See the best of Italy with our wine and food experience. Relax, explore, learn, and sample first-class food and wine as we journey through Italy’s premier wine regions, meeting family producers and learning directly from the winemakers.
Delight in a curated selection of our favorite restaurants, from Michelin-starred fine dining to lively osterias. Enjoy exquisite pairings of local wines with the fabulous produce of each region.
Whether traveling solo, as a couple, or with friends, our luxury tours provide the perfect escape to relax and enjoy a spot of luxury. We handle all the details, so you can simply focus on enjoying your time together.
At Joy of Wine Journeys, we specialize in showcasing the best of Italy, making your milestone birthday, anniversary, honeymoon, family gathering, or class reunion truly unforgettable! Come and discover the magic of Bella Italia.
Any questions about this tour experience? Please get in touch. If you’re also passionate about French wine, please also consider our 11-Day Wine and Food Tour in France.
Our tour begins in the Piedmont region, a cultural and culinary gem nestled between the Alps and the Ligurian Sea in northwest Italy. To welcome you and your travel companions to Northern Italy, we will gather at a hotel adjacent to the Milan Malpensa Airport (MXP) for an introductory reception.
Together, we will transfer by private coach to the Tenuta Santa Caterina Winery, located in the village of Grazzano Badoglio in Monferrato’s province of Asti. The winery is built around a Benedictine abbey dating back to 961 A.D. and boasts an ancient underground cellar. Here we will experience the first tour and tasting of our journey together, led by the winemaker himself, followed by a lunch celebrating the wines and local cuisine of Monferrato.
Travelling on, we will arrive at our extraordinary home for the next three nights—Castello di Gaurene, a breathtaking castle built in the 18th century and renovated into a luxury five-star hotel in the heart of the rolling hills of the Roero.
After time to unpack, relax, and refresh, the day finishes with an indulgent welcome dinner where you can get to know your fellow travelers and ease into the rhythms of La Dolce Vita.
Wines: Arneis, Barbera, Nebbiolo, and Chardonnay
Meals: Lunch at Tenuta Santa Caterina; Multi-course welcome dinner with wine pairings
Activity: Welcome reception; Winery tour and tasting
Accommodation: Luxury 5-Star Castle built in the 18th century perched atop a hill overlooking the rolling vineyards of the Langhe and Roero (a Relais and Chateau property)
After enjoying a leisurely breakfast at the Castello, we will depart for the Demarie winery in the Roero.
Third-generation winemaker Paolo Demarie will guide us through a tasting at his family cellar in Vezza d’Alba, sharing his deep knowledge about his vineyards and his remarkable wines. A traditional lunch in his cellar will give us more time to absorb Roero’s history and savor local flavors, including the famed Alba truffle (when available).
Following lunch, we will embark on a short tour through the heart of the Langhe hills, home to Italy’s most famous and important vineyards, with a stop in Barolo wine country to admire the breathtaking views. The rolling hills are blanketed with picturesque vineyards, dotted with castles, and framed by the snowcapped Alps.
You will then have free time to meander the winding cobblestone streets of the village of Barolo and to sip glasses of the eponymous wine as you take in this magical UNESCO World Heritage zone.
With time to refresh back at our hotel, the day will finish with dinner at one of our favorite, family-run osterias. Generations of the family will offer us their warm attention as we luxuriate in several courses of rustic, rich Roero cuisine, including freshly-made pasta, paired with excellent local wines.
Wines: Barolo DOCG, Barbaresco DOCG, Roero DOCG, Nascetta, Arneis, Ruche, Barbera and Nebbiolo
Meals: Lunch at the winery with plenty of shaved Alba Truffle (white when in season); Dinner at our favorite osteria with wine pairings
Activity: Winery Tour & Tasting; Free time to explore Barolo wine country, enjoy a glass of Barolo in the village bearing its name
Accommodation: Luxury 5-Star Castle built in the 18th century perched atop a hill overlooking the rolling vineyards of the Langhe and Roero (a Relais and Chateau property)
After breakfast at the Castello, you will have the opportunity to join our private, guided hunt for the region’s rare and delicate Alba truffles with a fourth-generation truffle hunter and his truffle-hunting dog.
If you prefer not to adventure in the woods, you can opt to enjoy the morning at your leisure in Alba, where the truffle hunters among us will also return for an afternoon of exploration and sightseeing. Food is the historical passion, art, and entertainment of the Piedmont region, and there is no shortage of excellent eateries in Alba you may choose from for lunch alfresco while taking in the small-town, Italian pace of life!
With plenty of time to refresh in our hotel’s gardens or spa, the day will finish with a remarkable dining experience at one of our favorite Michelin-starred restaurants located in the Langhe countryside.
It’s the perfect way to say goodbye to Piedmont.
Wines: Barolo DOCG, Barbaresco DOCG, Roero DOCG, (Nebbiolo) Barbera and Arneis
Meals: Breakfast; Multi-course dinner with wine pairings at a Michelin-starred restaurant
Activity: Free time to explore Alba; Truffle hunting with a guide & his highly trained truffle-hunting dog.
Accommodation: Luxury 5-Star Castle built in the 18th century perched atop a hill overlooking the rolling vineyards of the Langhe and Roero (a Relais and Chateau property)
Today we will motor east to the region of the Veneto.
We will break up the drive by spending the morning exploring the estate of Le Morette winery, surrounded by vineyards and vistas that are sure to become lifelong memories. The winery itself is a spectacular sight, with classic architecture, a gothic cellar for barrel aging, and a quintessentially romantic courtyard. The wine it produces is no less remarkable, and we will be treated to a private tour and tasting with the third-generation owner and winemaker, followed by a classic, wine-paired lunch.
On we will proceed to Verona, a city steeped in romance, with idyllic marble streets and quaint shops interspersed among Roman ruins. We will check into the five-star Hotel Due Torri, a 13th-century palace nestled in the city’s historic center, where we will stay for the next three nights. Its rooms have hosted historically prestigious guests, including King Louis XVII of France, the Hapsburg royal family, Napoleon III, and Mozart.
After a brief orientation walk of the heart of the city, this evening is completely free for you to relax and explore some of our superb dining recommendations on your own.
Wines: Monferatto DOC, Gignolino, Freisa, Lugana DOC, Bardolino DOC, Valpolicella DOC, Refosco, and Amarone
Meals: Breakfast; Lunch at le Morette
Activity: Winery tour and tasting; Orientation walk of Verona.
Accommodation: Luxury 5-star hotel in a historic palace
Your morning will be free to enjoy a little extra rest or a massage in the Palace Spa.
Then we will venture into the verdant Valpolicella countryside for a driving tour past picturesque vineyards, olive groves, and rolling green hills. Lunch will be an unforgettable pasta tasting at a family-owned trattoria that hand-rolls what was voted some of the best pasta in Italy. Mama is still in the kitchen, always willing to sign copies of her cookbook, Polenta & Amarone.
Following lunch, we will return to our hotel in Verona, leaving plenty of time to relax and refresh or to continue exploring this romantic city as you like.
Later that evening, a father-and-son team of chefs will welcome us to dinner for another stunning, Michelin-starred experience. A frescoed dining room will be our stage for an incredible culinary performance as the chefs send out an imaginative and elegant tasting menu.
Wines: Valpolicella DOC (Ripasso & Amarone), Lugana DOC, Bardolino DOC
Meals: Breakfast; Pasta tasting Lunch; Michelin-star restaurant with wine pairings
Activity: Driving tour of Valpolicella countryside
Accommodation: Luxury 5-Star hotel in historic palace
Today is your day to explore the beautiful city of Verona on your own, but of course, we have lots of incredible suggestions for ways to spend your leisure day.
Verona is the perfect city to stroll through hand-in-hand, meandering its charming streets and piazzas. Piazza Bra, Piazza Erbe, Piazza Dante, and the bridge of Ponte Pietra are not to be missed. At the heart of the city is a preserved Roman amphitheater that was one of the largest in the empire. As you explore, you will quickly realize why Shakespeare decided to use this city as the setting for Romeo and Juliet.
Mid-morning, you will have the opportunity to learn the art of pasta and risotto making with our friend, Chef Maria. Lunch will follow, with thoughtfully chosen wine pairings.
You may wish to spend your afternoon shopping at Verona’s many designer boutiques, such as Louis Vuitton, Gucci, Max Mara, Burberry, Givenchy, and Valentino, just to name a few.
Or, if history is of interest, consider touring some of the city’s historic churches and museums, including Castelvecchio, a Gothic castle built in the 13th century. Now it houses a museum with an impressive collection of sculptures, paintings, and ancient weapons, mostly from the Romanesque period of Verona.
In the early evening, we will join our private guide on a sunset walking tour as she explains more about the history of this beautiful city.
The Passeggiata, an evening stroll, is a ritual here in Verona. Start with a spritz in Piazza Bra and then follow the couples young and old slowly winding through the marble streets taking in the elaborate window displays.
Verona is full of excellent cuisine, from seven-course tasting menus to simple osterias that serve delicate small plates, offering a plethora to choose from for a romantic date night on your own.
Wines: Valpolicella DOC (Ripasso & Amarone), Lugana DOC, Bardolino DOC
Meals: Breakfast; Lunch – optional cooking class including a pasta lunch
Activity: Free time to explore Verona; Optional pasta & risotto making class; guided sunset walking tour
Accommodation: Luxury 5-star hotel in a historic palace
After a leisurely morning, we will depart for the quaint village of Dosson. Here, we will take a break from multi-course dining to enjoy a classic pizza at one of our favorite spots. An Italian tour wouldn’t be complete without a handmade pizza topped with the freshest ingredients, followed by incomparable homemade gelato.
Then we will continue our trip eastward to pristine Friuli-Venezia Giulia. Friuli is a tranquil region full of welcoming locals, boutique vineyards, and a backdrop of the Alps that forms the border with Austria and Slovenia.
Once in Trieste, the region’s capital city, we will check into our grand hotel for the next three nights, Starhotels Savoia Excelsior Palace, a four-star waterfront palace opened in 1911 and awarded 2021 World’s Best by Travel+Leisure magazine. Perfectly situated on Trieste’s waterfront with stunning views of the sea, it is just steps away from one of the most elegant piazzas in all of Europe.
After some free time to unpack and refresh, we will regroup for a brief orientation walk in this piazza, Piazza Unita, the main square of the city. You will quickly discover the charm and ease of navigating this historic city center that lies at our hotel’s doorstep.
In the evening, we will savor unforgettable, traditional Triestine cuisine, unique in Italy for its Austrian and Slavic influence. After dinner, we can suggest some favorite spots for a nightcap or take in the city’s fabulous nightlife.
Wines: Grave DOC, Pinot Bianco, Cabernet Franc, Soave DOC, Prosecco DOC, Valpolicella DOC
Meals: Breakfast; Pizza lunch; Traditional Triestine dinner
Activity: Orientation walk and leisure time to explore the city of Trieste
Accommodation: Luxury 4-star palace with views of the Adriatic Sea
After enjoying a relaxing morning and breakfast at the hotel, you will have some free time to explore Trieste on your own.
Spend the morning perusing the one-of-a-kind boutiques selling everything from antique books to artisan-crafted eyewear. Or indulge in the Italian delicacies at Eataly Trieste, a vibrant marketplace offering a treasure trove of Italian food & wine.
We will regroup to travel one hour north to the BorgosanDaniele winery, an artisanal producer of the Collio region’s signature wines, and one of the most award-winning boutique wineries in Italy. Winemaker Mauro Mauri will guide us through his wines with passion and humility at one of the most tranquil winery settings we have ever visited. There we enjoy a casual lunch together.
Upon returning to Trieste, you will have this evening to take a break from group dining and savor a night on your own. We have several excellent restaurant recommendations for you.
Wines: White Blends from the Collio, Pinot Grigio Isonzo DOC, Friulano Isonzo DOC, Ribolla Gialla, Pignolo and Schioppettino Collio DOC
Meals: Breakfast; Optional excursion with winery tour and lunch
Activity: Free time in the morning to explore Trieste’s café culture; Optional winery tour and tasting
Optional Add-ons: Pamper yourself with a massage
Accommodation: Luxury 4-star palace with views of the Adriatic Sea
This day is completely free to experience the elegant city of Trieste; however, we do have a few suggestions of things not to miss.
Trieste is the coffee capital of Europe and the home of Illy coffee—as a result, the locals take their coffee very seriously. We suggest starting your morning by exploring one of the many charming cafés, some dating back to the 18th century. Find our favorites along the Grand Canal.
You can opt to join our private guide as we depart for a visit to the breathtaking, seaside Miramare castle and gardens, built in 1856. If you join us, you will lunch in the castle’s garden café, or you may lunch on your own in Trieste with many great recommendations to choose from.
This afternoon, if you feel like a bit more history, you will have the opportunity to join our private guided walking tour focused on the royal Habsburg family and the history of the city. Go deeper with your visit as you get important historical context on the city’s main landmarks, from Roman ruins to Byzantine mosaics and stunning Habsburg buildings. Stroll along the elegant seafront and learn why Trieste is nicknamed “The Little Vienna on the Sea.”
In the evening, we will feast together one last time! Down a secret alleyway waits an incredible epicurean experience, an unforgettable evening of grilled delicacies paired with beautiful local wines.
Wines: White Blends from the Collio, Pinot Grigio Isonzo DOC, Friulano Isonzo DOC, Ribolla Gialla, Pignolo and Schioppettino Collio DOC
Meals: Breakfast; Multi-course dinner of local Triestine cuisine with wine pairings
Activity: Optional visit to the Castle of Miramare; Optional private guided walking tour of Trieste
Optional Add-ons: Pamper yourself with a massage
Accommodation: Luxury 4-star palace with views of the Adriatic Sea
Many of our guests like to extend a few days in Venice, and the Venice airport is just a high-speed train connection away from the Grand Canal in the heart of the city. The trip is less than one hour, much quicker than the three hours by car and boat.
We would be happy to share recommendations if you wish to extend your exploration of Italy.
Meals: Breakfast
Activity: Transfer by private coach to (VCE) Venice airport
Learn more about Italian wine. Visit our Italian Vineyards page to learn more about some of the amazing Italian wineries we work with, and visit our Italian Wine Regions page to read more about our favorite regions and what makes them so special.
