Tuscany Wine Tour

Suggested Tailored Wine Tour Itinerary

1. Florence

   

   Private Art Guided Tour & Gourmet Dining

   • 5 * Boutique Hotel
   • Dinner with wine
   • Private Chauffeured Mercedes

   Your private chauffeur will meet you at the airport, and you will transfer to your boutique hotel in the beautiful heart of Florence, at walking distance from Piazza Santa Croce, Duomo, and Piazza Santa Maria Novella, just a few steps from the Renaissance church bearing the same name. Welcome to Florence! Check into your luxurious hotel.

   After you freshen up, your 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 Ponte Vecchio, the Uffizi gallery, the Piazza Della Signoria (the gorgeous square where Neptune’s fountain, Loggia Dei Lanzi and the Palazzo Vecchio are all located), and plenty of hidden gourmet gems en route. The city’s cobblestone streets, lively atmosphere, and stunning artistic history add to the enchanting atmosphere. Many writers and artists 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 go shopping or sightseeing. Tonight’s dinner is a special treat- dinner at Cibreo. This restaurant is one of the favorite gourmet haunts in Italy. The New York Times best described Fabio (Cibreo’s chef-owner) when they said, “he talks like a poet and cooks like a wizard.” Fabio is one of the best chefs in Florence, and indeed Italy, a maestro.

    

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2. Florence- Chianti Classico – Siena – Montalcino countryside

   

   Chianti Classico Wine Tasting

   • 5* hilltop castle in the countryside of Montalcino
   • 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 grape, and you will taste different expressions of this noble grape.

   Begin with Antinori’s Badia a 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, Brunello di Montalcino, 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 aforementioned following wines. Top class.

   After lunch, carry on with a visit to a historic estate such as the beautiful Castello di Ama property, with its art collection and manicured gardens. On a private tour, explore the grounds and finish with a tasting of their best wines, including single-vineyard crus Bellavista, La Casuccia and Supertuscan L’Apparita and even their precious Extra Virgin Olive oil, produced with handpicked Correggiolo, Moraiolo, Leccino, and Frantoio olives, pressed the same day at their on-site mill.

   Next is the spectacular town of Siena. Your art guide will meet you and take you on an “insider’s tour” of Siena. Discover some beautiful 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.

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3. Montalcino - Montepulciano

   

   Montalcino & Montepulciano VIP Wine Tastings

   • 5* hilltop castle in the countryside of Montalcino
   • Full breakfast, Lunch with wine
   • Private Chauffeured Mercedes

   Full breakfast in the castle. Today, you will taste incredible Brunello di 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 Casanova di Neri 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 Rosso di Montalcino Giovanni Neri, Brunello di Montalcino White Label, Brunello di Montalcino Tenuta Nuova, Brunello di Montalcino Cerretalto and Pietradonice.

   Lunch will be at one of our favorite traditional restaurants in Tuscany, intimate and exclusive, with breathtaking views. 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 , which 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 historical, 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 Bindella, Boscarelli, 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 resort.

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4. Montalcino- Pitigliano- Maremma- Castiglione della Pescaia

   

   Maremma, Home of the Super Tuscans

   • 5* Ultra Luxury Villa style hotel
   • 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 exciting 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 most significant 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 to your beautiful and villa hotel. Lunch in this gorgeous town called Italy’s “Little Jerusalem” for its Jewish heritage and an ancient synagogue. Afternoon, sightseeing in beautiful little villages.

   In the evening you will arrive at your country villa-style hotel, a delicious property. This five-star hotel that was once an aristocratic hunting lodge. It is undoubtedly one of the most luxurious properties in Southern Tuscany, and you will love it! Enrico Bartolini, an Italian chef with a total of 8 Michelin stars, created a Tuscan inspired creative menu, delicious!. This evening is free to enjoy the restaurant at the hotel.

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5. Castiglione della Pescaia - Bolgheri

   

   Iconic Wine Tastings at Guado al Tasso, Sassicaia & Ornellaia

   • 5* Ultra Luxury Villa style hotel
   • Full breakfast, full lunch with wines
   • Private Chauffeured Mercedes

   Today is all about Super Tuscans! In the last three decades, there has been an explosion of wineries making some of the world’s best (and most expensive) wines, mainly Bordeaux-style blend. 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 Guado al Tasso and Ornellaia in the castle-crowned village of Bolgheri (one of the best cellars in Italy).

   Lunch will be at lovely Enoteca San Guido, simple yet elegant. Your hosts are incredibly charming, and you will enjoy a vertical tasting of Tenuta San Guido Sassicaia during 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 hotel.

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6. Castiglione della Pescaia – Suvereto – Marina di Bibbona - Riparbella - Florence

   

   Seafood Michelin starred lunch and exciting Wine Experience

   • 5* Boutique Hotel
   • Full breakfast, Michelin starred lunch with wine
   • Private Chauffeured Mercedes

   Today you will travel on the coast of Tuscany, on the way back to Florence, visiting and tasting at stellar wineries such as Petra (designed by the famed Mario Botta) and Tenuta Prima Pietra, the last wine adventure by Ferragamo in Riparbella.

   In between, you will have one of the best meals on the tour: an unforgettable seafood lunch at our favorite restaurant in the region, right on the sandy beach, La Pineta.

   In the late afternoon, you can explore Pisa or head back into Florence.
   Upon arrival in Florence, you will stay in the same lovely boutique hotel as your first night. The evening is yours to relax and sip a glass of wine in a beautiful Florentine piazza.

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7. Florence- San Gimignano- Fiesole

   

   Olive Oil Tasting and San Gimignano

   • 5* Boutique Hotel
   • Full Breakfast, Picnic lunch with wines Farewell present in your room
   • Private Chauffeured Mercedes

   Full breakfast at an elegant hotel. Today you will enjoy an excursion to San Gimignano. San Gimignano is a gorgeous medieval village called “the Manhattan of Tuscany” because of its many towers (medieval, of course!).

   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.
   Arrive at Fiesole, at extra virgin olive oil farm on these beautiful hills overlooking Florence. 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 and indulge in a delicious picnic lunch with cured hams, local cheeses, salads, sandwiches, dips, wine and of course- olives!
   Enjoy the last night in Florence on your own, with a  gift waiting for you in your room. We recommend Enoteca Pinchiorri or Gucci Osteria for dinner if you want a famed Michelin starred chef or La Giostra or Da Mario if you are looking for something charming and lively.

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8. Florence

   

   Depart from Florence

   • None
   • Full Breakfast
   • Private Chauffeured Mercedes

   Full breakfast at an 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.

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