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Community Globetrotters - Luxury Cultural Experiences

A Culinary Journey Through Italy: Private Wine Tastings

A Culinary Journey Through Italy | Private Wine Tastings
12 Days from $16,528 per person
Multiple Dates
Florence, Montalcino, Bologna, Milan
Beginning in Rome, you'll be greeted by a private assistant and enjoy a welcome package at your hotel. In Florence, immerse yourself in Renaissance history with a guided tour of iconic landmarks and visit a vineyard in Northern Tuscany for wine tasting. A cooking class awaits in Florence, followed by a scenic transfer to Montalcino, where you can indulge in activities like golf, spa treatments, and wine tours. Journey to Bologna for a gastronomic adventure, including visits to cheese and vinegar producers. End your trip with a glimpse of Milan's historical and fashion delights before bidding farewell to Italy.

12-Day Itinerary
Day 1:  Welcome to Italy! Meet your private English-speaking assistant outside of airport customs. Waiting with a sign with your name on it, they will direct you to your awaiting private transfer, and accompany you to your hotel for check-in. A welcome package with a city map, train tickets (if relevant), and any other touristic information that we deem you may find useful, will be provided to you on your first day in destination.
Day 2:  Florence | Get a lay of the land - Travel back to the Renaissance period during a half-day walking tour exploring the renowned Tuscan city of Florence. Depart your hotel on foot with your private guide, strolling through Florence's UNESCO World Heritage-listed old city center, coming to renowned Cathedral Square where you can admire some of the city's most iconic sites. Spot the massive 13th-15th century Florence Cathedral and 277-foot Giotto's Bell Tower which dominate the skyline, as well as the nearby 11th century Romanesque Baptistery with its Paradise Door. In Signoria Square, effectively an open-air sculpture museum, view the imposing Palazzo Vecchio with its clock and bell tower, and marvel at the stunning Neptune Fountain and recreated statue of Michelangelo’s masterpiece, David. Head to the elegant 14th century Ponte Vecchio, known as the jewel bridge. After exploring the city, you will proceed with your guide to visit the Accademia Gallery where you will have the chance to view Michelangelo's David. Completed in 1504 after four years' work, this stunning statue attracts millions of art lovers from around the globe each year. 
You will be met at your hotel by your private driver to travel across Northern Tuscany to the wine area of Monecarlo di Lucca (Pinocchio's birthplace), passing medieval villages and green valleys covered in vineyards and olive trees to a beautiful farmhouse to taste prized wines and other local specialties. After a warm welcome at the vineyard, you will be shown theirs beautiful estate where some of the best Tuscan wine is produced. Learn about the wine making process and sample some of their house wines accompanied by local specialties such as salami, cheese and bread. Wine tasting included. You will also have the opportunity to purchase some wine prior to returning to your hotel.
Day 3:  Florence | Creative cuisine - Enjoy an afternoon cooking class at Chef Laura's home in the center of Florence. You will be provided the address to enjoy a nice cooking class consisting of the preparation of a 4 course typical Italian Tuscan dinner consisting of an appetizer, homemade pasta, main course and dessert. You will later enjoy eating what you prepared during your cooking class. 
Day 4: Florence to Montalcino | A dazzling drive - Meet your private driver and vehicle for a transfer to Montalcino. Approximate travel time is two hours.  Rosewood Castiglion del Bosco is well set up for activities on the estate. It features miles of picturesque hiking and biking trails that hug spectacular ridges and meander past streams, waterfalls and hidden historic sites. Handsome Maremma horses, used by traditional Tuscan herdsmen, can also be taken out through a network of riding trails extending to the far-reaching corners of the property. Immersed in the heart of the Val d'Orcia Artistic, Natural and Cultural Park, Castiglion del Bosco Golf Club centers on a spectacular eighteen-hole course designed by the legendary Tom Weiskopf. Golf enthusiasts will certainly be pleased with the course. Spa lovers will be truly content with the offerings at the Care Suite Spa which is a serene oasis that specializes in unique therapies based on organic ingredients from the Estate. Entrust yourself to the caring hands of the in-house team, who will pamper you with a complete range of exquisite beauty, spa and wellness treatments. Alternatively, relax by the heated infinity pool or enjoy a wine tasting on the property if you haven't already - Castiglion del Bosco is among the first five Brunello wine producers. The extensive Gardens are a magnificent amenity in their own right, and encompass a radiant Tuscan palette for all seasons, including flower-decked terraces, rustic olive groves, manicured fruit orchards and sprawling Sangiovese vineyards. The splendid vegetable garden, designed by the Vatican's garden landscaper, is home to more than 180 varieties of vegetables, fruits and aromatic herbs grown exclusively for La Canonica's restaurants and Culinary Academy.
Day 5:  Montalcino | Vineyards and vintages - Meet your private driver for a transfer to the beautiful Bolgheri region, approximately 2 hours from Montalcino. On arrival, enjoy an included lunch at a local restaurant known for its genuine Mediterranean flavors and typical Tuscan dishes (wine not included). After lunch, you'll head off to the famous Ornellaia Wine Estate located near the picturesque village of Bolgheri, near the unspoiled Tuscan coast. The uniqueness of the area was epitomized by the famous poet Giosue Carducci who gave eternal fame to the monumental Cypress Avenue leading up to Bolgheri. The coastal plain is a natural refuge to numerous migratory birds and other protected species. In the midst of all this natural beauty lie the vineyards of Ornellaia. It is here that you will enjoy a 3 hour visit of the vineyards and winemaking facilities, followed by a privately hosted tasting of five different Ornellaia wines: Le Volte dell’Ornellaia, Le Serre Nuove dell’Ornellaia, Ornellaia, and Variazioni in Rosso. Upon request (no extra cost), you can also have the opportunity to taste the Extra virgin olive Oil and Eligo dell’Ornellaia, their Grappa Riserva. Some free time will then be provided before driving back to your hotel.
Day 6:  Montalcino | Pedal through the past - You will be met at the hotel by your private driver for a 20 minute drive to the meeting point where your guide and private mountain bikes will be awaiting you. Based on your biking ability, together with your guide you will set up a maximum 4 hour biking tour. Upon completion, you will then be provided with some free time (about 3 hrs) to explore the charming Montalcino; one of the loveliest little wine villages in Italy, home to the famed Brunello di Montalcino wine. The hill-topped village of Montalcino exists since the time of the Ancient Etruscans and the nearby Sant Antimo monastery was founded in the 8th century! The village as seen these days contains many reminders of medieval times and also offers great views over the whole Orcia Valley with its rolling hills and Cyprus lined country roads. At the end of the tour, a transfer will be provided to you to return to the hotel.
Day 7:  Montalcino to Bologna | The journey continues - This morning, enjoy time at leisure to explore at your own pace, or relax at your hotel. Meet your private driver for a transfer to Bologna. Approximate travel time is 2 hours and 45 minutes.


Day 8:  Bologna | Pound the pavement - Discover the tastes of the Emilia Romagna region on a private tour designed for the gastronomical lovers where you'll learn about the process of vinegar creation, Parmesan cheese, and Culatello Prosciutto ham, all famous local products of the area. Setting out with a private driver, begin with a scenic two-hour drive to a small village in the heart of Emilia Romagna where you'll visit a famous Parmesan producer. A staff member will detail the entire Parmesan-making process, and treat you to a delightful tasting of three separate categories of the famed cheese that they produce. Continue along a scenic road towards another small local village where you'll meet a local producer of high quality Culatello ham. Delight in a visit of the facility along with an explanation on how the famous ham is being produced followed by a tasting of the mouthwatering Prosciutto. After, head to a nearby local restaurant where you'll be treated to an excellent 4-course typical lunch, paired with two different wines. Rejoining your driver, continue toward your third and final visit, a small family-run balsamic vinegar producer. Discover the barrels where the vinegar is being stored and aged as you enjoy a guided visit of their property, culminating in a tasting of three different categories of vinegars, aged to 10, 25 and 50 years. With a dazzled palate, conclude with a return transfer to your hotel. Please note that the order of the visits might run in reverse based on availability in each location.
Day 9:  Bologna | Gourmet delights - Emilia Romagna region owns a rich treasure holding oenological wealth. Travelling from West to East, you will discover vineyards of different grape varieties such as Barbera, Bonarda, aromatic Malvasia di Candia, Lambruscos, Pignoletto on the Bologna hills and Sangiovese and Albana in the southern part Romagna.  Wines produced with these varieties are the result of a balance between tradition and modernity and reflects the personality of the people of this Region being lively and friendly in Emilia, deep and intense in Romagna (7 million hectoliters per year on average is produced, one third is exported). You will be transferred by your private driver to Dozza where your local guide will be waiting for you. Enjoy a walking tour of the town followed by a visit of the fortress built in 1250 and renewed in the 15th century. It was converted from a purely military building to a residential complex by the feudal lords in the 16th century. In the apartment are displayed 17th and 18th century furnishings. Since 1970 the cool underground vaults of the fortress have been home to the Emilia Romagna Regional Wine Cellar (Enoteca). The picturesque vaults contain a permanent collection of specially selected wines.  Here, over 800 different labels, representing 250 associated producers selected from the best in Emilia Romagna, It is here that you will meet your private sommelier to enjoy a private wine tasting of 6 separate wines paired with appetizers (Included) in order for you to find out about wine and regional food matching. Upon completion of your wine tasting you will enjoy a tasty 4 course lunch accompanied with by a glass of wine at a nearby local restaurant. The restaurant offers a unique decor that features items that once belonged to the castle. Tuesdays a different restaurant venue will be provided as this specific one is closed.  Then, you will have some free time prior to transferring back to your Bologna hotel. Entrance fee to Dozza fortress is included.
Day 10:  Bologna to Milan | On the road - Meet your private driver for a transfer to Milan. Approximate travel time is 2 hours and 45 minutes. Meet your private guide and driver, setting out on a half-day tour of monumental Milan. Admire the stunning exterior of the great Cathedral of Milan, a 515-foot long Gothic masterpiece which took six centuries to complete. It's the largest church in all of Italy, and the third largest in the world. Walk around the perimeter of the red and brown stone Sforza Castle, a Renaissance palace built in the 15th century by the Duke of Milan. Over years of expansion, the complex eventually became one of Europe's largest citadels. Continue on with views of La Scala, Milan's 18th century Opera House, one of the most prestigious in the world. The highlight of your tour will be a visit to the Santa Maria delle Grazie Church - a beautiful 15th century Renaissance convent, where you'll get to see the world-famous painting the Cenacolo (Last Supper) by Leonardo da Vinci. Conclude with a return transfer to your hotel.

Please note, tickets for the Last Supper cannot be guaranteed due to extremely limited availability. Every effort will be made to secure tickets in the days leading up to your trip.


Day 11:  Milan | Shop the shoppes - Milan is recognized throughout the world as the capital of pret-a-porter and a temple of fashion: Gucci, Armani, Prada, Valentino, the list of high-end designers found in this city goes on. Set out on foot with a personal shopper in the upscale shopping district, Quad d'Oro, to discover the most beautiful shops of the city. Having assisted numerous royals during their visits to Milan, your expert personal shopper will tailor your experience to your personal interests, ensuring you get the most out of your private fashion tour.
Day 12: Milan | Journey home - Transfer to the airport for your journey home. Until next time!

Trip Highlights
  • From Bologna, experience the gastronomy of Emilia Romagna with a private guide.
  • Vineyard visit and wine tasting in Tuscany.
  • Cook with a chef during a private cooking class in Florence.
  • Discover the highlights of Florence and Milan with a private guide.
  • Luxury accommodations throughout.

Available Packages

Price Per Person (Double Occupancy)
Unavailable as of February 19, 2024

Deposit: $1,000.00 per person