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’ll 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’ll 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’ll 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’ll 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.

Tour Highlights:

  • Private Chauffeured Mercedes
  • Wine Tastings in Chianti, Montalcino, Montepulciano and Maremma
  • Private tours of Florence and Siena
  • Special Gourmet Experiences
  • Luxury small boutique hotels
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Below is a suggested Day By Day Itinerary for your private Wine Tour in Tuscany

Day One - Private Art Guided Tour & Gourmet Dining

Boutique Hotel

Your special boutique hotel

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’ll 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.

Overnight: 5* Star Villa Style Hotel, Florence

Meals Included in Price: Dinner with wine

Transfers: Airport transfer, guided walking tour of Florence

Day Two - Chianti Classico Wine Tasting

Badia Coltibuono

Badia Coltibuono´s Historic Wine Estate

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´ll 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’ll travel to your hotel for the next two nights- a hill-topped castle! Free evening to enjoy the restaurant of the hotel on your own.

Overnight: 5* wine resort in the countryside of Montalcino

Meals Included in Price: Full breakfast, wonderful Tuscan lunch with wine

Transfers: Florence- Chianti Classico wine villages- Siena

Day Three - Montalcino & Montepulciano VIP Wine Tastings

Luxury Wine resort

Luxurious wine resort

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’ll 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.

Overnight: 5* wine resort in the countryside of Montalcino

Meals Included in Price: Full breakfast, Lunch with wine in private setting at winery

Transfers: Hotel- Montalcino- Montepulciano- Hotel

Day Four - Maremma, Home of the Super Tuscans

Luxury Hotel Room

Your elegant hotel

Full breakfast at your castle hotel. Check out.

Today, you'll 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 to 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. Overnight on your own to enjoy the restaurant of the hotel.

Overnight: 5* Ultra Luxury Villa style hotel, deluxe room

Meals Included in Price: Full breakfast, Lunch in Pitigliano (with wine)

Transfers: Montalcino- Pitigliano- sightseeing in Maremma- Castiglione della Pescaia

Day Five - VIP Wine Tastings at Petra & Ornellaia

Petra Winery Cellars

Petra Winery Cellars

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’ll 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 go back to your ultra luxury little hotel to enjoy it.

Overnight: 5* Ultra Luxury Villa style hotel, deluxe room

Meals Included in Price: Full breakfast, wine tastings, olive oil tasting, full lunch with wines

Transfers: Castiglione della Pescaia- Maremma wine villages- Castiglione

Day Six - Return to Florence via San Gimignano

San Gimignano

San Gimignano

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, etc. 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.

Overnight: 4* Luxury Hotel, Stylish converted mansion in Florence, in a superior room

Meals Included in Price: Full Breakfast Farewell present in your room

Transfers: Maremma- San Gimignano- Florence

Day Seven - Olive Oil Tasting and Farewell Wine Experience in San Miniato

Poggio Cappiano

Poggio Cappiano Olive Oil

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´ll 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

Overnight: 4* Luxury Hotel, Stylish converted mansion in Florence, in a superior room

Meals Included in Price: Full Breakfast, Brunch with wine

Transfers: Florence- Ponte a Cappiano- San Miniato- Florence

Day Eight - Depart from Florence

Il Duomo, Florence

Il Duomo, Florence

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 for extra days in Rome or Venice, contact us for details.

End of Services.

Meals Included in Price: Full Breakfast

Transfers: Airport transfer to Florence

Past Customer Testimonial

Villa Antinori (Badia Passignano) was unbelievable. Their grounds are gorgeous and their service was outstanding. Everyone was attentive and informative. The tour was lovely and the lunch and tasting that followed was incredible. This was hands down the most impressive winery of all our visits. Altesino was also a wonderful winery! We loved getting to see wineries of all sizes. The landscapes were beautiful, and our tour guide was great! The lunch they served was delicious! We very much enjoyed our visit to their winery! Casato Prime Donne was a unique winery! I was unaware of the history behind this company prior the visit, but they quickly capture your attention. Stefano, our driver, was absolutely wonderful!! What an incredibly patient and friendly man! He was early every morning and had bottles of water for us. He was incredibly accomodating. Whenever we saw a beautiful landscape where we'd like to stop, he would pull over and take pictures for us. We very much enjoyed having him as our driver, as would anyone else! The Castello del Nero hotel was beautiful and their spa was simply amazing. The food was outstanding, and we really enjoyed our stay. I would absolutely recommend Cellar Tours! The experience was incredible! We undoubtedly saw and experienced things that we would never have been able to organize on our own. It was a process where we voiced our interests and preferences, and trusted that paired with your local expertise, this part of our honeymoon would be everything we dreamt of - and it most certainly was! Thank you for orchestrating such an amazing vacation that we will always hold dear to our hearts!”

Alicia Winn, Dallas, Texas

What's Included

  • All luxury Transportation and transfers for 7 days/ 6 nights
  • Bilingual driver guide
  • Special additional wine guide for 4 days
  • Local certified art guides in Florence and Siena
  • All accommodation in luxury hotels (superior 4 and 5 stars) in superior rooms and junior suites
  • 6 Full Breakfasts
  • 4 wonderful wine country Lunches with wines, mineral water, other beverages (1 at Michelin star)
  • 1 spectacular welcome dinner with extra special wines selected
  • Welcome aperitif cocktails (Champagne/Campari Fizz/Negroni, etc)
  • Professional Wine Tasting Presentations with Winemakers/Owners/top staff
  • All VIP Winery Visits and Wine Tastings: minimum 5 Boutique and Premium wineries incl. Super Tuscans, Brunello di Montalcino and Chianti Classico
  • Olive Oil and Wine gifts
  • Various Wine Gifts with bottles signed by the winemakers
  • All Entrance Fees to Cultural Sites (Art museums, etc)
  • Excursions to Siena, Pitigliano and San Gimignano
  • Detailed Itinerary of Tour- Keepsake Book
  • Keepsake personalized menus
  • Welcome gifts and farewell gift
  • Bottled water, juice, soft drinks and snacks available during the drives
  • All local taxes

What's Not Included:

  • Flights
  • Meals and Drinks not Specified
  • Personal Expenses such as Telephone, Minibar, etc
  • Tips and Gratuities (Guides, Restaurants, etc)
  • Travel Insurance (Strongly recommended)
  • Cancellation Insurance


This is a SAMPLE TOUR ITINERARY. Please note that our private chauffeured luxury tours are totally customized to your needs and price varies according to the number of people in your group (please note tours require minimum 2 guests), specific suppliers included, number of services included,specific dates, transport type etc. Contact us today for more information and we would be delighted to get started on a tailor made detailed itinerary with pricing for you.

  • Final price depends on chosen style of accommodation and dining. Please contact us with your group size (minimum 2 guests, no maximum group size), travel dates and preferences and we will send you custom pricing.
  • Discounts available for larger groups
  • Please note that our tours are available upon demand for PRIVATE GROUPS and are not scheduled tours for mixed groups.

More Information:

All of our tours are available year round upon request for your private group of minimum 2 people. We organize unforgettable packages in Italy that include wine and adventure touring. If you would like us to customize a private high-end tour of Italy for you

For Your Personalized Quote!

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