffeur for all intercity travel, day trips and excursions
  • Airport / Train station transfers with baggage assistance
  • Private touring with professionally licensed local guides and cultural experts
  • Flexible guided time with local experts based upon your preference
  • 3 Gourmand dinners
  • 5 Regionally authentic lunches
  • Exclusive winery visits and tastings
  • Daily breakfasts
  • Museum tickets & entrance fees
  • All gratuities & taxes
  • Traveler welcome package including customized Culture Guide
  • Please note that transfers to airports and/or train stations outside of Florence Peretola Airport and Santa Maria Novella Train Station for arrival/departure, are available upon request for an additional, supplemental fee. Airfare is not included.

Featured Deluxe Hotels

Palazzo Magnani Feroni

A fixture of Florentine society for more than 500 years, the magnificent Palazzo Magnani Feroni has been enchanting visitors since its days as the private residence of the aristocratic Feroni family during the Renaissance. Nestled in one of the city’s most cherished historic quarters, the Borgo San Frediano, Palazzo Magnani Feroni is one of the oldest and most esteemed palaces to stand amongst the noble residences and medieval towers that so uniquely characterize the neighborhood. Today a five-star, all suite luxury hotel, the Palazzo retains the ambiance of a noble Renaissance home, transporting guests to the opulence of the 1500′s and offering a window into the cultural heritage of Florence’s golden age.

Villa Poggiano

Situated in a lush park overlooking the green hillsides of Val d’Orcia, Villa Poggiano is the perfect luxury country retreat from which to experience the best that Montepulciano wine country has to offer. Proudly owned and operated by the Savini family, the villa has been completely restored to its original splendor as an exquisite 18th century aristocratic summer home, first built by the Poliziana Gagnoni family. An architectural gem that retains the charm and character of a refined Tuscan residence, the villa incorporates all of the deluxe touches one would expect of a luxury accommodation while also paying special attention to retain the warmth and welcoming spirit of a family owned establishment. Each room is adorned with antique furnishings, classical artwork and elegant trimmings to create a warm and comfortable atmosphere that is consistent with the overall ambiance of the villa. The guestrooms also feature oversized windows for enjoying ample sunshine and splendid views of either the villa’s expansive Italianate garden and marble swimming pool or breathtaking views of the vineyards and olive groves that are so characteristic of Val d’Orcia.

Encounter Something Unexpected

Experiential travel takes time, passion and local ingredients to make something truly special. When you travel with CountryBred, you can look forward to the following:

      • A personalized and private travel experience, whether you’re a solo voyager, a couple, group of friends, family or an organization


      • A well crafted itinerary that is a reflection of your cultural interests, which we bring to life through our unparalleled insider knowledge, local access and dedicated team


      • A thoughtful travel pace that leads you down roads less traveled while leaving time to enjoy the quiet moments that make for remarkable memories


      • Enriching activities that immerse you in local culture and traditions


      • Premium accommodations that are distinct reflections of the regions they reside in, with real histories and real people behind them


      • Regional ambassadors and local cultural experts that go beyond educating, to invite you into their community and introduce you to their unique corner of the world.


    • Authentic dining that ensures you enjoy the finest in regional culinary traditions from quaint family owned eateries to innovative Michelin-starred restaurants. Each meal is in itself a work of art, passionately prepared and uniquely local.


Authentic is Premium