Custom Cultural Italy Tour in 2 Weeks

What to expect on this itinerary
Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.
Customizable Itinerary
Rome - Welcome to Italy!
When you arrive in Rome, your driver will be waiting for you at the airport to take you to your hotel. Relish the fact that you’re in one of the world’s most amazing cities. Start exploring the city by wandering the ancient streets just beyond your hotel to get your bearings and get into the local culture. When in Rome, do as the Romans do! Soak up the sun at an outdoor café with an espresso and stroll through the piazza while savoring gelato. For dinner, take a walk over to the Piazza Navona, with its hopping nightlife, illuminated fountains, street performers and sidewalk musicians. The piazza is ringed with restaurants and their tables sprawl out into the piazza, making it easy to find an osteria serving traditional Roman cuisine. Try the simple dish of cacio e pepe (pasta with pecorino romano sheep cheese and black pepper), or enjoy the classic spaghetti alla carbonara.
What's Included:
Rome - Walking Tours of the Roman Forum and Famous Monuments
Rome - Guided Tour of the Vatican City and Leisure Time
Florence - Travel from Rome to Florence - Afternoon Guided Tour of Florence
Florence - Explore Renaissance Art in Florence
Florence - Full-Day Excursion in Charming Tuscany
Florence - Leisure Time in Florence and Excursion to Pisa
Florence - Wine-Tasting in the Chianti Region
Venice - Travel from Florence to Venice
Venice - Discover Glorious Art and Culture
Venice - Tour the Lagoon Islands and Enjoy Classical Opera
Milan - Travel from Venice to Milan
Milan - From Medieval Wonders to Leonardo’s Last Supper
Milan - Depart Milan
Trip Highlights
- Imagine life of the ancients as you stroll through the Roman Forum
- Visit the Pantheon, an ancient Roman temple that had the largest dome in the world until the Renaissance
- See the awe-inspiring Saint Peter’s Cathedral and the Sistine Chapel
- Stroll through the piazzas, enjoying daily gelato stops and people watching
- Explore a treasure trove of Renaissance art and architecture in Florence
- Take an excursion to Pisa to see the Leaning Tower and other architectural marvels
- In Venice, sail down the Grand Canal, the most beautiful “main street” in the world
- Soak up the enchanting ambience, beautiful art and exquisite architecture in Venice
- Elegant window shopping and coffee stops in the fashionable city of Milan
- See Leonardo da Vinci’s “Last Supper” painting, by special appointment
Detailed Description
The tour begins in Rome, a fascinating city that is a foundation of Western Civilization. Imagine life in ancient times as you walk in the steps of Julius Caesar at the Roman Forum. Become awe-inspired at Saint Paul’s Cathedral, one of the most important churches in the world. With a monument, fountain or statue to admire at every turn, everyday life in Rome is a work of art in itself.
Next you’ll visit the idyllic countryside of Tuscany. In Florence, visit the renowned Uffizi Gallery, where the list of masterpieces reads like a veritable who’s who of art history. After immersing yourself in culture, enjoy an excursion to Pisa for a look at the world-famous Leaning Tower. In the rustic Chianti region, take a drive through the picturesque country roads on your way to ancient vineyards. You’ll experience the dreamy atmosphere of tiny medieval hilltop villages that seem frozen in time.
Serene and surreal, Venice awaits you next. With its mysterious mist-shrouded ambience, hidden bridges and tiny passageways, Venice will take your breath away! Wander off the beaten path and get lost in a maze of medieval streets and hidden Renaissance courtyards. Romantics will want to sip a Bellini at Harry’s Bar and then take a musical gondola ride under the moonlight.
Finally visit bustling Milan, where you’ll be marveled by the medieval castles, gothic grandeur and designer labels. In one day, you can shop at Prada, dine on ravioli at the Dolce & Gabbana Gold Restaurant, and sip champagne at the La Scala opera house before watching a performance. Conveniently scheduled for the last days of the trip, Milan is the ideal place to shop for specialty items and designer fashion pieces before you return home.
Starting Price
$6,300 per person (excluding international flights)
Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.
What's Included
- Accommodations
- In-country transportation
- Some or all activities and tours
- Expert trip planning
- 24x7 support during your trip
Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.
Verified Traveler Reviews
Based on 1881 reviews
The 2 weeks in Italy our travel agent planned for us was fantastic. We has a fantastic schedule with experienced and excellent guides. This was my first time in Italy, a 60th birthday trip with my sisters, we have varied interests and she hit the mark on them all! The hotel location in Sestri Levante was the perfect location. The weather was beautiful for late Sept., we enjoyed the beach and calm Mediterranean waters when we were relaxing back at the hotel. The guide on our hike in Cinque Terra was very good. We did not know what to expect. His knowledge on the history of the area kept us more than expected. The guide knew the area and was able to rearrange our schedule due to rough winds that cancelled the ferry.
I would have never taken a pesto making class, but it was a highlight!
The sailing day was absolutely perfect. The weather was beautiful, and the skipper was a true sailor!
On our way to Florence we stopped in Lucca and a winery that were fantastic. The driver was prompt and informative. Our hotel in Florence had the perfect location! Close to both sides of the river to explore by foot every day. The 2 days with our guide were fantastic! She was excellent in every way, she knew the history, art and even helped with restaurant suggestions and reservations. Having a guide was the perfect way to not only see the sights but understand the time period and history. The day trips out of Florence to Chianti, Siena and San Gimignano, were perfect with wine-tasting interspersed with visiting the smaller towns in the Tuscany region. The weather was beautiful both a weeks we were in Italy.
The trip exceeded our expectations in every-way and we will all be repeat customers!!
Thanks for making my 60th birthday trip, the trip of a lifetime!
See more
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!
See more
See more
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
See more
Locations Visited: Venice, Verona, Florence, San Gimignano, Siena, Pienze, Rome, Pompeii, Positano
My husband and I planned this trip for our 10-year anniversary. I’m a person with high expectation and this travel agency exceeded all my expectations. The entire trip was dream.
We opted for personalized tours and transport for 95% of our trip. All of our drivers were wonderful. They arrived on time and made sure we made it to all of our destinations without issue. They had the contact information for the tour guides we were meeting. Upon arrival to our first hotel, a local cell phone and gift were given to us. Having the iPhone during our trip made any needed communication with our agent and his team a breeze. In addition, we used the phone apps for navigation throughout the cities we visited. We made a last-minute request for an additional private transport, and our agent was able to make it happen. We greatly appreciated their customer service.
We participated in a several unique experiences while in Italy. We went truffle hunting in Pienza, which was amazing. After, we were served a meal that highlighted truffles and the cheeses made locally. In addition, we did a cooking day in Rome. This was a private cooking class where we made pasta, several sauces, and appetizers. The one disappointment is that we never received the recipes from the chef (we were told by the chef that they would be emailed to us). However, this is a knock on the chef and not our travel agent. Once the class was done, we were served a meal in a private garden area. Lastly, we did a food walking tour in Rome. This was an amazing way to find local cuisine that we wouldn’t have known about otherwise. A wonderful experience.
All of our tour guides were excellent. They were knowledgeable, friendly, and familiar with the cities. We had one guide that really went into the details and reasons for expressions in the art. We didn’t care for that, but we didn’t specify that ahead of time or to the guide. It was wonderful seeing her excitement and passion for all of the amazing working works of art and sculpture that we saw.
Overall, I would highly recommend this travel agent and his team if you are traveling to Italy!! You will not be disappointed. We gave him our wish list of activities, accommodation preferences, etc. ahead of time and he made sure we got them all! Thank you for such a wonderful and memorable trip. If we are able to return to Italy, you will be hearing from us.
See more
If I could give more than five stars I would!
I just returned from the best vacation of my life. I have traveled extensively through different tours, cruises and travel agents. This agent is a travel Goddess. The trip to Italy she set up for myself, my mom and my daughter exceeded all of our expectations. This agent and I worked together on the itinerary for a few months prior to my vacation, she listened to what I wanted, and what I didn’t want and put together the most perfect tour package. Never in my life have I had a trip to multiple cities, go so smoothly, there was zero stress for us during our trip. We did not go with a tour group this is a tour she set up for the three of us. Our agent meticulously thought through each and every detail of our trip. There were maps and pictures to help us find where we needed to be to go on our tours.
Venice-was marvelous, the hotel was quaint and in a perfect location to walk to all the sites in Venice. The staff was friendly and the room was very nice. We had a group tour of the Doge Palace and St. Marks, our tour leader was interesting and knowledgeable.
A driver picked us up and took us to Verona, a beautiful city. At the hotel, the staff was friendly, and the hotel was in the center of the city, where it was easy to walk around.
A driver picked us up from Verona and drove us to Florence, we stayed at a beautiful hotel, and our room was spectacular, with high ceilings and a lot of space. The hotel staff was fantastic, friendly and helpful. They went above and beyond for anything we needed. In Florence our agent set us up with a fabulous cooking class, this class is a must if you visit Florence, we made potato soufflé, eggplant, homemade pasta, chicken and Tiramisu. The class was a perfect size about 10 people, we laughed, we cooked and had a blast. Once the cooking was done, we all went downstairs where they served us the delicious meal we just made, with wine. At the end they gave us a recipe book for everything we cooked. The chef was delightful, it was one of the many highlights of our trip. The following day we had our tour of Florence with a fabulous guide—she shared her incredible in depth knowledge of Florence. This was a private tour with just the four of us, she shared, interesting facts about the beautiful city of Florence without overwhelming us with information. Took us for coffee, showed us how the locals do it. She is perfection. We really enjoyed our tour with our guide.
The Chianti vineyard dinner was fabulous, this is also a must. We arrived by bus to this beautiful family run vineyard. There were tables and antipasti set up for us on the top of the hill near the restaurant. There also provided blankets for everyone, as it got cold once the sun went down. We were served tasty Chianti and met the rest of the guests before heading down the hill to one of the most delicious meals we had eaten. There was so much food and wine. Everything cooked to perfection. Everyone who attended quickly bonded and were fast friends by the end of the night. Did I mention the delicious wine? It flowed freely. Good thing we were on a bus on the way home. This was another highlight of our trip.
The following day we had a day trip to Siena and San Gimignano, our driver and tour guide kept us laughing with stories and history of the area. He was the perfect host and made our tour of these two beautiful cities fun. We were a bit tired and sluggish (remember the wine from the night before?) He showed us some of the most beautiful spots around the area and would always pull over so we could take a photo. We adored him. If you get to Florence, have the agent book you with this guide!
From Florence we went to Rome, our agent set us up at a lovely hotel in the heart of Rome. The tours we did in Rome were educational and inspiring. We did a small walking tour the evening of the first night. This was helpful as it helped us know where things were for our next few adventures. The tour guides were very nice.
After three days in Rome a driver took us to Ceccano where we stayed at a quaint ville. The beautiful woman who runs the hotel was incredibly nice and accommodating. She made us feel like family. We enjoyed our stay at that hotel.
Our final days were spend it Positano. Positano is picture perfect, the town is gorgeous, there is great shopping. The factories that create the beautiful lacy clothing is in Positano. Let me start with our hotel, it was beautiful, our view from the balcony was the water. It was perfection. The staff at the hotel, especially the two gentlemen behind the desk. They were the best. They were incredibly helpful, charming, and funny we adored them. They made our trip even better. The room was spacious, clean and had a lovely balcony with a view.
This trip was just fabulous, we had the best time, it was relaxing, exhilarating, educational and most of all fun. To our agent, we thank you from the bottom of our hearts. You made this trip everything we wanted and more.
See more





