Tour description
Tuscany, Food Valley & Lake Como Custom Tour
Experience Italy through its most iconic cultural landscapes and gastronomic heartlands on this 18-day private journey from Rome to Milan. Explore the Eternal City, the medieval hill towns of Umbria, the UNESCO-listed Val d’Orcia, the vineyards of Brunello di Montalcino and Chianti Classico, the artisanal food traditions of Emilia-Romagna, and the serene elegance of Lake Como. With boutique hotels, family-run wineries, artisan cheese makers, balsamic masters, and local guides, this tailor-made itinerary blends wine, culture and slow luxury travel into an unforgettable insider’s Italy experience.
DAY 1 ARRIVAL ROME
Your private chauffeur will greet you at Rome Fiumicino Airport and transfer you to your boutique hotel in the historic center. All the 4 and 5 star boutique hotels we work with are hand picked, with lovely rooms, great breakfast and service.
You have arrived in the Eternal City – where over 2,800 years of history, art and architecture unfold in every direction. From your privileged location, stroll to landmarks such as the Trevi Fountain, Piazza di Spagna, the Quirinale district or even the Roman Forum. Enjoy an aperitivo in a lively piazza or relax with a cappuccino for classic Italian people-watching.
If this is your first visit to Rome, we recommend extending your stay for a private tour of Ancient Rome (Colosseum, Forum & Palatine Hill) and/or a dedicated Vatican Museums experience, options we will be delighted to arrange. We will also include personalized suggestions for the best local restaurants close to your hotel in your Personal Travel Website.
Tour in a Nutshell: Private transfer. Overnight in a central 4* boutique hotel in Rome.
DAY 2 UMBRIA: ORVIETO & CIVITA DI BAGNOREGIO
This morning your private chauffeur will collect you in Rome as you begin your journey toward Tuscany, with enriching stops along the way in the beautiful region of Umbria. Start in the dramatic hilltop town of Orvieto, known for its magnificent Gothic Cathedral, medieval streets and sweeping views of the surrounding countryside. Continue to the ethereal Civita di Bagnoregio, reachable only via its iconic footbridge. Often called “the dying town” it offers breathtaking panoramas and a captivating sense of history suspended in time. Enjoy an Umbrian lunch before continuing into southern Tuscany and the tranquil thermal village of Bagno Vignoni.
Check into your 5* boutique spa hotel Posta Marcucci, with its gorgeous natural hot springs surrounded by the rolling hills of the Val d’Orcia.
Tour in a Nutshell: Chauffeured day. Visit Orvieto & Civita. Local cuisine lunch. Overnight in a 5* boutique spa hotel in Val d’Orcia.
DAY 3 VAL D´ORCIA, MONTALCINO & PIENZA
Today you will set out with your guide/driver for a full-day exploration of Southern Tuscany, one of Italy’s most celebrated and photogenic regions. Your journey begins in the UNESCO-listed Val d’Orcia, a landscape of soft, undulating hills, cypress-lined drives, stone farmhouses, and medieval villages that seem untouched by time. You will make scenic stops along the way, allowing you to take in breathtaking views and capture some unforgettable photos.
Continue onward to the village of Montalcino, home of Brunello di Montalcino DOCG. Here you will enjoy a private visit at one of our favorite family-run cellars such as Tenuta Fanti, Caparzo or Cordella, learning about the local Sangiovese grapes and Brunello’s aging methods, followed by a Tuscan lunch.
In the afternoon, you will visit Pienza, the Renaissance “ideal city” created by Pope Pius II, a perfect stop for an aperitivo with sweeping views of the Tuscan rolling hills. Pienza is famous for it s Pecorino di Pienza Cheese and you will enjoy a private tasting at your favorite cheese artisan, discovering the flavors and techniques behind the region’s iconic cheese.
After a day immersed in the beauty, flavors, and traditions of Tuscany, your driver will return you comfortably to your hotel.
Tour in a Nutshell: Chauffeured day trip to Val d’Orcia, Montalcino & Pienza. Private visit to a family-run Brunello winery with tastings and a local cuisine lunch. Visit to a traditional pecorino cheese producer with tastings. Overnight Val d’Orcia.
DAY 4 PERUGIA & UMBRIAN VILLAGES
Today you will embark on a private chauffeured excursion into Umbria, Tuscany’s serene and soulful neighbor. Known as the “green heart of Italy,” Umbria is dotted with rolling hills, ancient towns, and enduring traditions that offer a wonderfully authentic experience.
Your first stop is Perugia, a vibrant university city rich in Etruscan, medieval and Renaissance heritage and famous for its delicious chocolate, which you will enjoy at our favorite tiny shop. Continue to Spello, one of Italy’s most picturesque hilltop villages, famed for its narrow, flower-lined lanes and beautifully preserved Roman mosaics. You will then continue to Montefalco, home of the bold Sagrantino di Montefalco DOCG, for a private tasting and hearty Umbrian specialties lunch, before returning to your hotel.
Tour in a Nutshell: Chauffeured day trip to Umbria. Private winery visit and tastings. Local cuisine lunch. Overnight Val d´Orcia.
DAY 5 MONTEPULCIANO
Spend the morning exploring the hilltop village of Montepulciano, admired for its Renaissance palaces, atmospheric lanes and the noble Vino Nobile di Montepulciano DOCG. Enjoy time to browse a selection of our favourite enotecas and small historic cellars, and take in the sweeping views across the Tuscan countryside.
A private visit and relaxed lunch awaits at Tenuta Boscarelli, one of our trusted family-run Vino Nobile estates. Here, the owners will warmly welcome you and share engaging insights into the traditions, terroir and character that define this prestigious wine.
In the afternoon, return to your hotel and unwind at the natural hot springs of Bagno Vignoni. Whether you choose to relax in the warm thermal waters, book a spa treatment or simply enjoy the peaceful setting by the pools, this is the perfect moment to savor the restorative atmosphere of the Val d’Orcia.
Tour in a Nutshell: Chauffeured visit to Montepulciano. Private winery visit and lunch. Free afternoon to enjoy Bagno Vignoni hot springs. Overnight in Val d’Orcia.
DAY 6 CHIANTI
This morning your private chauffeur will collect you for a private visit to the charming town of Siena and the nearby Chianti wineries. In Siena, our passionate local guide – a member of one of the city’s historic Contrade – will bring the medieval city to life with fascinating insights into the Palio traditions, centuries-old rivalries and everyday Sienese culture. Enjoy a guided stroll through Siena’s atmospheric streets, visit the stunning Duomo di Siena, and enjoy a few curated tastings of regional specialties along the way.
Continue into the heart of Chianti Classico DOCG for a private visit and lunch at one of our favorite small family-run wineries, paired with their elegant Sangiovese-based wines. Then, you will stop at the historic Castello di Brolio, considered the cradle of Chianti wine. Explore the estate’s grounds and taste a selection of its iconic reds, deepening your understanding of Chianti’s winemaking heritage.
Before heading to your hotel, stop briefly in Monteriggioni, a perfectly preserved medieval fortress village encircled by ancient stone walls. Enjoy a relaxed wander through its charming piazza and quiet lanes.
In the late afternoon, arrive at your luxurious 5* countryside hotel near Radda in Chianti – an elegant historic castle surrounded by vineyards and olive groves, an ideal peaceful retreat to unwind and ease into the gentle rhythm of Chianti life.
Tour in a Nutshell: Chauffeured tour with guided visit of Siena. Lunch and wine pairing at a family-run Chianti Classico estate. Visit to Castello di Brolio with wine tasting. Stop in Monteriggioni. Overnight at a 5* boutique countryside hotel in Chianti.
DAY 7 CHIANTI
Today is yours to relax and enjoy the slower pace of Chianti at your historic countryside hotel. Start the morning as you wish – over a generous breakfast, in the comfort of your room, or simply appreciating the views of vineyards, olive groves and wooded hills that surround the property. With the medieval village of Radda in Chianti just a short stroll away, it’s an ideal setting to unwind and enjoy the charm of rural Tuscany.
You may wish to spend part of the day in the hotel’s wellness area, with access to the heated indoor pool, sauna, Turkish bath and quiet relaxation spaces. Alternatively, walk into Radda to explore artisan shops, enjoy a cappuccino in the piazza, or settle into a local trattoria for lunch.
For those who like to be outdoors, the countryside offers excellent walking paths through vineyards, chestnut woods and gentle ridgelines. We will share route suggestions tailored to your interests.
As the day winds down, you might sample some of the local products gathered along your journey, perhaps accompanied by a glass of Chianti Classico while taking in the evening light over the hills.
Tour in a Nutshell: Free day Chianti. Overnight Chianti.
DAY 8 SAN GIMIGNANO
This morning your private chauffeur will collect you as you depart the peaceful Chianti countryside and make your way toward Florence, enjoying a beautiful day of exploration along the way. Your first stop is the magnificent hilltop town of San Gimignano, famed for its soaring medieval towers, atmospheric stone lanes and spectacular views over the Tuscan countryside. Enjoy free time to browse artisan boutiques, taste Vernaccia di San Gimignano DOCG, and admire the skyline that has earned the town its nickname, the “Medieval Manhattan.”
Continue to Castello Monterinaldi for a private visit and lunch. Set along an ancient Etruscan route, this family-run estate is known for its terroir-driven Chianti Classico, organic vineyards and its dedication to traditional aging in oak and concrete. Explore their hands-on winemaking philosophy before sitting down to a relaxed lunch paired with their elegant, estate-grown Sangiovese.
In the afternoon, visit the remarkable Antinori nel Chianti Classico estate – an architectural masterpiece seamlessly integrated into the hills of Bargino. During your premium tour, learn about the Antinori family’s 26 generations of winemaking, their pivotal role in shaping modern Tuscan wine (including the rise of the Super Tuscans), and their forward-thinking techniques. After your guided tasting of flagship labels, you will have time to stop at the estate’s sophisticated wine lounge – an excellent opportunity to compare vintages and discover limited releases such as Tignanello, Solaia, Guado al Tasso, and other celebrated Antinori wines.
Later in the afternoon, depart the estate for a scenic drive into Florence, where you will check into your charming 4* boutique hotel in the historic center. If this is your first visit, we will be delighted to arrange an extended stay and a private tour with one of our outstanding Florence guides. If you have been before, Florence is always a joy to revisit – perhaps with an evening stroll along the Ponte Vecchio, through Piazza della Signoria, or a relaxed dinner in a favourite Florentine trattoria.
Tour in a Nutshell: Chauffeured transfer from Chianti to Florence. Visit to San Gimignano. Private winery visit and lunch. Premium tour and tasting at Antinori nel Chianti Classico. Overnight at a 4* boutique hotel in Florence.
DAY 9 BOLOGNA
If you prefer to continue your journey north, this morning you will take a comfortable high-speed train from Florence to Bologna, Italy’s beloved food capital. Upon arrival, check into your charming 4* boutique hotel in the heart of the city – an ideal base for exploring Bologna’s medieval streets, porticoed avenues and vibrant culinary scene.
Our private local guide will meet you for an engaging private culinary and cultural walking tour through the heart of the city. Explore Bologna’s historic markets, artisan food shops, and medieval portico-lined streets while learning about the traditions, ingredients, and stories that define its world-famous cuisine. Along the way, you will enjoy generous tastings of regional specialties – fresh egg pasta, artisanal cured meats, aged Parmigiano Reggiano and classic Bolognese treats and other iconic delights that make Emilia-Romagna a paradise for food lovers.
Your guide will give you the best tips for the rest of your afternoon – wander the elegant arcades, explore the city’s stylish boutiques, climb the medieval Torre degli Asinelli for sweeping views, or settle into a lively piazza for an aperitivo as the city comes to life. Your Personal Travel Website will also include many personalised recommendations for the rest of your day.
Tour in a Nutshell: High-speed train from Florence to Bologna. Private guided culinary & cultural walking tour with food tastings. Overnight at a 4* boutique hotel in the heart of Bologna.
DAY 10 FOOD & MOTOR VALLEY
This morning your private chauffeur will take you into the heart of Emilia-Romagna’s legendary Modena & Motor Valley area for an exciting day devoted to Italy’s most iconic automotive brands. Visit the Lamborghini or Maserati museum, where beautifully curated collections, historic models, and cutting-edge supercars trace the evolution of these world-famous marques.
Continue to a traditional Parmigiano Reggiano DOP producer, where you will discover the centuries-old techniques behind this celebrated cheese. Enjoy a guided visit through the production areas and aging rooms, followed by tastings of different maturations that reveal the depth and character of real Parmigiano.
Afterwards, visit the cute little town of Modena, enjoy a private visit to our favorite historic Aceto Balsamico producer, or, if you are passionate about Italian automotive heritage, you can opt to visit to the Ferrari Factory and Museum in Maranello (the factory visit is only of the exterior of the production plant), allowing you to immerse yourself even further in the craftsmanship, design, and innovation that define Italy’s most prestigious automotive houses.
You will return to your hotel in Bologna to enjoy the remainder of your evening.
Tour in a Nutshell: Chauffeured day trip. Visit to Lamborghini or Maserati museum. Private tour and tasting at a Parmigiano Reggiano producer. Overnight in Bologna.
DAY 11 RAVENNA
Today your private chauffeur will take you on a delightful day trip to Ravenna, a city celebrated for its extraordinary early Christian and Byzantine mosaics – some of the most remarkable in the world and all recognized as UNESCO World Heritage. Enjoy free time to wander through Ravenna’s elegant historic center, visit its stunning basilicas, and admire the shimmering gold mosaics that have inspired artists for centuries.
You may also choose to visit Ferrara instead – a beautifully preserved Renaissance city once ruled by the powerful Este family. Ferrara is renowned for its sophisticated palaces, broad streets, and exceptional cultural heritage. Highlights include the moated Este Castle, the striking Palazzo dei Diamanti, and the city’s impressive medieval walls. With its relaxed pace and refined atmosphere, Ferrara is an ideal choice for history and art lovers.
After your visit, your chauffeur will return you to Bologna for a relaxed evening in the city.
Tour in a Nutshell: Chauffeured day trip to Ravenna (or optional Ferrara). Overnight Bologna.
DAY 12 LAKE COMO
This morning you will travel from Bologna to Milan aboard a comfortable high-speed train, enjoying a smooth and scenic journey through northern Italy. Upon arrival in Milan, your private chauffeur will meet you and drive you into the tranquil beauty of Lake Como, one of Italy’s most enchanting and romantic destinations.
You will check into your charming 4* lakeside hotel in the picturesque village of Varenna. Set directly along the water, this historic property offers elegant rooms, serene gardens, and beautiful views of the lake and surrounding mountains – an idyllic base for the coming days.
The rest of the afternoon is yours to unwind. You may choose to relax by the pool, stroll through Varenna’s peaceful waterfront, or simply enjoy the calm atmosphere from the comfort of your hotel. We will include personalized suggestions for dinner and evening walks.
Tour in a Nutshell: High-speed train from Bologna to Milan. Private chauffeured transfer to Lake Como. Overnight in a 4* lakeside hotel in Varenna, Lake Como.
DAY 13 LAKE COMO
This morning you will explore Lake Como with our charismatic local skipper, who will share stories, history and insights about the lake, its surroundings and its famous visitors.
Admire iconic lakeside villas including Villa Carlotta, Villa Melzi, Villa Oleandra (George Clooney) and the enchanting Comacina Island aboard a beautiful wooden Venetian boat. Your skipper will also give you a lot of practical local info on how to move around the lake with public ferries, he will also be more than happy to take some delightful pics of you too!
The rest of the day is at your own leisure and we will provide many free time suggestions.
Included: Private Lake Como boat tour. Overnight in Lake Como.
DAY 14 SWITZELAND: LAKE LUGANO
This morning your private driver will take you across the border into Switzerland for a scenic day exploring the refined landscapes of Lake Lugano. Enjoy beautiful views of alpine peaks, palm-lined promenades and the shimmering lake as you arrive in the elegant town of Lugano, the cultural center of Ticino.
Stroll along the Lakeside Promenade, admire views of Monte Brè and Monte San Salvatore, and wander the charming streets of the old town. You may browse luxury boutiques on Via Nassa, visit peaceful Parco Ciani, or linger in the lively Piazza della Riforma, lined with cafés and pastel façades.
You will enjoy the excellent local Swiss-Italian cuisine at our favorite lakeside restaurant and visit Gandria, a picturesque lakeside village known for its steep lanes and timeless atmosphere, before your return to Varenna to enjoy a relaxing evening on Lake Como.
Included: Chauffeured day trip to Lugano, Swiss Italian cuisine lunch. Overnight in Lake Como.
DAY 15 VALTELLINA
Today you will enjoy a chauffeured excursion into the alpine wine region of Valtellina, one of Italy’s most dramatic viticultural landscapes. Near the town of Sondrio, steep stone terraces rise along the mountainsides, planted with Nebbiolo – locally called Chiavennasca – which thrives in the sunny, south-facing slopes of the valley.
You will begin with a private visit to a boutique winery in the Valtellina Superiore area, where you will learn about the region’s heroic viticulture and taste elegant mountain wines, including Valtellina Superiore and the concentrated Sforzato di Valtellina. A relaxed lunch at a local osteria follows, featuring alpine cuisine paired with expressive Nebbiolo.
Continue with a visit to a traditional casera cheese producer to sample local specialties such as Bitto and Valtellina Casera, before a short stroll through a nearby village like Tirano or Chiuro, known for their quiet streets and sweeping mountain views.
Return to your hotel in the late afternoon for a peaceful evening on Lake Como.
Included: Chauffeured day trip to Valtellina, private winery visit and tasting, local cuisine lunch, cheese tasting. Overnight in Lake Como.
DAY 16 MILAN
This morning your private chauffeur will transfer you to Milan, Italy’s sophisticated capital of fashion, design and contemporary culture. Upon arrival, check into your elegant 4* boutique hotel in the historic center and take a moment to settle in.
In the early afternoon, our engaging local guide will await you for a private introduction to Milan’s most iconic landmarks. Begin at the magnificent Duomo di Milano, where you may ascend to the Duomo Rooftops for panoramic views over the city’s skyline. Continue through the historic Galleria Vittorio Emanuele II, Italy’s oldest and most glamorous shopping arcade, before strolling toward the atmospheric Brera district – known for its cobbled streets, artisan workshops and artistic heritage. Along the way, enjoy curated tastings of classic Milanese specialties.
Your tour concludes with a visit to Leonardo da Vinci’s Last Supper at Santa Maria delle Grazie -one of Milan’s most coveted cultural experiences and a profound highlight for art lovers.
Tour in a Nutshell: Private transfer to Milan. Boutique 4* hotel check-in. Private guided tour including the Duomo and the Last Supper. Overnight in Milan.
DAY 17 MILAN
Today is free for you to explore Milan at your own pace. As with every day of your journey, your Personal Travel Website will offer tailored suggestions based on your interests – whether that means browsing the luxury boutiques of the Quadrilatero della Moda and Via Montenapoleone, discovering the artistic charm of Brera, admiring the contemporary architecture of Porta Nuova and Piazza Gae Aulenti, or enjoying an aperitivo along the bohemian Navigli canals.
If you prefer a change of scenery, you may opt for a high-speed train to Venice. Here you can enjoy a privately guided walking tour through the city’s atmospheric calli and campi, a classic gondola experience, or a visit to the lagoon islands – Murano, Burano, or Torcello – each offering its own cultural and artisanal traditions.
Tour in a Nutshell: Free day in Milan with personalized recommendations, or optional Venice extension. Overnight in Milan.
DAY 18 DEPARTURE MILAN
Private chauffeured transfer to the main Milan airport of Malpensa or to the smaller Linate Airport for your departing flight.
Tour in a Nutshell: Private Transfer to Milan Airport.
Tour quotation
Tuscany, Food Valley & Lake Como Custom Tour Details
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