Immersive Couple’s Tour of Tuscany and Cinque Terre

Couple relaxing and enjoying the view of the Tuscany countryside in Italy

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.

Countries Visited

Italy

Places Visited

Florence, Siena, Lucca, Riomaggiore, Monterosso al Mare

Suggested Duration

9 Days

Customizable Itinerary

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Day 1

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:

Transfer
Accommodation
Tour
Day 2

Florence – Art of the Renaissance

Day 3

Siena – Wine Tasting in Chianti

Day 4

Lucca – Walking Tour of Highlights

Day 5

Lucca – The Enchanting City of Pisa

Day 6

Riomaggiore – Cinque Terre and Sunset Dinner

Day 7

Riomaggiore – Manarola, Corniglia, and Vernazza

Day 8

Monterosso al Mare – Relax on Pristine Beaches

Day 9

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.

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Verified Traveler Reviews

Based on 1215 reviews

Portugal, Croatia, Italy Vacation Review: Hiking, Florence American Cemetery and Memorial, Wine Tasting, Cuisine, 18 Nights
"Our Zicasso travel specialist was very patient and accommodating. Each tour guide was excellent. Each of the hotel accommodations was fabulous."

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Italy Tour Review: Monterosso al Mare, 10 Nights

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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Italy Travel Review: Rome, Florence, Naples, Ischia, Vatican Museums, Skywalk, Wine Tasting, Olive Oil Sampling, 2 Weeks

Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.

The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.

In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.

Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.

At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.

Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.

We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.

We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.

We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.

I can’t wait to use the travel company again next year.

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Italy Vacation Review: Tuscany, Siena, Florence, Wine Tasting, Cooking Class, 11 Nights

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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Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

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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Italy Vacation Review: Venice, Florence, Cinque Terre, Fabric Weavers, Cooking Class, Boat Ride, 11-Day Trip

We had a wonderful trip! Everything went perfectly! All our guides were great and always on time to the meeting point. Our two favorite guides were in Venice and Florence.

Our guide in Florence went above and beyond, making our tour exactly what we were looking for. He was so knowledgeable, I don't know how he keeps all those details in his head. He gave us such insights into the history and artworks we saw. My husband is a painter and really enjoyed his information on so many of the little details.

We also really enjoyed the visit to the fabric weavers very much!

All the hotels were fabulous and in perfect locations.

We also loved our cooking class in Portofino.

Our boat ride in Cinque Terre was wonderful.

I will definitely be recommending Zicasso to my friends! Thank you for a wonderful trip!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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