Vineyards on the rolling hills in Chianti, Italy
country flag

Italy Wine Tours & Vacation Packages

Ratings of Zicasso's Service
<p>Nothing is more quintessentially Italian than elegant wines enjoyed in the rolling hills of Tuscany or along the stunning cliffs of Sicily. Encounter these iconic destinations and the many marvelous wine-producing regions in between with Zicasso’s customizable Italy wine tours and discover the cultural depth and pride that is carried in each delectable varietal.</p>

Nothing is more quintessentially Italian than elegant wines enjoyed in the rolling...

Nothing is more quintessentially Italian than elegant wines enjoyed in the rolling hills of Tuscany or along the stunning cliffs of Sicily. Encounter these iconic destinations and the many marvelous wine-producing regions in between with Zicasso’s customizable Italy wine tours and discover the cultural depth and pride that is carried in each delectable varietal.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
Vineyards in Langhe region of Piedmont, Italy
Luxury Italy Wine Tour of the Top Regions

9 Day Custom Tour

Dynamic pricing from $7,015

Embrace the marvels of Italian flavor and the splendor of Italy's scenery during this 9-day luxury Italy wine tour. You will have an immersive experience of the wine culture and Italy's fabulous history of wine consumption, which will reveal sumptuous vines, elegant tastings, and exclusive excursions. From regal estates to stately panoramas, you will wander through antique cellars, stroll through medieval towns, and sample the spirit of Italy through its illustrious wines.

View Custom Itinerary
Famous Valpolicella Verona, Italy
Veneto Region Wine Tour: Indulging in Tradition

8 Day Custom Tour

Dynamic pricing from $2,859

The vineyards of Italy’s Veneto region spread from the edges of the Venetian Lagoon to the foothills of the Alps and produce unforgettable flavors that are influenced by the sea breeze and undulating terrain. Wine trails crisscross the region to connect the vines to the local villages that brim with historical culture and preserved architecture. During your custom tailored tour you will traverse the countryside to sample celebrated wines, from hidden accumulations of Malbec to the offerings of effervescent Prosecco. Castles decorate the hillsides as bell towers chime at midday and gondolas glide down the narrow canals. You will find the wines of Veneto are as iconic as the monuments.

View Custom Itinerary
San Gimignano village surround by vineyards in Tuscany, Italy
11-Day Luxury Wine Tour of Tuscany

11 Day Custom Tour

Dynamic pricing from $8,575

With layers of wine and preserved tradition to guide you, your 11-day Tuscany luxury tour revels in art from the museums to the kitchens, the piazzas to the markets. Witness architectural grandeur, sample the delicacies of restraint, and embrace the essential tastes of the grapevine. The Uffizi to Montepulciano’s terraced vineyards, the Accademia to San Gimignano’s towers, when discovering Tuscany, even the simple can feel opulent.

View Custom Itinerary
Vineyards in Piedmont with snow capped mountains in the background
An Italian Wine Tasting Journey: From Piedmont to Tuscany Wine Tour

9 Day Custom Tour

Dynamic pricing from $3,217

Italy should be devoured on your 9-day Italy wine tour! Piedmont with its mountains and Tuscany with its hills: fill your senses with tastes from award-winning vintners, wines that range from robust to comforting, old to young, and food that sings and melts in your mouth, all with medieval towns at your fingertips. Italy allows you to slow down, smell the grass, smell the food, smell the wine, and devour it all.

View Custom Itinerary
Woman raising a glass of wine, enjoying the view at sunset in Tuscany
Finest Wines of Tuscany & Central Italy Tour

10 Day Custom Tour

Dynamic pricing from $3,575

On this 10-day tour of Tuscany and Central Italy, immerse yourself in the encompassing culture of Italy and enjoy the sumptuous luxuries that the country has to offer. Taste wine from boutique wineries that have mastered the craft over centuries. The authentic Tuscan culture, the appetizing food, and the delectable wine are all within arms reach in this luxury Tuscany vacation.

View Custom Itinerary
Todi Terrace in Umbria, Italy
Culinary Delights of Umbria: Wine, Food, and More

7 Day Custom Tour

Dynamic pricing from $2,501

Umbria is for romance, for lovers of food, wine, history, and more. From the golden landscape that sweeps across the region, to the rich, red wines that are produced throughout the area, experience first hand why Umbria brings out the romantic in everyone. On this Umbria wine tour, you will discover that Umbria doesn’t wait for romance, it inspires it.

View Custom Itinerary

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
Harvested grapes in basket at Italian vineyard on Mount Etna, Sicily
Highlights of Sicily Wine Tour

9 Day Custom Tour

Dynamic pricing from $3,217

The incredible diversity of flavor and the captivating complexity of history will keep you engaged during your exclusive wine and highlights tour of Sicily that will unveil the distinctive characteristics of the local grapes and the undeniable charm of the unique culture. The cities possess a quintessential Mediterranean ambiance while the smaller towns reflect a sense of ancient history that dates back to the Greek settlements and the Arab traders. An incredible diversity of varietals embodies the long heritage of winemaking on the island that binds together the past and the present while the scenery is an incredible setting where you will discover transcendent beauty.

View Custom Itinerary
Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily
Romantic Sicily Wine Tour

9 Day Custom Tour

Dynamic pricing from $3,217

Capture the romance of Italy during your custom-tailored Sicily wine tour for couples. Revel in the perfect mixture of seductive history and enchanting flavors with private tours that offer exclusive access to boutique vineyards from Palermo to Marsala. The art and artistry of tradition bring a deep well of heritage that spans the millennia and shapes the captivating ambiance in which you will find Byzantine mosaics, ancient Greek architecture, delicate olive oil, and complex wines. Relax in the beauty of seaside towns, indulge in the splendor of golden architecture, and embrace the immersive panoramas seen during your luxurious wine tour of Sicily.

View Custom Itinerary
Vineyards in Sicily with Mt. Etna in the background
Sicily Wine Tour: History & Culture Exploration

9 Day Custom Tour

Dynamic pricing from $3,217

Italy is famous for its wine and its cuisine but beyond the mainland the gastronomic traditions and ancient marvels the best of Italian heritage will be yours to enjoy during your customizable wine, culture, and history tour of Sicily. The vines on the island have become legendary for the rocky plateaus, the fertile valleys, and the vineyards found along the slopes of soaring Mount Etna. With culinary and oenological traditions dating back to Phoenicians and Greeks with hints of Arab and Norman customs, your tour of Sicily will be an incredible immersion into a cornerstone of the Mediterranean filled with ancient wonder, Baroque opulence, and endless mouthwatering delights.

View Custom Itinerary
Couple eloping at Villa del Balbianello on Lake Como, Italy
Eloping in Italy Itinerary

9 Day Custom Tour

Dynamic pricing from $3,217

Your Italy tour celebrates elopement, the ultimate symbol of love and passion. Your romance guides the way on a personalized Italy tour leading from the base of the Italian Alps to the rolling hills of Tuscany. Choose your favorite destination in which to pledge your love and devotion. Rejoice with a multi-course meal inside the former palace of the Venetian doge, then sneak a kiss underneath the imposing figure of Michelangelo’s David. Sip wine on a quiet terrace offering an entrancing panorama over Lake Como and the lakeside towns, and seal your love with a perfect embrace during your unforgettable elopement in Italy.

View Custom Itinerary
Landscape of Tuscany, Italy.
7-Day Food and Wine Tour of Tuscany

7 Day Custom Tour

Dynamic pricing from $2,501

During this custom-tailored 7-day food and wine tour, immerse yourself in the great beauty of Italy, which is featured in soaring cypress trees, rolling hills, sprawling vineyards, and medieval towns. Sample noble vines, discover authentic local cuisine, and bask in the sumptuous flavors of sensational treats, from chocolate to gelato, for a sensational introduction to the food and wine of Tuscany.

View Custom Itinerary
Pathway thru vineyards above Manarola in the Cinque Terre, Italy.
Indulgent Food and Wine Tour of Tuscany and Cinque Terre

8 Day Custom Tour

Dynamic pricing from $2,859

Indulge in the delicious food and wine of Tuscany and Cinque Terre during this 8-day journey. Uncover the beauty and history of the region as you taste your way from scenic cities to historical landmarks. From the Leaning Tower of Pisa to the Renaissance art of Florence, discover all Tuscany has to offer. Savor the renowned wine of the area, indulge in private cooking classes, and visit the seaside haven of Cinque Terre.

View Custom Itinerary
Quintessential 10-Day Tuscany Food and Wine Tour

10 Day Custom Tour

Dynamic pricing from $3,575

During this 10-day Tuscany wine and food tour, indulge in the grandeur of rustic cuisine and develop an intimate understanding of the gorgeous landscape. Your private tours led by specialist guides offer insight into the heritage of local flavors. This customizable tour will shine a brighter light on Tuscany’s culinary marvels, such as visiting renowned winemaking regions, basking in the enticing aromas of a private kitchen, and scouring woodlands for the elusive white truffle.

  Read More

A Luxury Wine Tour of Sicily

9 Day Custom Tour

Dynamic pricing from $7,015

The luxuries of Sicily emanate from every sip of wine, each bite of food, and the unforgettable panoramas of the landscape. Your Sicily wine tour is custom tailored to ensure comfort and elegance, flavor and culture. The sea shines a deep sapphire blue. The hills transition between golden grasses and verdant vineyards. The exquisite snowcapped peak of Mount Etna rises over the sandy beaches, and immense columns of ancient Greek temples continue to stand stoically against rolling hills surrounding the valley. From the moment you arrive, you will relish the splendor of Sicily.

  Read More

Show More(2 itineraries)

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Reviews of Zicasso's Referral Service

4.89 stars based on 5114 reviews.

Italy Tour Review: Venice, Rome, Florence, Pisa, Cinque...
"In a word, Zicasso's travel agent was extraordinary. She...

Reviewed By Janice F.

Italy Travel Review: Tuscany, Florence, Cinque Terre, Cheese-Making...
"It was a trip of a lifetime! From the first private driver...

Reviewed By Kathryn D.

Italy Anniversary Tour Review: Sorrento, Amalfi Coast, Florence,...
"We liked that we were matched with Luana because she had...

Reviewed By Karla R.

Italy Vacation Review: Umbria, Tuscany, Cheese Making, Truffle...
"We had a wonderful, well-organized vacation exploring many...

Reviewed By Marc K.

Italy Tour Review: Venice, Florence, Rome, Sorrento, Food,...
"Zicasso’s tour operator exceeded all of our expectations....

Reviewed By Jacob H.

Italy Tour Review: Florence, Vincenza, Cinque Terre, Venice,...
"We received great service from our travel company, which...

Reviewed By Phyllis P.