Vineyards on the rolling hills in Chianti, Italy
29,000+ 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 6201 verified traveler reviews.

Melanie E.
Italy Honeymoon Review: Rome, Florence, Tuscany, Pompeii, Vespa Tour, Food Tour, Wine Tasting, 12 Days

We had a wonderful honeymoon in Italy! It was easy to coordinate with Zicasso’s travel specialist; she heard what we were interested in doing and seeing, and she planned a seamless vacation. The travel from point to point was easy, we had knowledgeable drivers and guides as we visited new places, and the hotel and restaurant recommendations all led us to perfect spots we wouldn't have found on our own. We had a great time in Rome and Florence, and in the countryside in Tuscany, and would absolutely consider Zicasso again for future trips.

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Dirk S.
Italy Travel Review: 2 Weeks

The trip was excellent. Zicasso’s tour operator handled our special request and situation very well. They were very responsive and helpful.

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Laurie H.
Italy Trip Review: Naples, Lecce, Ischia, Mount Etna, Trulli Homes, 3 Weeks

Zicasso's was a great company to work with for our trip to Italy. Everyone replied promptly to questions or concerns. We liked the suggested tours. Most of the guides were very engaging and easy to understand.

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Joseph G.
Italy Travel Review: Florence, Cooking Class, 1 Week

The tour company did everything we agreed upon.

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Teresa V.
Italy Travel Review: Florence, Chianti, Private Guide, 5 Nights

Zicasso’s tour operator was superb! Their communication, understanding of our requests, and planning were excellent. They made our first trip to Italy unforgettable.

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Paula Z.
Italy Travel Review: Palermo, Agrigento, Sorrento, Amalfi Coast, Opera, Winery, Cooking Class, 10-Day Trip

Zicasso’s travel specialist did a wonderful job at listening to what we were looking for in our trip and the experiences we would like to incorporate. Her recommendations were spot-on! All of the tours, guides, cooking classes, and drivers were excellent. All details were taken care of and we had nothing to worry about but enjoying our vacation.

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