Discover Tuscany’s timeless beauty in this private food and wine tour through the cradle of the Renaissance. Experience Tuscany’s rich culinary heritage from Florence street food, to Chianti cooking, to farm-fresh cheese in the Val d’Orcia. Visit scenic vineyards and ancient cellars during private wine tours and wine tastings in Tuscany’s best appellations.
Luxury Tuscany Food & Wine Tour: Chianti Classico, Brunello, Super Tuscans

Overview
About the Region
Close your eyes and picture Italy, and there’s good chance you picture Tuscany, with winding roads lined with Cyprus trees and rolling hills blanketed with vineyards. For centuries, Tuscany’s romantic landscapes have inspired artists and travelers alike. This beautiful, fertile region of central Italy offers an incredibly rich concentration of history, art, craftsmanship, gastronomy, and winemaking. Eight localities in Tuscany have received UNESCO World Heritage recognition for their importance in human cultural history. Food and winemaking traditions are also integral parts of Tuscany’s fascinating story. Tuscan gastronomy emphasizes fresh, seasonal ingredients prepared simply to honor their quality and preserve their natural flavors. Viticulture in Tuscany has flourished since the Greeks introduced winemaking to the Etruscans in the 7th century BC.
Tour Highlights
Tour Overview
Taste your way through Tuscany’s best food and wine during this 10-day immersion in Tuscan culinary tradition and winemaking excellence. Our carefully chosen 5-star hotels in Florence and Chianti, and 4-star hotel in Lucca, offer luxurious hospitality with a distinctly Tuscan personality. Marvel at stunning works of art and sculpture in Florence. Unwind in the tranquil Chianti countryside surrounded by vineyards and olive groves. Experience Tuscany’s rich history and culinary culture at your own pace. Our Luxury Tuscany Food and Wine Tour features private drivers, private guides, and enough free time to be spontaneous and find serendipity.
Learn how to cook an authentic Tuscan meal during your private Chianti cooking class and discover even more of Tuscany’s flavors as you taste old-fashioned street food in Florence and farm-fresh cheese in Pienza. Our Luxury Tuscany Food and Wine Tour brings you into the vineyards and cellars of local winemakers in Chianti Classico, Montalcino, Montecarlo di Lucca, and Bolgheri to discover Tuscany’s most emblematic wines as well as off-the-beaten track appellations. By walking the vineyards, touching the soil, and wine tasting with local experts, you’ll understand the influence of terroir, tradition, and innovation on the story of Tuscan winemaking.
Tour Dates & Pricing
This tour is available year-round. Contact us to request dates and check availability. Pricing is based on your travel dates, group size, and tour customizations. Contact us for a free quotation to get started.

Tour Itinerary
Welcome to Florence

Benvenuti a Firenze! Arrive at Florence airport or Santa Maria Novella train station. Your friendly private driver will greet you on arrival and transfer you to Hotel Lungarno, your 5-star accommodations in Florence city center.
Today is free time to begin exploring Florence on your own. From your luxurious hotel in the city center, Florence’s most important historical and artistic treasures are all easily walkable. Time permitting, you may want to visit the Uffizi Gallery this afternoon or discover the Oltrarno district’s neighborhood wine bars, trattorias, and local artisan boutiques.
For dinner this evening, we offer reservations at some of our favorite Florence restaurants.
What’s Included
Hotel Lungarno
Located on the River Arno just next to the iconic Ponte Vecchio, the 5-star Hotel Lungarno welcomes you for the first two nights of your private luxury wine tour in Tuscany with the ambiance of an art collector’s private townhome in the heart of Florence. The hotel’s collection includes pieces from Picasso, Cocteau, Bueno, and Italian artists such as Cassinari, Guidi, Fusi, Morlotti, Rosai, Sironi, and Tosi. At both the hotel’s Michelin-starred restaurant, Borgo San Jacopo, and its Picteau Bistrot & Bar, Executive Chef Claudio Mengoni’s menus celebrate the purity of seasonal Tuscan ingredients from land and sea.
Renaissance Art & Florence Food Culture

Start your morning in Florence with fresh breakfast at Hotel Lungarno before your expert local guide meets you at the hotel to begin a private walking tour focused on Florence’s incredible artistic and culinary heritage. Florence is the cradle of the Renaissance and the city itself is a work of art. Journey through history, culture, and cuisine as you make your way towards the Accademia. Stop to taste traditional street food like lampredotto, a Florence specialty made with slow-cooked cow’s stomach and schiacciata, a Tuscan flatbread that makes a delicious snack by itself, or a great sandwich with cured Tuscan ham. Of course, an authentic food tour in Florence would not be complete without tasting Tuscan wine. Pair a local Tuscan vino served from one of the city’s famous buchette with these traditional Florentine flavors.
Conclude this morning’s private tour of Florence with a guided visit to the Galleria dell’Accademia. Avoid the wait with your skip-the-line tickets to experience in person one of the great artistic masterpieces of the Renaissance – Michelangelo’s David.
Complete this morning’s culinary exploration of Florence with lunch (included) at one of our favorite local trattorias. The rest of the afternoon is free to experience more of Florence on your own.
What’s Included
Florence Street Food
Florence’s street food is a delightful blend of history, tradition, and Tuscan flavors. Schiacciata, a Tuscan flatbread, is often topped with coarse salt and rosemary, making it a perfect snack or sandwich base. Lampredotto, a beloved Florentine delicacy, is made from the fourth stomach of a cow, slow cooked in a savory broth, and served in a crusty roll with a spicy or herb sauce. The fascinating buchette del vino (wine windows) are small, arched openings in the walls of noble residences date back to the Renaissance. Aristocrats used the buchette del vino to sell wine directly from their cellars to avoid paying taxes. Thirsty Florentines would knock on the window, leave their money and an empty bottle, and receive it back filled with Tuscan wine.
Wine Tasting in Chianti Classico & Tuscan Hilltop Villages

Enjoy a leisurely breakfast and a little free time in Florence this morning before your private wine tour in Tuscany transitions to Chianti. Your private driver will collect you from your hotel in Florence to begin your first day exploring Tuscan wine and cuisine in the Chianti countryside. First reach the charming hamlet of Montefioralle, one of Chianti’s oldest villages considered one of the prettiest towns in Italy. Spend some time strolling Montefioralle’s quaint cobbled streets and shops before continuing to a local winery for your first Chianti wine tasting.
The borders of Chianti have expanded over the years and now cover much of Tuscany itself. Today’s wine tasting is in Chianti Classico, the original Chianti and the only Chianti subregion to hold its own DOCG. Chianti Classico is the oldest appellation in Italy, legally delineated in 1716 around the villages of Radda, Gaiole, Castellina, and later Greve and Panzano. Soils in this hilly terrain are primarily marl with some limestone, yielding highly acidic Sangiovese that skilled winemakers finesse into full, complex, savory reds that improve with age. Meet a local winemaker near Montefioralle to visit their cellars and discover centuries-old viticulture. Enjoy a private Chianti Classico wine tasting at the winery along with a light lunch of seasonal Tuscan dishes.
Following your wine tasting and lunch, continue to Radda in Chianti to visit this picturesque medieval Tuscan village near the southern border of Chianti Classico, then arrive in the late afternoon to your luxurious accommodations at 5-star Borgo San Felice near Siena.
What’s Included
Borgo San Felice
Your home for four nights in Tuscany, Borgo San Felice, offers a serene escape amidst rolling vineyards and olive groves. The estate’s charm lies in its meticulous restoration, preserving the rustic beauty of its medieval origins while providing modern comforts. At the Michelin-starred Il Poggio Rosso, Chef Juan Quintero blends Latin influences with traditional Italian flavors. For a more relaxed dining experience, Osteria del Grigio offers rustic dishes in a cozy setting perfect for savoring Tuscany’s rich culinary heritage. From 179 hectares of vineyards, Borgo San Felice produces excellent Chianti Classico, Brunello di Montalcino, and Bolgheri under holistic vineyard management, ensuring the land remains fertile and biodiverse. Borgo San Felice operates with a Zero Waste Hotel Certification and uses 100% renewable energy.
Tuscan Cooking Class & Free Afternoon in Chianti

Wake up in the tranquil Chianti countryside and start your day with fresh homemade farm-to-table breakfast. Later this morning, your private driver will collect you from Borgo San Felice and bring you do a nearby cooking school for a private Tuscan cooking class. This fun, hands-on culinary experience will teach you how to cook authentic Tuscan recipes. You’ll learn how to select fresh, quality ingredients and how to prepare a seasonal, multi-course Tuscan lunch or dinner for your family and friends back home. Enjoy a relaxed lunch to follow, with local Tuscan wine.
After your Tuscany cooking class and lunch, return to Borgo San Felice and enjoy free time for the remainder of the afternoon. Perhaps use the resort’s e-bikes to explore the Chianti countryside. Siena is only a 20-minute ride. Walk in the gardens and the olive groves, swim and relax by the pool, or take rejuvenating treatments in the botanic spa. We can also arrange a private visit to Borgo San Felice’s cellars and a tasting of their Chianti, Brunello, and Bolgheri wines.
What’s Included
Borgo San Felice Wine Tastings (Optional)
For an in-depth discovery of the estate’s winemaking, an optional private visit to the vineyards and cellars is available this afternoon (confirmed in advance), according to your knowledge and interest. The estate’s winemaker will be delighted to show you around the vineyards, explaining the daily work, seasonal rhythms and sustainable soil management. Explore the wine library’s most prestigious vintages, including the Super Tuscan which launched the reputation of San Felice. Enjoy tastings with small plate pairings by Chef Juan Quintero. Barrel tastings are available for a deeper insight into the wine making process, or you can begin with a briefer introduction with wines from current vintages across their three Tuscan estates, served with homemade bread and San Felice DOP olive oil.
San Gimignano & Siena

Farm fresh breakfast at Borgo San Felice this morning before setting off with your private driver for a full visiting two of Tuscany’s most scenic and historic cities – San Gimignano and Siena.
San Gimignano is unique in Italy for how many of its medieval towers have survived through centuries of war and disaster to the present day. 14 of its 72 original towers still cut a medieval skyline against the Tuscan landscape. Take free time this morning to explore San Gimignano’s piazzas, shops, and UNESCO World Heritage city center on your own. In addition to its historical significance, San Gimignano is a locus for several distinct Tuscan culinary specialties — saffron infused dry aged Tuscan ham, pecorino cheese made from local sheep’s milk, and the distinctly Tuscan white wine Vernaccia di San Gimignano. Tuscan Vernaccia is a distinct varietal from the Sardinian and Le Marche grapes of the same name. Try a glass of Tuscan Vernaccia with some of the local pecorino! You’ll have time for lunch before continuing your journey through Tuscan history to Siena.
Siena’s historic center is also designated a UNESCO World Heritage site. It hosts the wild Palio di Siena in July and August. Bareback riders representing 10 of the city’s 17 contrade (wards) compete for the glory of their neighborhood over three no-holds-barred laps around the Piazza del Campo. Visit Siena with an expert local guide who will bring the city’s colorful history to life with stories of the Palio and Siena’s famous rivalry with Florence. Stop in a local pasticceria to taste Siena’s sweet treat, Ricciarelli – soft, chewy cookies made from almonds, sugar, and egg white.
Enjoy dinner tonight in Siena. The city hosts many excellent, atmospheric restaurants to discover on your own, or with our recommendations. Private transfer back to Borgo San Felice after your evening out in Siena.
What’s Included
Palio di Siena
Called simply Il Palio, Siena goes bananas on July 2 and August 16 when 10 riders representing their Siena neighborhood horserace bareback around a dirt track in the Piazza del Campo. The race dates to the Middle Ages and is intimately connected with the Sienese culture of fierce loyalty to the contrade in which they were born. On Palio days, married couples born in different contrade will separate and return to their original neighborhood’s cheering section in the Piazza del Campo. The race is notoriously dangerous. Riders are routinely thrown from their horses and injured making the hairpin turns. The first horse across the finish line after 3 laps is victorious, with or without its rider.
Private Val d’Orcia Food & Wine Tour: Pienza & Montalcino

Begin the morning with another fresh homemade breakfast at Borgo San Felice in the Chianti countryside before departing with your private driver for a full day exploring the quintessential Tuscan landscape and oenogastronomic traditions of the Val d’Orcia. Your first stop during today’s private food and wine tour in the Val d’Orcia is the Renaissance town of Pienza, the first example of Renaissance era humanist urban planning, a model that became replicated throughout Europe. This cultural legacy earned Pienza UNESCO World Heritage status in 1996.
Gastronomically, Pienza is renowned for its local Pecorino cheese. Soils in this part of southern Tuscany are a mix of clay, limestone, and lava flow deposited by the extinct Mount Amiata volcano complex. Grasses, herbs, and wildflowers thrive in these conditions and contain a mineral profile unique to the valley. But authentic Pecorino di Pienza is as much a product of the sheep that graze in the Val d’Orcia as what the ewes eat. True Pecorino di Pienza should be made from the milk of Sardo ewes grazed in natural local pasture. After a morning exploring historic Pienza on your own, you’ll meet a local artisanal cheesemaker and organic farmer producing authentic Pecorino di Pienza. Discover their artisanal cheesemaking process, organic farm, and taste a selection of cheeses with lunch at their farm-to-table restaurant.
After lunch at the farm, continue your food and wine tour in the Val d’Orcia towards another Tuscan hill town, Montalcino. Take free time discovering Montalcino’s charming medieval center on your own. From the highest point in town, the views from Montalicino’s imposing Sienese fortress, La Fortezza, are not to be missed. Perhaps visit Enoteca la Fortezza at the base of the fortress to survey the huge collection of Brunello. Your afternoon continues to a local winery to visit the all-important cellars that age Brunello from Montalcino into some of Italy’s most impressive wine. Enjoy a private Brunello di Montalcino wine tasting before returning to Borgo San Felice in the early evening. Dinner tonight at your leisure in one of Borgo San Felice’s farm-to-table restaurants.
What’s Included
Brunello di Montalcino
Brunello is a local Montalcino clone of Tuscan Sangiovese Grosso. Brunello’s thicker-skinned berries produce wines with bold fruit flavors, high tannins, and high acidity for long aging potential. Brunello di Montalcino DOCG regulations require aging for a minimum of two years in oak and four months in bottle, and it cannot be released for sale until five years from harvest. After 10+ years, Brunello’s fruit flavors go from fresh to dried or candied, tannins smooth out and become chocolatey, and its acidity perfectly balances the wine’s richness. Wine from Montalcino was among the earliest Tuscan vino considered high quality enough for international markets. References to Montalcino’s reputation for good wine appear as early as 1551. By the mid-1600s, wines from Montalcino were regularly exported to England, including to the court of King William II. But Montalcino’s reputation among wine lovers today can be traced to the vision of one winemaker, Clemente Santi. In the 1860s, Clemente Santi began aging his Brunello in barrels for 4 – 5 years, a technique almost unheard of in Italy at the time. His vision for orienting Montalcino’s wine industry towards export quality, vintage wines created Brunello di Montalcino as we know it today.
Pisa & Lucca

Savor a final morning breakfast in the Chianti countryside at Borgo San Felice, then meet your private driver as your food and wine tour in Tuscany continues to Pisa and Lucca. Pisa, one of Italy’s four great maritime republics, has a long and fascinating history. Did you know that Pisa’s cathedral with its famous leaning bell tower was financed with treasure seized from Saracen pirates in Sicily? Discover Pisa’s exciting story during a private tour with a local expert guide. Pisa’s Piazza dei Miracoli which contains the Leaning Tower, Baptistry, Cathedral, and Cemetery is a stunningly beautiful work of art and architecture. Look closely at the Duomo’s gray marble and white stone façade, inlaid with colored marble, as sunlight and shadow interplay to gorgeous visual effect.
Enjoy free time to visit more of Pisa on your own and have lunch, then continue to Lucca, a Tuscan architectural gem. Check in to the 4-star Hotel Grand Universe Lucca in the historic city center. Lucca is a remarkably well-preserved city. Its Renaissance era defensive city walls remain completely intact, and its historic center is a mix of Roman, Medieval, and Renaissance architecture. The rest of the afternoon is free to explore beautiful Lucca on your own.
What’s Included
Grand Hotel Universe Lucca
Your home for the final three nights of your food and wine tour in Tuscany, the 4-star Grand Hotel Universe Lucca is perfectly positioned for discovering Lucca’s art galleries, shops, restaurants, cafés, and historical treasures. Overlooking the charming Piazza del Giglio and Piazza Napoleone, the hotel itself embodies Lucca’s artistic spirit. Its foundations date to the Roman era when the hotel was the site of a glassblowing factory. During the Renaissance, it evolved into an elegant private Palazzo for the local Paoli family, before becoming a hotel in 1857. The Grand Universe has welcomed many famous artists, composers, poets, writers, and royalty during its long history. In 2020, a complete restoration fully modernized the hotel to contemporary luxury standards while preserving its historical character.
Pietrasanta Marble Artisans & Montecarlo Tuscan Wine Tasting

Breakfast at the Grand Universe Lucca, then depart the hotel with your private driver towards Tuscany’s Versilia coast to visit Pietrasanta. Located in the foothills of the Apuan Alps with their huge deposits of Carrara marble, Pietrasanta is a global destination for sculptors and artists. Michelangelo took the enormous block of Carrara marble from which he sculpted David from a Roman quarry in the Apuan Alps near Pietrasanta. With your local guide this morning, visit Pietrasanta’s charming village center, marble studios, and art galleries.
In the late morning, your private wine tour in Tuscany continues to the small hilltop village of Montecarlo, east of Lucca. Less well known internationally than Tuscany’s star wine regions to the south, Montecarlo and the nearby Colline Lucchese (Lucca Hills) are well regarded by Tuscan locals for very good regional wines, especially white. Today is an opportunity to discover a corner of Tuscany’s wine world that most international visitors never experience. Visit a winemaker in Montecarlo to discover this interesting production in northern Tuscany and enjoy a private wine tasting, along with a light lunch at the winery.
Olive farming is another important activity for the rural economy in the province of Lucca, and Montecarlo is within the boundaries for producing DOP Lucca Extra Virgin Olive Oil. DOP Lucca EVOO is lightly fruited, primarily sweet on the palate with spicy finish.
After your wine tasting and lunch in Montecarlo, return to Lucca for free time to discover more of the city on your own.
What’s Included
Montecarlo DOC
While the village of Montecarlo is very small, under 4,500 inhabitants, this small DOC has around 20 local wineries. Montecarlo wines depart from the usual blend and varietals found in Tuscany, especially for white wine. Montecarlo DOC allows blends between 40% – 60% Trebbiano and 40% – 60% Semillon, Pinot Bianco, Pinot Gris, Vermentino, Sauvignon Blanc, and Roussane. Dry, aromatic Montecarlo Bianco pairs beautifully with Tuscan seafood.
Private Super Tuscan Wine Tasting in Bolgheri

After starting the morning with fresh homemade breakfast at the Grand Universe Lucca, your driver will collect you from the hotel to set off for today’s private wine tasting tour in Tuscany focused on Super Tuscans. Travel from Lucca to the Maremma Toscana, a stretch of coastal Tuscany running along the Tyrrhenian Sea from Livorno south to the Argentario Peninsula. This wild, natural section of Tuscany’s coast does not have a long history of wine production. But since one of Piedmont’s oldest winemaking families began planting Cabernet Sauvignon in Bolgheri in the 1940s, the Maremma has rapidly transformed into Italy’s Napa Valley, attracting large investments and land acquisition from big names in Italian and international winemaking.
Your first stop during today’s Super Tuscan wine tour is the village of Bolgheri. In the 1940s, Marchese Mario Incisa della Rocchetta planted Cabernet vines on his wife’s San Guido estate in Bolgheri, and the proto Super Tuscan, Sassicaia was born. His nephews, Ludovico and Piero Antinori thought their uncle was onto something and began selling Sassicaia with the 1968 vintage. Sassicaia achieved sensational success in the 1970s, prompting Ludovico and Piero Antinori to follow suit and plant Bordeaux grapes in their own Bolgheri plots, creating the now legendary Super Tuscans Ornellaia and Guado al Tasso. Discover the Super Tuscans’ star turn today as you visit this charming little village, then proceed to a local Bolgheri estate for a private tour of the vineyards, cellars, and a private wine tasting accompanied by light lunch at the winery.
After your wine tasting and lunch in Bolgheri, continue to another hill town in Tuscany’s Maremma, nearby Castagneto Carducci. The Etruscan Coast Wine and Olive Oil Train runs through Castagneto Carducci, making this beautiful medieval village an ideal combination of culture and cuisine. Take time to explore the village’s quaint piazzas and if you’re still thirsty, survey more Super Tuscan blends in Castagneto Carducci’s local enotecas.
What’s Included
Super Tuscan Wines
Super Tuscan is an unofficial name that began as an act of rebellion against Italy’s DOC and DOCG laws in the 1960s. Some winemakers in Tuscany found the regulations too constraining for producing high quality, modern wines. They wanted to blend Tuscan Sangiovese with French varietals like Cabernet, Merlot, Syrah, in addition to aging in smaller oak barriques. Despite their very high quality, these Tuscan blends of Sangiovese with Bordeaux grapes were forced to bear the lowly Vino da Tavola label, the lowest tier in Italy’s classification until the IGT category (Indicazione Geografica Tipica) was created in the 1990s as a compromise between the highly regulated DOCG and DOC classifications and the totally unregulated Vino da Tavola. Italian IGT wines must only display a vintage, the name of the producer, and the region of origin. IGT Toscana can be produced anywhere in Tuscany, in any style, with any blend. Some of the original so-called Super Tuscans were ultimately elevated to their own DOC classification – Bolgheri and Sassicaia now each have their own DOC, for example, but given how broad a category IGT Toscana is, knowing a good Super Tuscan from a bad one, requires building some knowledge of individual producers and their quality. The best Super Tuscans fetch some of the highest prices in Italian wine.
Depart Lucca and Transfer to Florence Airport.

Savor a final breakfast at the Grand Universe Lucca this morning before hotel pickup and private transfer to Florence airport for your journey home.
Arrivederci, Tuscany. Until soon!
What’s Included
Your Luxury Tuscany Food & Wine Tour in Review
From the cradle of the Renaissance in Florence to the unspoiled Tyrrhenian Coast in the Maremma, these 10 unforgettable days in Tuscany have been a luxurious immersion into the heart of Italy’s food and wine culture. You’ve gained new insights into Tuscany’s rich historical legacy during fascinating guided visits to UNESCO World Heritage sites in Florence, Pisa, San Gimignano, Siena, Pienza, and the Val d’Orcia. You leave Tuscany with both an appreciation for its centuries-old culinary traditions, and your own skills to cook authentic Tuscan dishes for friends and family back home. During your private visits and tastings with winemakers in Chianti Classico, Montalcino, Montecarlo, and Bolgheri, you’ve enjoyed some of Italy’s best wines while experiencing firsthand how important winemaking is for Tuscany’s economy, its gastronomy, and to people’s pride in their territory and local traditions. Let the creative artisans you’ve met in Tuscany and the new friends you’ve made inspire your own pursuits and passions.
Not ready to head home? Let us customize your Italian travels onwards from Lucca or Florence. Contact us for ideas and inspiration. Tuscany can be easily combined with Piedmont, Liguria, Emilia-Romagna, the Veneto, Umbria, or Rome.

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