
8 Day Italy Itineraries & Vacation Packages
Uncover discoveries long held to legend as you venture to Italy for an experience unlike any other. From ancient monuments and tantalizing mythology to winding vineyards and a thriving culture, an 8-day Italy itinerary has so much to offer. Enjoy the luxury of expert guidance as you plan your trip of a lifetime with Zicasso’s travel specialists.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

8 Day Trip IdeaFrom $7,800
8 Day Luxury Tour of Sicily Highlights: Taormina, Syracuse, Agrigento, Palermo

8 Day Trip IdeaFrom $3,600
Adriatic to Mediterranean: Explore Venice, Lake Garda & Cinque Terre Tour

8 Day Trip IdeaFrom $3,600
Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo

8 Day Trip IdeaFrom $3,600
Soulful Italy: Umbria, The Marches, and Abruzzo Tour

8 Day Trip IdeaFrom $3,600
Gastronomic Traditions of Italy Tour: Cheese Making, Olive Oil Pressing & More

8 Day Trip IdeaFrom $3,600
Basil & Chocolate: Indulging in Italian Riviera and Umbrian Countryside Tour
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
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.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.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.

8 Day Trip IdeaFrom $3,600
Pleasures of Piedmont Tour: Wine, Truffles & Celebration

8 Day Trip IdeaFrom $3,600
True Flavors of Northern Italy: Food & Wine Tour of Veneto

8 Day Trip IdeaFrom $3,600
Tuscany Tour of Charming Villages, Ancient Towns & Unforgettable Landscapes

8 Day Trip IdeaFrom $3,600
Off-the-Beaten-Path Puglia Discovery Tour

8 Day Trip IdeaFrom $3,600
8-Day Rome and Neapolitan Coast Tour

8 Day Trip IdeaFrom $3,700
Heart and Soul of Italy Tour: Umbria to Abruzzo
Reviews of Zicasso's 8 Day Italy Itineraries & Vacation Packages
Based on 1209 verified traveler reviews.
We had a lovely tour of Sicily and we thoroughly enjoyed the scenic villages, mountains and coastal areas, the delicious food, the history and culture of the region, and, of course, the many lovely Sicilians we met on our journey! This was made possible by the travel company we went with when we first engaged Zicasso. They met with us (online) and developed a great tour, for which a few highlights are summarized below. They were also very helpful during the trip to offer us assistance if we needed it. In short, they made our trip truly memorable!
On our visit to Palermo, we experienced its ancient history and fine cuisine. Touring some of the smaller towns and villages, such as Cefalù, Modica, Scicli, Marzamemi and Noto, we enjoyed many scenic streets and alleys with their many shops and restaurants, and also seeing some beautiful artwork in their ancient cathedrals. The countryside of Sicily is also lovely to see and on our tour, we were privileged to visit some farms and talk with some locals who make their living off the land.
We were captivated by the rich historical underpinnings of Sicily, as we saw when we toured Agrigento to visit the Valley of the Temples. In other larger towns/cities we visited, such as Ragusa, Syracuse and Taormina, we had many opportunities to tour food markets and taste (and to learn to prepare) some specialty dishes of the local area.
Having a walking tour around Mount Etna with a local guide provided us with a refreshing outdoor nature hike that was a great way to learn about the area. Capping off our nature walk with a gastro/wine tour at a local winery was a great finale to our two-week vacation! In the end, our only regret was that we didn't want the vacation to end!
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We had a fabulous time in Sicily. It was our first visit and Zicasso’s travel company planned an excellent itinerary, with great recommendations on the cities and towns to visit that felt like a truly local experience. (Other agents focus on the big cities of Palermo and Taormina, but the travel company recommended we spend more time in Syracuse/Noto, Ragusa, and Modica.)
We loved our primary driver and the boutique hotels they selected for us. Communication and documents were all easy to follow.
The only piece we wish might have been curated a little more was the recommended dining options. There were too many and not necessarily great restaurants.
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We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.
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Our 16-day trip through Venice, Florence, Tuscany, Sorrento and the Amalfi Coast, and Rome was outstanding in every detail. Every transfer ran on time, every guide was knowledgeable and warm, and every hotel was a great choice.
Our favorites were the private lagoon boat trip in Venice, the Brunello wine and cheese tour, the pasta class at a Tuscan farm, Pompeii, the Capri cruise, and the Vatican tour. We couldn’t have asked for better planning or support. We highly recommend Zicasso's travel company.
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We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.
The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.
The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.
One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.
Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.
While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!
Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.
Every experience felt personal, meaningful, and special.
This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!
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My wife and I spent two weeks in Sicily and four more days in Rome. The trip was seamless: no glitches and no problems. Zicasso's travel specialist and others were promptly responsive, friendly, and cooperative. They made excellent suggestions and respected our preferences.
The transportation and the guides were all very good. The hotels were appropriate for our desires and budget. They provided wonderful sunset cruises in Palermo and Taormina, and they got us restaurant reservations for dinner each night at non-touristy places.
Surprisingly to us since we have been there before, Rome was especially enjoyable. The art in the Borghese Gallery and in the Pope's museum at the Vatican was overwhelming.
My wife and I have traveled extensively, particularly with agents obtained through Zicasso. They have all been good, and this one was one of the best. I can recommend our travel company without reservation.
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