Vineyards on the rolling hills in Chianti, Italy
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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 6143 verified traveler reviews.

Ty E.
Italy Anniversary Trip Review: 2 Weeks

We had extremely high hopes for our first trip to Italy and Zicasso’s travel agent and the entire tour operator vastly exceeded all of our expectations! From the way they took our input on our likes/dislikes and created a perfect two-week itinerary for my wife and I for our 10-year wedding anniversary to the way they covered every logistical aspect of the trip to ensure that even though we were traveling to five cities over a two-week period, we never experienced any type of stress.

The only time we even had to touch our bags was getting on/off the trains! I have never experienced a trip that was so meticulously crafted as the one the tour operator put together for us, and thanks to that care and attention to detail, they helped my wife enjoy a trip of a lifetime. We could not be more thankful!!!

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Cynthia F.
Italy Vacation Review: Florence, Amalfi Coast, Local Cuisine, 9 Nights

Zicasso’s travel consultant and the entire tour operator were beyond wonderful: their customer experience is second to none. They are accommodating, providing the ultimate travel organization and follow-up. I would highly recommend their team and services to everyone. In fact, I've already done so! I am deeply grateful for their knowledge and expertise in planning an unforgettable experience for my first trip in 15 years.

My deepest appreciation to all!

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Kathy D.
Italy Vacation Review: Pompeii, Vatican Tour, 10 Nights

Zicasso's trip coordinator was so helpful. Her two "pre-meetings" really made me feel comfortable with the whole trip planning process, especially traveling with two young kids.

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Amelia K.
Italy Vacation Review: History, Art, Private Guides, 10-Night Trip

This was a trip of a lifetime, crafted to be everything I dreamed about. We will definitely use this travel agency to plan our visits to other areas of Italy. Thank you, Zicasso, for making this connection for us. The private guides were unbelievably knowledgeable and super-special. Hotel locations were perfect. Even our drivers were top-notch!

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Marisol K.
Italy Travel Review: Rome, Tuscany, Vespa Sidecar Ride, Wine Tasting, 8 Nights

Overall, this was a wonderful trip! The initial planning was new to us, as we had never hired a travel planner before, but Zicasso’s travel designer, our primary contact for the tour operator, was so responsive and made the process very easy. She was exceptional at putting together a plan that was so comprehensive, even though we were not in Italy very long, and we were so appreciative of her including our friends in some of our plans, at the last minute!

Our trip was very stress-free because of the meticulous planning by the travel designer and the travel partner. It was so wonderful to arrive and have a driver there to meet us at the various stops, have our hotel arranged, and all of our tours. She really listened to our interests, which we appreciated.

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John K.
Italy Tour Review: Venice, 3 Weeks

The trip was exceptional. The drivers and guides selected were top-notch. The staff was helpful and available when needed.

Our guide in Venice was excellent. A strike in Venice was difficult. Her commitment to arrive early and arrange transportation in the middle of a strike was spectacular. This is a reason for using this top-notch travel company. Planning and execution of the trip were great.

Our only feedback is that the trains in Italy take a minute to understand. More discussion on the lounges, with local trains not being reliable, would be helpful for future trips. More education is needed on this part of the travel plans.

Overall, it was a fantastic trip and we have much appreciation for the professionalism of Zicasso’s tour operator.

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