Vineyards on the rolling hills in Chianti, Italy
30,000+ Verified Traveler Reviews

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.

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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 6051 verified traveler reviews.

Italy Travel Review: Sorrento, Taormina, Rome, Pompeii, Mount Etna, Wine Tasting, 2 Weeks

We had a fabulous trip to Italy, including to Sorrento, Taormina, and Rome. Zicasso’s travel specialist made sure every detail was taken care of, including stays in beautiful, well-located hotels and excursions that were interesting and fun for our family.

For example, she arranged for an airport host to assist us with our arrival to and departure from the Rome airport, and she was simply amazing, whisking us through the airport and eliminating stress for our family.

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England, Italy Vacation Review: London, Rome, 3 Weeks

In all respects, a well-planned and well-executed trip to London and Rome. The guides were exceptional in knowledge, kindness, and sense of humor. The best restaurant recommendation was the one in London.

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Italy Travel Review: 2 Weeks

The trip was seamless. Zicasso's travel specialist was always available for any questions or concerns, and even came up with ideas that I would never have come up with.

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Italy Travel Review: Lake Como, Cinque Terre, Florence, Rome, Boat Ride, Hiking, Cooking Class, 10 Days

Amazing!! Everything from start to finish was simply amazing! The process, from the beginning with Zicasso to the end with Zicasso’s travel consultant, was flawless. She was in touch throughout the whole process. In preparation, she was very responsive and, once we were there, every little detail was thought through.

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Italy Tour Review: Vatican, Cooking Class, 1 Week

Zicasso’s travel specialist put together a perfect trip for us. We were a large group, with large age and ability ranges—in addition to traveling over the holidays, so places being closed for the holidays was also a challenge. She made magic happen and, honestly, our trip could not have been more seamless.

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Italy Tour Review: Family Heritage, 8 Nights

We received fantastic and speedy communication from Zicasso's travel specialist. It took time to gain an understanding of our group’s needs and goals for the trip. We had comfortable, high-end transportation and professional service.

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