Vineyards on the rolling hills in Chianti, Italy
28,000+ 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.

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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 $3,300

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 $3,300

Romantic Sicily Wine Tour

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

9 Day Trip IdeaFrom $3,300

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 $3,300

Eloping in Italy Itinerary

Lecco, Venice, Tuscany
Landscape of Tuscany, Italy.

7 Day Trip IdeaFrom $2,600

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 $2,900

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 2637 verified traveler reviews.

Luxury Italy Group Tour Review: Rome, Tuscany, Chianti, Montepulciano, Montalcino, Siena, Florence, Pisa, Lucca, San Gimignano

THE BEST VACATION EVER!!!!

I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone.  However, after my first communication with our agent -- I knew that she “had it.”  She understood exactly what we wanted to do.  She was right-on in both concept and execution.

Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome.  During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums.  Extremely knowledgeable, English-speaking guides led all of our tours.  Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.

After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany.  The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano.  The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip.  In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca.  On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it.  Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.

When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.

Thanks to this travel company and our agent for designing the perfect vacation for our group.  The only complaint that I heard was that we ate too much — wow was all the food delicious.  I really don’t know how she did it.  All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular.  Our stay in the villa was a great experience.  We were treated royally everywhere.  We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time.  She is a genius!!!!

Jeff E

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Travel Review: Italy Vacation, Tuscany, Florence, Venice, Chianti, San Gimiagnano, Siena, Cortona, Volterra, Assisi

~~OUR STORYBOOK VACATION CREATED BY ZICASSO

The most beautiful vacation was created for my husband and me by this agent, partner of Zicasso. At our initial contact with Zicasso, we advised them of our dream vacation which we wanted in the Tuscany and Umbria regions of Italy.  Very soon thereafter we received an e-mail from our agent wanting to know what we wanted to see and do on this vacation.  We provided a short list of our desires and she got to work.She contacted us by phone from Florence, Italy where she is located and spent 45 minutes getting to know us and detailing the itinerary with us.  That was only the beginning!Within a few days, she set up the itinerary which was perfect for us.  We began our journey by flying to Venice (a gondola ride was scheduled, of course).  A couple of days later, took a train to Florence (beautiful experience, because our reservations and tickets were already in hand).  A private driver met us at the platform and took us to our hotel).  A few more days and we were off by rented car (already paid for and ready to go thanks to our agent) and drove off to other parts of Tuscany (Radda in Chianti, Montalcino, Bevagna and the small villages along the way of Volterra, San Gimignano, Siena, Val d’Orcia area with the beautiful Abbey of Sant’ Antimo and listening to the spiritual and beautiful Gregorian chants during Mass, followed by our next stop in the Umbria region - Cortona, and staying in Bevagna.  Of course, we cannot forget our inspirational visit to Assisi with a private guide.  Everything was perfectly orchestrated by our agent.  The train, the car, the hotels, the private tour guides, the tickets, were all taken care of. She also provided her emergency number should there have been any problem at all.We are so happy we chose this wonderful travel agency and, we must say, most dedicated and pleasant agent, to handle this dream vacation for us.  One which we will remember forever!!Thank you – BRAVO!!!

Sincerely,

Veronica and Leonard B

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Italy Trip Review: Rome, Florence, Tuscany, Chianti, San Gimignano, Montepulciano, Montalcino, Lake Como, Cooking Class

My husband and I just returned from a two-week vacation in Italy. With the help of Zicasso and our travel company, we were able to fit every wish into this short time.

We started out in Rome, then went on to Florence for some amazing history. We then traveled to the Tuscany and Chianti countryside for private cooking and wine experiences. We loved the small villages we explored and the little family-owned wineries and olive farms.

A highlight was staying in a bed and breakfast in Ponzano that overlooked the beautiful olive gardens and countryside. We explored the small villages of San Gimignano, Montepulciano, and Montalcino, and felt like we had discovered authentic local life.

The tail of our trip was spent in the beautiful Lake Como area, with a day trip to Lugano, Switzerland.

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Review: Luxury Italy Vacation, Rome, Tuscany, Florence, Chianti, Siena, San Gimignano, Greve, Vatican, Trastevere Food Tour

Wonderful 10 day trip to central Italy planned by this Italy travel company.   We spent the first part of the trip at Castello di Casole in the Tuscan countryside, then Florence and the final part of the trip in Rome.    While in Tuscany, we took day trips to Montalcino, Siena, Montepulciano, Pienza, San Gimignano and Greve.   We had walking tours in Florence and Rome. our agent at this travel company planned all the details, transfer drivers, tour guides and hotel arrangements.   Everything went according to plan and was of outstanding quality.   The agency gave us a very detailed package of information with all the relevant details for each day.   

Great Vacation

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Vacation Review: Italy Mother/Daughters Trip, Civita di Bagnoregio, Milan, Cinque Terre, Local Cuisine, Culture & Natural Beauty
Rome, Civita di Bagnoregio, Tuscany ( Pisa, Florence, Chianti, San Gimignano) Cinque Terre, and MilanIncredible, life changing trip with my 17 year old twin daughters. From the initial planning, final itenerary , drivers and private guides our VIP experience was phenomenal.Every detail was thought out by the travel company. Gulio and team are amazing and would definitely book with them again.Ciao Italia! è stato un grande piacere vivere il tuo fascino, la tua storia, la tua rinomata cucina, la tua cultura e la tua bellezza geografica. Ci vediamo

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Review: Honeymoon in Italy, Rome, Venice, Florence, Tuscany, Siena, San Gimignano, Lucca, Sorrento, Pisa, Capri, Pompeii

When we inquired about a trip on Zicasso, they told us a few companies would reach out to us with different offers on our desired location. It only took one reply back from this agent for me to know that we would have a more personable experience with this travel agency. (Mainly because he was straight up with us concerning itinerary ideas, especially regarding weather and how it is unpredictable in March. He patiently worked with my fiance and me for quite a while before we approved the final itinerary filled with transportation to and from hotels, private tours (some meant to be small group, but we ended up being only ones), and pre-planned relaxing train-rides. There wasn’t a moment of our trip that we had to worry or even think about- really. Our first stop was Rome, where we spent 3 days. Upon arrival at the airport in Rome, we had a driver waiting for us, which was a huge relief since we were tired and last thing we wanted to stress about was how to get to our hotel. Our local point-of-contact for the agency also called once we arrived to make sure we had everything we needed. He was great! Once we reached our hotel, we slept off the jet-lag and then our holiday started. March is the early beginning of the tourist season, so we were able to do many things without waiting. Not saying it was empty, but we had room on the sidewalks and were in and out of restaurants in no time at all. I also highly recommend planning free days in each city, as you will want to look around for yourself and take your time in certain parts. Even if you spend a week in every city, you always leave feeling like you needed much more time, as there is so much to do and so little time in a day. We spent 3 days/4 nights in Florence. It was in Florence that we were able to easily tour a good bit of what Tuscany has to offer. Through tours our agent set up for us, we visited the beautiful cities of Siena, San Gimignano (Our Favorite), Lucca, Pisa, and the Chianti Region. We tasted sooooo many wonderful wines and privately ate at local restaurants for lunch. We also took a short train ride to Venice for a day trip, as I craved a gondola ride. Everything was planned so perfectly. The minute we stepped off the train in Venezia our guide to get us to our marked location was there with a water taxi to take us to St Mark’s Square. There, she directed us to our gondola and we spent the day wondering around Venice until meeting up back with her and the water taxi to take us back to the train station. After Florence, we traveled to Sorrento (our other favorite!) along the Amalfi Coast. It was magical and the weather was perfect. We had our own boat to visit the grottos (no wait for the Blue Grotto either!) and to the Isle of Capri; and although most of the shops were closed on the isle (early season still), it was beautiful and we were able to relax on the beach. We saw Pompeii and even hiked up Mount Vesuvius. Sorrento was a quaint and charming city and we made friends with quite a few locals. We truly had a wonderful honeymoon and I would recommend this agency to everyone. We could not be happier!

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