Tuscany & Cinque Terre Tour: The Bountiful Beauty of Italy's West

Church of San Giovanni Battista in Riomaggiore, Cinque Terre, Italy

What to expect on this itinerary

Tuscany and Cinque Terre embody the word Renaissance, which means rebirth. Immerse yourself in towns built to encapsulate the artistic spirit, with rosy brickwork and dreamy paintings decorate the Cathedrals. Vineyards cover the rolling hills and take their nutrients from the diverse soil as fishermen take their daily catch to the morning market to showcase their fresh wares. Trails meander along cliff-sides and plateaus and open to the unforgettable Ligurian Sea. Your tour is custom tailored so you can indulge in bright pesto, climb medieval towers, and enjoy the lasting connection you make with the people and landscape.

Countries Visited

Italy

Places Visited

San Gimignano, Montepulciano, Siena, Val d’Orcia, Arezzo, Florence, Carrara, Lucca, Pisa, Corniglia, Vernazza, Riomaggiore, Monterosso, Manarola

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Montepulciano – Arrive in Florence and Travel to Charming Montepulciano

Your flight will descend into the Florence airport, and you will see the lush greenery that surrounds the tarmac. The city rises above the verdant landscape in the distance, bordered by rolling hills along the horizon. Your private transfer will meet you at baggage claim and lead you on a scenic drive through the Tuscan countryside before you arrive at your luxurious villa-style accommodation in Montepulciano. The walled town has preserved its medieval architecture, along with the updates procured during the 16th-century Renaissance. Montepulciano rises above the cypress and oak trees on a limestone ridge that reaches 2,000 feet above sea level.

Small hills and flatland spread across the valley below as the 14th-century Palazzo Comunale borders the western edge of the central piazza. The present Duomo was constructed between the late 16th and early 17th-century over the original parish church. The rough exterior stonework contrasts with the interior Renaissance beauty, including a 15th-century triptych of the Assumption by Taddeo di Bartolo. Your guide will meet you at the hotel after you’ve had a chance to settle in and lead you to a private vineyard outside of town. Wineries encompass approximately 2,500 acres of Sangiovese style grapes known as Prugnolo. The winery you visit was established in the 18th-century and houses the barrels in the same cellar as when the winery began.

The hills reach a height of nearly 1,500 feet above sea level and the change in elevation and sediment allows the vines to absorb the different nutrients from the soil. Your guide will lead you along the vines used to produce Vino Nobile, one of the most celebrated wines produced in all of Italy, let alone Tuscany. The cool air of the cellar preserves the wine, and here you find a tasting table amongst the barrels. Your guide will pour you a sample of the most recent vintage of Vino Nobile that the winery has produced. You will find the aroma of violet and rose petals mixed with cassis as the wild cherry flavor lingers on your palate with hints of cinnamon and white pepper. It is the perfect welcome to the Italian countryside.

What's Included:

Accommodation
Transfer
Tour
Day 2

Montepulciano – Indulge in the Val d’Orcia and the Town of Arezzo

Day 3

Siena – Enjoy the Tuscan Scenery and Tour San Gimignano and Siena

Day 4

La Spezia – Discover Pisa and Trek the Cinque Terre Trail Steps to Corniglia

Day 5

La Spezia – Relish a Private Cruise Before Touring the Town of Vernazza

Day 6

La Spezia – Relax On the Trails or Beaches in the Towns of Cinque Terre

Day 7

Florence – Visit the City of Carrara and Explore the Walls of Lucca

Day 8

Florence – Depart for Home

Trip Highlights

  • Enjoy a relaxing outing on the Mediterranean Sea during a private cruise to bask in the sun or cast a line into the water
  • Learn the art of sculpting with hands-on instruction in Carrara, home to Italy’s most famous marble quarries
  • Sample one of Italy’s most popular wine varietals near Montepulciano, home to the Vino Nobile
  • Discover the enchanting ambiance and scenery of Cinque Terre by traversing a portion of the celebrated cliff-side trails
  • Learn the secrets of Tuscan cuisine with a private cooking tour at a farmhouse near San Gimignano
  • Witness the elaborate Leaning Tower of Pisa, along with the magnificent history and monuments of the entire city
  • Immerse yourself in the Renaissance splendor of Pienza, a town embodying the spirit of artistic and spiritual rebirth in Italy
  • View the glinting bronze panels of Ghiberti’s Gates of Paradise located in the Museo dell’Opera del Duomo in Florence 

Detailed Description

It’s time to discover that people’s praises of Tuscany and Cinque Terre are more than true, and nothing compares to the majesty of the countryside and splendor of the Ligurian coastline. Your 8-day vacation uncovers the beauty of the Tuscan hills set in the charming villages, vineyards, and villas, while the towns of Cinque Terre radiate vintage charm as they overlook the turquoise waters of the Mediterranean. Your tour begins with your arrival at the Florence airport as your private transfer meets you at baggage claim to escort you to Montepulciano, a hilltop town above Val d’Orcia with hints of Renaissance, Medieval, and Baroque architecture. After an introductory walking tour of the city, your guide will take you to a small winery on the outskirts of town for a welcoming taste of Vino Nobile.

Venture next to Val d’Orcia to explore the sensational fields, vineyards, and towns along the valley floor en route to the ancient town of Arezzo. Discover the remarkable Renaissance town of Pienza before you wander through the quiet streets of Arezzo. Travel along the scenic roads of Tuscany to San Gimignano to explore the towers and cobbled streets before your private cooking lesson and lunch at a Tuscan farmhouse. Learn the delicious secrets of the countryside, from fresh produce to the homemade cheeses. In the afternoon, you will enjoy a half-day tour of the captivating medieval city of Siena, which once rivaled Florence for regional supremacy.

Travel next to Pisa to discover the wonders beyond the Leaning Tower. Take a local train from La Spezia to the secluded beaches of Cinque Terre, a collection of five towns located on the Ligurian Sea. Traverse the stairway of Corniglia, the center town, for an initial view of the coastline and the villages. Next day, board your boat in the town of Vernazza for a private cruise on the Mediterranean and cast a fishing line out into the water if you desire.

When you return to Vernazza, relax into the serene view. If you caught a fish, take it to a local restaurant that will be happy to cook your catch with regional flavors. The next day at your leisure to enjoy Cinque Terre as you please as you follow one of the various trails that connect the towns together or visit the Gulf of Poets to see more of the Italian Riviera.

Next, your private transfer will escort you to Carrara, home of Italian marble. Visit the famed quarries, witness the treasured artworks developed by famous masters, or try your hand at sculpting during a private workshop. Continue to the walled city of Lucca for an in-depth tour of the enchanting medieval and Renaissance streets before you arrive in Florence. Extend your vacation to spend more time luxuriating in the pleasures of Tuscany and Italy, but if time is short, your private transfer will greet you at your hotel and escort you to the airport for your flight home. 

Starting Price

$3,600 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.

4.9

Verified Traveler Reviews

Based on 709 reviews

Italy Birthday Trip Review: Tuscany, Cinque Terre, Florence, Monterosso al Mare, Boat Ride, Wine Tasting, Cooking Class, Paper-Making Class, 10 Days

Zicasso’s travel specialist and her team crafted a wonderful 10-day trip to Tuscany, Cinque Terre, and Florence for my husband's 60th birthday. All the hotels were beautiful boutique hotels that we probably would not have found if we were planning it ourselves. The same was true with the experiences they booked for us. They have the local connections and can provide experiences you may not easily find by searching the internet.

We loved that our wine tastings were at smaller local wineries. All our guides were very friendly and very knowledgeable. All our drivers were always on time. They took care of reserving our train tickets, as well as dinner reservations. We felt very well taken care of throughout the entire trip.

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Italy Trip Review: Rome, Florence, Tuscany, Cinque Terre, Venice, Pizza-Making Class, 2 Weeks

We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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Italy Tour Review: Florence, Cinque Terre, Capri, Boat Ride, 2-Week Trip

Our Zicasso travel agent did a great job planning and executing our two-week tour of Italy. Transfers were seamless and guides were knowledgeable and experienced. We particularly loved Florence, our hotel, its staff, and its walkable location to so many sites. We loved the guide in Cinque Terre; he knew the area, specifically a restaurant where we were away from the crowds. Thanks to the travel agent for a job well done.

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Italy Tour Review: Pompeii, Amalfi Coast, Florence, 12 Nights

Zicasso’s travel company and every single guide and driver were stellar. All four hotels were good or excellent. There was one error on the schedule for the day outside of Florence when we had a driver to take us to the Siena region. The schedule stated three hours, so we paid for tickets to the Pitti Palace/garden, which turned out to be wasted money as the driving tour was actually nine hours. It was a beautiful day, though.

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Italy Travel Review: Venice, Cinque Terre, Pisa, Florence, Impruneta, Rome, St. Mark's Basilica, Vatican, Cooking Class, Winery Tour, Art, 9-Day Trip

The trip was awesome. The accommodations were very nice. We just did not realize how much walking we would do, but we managed. There were a few hiccups, but nothing major.

Our transport from the airport to the hotel in Venice went smoothly. We definitely appreciated the private transfer after seeing the crowd on the public transportation. My sister was a little disappointed that the gondolier did not sing to us in Italian, but she thought the ride was very relaxing. The tour guide for St. Mark's was very knowledgeable and informative. Venice was a lovely and unique city. We were surprised by the narrow walkways/streets and canals; but came to appreciate them. It gave Venice its charm. The transport from the hotel to the train station was right on time and the guy at the train station was great. He explained exactly what we needed to do to catch the train to our next destinations. We really appreciated his help.

The transport from the train station to the car rental agency was okay. The driver spoke little English and the A/C did not work in the vehicle. The driver did try everything to work the A/C and did apologize that it was not working. The driver dropped us off at the wrong spot at the rental car place. He dropped us off where you turn in the cars.  We had to walk to where you rent the cars with our luggage. The car-rental line was extremely long and somewhat confusing. There were no instructions to take a number. We only knew because a nice couple informed us to do so. And there were so many other car-rental places with no lines. 

We explored Cinque Terre, Pisa, and Florence during our time in Impruneta. We really enjoyed the cooking class and winery tour you scheduled for us; our guide was a great teacher. Driving in Florence was a little confusing with the ZTLs, but I think we did okay. Little did we know how much we would appreciate the ZTLs while walking around in Florence. We walked and shopped in Florence. We even did a tour at the Accademia Gallery to see the statue of David. 

Returning the vehicle was way easier than renting it and our next transport picked us up right where we were dropped off. We felt very comfortable navigating the train station for our train ride to Rome, thanks to the train station lesson we received from the guy in Venice. The train rides went very smoothly. The transport from the station in Rome to our hotel went very well. He literally dropped us off right in front of the hotel.

Rome was different. It had the narrow, quaint streets between buildings which made Rome very walkable. However, we did not expect cars/motorcycles to be driving down these narrow streets as well. It made for interesting walks. We really enjoyed our tours with our guide. She was very knowledgeable and informative. She also allowed us to go at our own pace. Needless to say, our pace became slower than usual from all the walking we already did in Venice and Florence. Our feet were starting to hurt, even though we wore comfortable shoes the whole time. We also enjoyed the Vatican Necropolis. I was extremely humbled that I was able to kneel and pray before the actual remains of St. Peter. I am very grateful we were allowed to get into that tour. Although Rome was different, it was very historical and a lot to take in. There was just so much history everywhere you turned. Rome was really inspiring.

Our transport from the hotel back to the airport was on time and went very well. The driver spoke very good English and gave us some additional interesting facts while on our way to the airport. We were ready to go home, but also sad to be leaving.  

Thank you for putting the details of the trip together. The trip would not have been as great as it was without you.

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Switzerland, Italy, Germany Tour Review: Bologna, Florence, Zermatt, Wengen, Lake Como, Matterhorn, Tuscany, Winery Visit, Truffle Hunt, 9 Nights

This travel company was incredibly difficult to work with, and I would not recommend them. The travel agent seemed very annoyed when we asked basic questions about our itinerary. For example, the itinerary he sent us did not have the correct number of rooms booked for our party. When I asked him about it, he rudely told me, "Of course I have booked the right rooms". Later, we found out he was working off the wrong itinerary - our final invoice was based on this wrong itinerary and had a much higher amount than we actually owed. When we pointed that out, he went from being annoyed to flat out rude.

We also identified many gaps in transportation and logistics, with the travel agent continuing to be rude when we asked for clarification or support in fixing the gaps. For example, he had us driving a rental car to the Bologna airport at around 3 AM from rural Italy to make an 8 AM flight. We would be driving right through Florence on the way to Bologna. When I asked why we didn't simply take a later flight out of Florence, I was told there were no options to do this. A simple Google search identified several flights out of Florence at a more reasonable time.

We finally had Zicasso step in, and they were incredibly helpful in cleaning up our itinerary. Unfortunately, we still experienced several logistical issues during our trip despite Zicasso's support. For example, we were dropped off by drivers at train stations and were then on our own to figure out how to get to our hotels - all required lengthy walks up hills to access, and my 81-year old father was not able to do that. So we had to find our own transportation or have my dad attempt to walk (not good at all). As another example, my father really wanted to see the Matterhorn. The travel agent said it was an easy "day trip" from our hotel to the Matterhorn. It turned out to be a 3.5 hour drive each way. The driver left us at a train station below Zermatt (town below the mountain) to figure out on our own how to navigate the city of Zermatt. We had no guidance from the travel agency on how to best see the Matterhorn, and Zermatt was another town with steep hills that my dad had to walk through (with a cane) as we tried to figure out how to best see the mountain. Due to the length of the drive to Zermatt from our hotel, we had less than two hours in Zermatt because the travel company had booked us on a 6:15 AM train the next morning to leave Switzerland. It was a wasted day instead of being the wonderful experience my father had hoped for.

The best part of the trip was the hotels, and the travel company gets credit for selecting hotels with wonderful views and great breakfast options. They were not easily accessible from the local towns, so we had to figure out taxis and shuttles to get to nearby sites.

Most of the time, we were left on our own to find our way around. But we did have a guided tour in Florence and a knowledgeable driver that took us to a winery in Tuscany. Both of these guides were amazing, and it would have been nice to have more guided support throughout this trip (especially in Zermatt).

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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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