Vineyards on the rolling hills in Chianti, Italy
29,000+ Verified Traveler Reviews
Zicasso in the News

Italy Wine Tours & Vacation Packages

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.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

Wine tasting tour in Tuscany, Italy

9 Day Trip IdeaFrom $8,800

Luxury Italy Wine Tour of the Top Regions

Piedmont, Lombardy, Chianti 
Famous Valpolicella Verona, Italy

8 Day Trip IdeaFrom $3,600

Veneto Region Wine Tour: Indulging in Tradition

Venice, Bardolino, Soave, Arqua Petrarca, Friuli 
San Gimignano village surround by vineyards in Tuscany, Italy

11 Day Trip IdeaFrom $10,800

11-Day Luxury Wine Tour of Tuscany

Pienza, Montepulciano, Bagno Vignoni, Chianti, Siena +8 more
Vineyards in Piedmont with snow capped mountains in the background

9 Day Trip IdeaFrom $4,100

An Italian Wine Tasting Journey: From Piedmont to Tuscany Wine Tour

Barolo, Barbaresco, Alba, Greve in Chianti, Radda in Chianti +1 more
Woman raising a glass of wine, enjoying the view at sunset in Tuscany

10 Day Trip IdeaFrom $4,500

Finest Wines of Tuscany & Central Italy Tour

Italy, Tuscany, Rome, Umbria, Pisa +9 more
Todi Terrace in Umbria, Italy

7 Day Trip IdeaFrom $3,200

Culinary Delights of Umbria: Wine, Food, and More

Umbria, Todi, orvieto, Montefalco, Torgiano +3 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

Learn More
Harvested grapes in basket at Italian vineyard on Mount Etna, Sicily

9 Day Trip IdeaFrom $4,100

Highlights of Sicily Wine Tour

Palermo, Cefalù, Vallelunga, Segesta, Mazara +4 more
Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily

9 Day Trip IdeaFrom $4,100

Romantic Sicily Wine Tour

Palermo, Marsala, Cefalù, Erice, Selinunte 
Vineyards in Sicily with Mt. Etna in the background

9 Day Trip IdeaFrom $4,100

Sicily Wine Tour: History & Culture Exploration

Catania, Siracusa, Vittoria, Caltanissetta, Mt. Etna 
Couple eloping at Villa del Balbianello on Lake Como, Italy

9 Day Trip IdeaFrom $4,100

Eloping in Italy Itinerary

Lecco, Venice, Tuscany 
Landscape of Tuscany, Italy.

7 Day Trip IdeaFrom $3,200

7-Day Food and Wine Tour of Tuscany

Florence, Arezzo, Siena, San Gimignano 
Pathway thru vineyards above Manarola in the Cinque Terre, Italy.

8 Day Trip IdeaFrom $3,600

Indulgent Food and Wine Tour of Tuscany and Cinque Terre

Pisa, Florence, Lucca, La Spezia, Riomaggiore +1 more

4.9

Reviews of Zicasso's Italy Wine Tours & Vacation Packages

Based on 6175 verified traveler reviews.

Rick T.
Italy, Poland, France Tour Review: 17-Day Trip

We had a wonderful experience with Zicasso. Every detail was thought through and our trip went perfectly. We had frequent communications on our experiences and also to tell us what was happening the next day. We highly recommend this tour company and we will be using them again.

See more

Bernadette B.
Italy Vacation Review: Assisi, Cooking Class, Wine Tour, 1 Week

Zicasso’s tour operator was wonderful to work with. They answered all our questions quickly. All the arrangements they made for us went smoothly. They created a WhatsApp group for us, so if there was an emergency or just a quick question, we could reach them. They even called us on our first day to review the itinerary with them! They planned a great trip for us! They stayed within our budget, which was tight, but gave us a first-class trip.

See more

Craig J.
Italy Vacation Review: 1 Month

All aspects of the trip were laid out and executed, with absolutely not one item missed or left out. It truly took all travel pressure off; we just had to show up, wake up, and start each day and end each day with a smile.

See more

Sue S.
Italy Tour Review: Sicily, Syracuse, Taormina, Catania, Wine Tasting, Food Tour, Mount Etna, 8 Nights

Our overall experience on our Sicily trip was excellent. Every day's events were amazing and perfect for my husband and me. We truly enjoyed having drivers for most of our tours, as it made it easier for us, and we did not have any worries.

I did have to call the number that was available for problems, and the gentleman who helped me was very good and prompt. Things were easily resolved.

Our only glitch was the inconsistency of English-speaking drivers, or at the minimum, being able to understand English. The driver who drove us from Syracuse to our hotel in Taormina was very bad. She did not speak or understand much English and, worst of all, we felt like she dropped us off at the back of our five-star hotel in Taormina without any instructions except “there’s your elevator.” Fortunately, I called that number and things were resolved. The driver who took us to the airport in Catania had the same issue, no English or understanding. He left us at the airport unable to give us direction as to what to do. It would have been ideal for our drivers to have at least minimal ability to communicate in English.

Zicasso’s travel specialist gave us a full and genuine experience of what Sicily is. Every day was planned out perfectly to suit our needs and abilities. We would recommend her to everyone to see and learn Sicily.

See more

Kevin M.
Italy Tour Review: Sorrento, Florence, Rome, Pompeii, Winery, Private Tours and Guides, 13 Nights

Zicasso’s travel specialist was a fantastic travel advisor. This tour operator helped us plan our perfect Italian vacation by listening to our desires, from wanting boutique hotels with a view to private tours. They secured transportation from Sorrento to Florence to Rome.

Our driver to the winery was exceptional. He went above and beyond to find a quaint restaurant that served my favorite meal: white-truffle pasta. We also had an amazing guide in Pompeii. He was very informative and even surprised us with his beautiful singing voice in the amphitheater inside Pompeii. This trip was magical. We could not have asked for a better organized, non-stress trip.

See more

Corie D.
Spain, Italy Travel Review: Granada, Alhambra, 2 Weeks

All information was thorough and the planned itinerary met our needs. Our hotels were acceptable and our guides were top-notch and very knowledgeable. The highlight for me was the Alhambra in Granada. Thank you very much.

See more