Immersive Couple’s Tour of Tuscany and Cinque Terre

What to expect on this itinerary
This 9-day couples trip to Italy’s Tuscany and Cinque Terre regions is a discovery of rich history and natural beauty. Experience the culture, history, and cuisine of Italy in addition to the iconic la dolce vita during this unforgettable couple’s vacation. Indulge in a private wine tasting in the Chianti region, explore the idyllic haven of Cinque Terre, and enjoy private time on some of Italy’s most pristine beaches.
Customizable Itinerary
Florence – Tour of Florence Cathedral
Your 9-day journey will begin when you land at Florence International Airport. A private driver will greet and transfer you to your luxurious accommodation. After having some time to relax and settle in to your new surroundings, your guide will lead you on a private tour of the Florence Cathedral. The colorful marble of the Cathedral will be a fascinating sight, and you will begin to learn about the intriguing history of the church from your guide. Once your tour concludes, you will be free to explore more of Florence at your own pace.
What's Included:
Florence – Art of the Renaissance
Siena – Wine Tasting in Chianti
Lucca – Walking Tour of Highlights
Lucca – The Enchanting City of Pisa
Riomaggiore – Cinque Terre and Sunset Dinner
Riomaggiore – Manarola, Corniglia, and Vernazza
Monterosso al Mare – Relax on Pristine Beaches
Monterosso al Mare – Departure
Trip Highlights
- Explore the Florence Cathedral to admire its colorful frescoes and impressive dome
- Witness Michelangelo’s masterpiece statue of David during an engaging visit to the Accademia Gallery in Florence
- Taste the delectable wines of Chianti during a private tasting for two at a traditional winery
- Enjoy one night in the beautiful city of Siena, which is known for its historic buildings and unparalleled landscapes
- Ascend to the top of Guinigi Tower to enjoy the sweeping views and rooftop garden
- Visit the Square of Miracles and climb the famous Leaning Tower of Pisa
- Indulge in a delicious sunset dinner for two in Riomaggiore, one of the five towns of Cinque Terre
- Delight in clifftop views and a wonderful atmosphere in Manarola
- Relax at one of the idyllic beaches of Monterosso al Mare, the northernmost town of Cinque Terre
Detailed Description
The beautiful landscapes of Tuscany and Cinque Terre provide the perfect backdrop for a memorable couple’s vacation. Your 9-day journey will begin when you land in Florence. Your first taste of the city will come in the form of a private tour of the gorgeous Florence Cathedral. The following day, you will explore Florence with visits to the Uffizi and Accademia Galleries. At these galleries, art masterpieces can be found around every turn. After your final evening in Florence, you will depart the next morning for Siena.
During your journey through the winding roads of Tuscany, the delightful area of Chianti will be the perfect place to visit one of the area’s premier wineries. At the winery, you can enjoy a private tour and tasting. The next day, you will transfer to Lucca, where your guide will lead you on an immersive walking tour. The Lucca Cathedral and ancient Guinigi Tower will be just two of the places that you will see. As the sun rises the next morning, you will set out for an excursion to the charming city of Pisa. In Pisa, you will visit the city’s iconic sites.
As another morning begins in Lucca, you will transfer to the idyllic Cinque Terre area. After an enjoyable ride, you will arrive in Riomaggiore, which is the southernmost town of Cinque Terre. Here, you will explore the town’s highlights with a local guide before indulging in a delicious dinner for two. The next day, you will uncover more of Cinque Terre with tours of Manarola, Corniglia, and Vernazza. From the impressive churches to the ancient castles, you will enjoy every minute of your visit to this picturesque region. The following morning, you will venture to Monterosso al Mare, which will be your final destination. After an engaging tour and having time at one of the town’s pristine beaches, you will have nearly concluded your Italy tour. The next day, you will head home hand after a private transfer leads you to Pisa International Airport.
Starting Price
$3,300 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
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.
Verified Traveler Reviews
Based on 953 reviews
We loved the hotels you selected. The drivers were prompt and the guides were good. We especially loved our guide in Florence. Monterosso al Mare was beautiful.
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Zicasso's travel company planned the most amazing trip to Venice, Verona, Florence, Tuscany, Siena, and Rome for our family of five. It was the best trip I've ever taken, and having all the details covered by them and plans and tickets sent to us via WhatsApp allowed us to really live in the moment and not have to think about what was next. I loved every second. I cannot wait to plan another trip to Italy to experience the southern half of the country.
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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.
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The travel assistance from Zicasso's company was very helpful. All tour guides were wonderful, as well as the tours, with the exception of the all-day tour into Tuscany, ending in Siena.
As an elderly woman, I found it to be too long. Also, after the lovely lunch and wine tasting, it was difficult to go on a 3.5-hour walking tour, as well as walk a mile into Siena and a mile out of Siena. Also, the bus did not have great air conditioning and did not have a working bathroom.
The other issue I had was with the seven and nine flights of stairs in Venice and Florence in our hotels. With bad hips and knees, I was confined to going up and down the flights only once during the day. I suggest this be a question for guests in the future.
The travel company was very generous in paying for a wonderful dinner for me and my grandson due to my struggles.
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When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.
Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.
Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.
A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.
Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.
When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.
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