For the Perfect Tuscan Experience

If you consider yourself a wine connoisseur or even a wine lover and you want to experience the best wine country experiences that Tuscany has to offer, then this is the Wine Tour for you! You will spend a week visiting the best appellations in this gorgeous part of Italy. The tour begins and ends in Florence, and is a private chauffeured tour. You will spend your first night in Florence, home to Michelangelo, the Medici and some of the most beautiful architecture in the world. Dine at Cibreo, Florence’s hottest restaurants for Foodies. From Florence, you will travel through the scenic wine country of Chianti Classico, quintessential Tuscany. Cypress lined narrow roads and medieval hill topped wine villages are the classic images of Chianti, very photogenic. You will visit top producers such as Badia a Coltibuono (whose winery is one of the most beautiful in Italy).

Next on this fantastic Tuscan wine tour is a visit to the exquisite Tuscan town of Siena, famed for its medieval Palio, the zebra striped duomo and its “holy wine” (Vin Santo) served with cantucci. Enjoy a private guided tour of with a local art guide, to gain a deeper appreciation of this beautiful town. From Siena, you will visit Montalcino and Montepulciano (to top Brunello di Montalcino and Vino Nobile di Montepulciano producers) and you will sleep in a luxurious castle located at the top of a hill with dramatic views of the valley beneath. From Montalcino you will spend two nights in a luxurious villa in the wild Maremma, home to Italy’s famed “Super Tuscan Wines”. Savor amazing wines and enjoy some incredible meals in this lovely, quite undiscovered area of Tuscany. Your tour will conclude back in Florence, and you will leave Italy with many gourmet gifts and memories to last a lifetime.


Tuscany Wine Tour Highlights:

  • Private Chauffeured Mercedes
  • Winery Visits and Tastings in Chianti, Montalcino, Montepulciano and Maremma
  • Private tours of Florence and Siena
  • Special Gourmet Experiences
  • Luxury small boutique hotels

Below is a suggested Itinerary for your private Tuscany Wine Tour

  1. Florence

    Private Art Guided Tour & Gourmet Dining

    Beautiful Florence
    Beautiful Florence
    • 5* Star Villa Style Hotel
    • Dinner with wine
    • Private Chauffeured Mercedes

    Your English speaking private chauffeur will meet you at the airport, and you will transfer to your very special boutique hotel, in the wonderful Piazza Santa Maria Novella, just a few steps from the Renaissance church bearing the same name.

    Welcome to Florence! Check into your luxurious hotel, a small mansion that resembles an art gallery. After you freshen up, your own private art guide will pick you up and you will discover the best highlights of Florence. After a welcome aperitif with your charming guide, enjoy a guided walking tour of Florence’s “Centro Storico” including the Mercato Centrale (the mind boggling food market), the Piazza della Signoria (the gorgeous square where the Uffizi gallery, Neptune’s fountain and the Palazzo Vecchio are all located), and plenty of hidden gourmet gems enroute. The city’s cobblestone streets, lively atmosphere, and stunning artistic history all add to the enchanting atmosphere. Many writers and artist have been captivated by this city including, Henry James, Albert Camus, and Mark Twain.

    In the afternoon, sip a glass of wine on a stylish terrace or get in some shopping or sightseeing. Tonight’s dinner is a special treat- dinner at Cibreo. This restaurant is one of favorite gourmet haunts in Italy. The New York Times described Fabio (Cibreo’s chef owner) best when they said, “he talks like a poet and cooks like a wizard”. Fabio is definitely one of the best chefs in Florence, and indeed Italy, a maestro.

  2. Florence- Chianti Classico - Siena

    Chianti Classico Wine Tasting

    Badia a Coltibuono
    Badia a Coltibuono
    • Florence- Chianti Classico wine villages- Siena
    • Full breakfast, wonderful Tuscan lunch with wine
    • Private Chauffeured Mercedes

    Full breakfast in your sophisticated hotel. Today will be a wine tasting extravaganza!

    Your charming chauffeur guide will pick you up at your boutique hotel and you will transfer by Mercedes to the delicious Chianti Classico wine region, through the enchanting Chiantigiana route. This is the land of Sangiovese and you will taste different expressions of this noble grape. Begin with a visit to a historic estate such as the beautiful Badia a Coltibuono property, with its abbey and manicured gardens.On a private tour, explore the grounds and finish with a tasting of their best wines and even Balsamic Vinegars and Olive Oils.

    Carry on to Antinori’s Badia Passignano estate, our absolute favorite in Chianti. Your exuberant host will take you on a memorable tour of the property and you will taste some of Antinori’s mythical wines such as Tignanello, Cervaro della Sala, Chianti Classico Riserva Badia a Passignano, Guado al Tasso, and Solaia. After the cellar visit, enjoy an Extra Virgin Olive Oil tasting followed by an outstanding lunch at the Michelin starred Osteria, with dishes paired with the aformentioned following wines. Top class.

    After lunch, you will carry on to the spectacular town of Siena. Your own personal art guide will meet you and take you on an “insider’s tour” of Siena. Walk off that lunch and discover some wonderful hidden corners of this charming town.

    After your tour of Siena you will travel to your hotel for the next two nights- a hill-topped castle! Free evening to enjoy the hotel restaurant on your own.

  3. Montalcino- Montepulciano

    Montalcino & Montepulciano VIP Wine Tastings

    Montalcino Vineyards
    Montalcino Vineyards
    • 5* wine resort in the countryside of Montalcino
    • Full breakfast, Lunch with wine in private setting at winery
    • Private Chauffeured Mercedes

    Full breakfast in the castle. Today, you will taste incredible Montalcino and Vino Nobile di Montepulciano wines!

    Your chauffeur guide will pick you up and take you first to Montalcino. This ancient village is best known for its elixir red Brunello di Montalcino wines, made with the Sangiovese Grosso grape varietal. Enjoy a VIP private visit to a Brunello producer such as the prestigious Nardi estate. On the way to the winery, you can stop for a quick visit to the stunning ruins of the 9th century Abbazia di Sant’Antimo. At the winery you will tour the barrel caves, the installations, take in the gorgeous views and taste Brunello “Riservas” and also Rosso di Montalcinos.

    Lunch will be with your charming hosts at the winery itself in a private setting, intimate and special. After a delicious lunch, carry on to Montepulciano.

    Of Etruscan origin, Montepulciano is one of the most beautiful (and steepest) hill towns in Tuscany. The fortified hamlet was built along a narrow bridge made of natural tufa. Montepulciano is an absolute treat and of course a mythical name for wine lovers. Perfectly preserved and historic, there are darling enotecas (wine bars), gourmet shops and historic palaces, fabulous. The Vino Nobile wines of Montepulciano, were the first to be given the ultimate quality level of DOCG certification. Which is why you are here! You will visit a top estate such as Valdpiatta or Avignonesi and enjoy a tasting of Vino Nobile wines.

    In the late afternoon, enjoy free time on your own in Montepulciano and transfer back to your winery resort.

  4. Montalcino- Pitigliano- Maremma- Castiglione della Pescaia

    Maremma, Home of the Super Tuscans

    The stunning medieval town of Pitigliano
    The stunning medieval town of Pitigliano
    • 5* Ultra Luxury Villa style hotel, deluxe room
    • Full breakfast, Lunch in Pitigliano (with wine)
    • Private Chauffeured Mercedes

    Full breakfast at your castle hotel.

    Today, you will travel southwest, from Montalcino to the mythical Maremma Wine Region. The drive takes you from the cypress-covered hills of Montalcino into the beautiful and wild Maremma region. The Maremma is one of the most interesting areas of Tuscany, and curiously “undiscovered” by non-Italians. It is more famous locally for its glamorous beaches on the Tyrrhenian sea, and millionaire’s yachts in Porto Argentario. It is also, interestingly, famous for its cowboys. The ‘butteri’ (cowboys) notoriously beat Buffalo Bill in 1911 when he challenged them to a contest of breaking in the colts.

    For us wine lovers, it is also the home of some of the biggest wine names in the world such as Ornellaia and Sassicaia. We will save the wine tasting for tomorrow to give you a chance today to soak up some culture. You will visit Montemerano, Pitigliano and other little villages before checking-in into your beautiful and villa hotel. Lunch in this gorgeous town, called Italy’s “Little Jerusalem” for its Jewish heritage and ancient synagogue. Afternoon, sightseeing in wonderful little villages.

    In the evening you will arrive at your country villa style hotel, a delicious property. This is a five star hotel that was once an aristocratic hunting lodge. It is certainly the most luxurious property in Southern Tuscany and you will love it! Alain Ducasse, France’s most famous chef, is the consultant chef here and he has created a Tuscan inspired creative menu, wonderful. This evening is free to enjoy the restaurant of the hotel.

  5. Castiglione della Pescaia- Maremma

    VIP Wine Tastings at Petra & Ornellaia

    The Celebrated Ornellaia
    The Celebrated Ornellaia
    • 5* Ultra Luxury Villa style hotel, deluxe room
    • ull breakfast, wine tastings, olive oil tasting, full lunch with wines
    • Private Chauffeured Mercedes

    Full breakfast in your elegant Tuscan country hotel.

    Today is all about Super Tuscans! In the last 3 decades, there has been an explosion of tiny “garage” style wineries making some of the world’s best (and most expensive) wines. These days, the wines from Maremma can cost up to 500 dollars a bottle!

    You will enjoy a wonderful wine tasting day, taking in two superb cellars such as Petra (designed by the famed Mario Botta) and Ornellaia in the castle crowned village of Bolgheri (one of the best cellars in Italy). After your wine “breakfast”, you will have one of the best meals on the tour- an unforgettable lunch at our favorite restaurant in the region, Ombrone. This converted 13th century “Frantoio” (olive oil mill) is fabulous. Your hosts are extremely charming and you will enjoy an olive oil tasting before your Tuscan style lunch.

    In the afternoon, your chauffeur guide will be on hand and you can visit the beaches of the Maremma, do some sightseeing in medieval villages or enjoy some time back to your ultra luxury little hotel.

  6. Maremma- San Gimignano- Florence

    Return to Florence via San Gimignano

    San Gimignano skyline
    San Gimignano skyline
    • 4* Luxury Hotel, Stylish converted mansion in Florence, in a superior room
    • Full Breakfast Farewell present in your room
    • Private Chauffeured Mercedes

    Full breakfast at elegant hotel.

    Today you will enjoy an excursion to San Gimignano on the way back to Florence. San Gimignano is a gorgeous medieval village called “the Manhattan of Tuscany” because of its many towers (medieval, of course!).

    From the wild Maremma you will drive northeast into the beautiful rolling hills covered in vines, olives and historic villages. Stop in San Gimignano with your driver guide for a few hours. Take in the lovely cobblestoned streets lined with ristoranti, wine shops, ceramic shops. Visit the medieval palaces and art museums. Sit on a terrace before you leave, tasting the local white tipple, Vernaccia di San Gimignano.

    Upon arrival to Florence, you will stay in the same lovely boutique hotel as your first night. Enjoy a last night in Florence on your own, with a last gift waiting for you in your room. We recommend Enoteca Pinchiorri for dinner if you want a famed Michelin starred chef or Alle Murate if you are looking for something charming and lively, enjoy your last notte in Florence.

  7. Florence- Ponte a Cappiano- San Miniato

    Olive Oil Tasting and Farewell Wine Experience in San Miniato

    Leonardo Beconcini, Pietro Beconcini Winery
    Leonardo Beconcini, Pietro Beconcini Winery
    • 4* Luxury Hotel, Stylish converted mansion in Florence, in a superior room
    • Full Breakfast, Brunch with wine
    • Private Chauffeured Mercedes

    Enjoy a lighter breakfast today as you will delight in a hearty Italian brunch later on this morning.

    You will travel west towards the hills of Ponte a Cappiano, a historic hamlet located on the ancient Via Francigena and sprinkled with olive groves. Your first experience of the day is a convivial and unique olive oil tasting at a top quality producer Poggio Cappiano. Enjoy a walk through the olive trees (magnificent in late autumn) and learn about Tuscany’s olive varietals and the process of making extra virgin oils. Finish the visit with a tasting of the full range of their premium olive oils as well as a delicious brunch of cured hams, local cheeses and of course- olives!

    Carry on towards the medieval hamlet of San Miniato, to the Beconcini wine estate, one of our favorite wineries in Italy. Your hosts will warmly welcome you to their small high end estate, show you the vineyards, collect fossils along the way (the soil here is rich in ancient fossils), and you will conclude your terrific visit with some wine tasting and home cooked food in their family home. Very unique experience and a definite highlight of your wine tour in Tuscany. In the late afternoon you can explore Pisa or head back into Florence. The evening is yours to relax and sip a glass of wine in a beautiful Florentine piazza.

  8. Florence

    Depart from Florence

    Buon Viaggio!
    Buon Viaggio!
    • None
    • Full Breakfast
    • Private Chauffeured Mercedes

    Full breakfast at elegant hotel.

    This concludes your wine tour of Tuscany, with wine tasting in Chianti, Montalcino, Montepulciano and the Maremma. You will leave with many gourmet goodies and gifts, and above all with a deeper appreciation of Tuscan wines, art and architecture.

    We can arrange extra days in Rome or Venice, please contact us for details.

More information

If you would like us to customize an exclusive, luxury tour for you, get in touch with us and let us know your travel plans. We offer luxury food and wine tours for private groups of minimum 2 guests. All of our private, chauffeured tours are available year round upon request.

Contact us for your personalized quote!
Cellar Tours Private Luxury Food & Wine Tours

Cellar Tours

Cellar Tours is a Luxury Travel Specialist, operating since 2003 and offering exclusive Mercedes chauffeured Gourmet Vacations in Chile, France, Italy, Ireland, Portugal, South Africa, and Spain. We specialize in luxurious custom designed vacations, events and incentives related to food and wine. We are proud members of Slow Food, UNAV (Travel Agency Association in Spain), and the IACP (International Association of Culinary Professionals).

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