Vineyards on the rolling hills in Chianti, Italy
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Italy Wine Tours & Vacation Packages

Ratings of Zicasso's Service
<p>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.</p>

Nothing is more quintessentially Italian than elegant wines enjoyed in the rolling...

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.

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Ratings of Zicasso's Service
Vineyards in Langhe region of Piedmont, Italy

Luxury Italy Wine Tour of the Top Regions

Places Visited: Piedmont, Lombardy +1 more
Places Visited: Piedmont, Lombardy, Chianti 

9 Day Custom Tour

From $8,800

Famous Valpolicella Verona, Italy

Veneto Region Wine Tour: Indulging in Tradition

Places Visited: Venice, Bardolino +3 more
Places Visited: Venice, Bardolino, Soave, Arqua Petrarca, Friuli 

8 Day Custom Tour

From $3,600

San Gimignano village surround by vineyards in Tuscany, Italy

11-Day Luxury Wine Tour of Tuscany

Places Visited: Pienza, Montepulciano +11 more
Places Visited: Pienza, Montepulciano, Bagno Vignoni, Chianti, Siena +8 more

11 Day Custom Tour

From $10,800

Vineyards in Piedmont with snow capped mountains in the background

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

Places Visited: Barolo, Barbaresco +4 more
Places Visited: Barolo, Barbaresco, Alba, Greve in Chianti, Radda in Chianti +1 more

9 Day Custom Tour

From $4,100

Woman raising a glass of wine, enjoying the view at sunset in Tuscany

Finest Wines of Tuscany & Central Italy Tour

Places Visited: Italy, Tuscany +12 more
Places Visited: Italy, Tuscany, Rome, Umbria, Pisa +9 more

10 Day Custom Tour

From $4,500

Todi Terrace in Umbria, Italy

Culinary Delights of Umbria: Wine, Food, and More

Places Visited: Umbria, Todi +6 more
Places Visited: Umbria, Todi, orvieto, Montefalco, Torgiano +3 more

7 Day Custom Tour

From $3,200

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
Harvested grapes in basket at Italian vineyard on Mount Etna, Sicily

Highlights of Sicily Wine Tour

Places Visited: Palermo, Cefalù +7 more
Places Visited: Palermo, Cefalù, Vallelunga, Segesta, Mazara +4 more

9 Day Custom Tour

From $4,100

Couple at a luxury resort pool surrounded by vineyards in Selinunte, Sicily

Romantic Sicily Wine Tour

Places Visited: Palermo, Marsala +3 more
Places Visited: Palermo, Marsala, Cefalù, Erice, Selinunte 

9 Day Custom Tour

From $4,100

Vineyards in Sicily with Mt. Etna in the background

Sicily Wine Tour: History & Culture Exploration

Places Visited: Catania, Siracusa +3 more
Places Visited: Catania, Siracusa, Vittoria, Caltanissetta, Mt. Etna 

9 Day Custom Tour

From $4,100

Couple eloping at Villa del Balbianello on Lake Como, Italy

Eloping in Italy Itinerary

Places Visited: Lecco, Venice +1 more
Places Visited: Lecco, Venice, Tuscany 

9 Day Custom Tour

From $4,100

Landscape of Tuscany, Italy.

7-Day Food and Wine Tour of Tuscany

Places Visited: Florence, Arezzo +2 more
Places Visited: Florence, Arezzo, Siena, San Gimignano 

7 Day Custom Tour

From $3,200

Pathway thru vineyards above Manarola in the Cinque Terre, Italy.

Indulgent Food and Wine Tour of Tuscany and Cinque Terre

Places Visited: Pisa, Florence +4 more
Places Visited: Pisa, Florence, Lucca, La Spezia, Riomaggiore +1 more

8 Day Custom Tour

From $3,600

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Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Reviews of Zicasso's Referral Service

4.9 stars based on 5972 reviews.

Italy Trip Review: Rome, Amalfi, Positano, 12 Days

The trip Zicasso's travel specialist arranged for us exceeded all our expectations. It was absolutely wonderful; not a single detail was overlooked. The hotels were excellent, the tours were great, and the drivers were always on time. I totally recommend Zicasso and the agency, and will undoubtedly use them for future travel plans.

Reviewed By Philip S.

Italy Travel Review: Lake Como, Ostuni, Private Boat Tour,...

Zicasso's travel designer did a terrific job. We had the initial phone consult, after which she delivered a first draft of the itinerary. From there, she helped guide us through a few revisions until we got the details smoothed out. We are experienced travelers and can appreciate a well-constructed trip, and that's what our experience with our agent reflected.

One crucial thing is that all the drivers who are engaged to move you around are prompt. Every one of them was right on time and friendly and helpful to boot. It was much appreciated.

To sum up our experience, I would do it all again with Zicasso and the agency and our agent. Our trip to Italy in the late summer of 2025 was something we will not soon forget!

Reviewed By tony B.

Italy Tour Review: Calabria, 11 Nights

Zicasso's travel partner is very thorough and makes sure the trip is tailored to your vision. They are flexible and very responsive. We would recommend them to anyone traveling.

Reviewed By Evan C.

Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii,...

Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

Reviewed By Kevin S.

Italy Travel Review: Dolomites, 2 Weeks

Zicasso's travel designer made the whole trip run very smoothly. It was a pleasure working with her.

Reviewed By Joseph B.

Italy Vacation Review: E-bike Tour, Kayaking, 10-Night Trip...

This was the best trip ever!!! I am so grateful Zicasso introduced us to our tour operator. This team was amazing! They set up a call to learn more about us and jumped into action. Within a short time, they came back to us with a presentation on ideas, with recommendations. There is no chance our trip would have been half as good without them. They even had a text group on standby while we were here in case we needed anything.

Reviewed By Linda C.