Bolgheri Wine Tour
Visit top Super Tuscan estates with a private chauffeur, enjoy a gourmet lunch at Sassicaia, and explore Tuscany's medieval beauty. Book now!
If you consider yourself a wine connoisseur or even a wine lover and want to experience the best wine country experiences that Tuscany offers, then this is the Wine Tour for you! You will visit the best appellations in this gorgeous part of Italy for a week. 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 restaurant 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, which is very photogenic. You will visit top producers such as Badia a Passignano and Castello di Ama.
Next on this fantastic Tuscan wine tour is a visit to the beautiful 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 with a local art guide to better appreciate 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 fantastic wines and enjoy some incredible meals in this lovely, quiet, 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.
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.
Florence- Chianti Classico – Siena – Montalcino countryside
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.
Montalcino - Montepulciano
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.
Montalcino- Pitigliano- Maremma- Castiglione della Pescaia
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.
Castiglione della Pescaia - Bolgheri
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.
Castiglione della Pescaia – Suvereto – Marina di Bibbona - Riparbella - Florence
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.
Florence- San Gimignano- Fiesole
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.
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.
Cecelia and Ted Hoyt, Lousiana
Thank you so much for arranging the best vacation we've ever had!
Everything was perfect; nothing went wrong. We loved Suaro and the guides were wonderful. Accommodations, food, and wine could not have been better. We will travel with you again!
Nicholas & Veronica Brownlee, Massachusetts
The overall organization of the trip was excellent.
Everything worked, Stefano was always early or on time. There were no snafus for hotel reservations or restaurant reservations. Everyone was expecting us. The winery tastings and tours were well organized. I have already recommended cellar tours to several people in the week since I returned. Everything that was under your control worked. The choices of hotels were excellent but could have been better situated. You exceeded my expectations several times throughout the week. Wow!! We know how much work goes into planning this kind of trip. We appreciate your attention to the details.
Sharon Pulse, Washington
We can’t say enough how much we thoroughly enjoyed our trip.
One of the wonderful things about our trip was once we had gone through the planning stage and had come up with an itinerary, our work was done. You made all the reservations for our accommodations, directing us to the “right” wineries, fabulous restaurants, and our Drivers Sauro and Stefano, who were wonderful, were always on time, took great care in calling ahead to let the wineries and restaurants know when we would be arriving, and drove very professionally on some very interesting roads!! For two people who always are in charge to be able to sit back and enjoy beautiful Tuscany and Verona was “magical!”. We came home rested and that is saying something after all the wineries we visited!
Steve Beutler, California
The organization was great, and it flowed well.
The accommodations were perfect in terms of location and staff friendliness. Inn at Spanish Steps checked us in early and provided breakfast. Meals were very good, some memorable. Altesino served fresh and delicious food that paired well with their wine. The tasting room atmosphere enhanced the experience. Sassicaia lunch was delicious with good wine pairings. Roscioli provided an unusual, fun, and educational dining experience with fresh and delicious food. Il Palazzone winery in Montalcino, introduced by you, was a great discovery. Laura, the hostess, generously poured older vintages not on the tasting. The trip was wonderful and couldn’t have been more enjoyable. Thanks again, Gen!
We very much enjoyed our trip and are very pleased with Cellar Tours!
The experience was excellent and the order of events was well thought out. The wine tours were absolutely fabulous. Better than expected. Each tour was unique and we experienced a nice variety of tours and locations and people, so it was perfect
If you would like us to customize an exclusive luxury tour, contact us and let us know your travel plans. We offer luxury food and wine tours for private groups of a mininium two guests. In addition, all of our private, chauffeured tours are available year-round upon request.
Welcome to Cellar Tours, the premier Luxury Travel Specialist since 2003. Our goal is to provide you with the ultimate food and wine vacation experience, with exclusive Mercedes chauffeured tours that showcase the best of local cuisine and wines.
Our team specializes in crafting bespoke, custom-designed vacations, events, and incentives tailored to your unique tastes and preferences. Travel is not just about seeing new places - it's about creating unforgettable memories and indulging in the finer things in life.
As members of Slow Food, OTAVA (Travel Agency Association in Spain), and the IACP (International Association of Culinary Professionals), we promote sustainable tourism and support local communities. We work closely with top-rated hotels, restaurants, and wineries to provide you with the highest level of service and attention to detail.
Whether you're planning a romantic getaway, a family vacation, or a corporate retreat, let Cellar Tours be your guide. With our passion for food and wine, extensive knowledge of local culture, and dedication to exceptional customer service, we're confident we can exceed your expectations.
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