
Milan and Cinque Terre Itineraries & Tours
Blend the luxury of the House of Savoy with the charisma of hidden seaside towns overlooking the Tyrrhenian Sea with Milan and Cinque Terre itineraries. Wander along coastal paths that connect secluded cobblestone lanes and witness the marvels of classic masterpieces by the likes of da Vinci. Find hidden canals, embrace local flavors, or embrace the glamour of luxury shops. With thousands of custom trips planned to Italy, a Zicasso travel specialist tailors your itinerary to your wants, desires, and needs. Find inspiration for your personalized trip with our sample itineraries.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

8 Day Trip IdeaFrom $3,600
Romantic Getaway to Northern Italy and Cinque Terre Tour

10 Day Trip IdeaFrom $4,500
Culture and Coastal Treasures of Northern Italy

12 Day Trip IdeaFrom $5,400
Marvelous Piedmont, Cinque Terre, and Milan Tour

12 Day Trip IdeaFrom $6,400
Northern Italy Trip Between Opera and Culture

12 Day Trip IdeaFrom $5,400
Italy's Lakes District Tour with Cinque Terre

17 Day Trip IdeaFrom $7,700
Spirited 17-Day Journey through Italy: Highlights and Hidden Culture
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.

9 Day Trip IdeaFrom $3,300
Cultural Immersion Tour of Northern Italy & Cinque Terre

7 Day Trip IdeaFrom $3,200
A Perfect Seven-Day Itinerary to Cinque Terre

9 Day Trip IdeaFrom $4,200
Unbeaten Path of Italy Tour: Discovering Cinque Terre, Lake Garda & Venice
Reviews of Zicasso's Milan and Cinque Terre Itineraries & Tours
Based on 2404 verified traveler reviews.
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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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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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Thanks for helping me organize my family (of 10 with diverse age from 15 to 63) trip to Italy, from Dec 17 to Dec 31. Whilst different member of my family have different expectation and requirement, I would like to comment you and your team on having planned an excellent trip that not only met each and everyone's interest and expectation but truly exceeded it.
Your planning have brought us to the lovely cities of Parma, Modena, Florence, Orvieto, Civita Di Bagnoregio, Naples, Rome, Venice, Cortina d'Amprezzo and back to our starting point Milan. Throughout the trip, we have a well balance itinerary that covered
- beautiful churches such as the Duomo in Milan, Rome, Florence,
- archeological site like Pompeii, Colosseum, Roman Forum, Pantheon, Pisa, Verona (learning more about romeo and Juliet)
- great local eating places (recommended by the guides you chose)
- lovely country side and unique sight in San Gimignano, Civita Di Bagnoregio, Orvieto, Lake Como,
- great gallery likes Uffizi, Academia
- Interesting activity such as Snow Mobile excursion in Cortina, Learning Cooking
- Shopping activities
With so much, yet your team immaculate planning never have us rushing from sight to sight, we were both able to enjoy and learn as much as we can of each sight and at times added more activities.
The team of guides you chose, have truly turn stone and history into exciting stories that the provided the group deeper understanding of the sights we visited and saw. Really like to thank each on of them like our guides in Florence, Pisa, San Gimignano, Orvieto and Civita Di Bagnoregio, Naples and Pompeii, Rome, Verona, Venice and Milan.
But most importantly, thank you for getting our driver, he truly ensure our comfort whilst driving steadily through jams on our way to Naple and snow storm on our way to Cortina d Amprezzo and also took very good care of us ensuring we know what to do where we have no guides and leaving us clear instruction when we needed help. He is truly a wonder.
I will definitely tell my friends heading to Italy about this company.... A wonderfully great experience.
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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.
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We recently enjoyed a whirlwind trip through Italy. We began in Venice and ended this incredibly memorable trip in Positano. The fact that I had nothing to worry about is what really impressed me. Everything was outlined, our itinerary was planned out for us including suggestions about restaurants. My travel group consisted of myself, my spouse, my 12 year old and 5 year old daughters along with my mom, sister and 13 year old niece. Our private drivers were waiting for us at all destinations from the airport to boats in Venice to our train in Naples. The hotels were impressive, especially in Chianti although it was a little out of the way from Florence but the hotel provides a shuttle service. We had guided tours in Venice, Siena, Rome (Vatican City and the Colosseum) and Pompeii. We also had stops in Verona, San Gimignano and Montepulciano. We finish our trip in Positano and are able to unwind and relax. We fell in love with Italy but having someone driving us around and talking about their beautiful country made our trip special. My husband was very pleased with the service and having our agents available with just a phone call made it easier. I can't wait to go back!
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