Trekking the Italian Riviera Tour: Treasured Trails of Cinque Terre

What to expect on this itinerary
Redefine your ideas of comfort and luxury on the trails of the Italian Riviera as you relax in the natural landscape of the meandering cliffs and the stunning Mediterranean Sea. Your custom tailored tour will lead you along the ancient paths that connect medieval villages, secluded monasteries, and lush seaside towns. The scents of lemon trees and basil plants blend into the sea breeze as antique towers that have protected the coastline from pirates and maritime powers for centuries stand tall. Fishing boats return to the lively harbors with nets that burst with fresh fish. Indulge in the sun-soaked villages and the endless discovery of Ligurian splendor, from wine to frescoes, seafood to panoramic views.
Customizable Itinerary
Florence – Arrive in Florence
Florence stands at the heart of Tuscany and fills the famous region with the luster of its Renaissance influence lining the Arno River. As your flight descends into the Florence airport, you will see the cypress trees and vineyards that rise along the rolling hills of the countryside. Your private transfer will meet you at the baggage claim and lead you along the cobblestones of Florence’s city center. The massive dome of the Florence Cathedral soars above the palaces and historical buildings of the city. Your guide will meet you in the hotel lobby to show you the wonders of Florence on an introductory walking tour to highlight the city’s open-air museum characteristics.
The Cathedral of Santa Maria del Fiore, Giotto’s Campanile, and the Baptistery rise from the heart of the Piazza del Duomo. The inlaid marble shines pink, white, and green in the passing sunlight. The Museo dell’Opera del Duomo hides in an antique palace that borders the square behind the Cathedral’s main entrance. The Cathedral is often considered the symbol of Florence, from its incredible dome designed by Brunelleschi to the sheer magnitude of the church, which reaches a length of nearly 500 feet long. The interior contains hints of frankincense that linger from mass earlier in the day.
The 44 stained glass windows from the 14th and 15th-century continue to glow with sharp hues that bring a rainbow of light into the nave. Lorenzo Ghiberti, who designed the bronze panels of the baptistery doors, also created the stunning Biblical depictions in the three rose windows. Your elaborate introductory tour of the city ends at the Church of San Miniato that overlooks the Tuscan countryside and Florence. The aroma of lush cypress trees overtakes the air outside of the entrance. You walked up the hill that bordered the city, which provides access to Piazza Michelangelo. Inside the church, the local monks still chant nightly, as they have since the church’s inception in the 11th-century.
What's Included:
Santa Margherita – Introductory Hike
Santa Margherita – Trek to San Fruttuoso
Monterosso – Visit Levanto and Medieval Towns
Monterosso – The Cinque Terre Trails
Portovenere – From Riomaggiore to Portovenere
Florence – A Scenic Cruise
Florence – Depart for Home
Trip Highlights
- Experience the incredible Mediterranean coastline of Liguria as you trek along the ancient trails that connect secluded villages and towns
- Listen to monks perform traditional Gregorian chants while you absorb the panorama of the Florence skyline
- Discover the secluded San Fruttuoso Monastery only reachable by boat or walking trail
- Indulge in the luxuries of the medieval city of Portovenere and the beauty of the Gulf of Poets
- Sip wine on a private vineyard near Corniglia with a fantastic view of the Ligurian Coast
- Discover the vines and olive orchards that circle the ancient town of Volastra
- Indulge in the fresh flavors of Ligurian cuisine, from the seafood to the pesto
- Climb the watchtowers of the various towns of Cinque Terre erected to protect the coastline from pirates
- Visit elegant villas and graceful gardens that offer ample views of the mountains and sea
- Capture the fascinating aromas of the history of perfume at the Officina Profumo Farmaceutica di Santa Maria Novella
Detailed Description
Combine the pleasures of the Italian villages with the wonders of the Italian scenery during your active exploration of the Italian Riviera. Your 8-day scenic tour provides you with unparalleled views of the dramatic Ligurian coastline, filled with medieval fortresses and moored yachts. Follow unique trails that connect tranquil churches and flourishing vineyards. Each village contains a distinctive charm with its own cuisine based on the regional style. When your flight lands at the Florence airport, your private transfer will escort you into the heart of the Renaissance city. After settling in, your guide will lead you on an introductory walking tour to take in the open-air museum for which the Florentine streets are known. End your tour at the church of San Miniato to hear the monks’ Gregorian chant.
Venture next into the region of Liguria at the town of Santa Margherita. Enjoy the aroma of orange blossoms on the promenade before your brief hike to the nearby Portofino. Next day, trek along the cliffs of the Italian Riviera to reach the sheltered San Fruttuoso Abbey before you return to the town of Portofino. Enter next into the famed hamlet of Cinque Terre and leave the quiet, but luxurious, Levanto and cross over the prominent hills into Monterosso. Relish the marvelous vistas along the way as you eventually reach the picturesque region of Vernazza.
Next, you will follow the trails from Vernazza to Manarola. Pass through the middle of the Five Towns, known as Corniglia. Enjoy a visit to a local winery where vines overtake the hillside near the ancient town of Volastra. Once in Manarola, board the return train to Monterosso for the evening. Venture next to Riomaggiore, the southernmost town of Cinque Terre, by morning train and begin your outing for the day. The trail winds along pine and chestnut forests to reach the Gulf of Poets at the town of Portovenere, where you will indulge in the luxurious charms of the medieval city.
Continue to take the ferry to La Spezia to meet your private transfer. The remainder of the day is at your leisure to explore the splendor of Tuscany as you please, whether with a visit to the quintessential towns of Pisa and Lucca or by returning to Florence to relish more of the Renaissance influence on the culture. You could also visit the Officina Profumo Farmaceutica di Santa Maria Novella, the first perfumery in the world. To conclude, your private transfer will escort you to the Florence airport for your flight home.
Starting Price
$3,600 per person (excluding international flights)
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 6219 reviews
Our trip to Italy was absolutely amazing. Zicasso’s travel company provided exceptional service and attention to detail. We had never used a travel company for arrangements prior to this trip and we are so glad we did. It made the trip stress-free and truly over-the-top.
Our favorite time on the trip was at a location recommended by our travel agent in a very small area called Ciociaria. We loved this location and our resort in Ciociaria. The staff was incredible and we felt so relaxed.
I have been telling all my family and friends about the travel company’s services and that I will use them for future trips. I am so thankful to Zicasso for connecting me to an incredible experience with our travel company.
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This was our first time using a travel agency for a trip like this and Zicasso’s travel company completely exceeded our expectations. Traveling internationally with pre-teen children can be stressful, but from the very beginning, this travel company removed every bit of that anxiety. Every detail was thoughtfully planned, clearly communicated, and flawlessly executed.
From airport transfers to hotels, tours, trains, guides, and daily logistics, everything worked seamlessly. We never once felt lost, rushed, or unsure of what was next. Instead of worrying about schedules or navigating a foreign country, we were able to fully focus on our family and enjoy the experience. That peace of mind alone was invaluable.
What really stood out was how well the trip was tailored to our family. The pacing was perfect, the experiences were engaging for adults and kids, and every guide we worked with was knowledgeable, friendly, and professional. It truly felt like a curated, high-quality experience rather than a generic itinerary.
We came home with incredible memories and zero travel stress, something I didn’t think was possible with kids that age. This travel company was phenomenal and we would absolutely use them again, and recommend them without hesitation to anyone considering international travel, especially families.
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I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.
Trip Planning:
As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.
Transportation and travel between locations:
Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.
One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.
Venice:
Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.
The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.
Florence:
As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.
While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.
Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.
Day trip to Pisa:
The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.
The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.
Rome:
Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.
Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.
The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.
The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.
The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.
The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.
Sorrento:
We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.
During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.
Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.
On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.
Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.
Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.
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Thank you to Zicasso’s travel specialist and her amazing staff. The itinerary was fabulous. It was filled with food, wine, and highlights of the most important tourist places. Her guidance throughout the year-plus planning was the right amount of checking in and waiting. Thank you for the nudges to have reservations for all the holiday days. Things seemed to be pretty open overall, but it was nice not to worry.
All the restaurants set up for us were wonderful. The app was terrific to keep track of what we were doing when. All the drivers were very friendly, professional, and punctual.
Thank you for making our 35th wedding anniversary trip (December 22 2024 to January 6 2025) a most memorable one. We hope to return to Italy to enjoy the southern area and maybe some of the beaches and islands.
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We had an excellent itinerary and we really liked the accommodations provided, and their locations within walking distance of our must-see sites.
Excellent tour guides, drivers, and transportation were provided!
The Zicasso travel expert's recommended restaurants were also great and the guidelines were helpful!
My husband and I saw and enjoyed what we needed to see and experience!
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It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.
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