Signature Journey
7-Day Florence & Tuscany Wine Tour
A complete private itinerary combining Florence, Tuscan wine country, fine dining, cultural touring, chauffeured transfers, and handpicked luxury hotels.
Florence-based wine routes through Tuscany’s finest appellations.
Florence Wine Tours
Florence is one of the best places to base yourself for private wine touring in Tuscany, with routes to Chianti Classico, Montalcino, Montepulciano, San Gimignano, Bolgheri, and the Super Tuscan coast. Drawing on more than 20 years’ experience planning private food and wine tours in Italy, Cellar Tours designs tailor-made Tuscany wine tours from Florence with chauffeured transfers, expert guides, handpicked wineries, fine dining, and itineraries tailored to your tastes and pace.
Choose a private day tour from Florence or our signature 7-day Florence and Tuscany wine journey. Each itinerary is private and designed around your interests, whether you prefer classic Tuscan scenery, Brunello cellars, modern collectible reds, hill towns, Michelin-starred dining, or a slower countryside rhythm.
As featured in
Choose your signature route
Select a complete multi-day Florence and Tuscany journey, or compare private day routes through Tuscany’s most celebrated wine country.
Signature Journey
A complete private itinerary combining Florence, Tuscan wine country, fine dining, cultural touring, chauffeured transfers, and handpicked luxury hotels.
Classic Day Trip
The easiest and most iconic private wine route from Florence, with scenic vineyards, historic villages, and elegant Sangiovese-based wines.
View Itinerary
For Brunello Lovers
A premium private wine tour for guests interested in Brunello di Montalcino, cellar visits, and a refined Tuscan wine-country lunch.
View Itinerary
Collector Route
A longer private route to the Tuscan coast, ideal for Bolgheri DOC, Bordeaux-variety blends, and lovers of modern Italian fine wine.
View Itinerary
Wine & Hill Towns
A refined route combining Vino Nobile di Montepulciano, Renaissance architecture, and the landscapes of southern Tuscany.
View Itinerary
Lighter Tuscan Day
A scenic day with medieval towers, countryside views, and Vernaccia di San Gimignano, Tuscany's historic white wine.
View Itinerary
Culinary Route
A private Tuscan countryside day for food and wine lovers, with premium extra-virgin olive oil tastings, regional flavors, and relaxed rural scenery.
View ItineraryEvery private itinerary is tailored to your route, pace, and interests. These are the elements most commonly arranged across our regional wine tours.
Signature journey
This is a sample itinerary. Your final hotels, restaurants, winery visits and guides will be selected and confirmed in advance in your personal proposal.
This premium wine tour features vineyard walks at superb wineries in Chianti and Montalcino, and mouth-watering gourmet discoveries. Visits to Florence and Siena, two of the most spectacular cities in Italy, are also included, as well as hidden gems like Pietrasanta, Lucca, and Carrara and classics like Pisa. You will have your private chauffeur for the duration of this Luxury Tour, along with excellent local guides. The accommodation chosen for this tour is extremely luxurious, two of the most beautiful hotels in Europe and certainly in Italy.
Apart from sleeping in utter luxury, you will visit the beautiful cities of Florence and Siena; whose combined artistic heritage is more than most countries! Local art historians will lead you through the best galleries and museums (including the Uffizi Gallery), and you will have the chance to explore some lesser-known jewels, such as the Boboli Gardens, and picturesque medieval villages and towns like Pisa, Lucca, and Pietrasanta.
The cuisine featured on this tour is, as always, on our tours, a major highlight. Dine-in Michelin-starred restaurants along with rustic, mom-and-pop trattorias. The restaurants are hand-selected to show you the best Tuscany has to offer. The wines and specialties of Toscana are revered as being some of the finest in the world. On this tour, you’ll taste vintage Brunello di Montalcino and classic Chianti wines. Delicious local dishes include “Pappardelle Alla Lepre” (pappardelle pasta cooked with hare), Fagioli all’uccelletto (flavorful beans and tomato sauce), ribollita soup, wild boar cured sausage (“Prosciutto di Cinghiale”), topetti (hand made gnocchi from Versilia) and Lardo di Colonnata. Also on the menu is the famous Florentine dish “Bistecca Alla Fiorentina,” a huge T-Bone Tuscan steak usually big enough for two. You will taste it at Dario Cecchini, a veritable mecca for meat lovers. And, to finish off any proper Tuscan meal, perhaps while you are dining al fresco at one of the gorgeous hotels included in this tour, you must try the “Cantucci with Vin Santo” (Macaroons and “holy wine”). Divine! If you are looking for a luxurious food and wine orientated tour from Florence, with the “Best of” highlights of the region’s art treasures, then this tour is for you.
Day 1Florence

Florence at sunset
Your English-speaking driver for the tour will meet you at the airport, and you will transfer by comfortable Mercedes to your exclusive hotel, tucked away in a chic neighborhood in Florence. Arrive at your fantastic hotel, a true “urban resort” with Renaissance buildings surrounded by an immense park. Numerous personalities have stayed here through the centuries, including Pope Leo XI, whose pontificate lasted less than a month, the Viceroy of Egypt, and five centuries of Italian nobles.
Florence awaits! After check-in, your chauffeur will take you into the historic center of Florence, one of the most beautiful cities in the world.
You will experience your first velvety wines of the tour during a guided wine tasting in the stunning Bernardino Poccetti’s fresco room, before enjoying an authentic Florentine lunch at a lively local trattoria.
Next, you will take a private guided walking tour to see Florence’s highlights: Ponte Vecchio, Piazza della Signoria and its replica of Michelangelo’s David, and the Duomo with Brunelleschi’s great cupola.
In the evening, transfer back to the luxury hotel and have dinner on your own at the hotel’s Michelin-starred restaurant.
Day 2Florence

Uffizi Gallery
A free morning to enjoy this splendid hotel, its beautiful private garden, and amenities. Early afternoon transfer to historic Florence. Guided by your charming art historian, you will visit the marvelous Uffizi Gallery, one of the world’s most famous art museums, featuring Botticelli, Michelangelo, and Da Vinci. You will also visit the Vasari Corridor, a skywalk built in 1565 by order of Duke Cosimo I de’ Medici to connect his residence (Palazzo Pitti) and government palace, for security reasons. This is a real treat!
You will also enjoy a guided tour of the Boboli Gardens before going back to the hotel to freshen up.
A three-Michelin-star dinner will be waiting for you at Enoteca Pinchiorri in Florence, the crème de la crème venue to begin a gastronomic journey. Set in a magnificent historic palazzo, its celebrated cellar holds an extraordinary collection of Italian and international wines selected by Giorgio Pinchiorri. Founded by Giorgio Pinchiorri and French chef Annie Féolde, the restaurant is led in the kitchen today by chef Riccardo Monco. You will visit the cellar and choose your wine for dinner, exploring one of Florence’s great wine lists.
Day 3Florence – Chianti - Montalcino

Chianti Classico's Black rooster
Today will be a wine tasting extravaganza! Transfer from Florence towards Siena, via the most beautiful villages of the Chianti Classico region, including Greve in Chianti, Radda in Chianti, and Castellina in Chianti. Chianti Classico is part of the greater Chianti wine region, and you will find the best vineyards. It lies between Florence and Siena (the border was designated in 1716). Its climate, soils, and altitude have made Chianti Classico a top-notch region for premium wines. The symbol of Chianti Classico is the Black rooster, which is on all Chianti Classico bottles.
Stop for a VIP winery visit at the beautiful Capannelle. Enjoy a professional tasting of the full range of wines, with personalized tasting sheets and a personalized gift signed by the winemaker.
Your aperitif and lunch will be a carnivorous feast at Dario Cecchini’s establishment, called the “world’s best butcher” by the New York Times. Long shared tables, a pleasant atmosphere, and excellent yet straightforward food, combined with Dario’s unique and exuberant character, make this experience one to remember.
After lunch, enjoy a scenic drive through the nearby vineyards and wine villages, stopping to visit the perfectly manicured hilltop town of Montalcino. We will arrange a VIP private visit to an artisan Brunello producer (generally closed to the public), followed by a fantastic vertical tasting.
Transfer back to your luxury hotel and enjoy the night in Florence on your own.
Day 4Florence – Siena

Amazing Mercato Centrale in Florence
Full Breakfast at your Villa hotel, served in a historic patio, surrounded by ancient trees. This morning, you will visit Florence’s famous Mercato Centrale – San Lorenzo market with your private chef, where you will taste traditional gourmet treats, meet and talk with local food producers, and learn how to choose the best ingredients. Then you’ll be ready for your hands-on cooking class with traditional, authentic recipes using the fresh ingredients you purchased.
Before lunch with your charming host and chef, you will enjoy a professional extra virgin olive oil tasting, and each guest will receive a gift bottle of EVO.
After lunch, you will transfer from Florence to the historic center of Siena, one of Italy’s noblest cities, home to the gorgeous 14th-century main square called the “Campo,” where the world-famous “Palio” race is held twice a year. You will take a walking tour of the old town, then have free time for shopping or gallery hopping.
On the way back to Florence, stop in the charming, walled medieval hamlet of Monteriggioni for a nice walk. Dante Alighieri included Monteriggioni in his most famous work, The Divine Comedy.
Day 5Florence – Palaia – Pisa – Forte dei Marmi

Truffle Hunting
After breakfast today, you will leave the city of Florence and travel west to the Valdarno countryside (The Arno River valley), before arriving at the Tuscan beaches of Versilia and one of the most prestigious seaside resorts along the Tyrrhenian coast.
But first, a treat in store! You will experience a real truffle hunt, with your private tartufaio (truffle hunter) and his loyal dogs. On your truffle hunt, you will learn about the precious truffles and admire the skills of expert dogs, which smell, dig, and find them. Lunch will be a truffle extravaganza, from appetizer to dessert!
After this sumptuous lunch, you will explore the historic villa, gardens, and ancient cellar at Varramista estate, followed by a tasting of their wines. Giovanni Alberto Agnelli took over this estate in the 1990s, introducing the Syrah grape. Using this new varietal, along with the estate’s historic Sangiovese vines, the winery began producing high-quality wines.
Pisa is your next destination, and your private guide Alessandro will guide you through this lively small town that offers a lot more than the iconic Leaning Tower and Piazza dei Miracoli.
Arrive at your waterfront hotel, check in, and enjoy the evening at your leisure.
Day 6Forte dei Marmi - Pietrasanta – Lucca – Carrara marble quarries and Colonnata

Charming Lucca
After a full breakfast at your elegant hotel, you will meet your private dynamic art guide and begin the day with a relaxing electric bike ride to the nearby town of Pietrasanta. This quaint town is known as “Little Athens” because many artists have settled here (including Igor Mitoraj and Fernando Botero). The town is an open-air museum, with contemporary art and sculpture on display in its many galleries and piazzas.
Next, transfer to Lucca, where you will take a guided tour of this beautiful walled town, which dates back to ancient Etruscan times. Lucca is filled with cobblestone streets, surrounded by a medieval wall, and is the birthplace of Puccini. Admire the Romanesque churches, historic buildings, and the beautiful Piazza dell’Anfiteatro. You will fall in love with this romantic Italian gem.
Now for something completely different: a 4×4 adventure in the world-famous Carrara marble quarries. Michelangelo spent long periods in Carrara selecting marble for many of his sculptures, and the city’s white stone became inseparable from his work.
For lunch, you will stop in the quaint medieval hamlet of Colonnata. Colonnata is famous for its high-quality pork lard, spiced with sea salt, rosemary, garlic, and black pepper, and cured in marble tanks, called “conche,” for at least six months.
After this delicious lunch, you will return to your hotel and have free time to relax and freshen up. Before dinner, enjoy an aperitivo, as the Italians do!
Tonight, you have a treat in store! An amazing farewell dinner with keepsake menus (signed by the chef) arranged for you, paired with top-quality wines.
Day 7Forte dei Marmi – next port of call

Buon Viaggio!
Full breakfast at your elegant hotel. Your chauffeur will take you to your next port of call.
That concludes your ultra-luxury Florence Wine Tour. We can arrange extra days in the Italian Riviera, Piedmont, Bologna, and Emilia-Romagna; please contact us for details.
Chianti Classico and San Gimignano are among the most comfortable private day trips from Florence. Montalcino and Montepulciano work well as longer day tours, while Bolgheri is usually best for guests who are comfortable with a longer private drive or who wish to include it as part of a multi-day Tuscany itinerary.
Every Cellar Tours itinerary is designed around your dates, pace, wine interests, dining preferences, hotel style and preferred level of guiding. With more than 20 years’ experience organizing private food and wine tours in Italy, Simona personally designs and refines our Italian itineraries, conducts site inspections, meets with our winery, hotel and restaurant partners, and reviews client feedback, bringing first-hand knowledge of the places and people behind each journey.
Maria and Umberto Contestabile, Virginia Beach, USA
You were such a pleasure to deal with so understanding of all our issues
I can’t thank you enough for your caring and flexibility. The hotels were outstanding. The service aspect of each of the hotels was exemplary with exquisite care being given to every detail. Simone was also a delight. I was blown away by his knowledge of Florence and the Uffizi. I felt like I was walking with the encyclopedia Britannica. The restaurants…what can I possibly say? Pinchiorri is an experience one is not likely to forget. The food, the wine, the service – world class.
Ken and Phyllis Baker, Florida
This was our second trip with Cellar Tours and it was just as wonderful as our first.
Last year we toured the Prosecco region outside of Venice and this year we toured the Chianti region outside of Florence. The Chianti tour was very professionally organized and our driver was prompt and spoke English very well. Castello Di Monsanto was a wonderful experience and we were given an informative tour of their wine-producing facility. We then had a fabulous wine tasting of 3 of their delicious wines. Lunch at Albergaccio was one of the best meals we have had in Italy and this is our 3rd trip to Italy. We were given a personalized menu by the owner and had a 4-course lunch with matching wines. My wife and I travel to Europe for the food and wine, and this was definitely a highlight. We then traveled the short distance to Fonterutoli to have another wine tasting at Castello di Fonterutoli. The wines we tasted there were superb and we had a chance to purchase some. The trip was as good as we had anticipated and we hope to be traveling to Milan next year, and if we do, we will surely contact Cellar Tours to organize our third trip. We have no suggestions to give because you seem to cover everything in your tours. Thanks for everything again. Hope to contact you next year.
Phyllis Turner-Brim, Washington
Everything was exquisitely arranged and organized according to our requests.
I can’t think of anything you could have done better. The Four Seasons Florence was wonderful, worth every penny. Villa Armena – Beautifully done. The room was cozy and modern all at the same time. It was so peaceful and isolated we really enjoyed our time here. L’Andana – Jerry and I both liked this hotel the best. The combination of luxurious accommodations, spa services, and great food was outstanding. We enjoyed having champagne in the garden in the afternoon. Cibrèo in Florence was Fantastic. Really too much food, but we ate it all. The lunch at winery Beconcini – We enjoyed the homemade food and the conversation. Sauro was tremendous and took great care of us. He was punctual, courteous and professional. I have already recommended Cellar Tours to two friends. This was the most wonderful travel experience that we have ever had. We can’t even put into words how much we enjoyed our trip. Everything was organized in advance so that we didn’t have to make any decisions once we arrived. In my view, this is the only way to see Tuscany. We are looking forward to our next Cellar Tours experience!
Yes. Chianti Classico and San Gimignano are among the most comfortable private day trips from Florence. Montalcino, Montepulciano, and Bolgheri can also be arranged, though they work best for guests comfortable with a longer private day or as part of a multi-day itinerary.
Chianti Classico is usually the best first private wine tour from Florence because it combines classic Tuscan scenery, historic villages, elegant Sangiovese-based wines, and easier logistics.
Bolgheri can be arranged as a long private day trip from Florence, but it is usually more comfortable as an overnight or multi-day extension, especially for guests focused on Super Tuscan and coastal red wines.
Yes. Cellar Tours designs private, tailor-made itineraries with chauffeured transfers, selected winery appointments, regional dining, expert guides, and luxury hotels where required.
Our regional guides offer deeper background on the places, wines, classifications, and local food traditions behind our private tours.