Tuscany & Cinque Terre Tour

A 13 day trip to Italy 
4.87 out of 5 stars
15 reviews

From the lush green of Tuscany’s hills to the pearl blue water of Cinque Terre’s coastline, experience why Italy is one of the world’s top destinations. Tuscany and Cinque Terre are works of art that everyone can enjoy. In Tuscany and Cinque Terre you do not just view the art, you become a part of it. Find out for yourself what all the great reviews are about!

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General Information

Detailed Itinerary

Places Visited 

Tuscany, Cinque Terre

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 – Sensory Immersion

Arrive at the Florence airport and be transferred to a quiet Tuscan country estate along La Strada di Chianti, the historical road that has connected vineyards and olive groves in Tuscany for centuries. Settle in to the beauty of your accommodation, surrounded by the rich smell of the Tuscan hills. Walk around the grounds. Sneak a taste of a juicy grape still on the vine. Now is the time to relax and let go of your worries. Give in to the sweet scent of Tuscany, the lingering sunset, and the art that is Italy. 

What's Included: transfer, accommodation

Day 2 – Absorb the Art of Florence

Early in the morning the city smells like sweet brioche and rich coffee. Give yourself the morning to sit in la Piazza del Duomo, the square that houses the Duomo, with so many bakeries in the area. Choose a bakery and enjoy an Italian breakfast: the sweet, crunch of a pastry, the strong, hot espresso, and watch the city come alive. Become a part of the city, with its beauty at your fingertips.

The Duomo is the main church in Florence and can be seen from almost anywhere, towering over the city like a guardian. Arnolfo di Cambio designed the basilica; Giotto designed the campanile. Brunelleschi, inspired by the Pantheon in Rome, designed the dome. The dome is impressive from the outside; the basilica is breathtaking from the inside. The spicy smell of myrrh, the echo of footsteps, the stain glass windows that light the cathedral, the ethereal fresco that encircles the dome. Climb to the top of the dome and look out on the sprawl of Florence, from the Arno River, to the Tuscan hills that surround the city. 

While walking through the streets of Florence, don’t forget to look up; buildings in the city center that were mentioned in Dante’s Divine Comedy have plaques to commemorate them. Each plaque lists the book, (Inferno, Purgatory, Paradise), the canto (verse), and the line number. Some locations have more favorable mentions than others. 

Venture into the small museum behind the Duomo called Il Museo dell’Opera del Duomo. It houses most of the original art and sculptures that were once inside the Duomo, including Ghiberti’s Gates of Paradisewhich many people think are still located on the Baptistery. Head down via Calimala toward Piazza della Signoria, where the Old Palace sits. Like much of Florence, don’t let the antiquated look of the building fool you. Inside the palace you will see the impressive frescos that were meant for royalty, along with Dante’s death mask, a plaster mold of his face after his death. A replica of Michelangelo’s David guards one of the formal entrances of the palace.

You can’t miss the Uffizi Gallery in the same plaza, with hordes of people lining up to enter. Pay attention to the statues being photographed outside of the Uffizi’s entrance. If you look long enough you will see them move. It is a short walk to the Ponte Vecchio, the old bridge, where family jewelry shops have thrived for generations and continue their trade. The area is lively as the Arno River rushes beneath you, and the crowd is excited and boisterous. 

Go to the local market and grab some bread and cheese for a picnic, or head to The Oil Shoppe on Via Sant’Egidio. The owner and head chef, Alberto, has mapped out the best flavor combinations for all of his panini, or feel free to make your own. Alberto will clearly tell you if you’re combination of meat, cheese, vegetables, and homemade sauce will not go well together. Take the sandwiches portare via (to go); head to the Boboli Gardens, just across the Ponte Vecchio. The Boboli Gardens are 11 acres of superbly manicured grounds filled with sculptures and fountains that span centuries. Spend the remainder of the day traversing the grounds. The sound of running water can be heard from almost anywhere in the garden from fountains and streams. Explore the hedges that almost act like a maze and literally smell the roses that rest between them. Sit near Neptune’s statue, feel the soft grass, the cool air, and bite into the decadent sandwich or picnic that you brought with you. 

What's Included: breakfast, guided tour, accommodation

Day 3 – Florence Revisited

Having seen the luster of Florence’s architecture and gardens, start the day with the majesty of some of the Renaissance’s greatest art. The Uffizi Gallery, originally commissioned by Cosimo I de’ Medici in the 16th century, now houses some of the Western world’s greatest and most recognized art. Housing such artists as Da Vinci, Caravaggio, Titian, and Raphael, you can practically smell the smooth marble and paint when you stand in front of Botticelli’s The Birth of Venus. You could easily spend a full day wandering through the polished halls of the gallery, among some of the most notable names in art history. 

The Central Market located Piazza San Lorenzo, is close by. It is a large, open, and and easy place to grab a quick lunch. From a panino made of prosciutto and pana gradano, to a luscious ricci pasta, a long, threaded egg pasta in a light tomato sauce, surround yourself with locals and lunch like one too. San Lorenzo Market is also a popular shopping area, with merchants touting bargain scarves, hats, and ties. The area is mostly known for its accessible leather goods, from jackets and shoes, to purses and bags.  

The church of San Lorenzo was considered the “official” church of the Medici family, the oldest documented church in Florence. The interior shines with bronze and white marble. The air is quiet as people walk in the footsteps of the Medici. Michelangelo’s statues of Dawn and Dusk stare back at you in repose as you enter the doors of San Lorenzo.

The Medici mausoleums are also in the area, flanked by statues of Cosma and Damian, the Medici’s Patron Saints. The Medici-Riccardi Palace is also close to San Lorenzo. Don’t let the plain exterior fool you. Inside the palace is an eccentric and lavish courtyard full of seductive statues. The palace contains vibrant paintings that tell the history of religion, and of the Medici family. 

Allow yourself the Indulgence of a snack: a gelato from Perche No, a tasty gelateria just off of the main street of Via dei Calzaiuoli. Perche No has traditional flavors of gelato like stracciatella (chocolate chip) and fragola (strawberry), but also has flavors like Nutella, Tartufo (truffle), and green tea.

Cross the Ponte Vecchio for a luxurious and decadent dinner. Stay for a moment on the bridge and listen to the musicians that often play at sunset. Continue to Via dè Vellutin, a plaza close to the Pitti Palace. There you will find Quatro Leoni, a delicious restaurant known for its Bistecca Fiorentina, a hardy, juicy Florentine T-bone steak, and its sumptuous pear and Gorgonzola tortellini. 

What's Included: breakfast, guided tour, accommodation

Day 4 – Another Day of Art Exploration

With so many replicas of Michelangelo’s David, it is natural to assume that the original would be so similar. Today is the day to see how wrong that assumption is. The Academia not only houses historical musical instruments and incredible sculptures, but is also still a prestigious art school in Italy. Get to the museum early and take the time to walk among the statues, finished to the tiniest detail, with eyes that stare off into space. Walk into the gallery that houses David, a long white corridor with the gigantic statue at the end. The statue, with its size and detail, has always been, and continues to be, a tourist highlight. 

A light lunch at I Due Fratellini will hit the spot. It is a tiny spot where a delicious mini-panino and a glass of wine will cost about five-Euro. Continue your museum exploration with a trip to the Bargello, where Donatello’s David is housed. Different in size and in material, Donatello used bronze to create the first unsupported standing work of bronze of the Renaissance. Donatello’s David is also a bit cheeky, a noticeable smirk on his face with his bronzed foot resting on Goliath’s head. 

There is always time to see Piazzale Michelangelo. Take the stairs, mentioned in Dante’s Paradise, up to the piazza, for the best panoramic view of Florence at sunset. As the sun starts to dim and the lights of the city start to glow, you can see the largest buildings of the city radiant in the night sky, the octagonal bell tower of the Badia Fiorentina, Bargello, Palazzo Vecchio, and of course, the Duomo.

Later, indulge at La Giostra, a luxurious restaurant owned by Hapsburg royalty. With dishes that highlight the decadent white truffle, and wines that are both subtle and luscious, what better way to wind down your night than in a Florentine restaurant that rarely has the same menu twice.  

What's Included: breakfast, accommodation

Day 5 – Artistry Wanderlust

End your Florentine wanderlust with a walk through Piazza Santa Croce. The plaza holds some of the larger festivals of the city, such as the Christmas and Easter fairs. The Basilica is known, not just for its incredibly flush façade, but also for the famous Florentines that have been buried there, such as Machiavelli, Michelangelo, and Galileo. The church was also mentioned in E.M. Forester’s novel A Room with a View. 

Around the corner is Trattoria Baldovino, a delightful restaurant with traditional Tuscan dishes. Enjoy the selection of cheese, from light and creamy, to pungent and strong, with crostini and honey. They also have a light Tagliatelle with a traditional Tuscan meat sauce with porcini mushrooms. The combination of the smell of melted cheeses, sweet honey, juicy meats, and incredible art, is almost enough to fill you up - almost!

The Mercato delle Cascine is one of the largest markets in the city, open on Tuesdays from 7am-2pm. The market is full of locally made clothing and food; you can smell the slow cooked meat and aged cheese as you enter the park. Follow the crowd through the half-mile long market, browse, buy, taste, drink, devour. If you feel adventurous, try the rich tripe sandwich from one of the food stands.

When the crowd and the shopping have tired you out, Cascine Park is the largest park in Florence. Stroll through the trees and the grass, relax in the shade, possibly with some fresh pastries you bought in the market. A leisurely stroll down the Arno takes you back to the center of the city, and it is a nice reminder of the history you have experienced in this beautiful place. Also be rewarded as you watch the sun fade behind the hills. 

What's Included: breakfast, accommodation

Day 6 – The Art of Wine and Oil

Spend the day cruising through La Strada di Chianti, home to some of the regions best wines and medieval villages. The Tuscan landscape is filled with more than just the green hills, but with the ripening fruits and smooth flavors of wine and olive oil. 

Greve is the “Gateway into Chianti,” the first large town you reach heading south from Florence to Siena. One of the few Tuscan towns not located at the top of a hill, Greve in Chianti centers around the Piazza Matteotti, the lifeblood of the town. The square itself is a sight to see, a triangular shape with a portico that frames the local shops and restaurants. On Saturday mornings the square erupts with a boisterous crowd, the smell of fresh breads and pastries, local cheeses and winemakers for the weekly Saturday market. 

Stroll through the Museum of Sacred Art, full of historical and important artwork characterized by sculptures and colorful terracotta. The museum almost sums up the connection the area has between religion and art. For a delicate taste and instruction on the local flavor, the Wine Museum offers a history of Tuscany’s wine production. From antiquated tools that smell of rust, to old barrels that contain their earthy, smokiness, the museum has displays that will entice even those unaccustomed to the uniqueness of the region’s wine history, complete with 200 different Tuscan wines to taste. 

Farther down La Strada” is San Gimignano. The town rises above the hills of Tuscany with 13 of its original 70 towers still standing. The towers were originally constructed in the 14th century to show off economic power. It is easy to see the beauty of Tuscany from the top of one of the towers. You can almost smell the grass as the sun sets behind the hills. San Gimignano is also known for its Vernaccia, a white wine that Dante mentioned as leading to Pope Martin IV’s gluttony, eating Bolsena eels pickled in the wine.

If you enjoy Italian wines, you might also be interested in the Umbria wine tour.

What's Included: breakfast, transfer, guided tour, accommodation

Day 7 – The Art of Festivals

Tuscany is a superb place to celebrate food and wine as festivals sprout in autumn like grapes on the vine. The Chianti festival in Greve in Chianti is a delicious and fun way to not only taste the wines that Tuscany has to offer, but to mingle with the locals and catch an insider's view of the Italian lifestyle; experience Italy in the tasty way that Italians do. Buy a glass from the organizer’s booth and taste the varieties of flavor that Tuscany offers, from smoky, earth to dark fruits and spice.

If you prefer adventure to wine, Sagra del Tordo in Montalcino is a reenactment of a medieval archery tournament. The competition is between the four neighborhoods of the town. Join the energy of the crowd as they clap their hands, stomp their feet, and chant for their archer’s victory.  

What's Included: breakfast, accommodation

Day 8 – Another Pleasant Stroll

La Strada continues with a visit to Castellina in Chianti, a municipality between the valleys of Arbia, Pesa, and Elsa Rivers. The 14th century castle looms over the town as a reminder of its historical roots.  Observe the top point of the tallest tower, down to the museum that houses the Etruscan history of the area. 

Castellina in Chianti offers more than a tower and a beautiful view of the Tuscan countryside. The church of San Salvatore holds a fresco of Madonna with Child. A short distance from the city center is the Montecalvario Mound, four tombs from the 76th century BC. From the distance they look like a cluster of tiny hills situated close together. Step inside to see the burial rites of an ancient civilization. The beauty and luxury of La Strada will not be far behind. 

Indulge in the evening with a four-course meal at a gorgeous Tuscan estate, complete with a sampling of the estate’s wines. Tuscany is known for its use of simple flavors and ingredients, drawing attention to the luxury of simplicity. Enjoy the delicate flavor Affettati Misti (sliced meats), or fresh vegetables in olive oil. The lovely, salty crunch of crostini in chicken liver, the comfort of onion soup with grated cheese, the Florentine chicken in bread crumbs with spinach, and finish with rich chocolate profiteroles. You will be wishing you had space in your stomach to do the meal again.

What's Included: breakfast, dinner and wine, accommodation

Day 9 – Another Beautiful Adventure

End your final day in Tuscany with a trip to Lucca and Pisa. Lucca is another of Tuscany’s ancient city’s, a gem of antiquity and modernity still surrounded by its historic walls. As the walls lost military importance they became a pedestrian promenade, full of beautiful trees that change with the seasons, and a lovely place to relax and soak in the sights. From the intimidating facades of many of the basilicas, to the traces of the roman amphitheater in Piazza dell’Anfiteatro, there is even a museum to commemorate the composer Giacomo Puccini. 

Pisa has as much medieval history as Florence, often an adversary against the Florentine municipality. The tower was to commemorate the city’s conquests, now it is known for its tilt. Delight in not only the tower, but those around trying their hardest to fit the tower into their awkward pose. The baptistery and the cathedral are just as impressive, with their Gothic elements and grandiose gray marble. The piazza was once described by Gabriele d’Annunzio as the “meadow of miracles.” Although the tilt of the tower may intrigue you, the interior of the cathedral will blow you away. The pulpit has such an elaborate artistry that you could spend hours trying to find similarities in each person carved into the structure. The baptistery windows are stained with colorful glass that shine into the building making the floor sparkle. 

What's Included: breakfast, accommodation

Day 10 – The Luxury of Liguria 

Cinque Terre is part of the Italian Riviera, in Liguria. It is composed of five villages woven together on the coastline through a hiking trail and railway. Riomaggiore, Manaorla, Corniglia, Vernazza, and Monteroos al Mare all offer different attractions, and are all equally as stunning. 

Experience each town and what they have to offer independently from another. Most people begin in Riomaggiore, the southern most town of the five. The buildings are painted with bright colors that can be seen from the horizon to help guide fishermen home. Relax in sun and sand, see the wharf framed by tower houses, and taste the difference of the Ligurian cuisine from that of Tuscany, most notably the pesto. Plants can grow as tall as five feet with an earthy sweet taste that graces pastas and pizza. 

What's Included: breakfast, transfer, accommodation

Day 11 – Nature’s Beauty

Begin the day with a Genoese breakfast, one of caffe and focaccia; in this area focaccia is considered to be a delicacy at any time of day. Hit the trail to Manarola, the delicate smell of tomatoes and basil fill the trail. Or you can take a boat from one town to the next; the buildings built into the cliff are both impending and stunning. Manarola historically was known for its fishing and its wine, and the town smells of salty bread and rich seafood. Take a seat in a trattoria that looks over the water, taste the ruggedness of the wine, and the delicate salty fish that graces the table. Manarola is also the oldest town of the five, the cornerstone of San Lorenzo Church dating back to 1338.

Continue the journey by land or sea to Corniglia. Terraces and vineyards on three sides surround the town; the fourth side has a steep dive into the water. If you do choose to take a boat be ready for the hike up the Lardarina, 382 brick steps. Traverse the narrow roads of the town and up to the tallest terrace where the four other towns can be seen. Corniglia is a wonderful place to watch the sun dip behind the horizon and down into the pearl blue sea. 

What's Included: breakfast, accommodation

Day 12 – One More Day

Two more towns to see along the sea, and Vernazza is as colorful as the towns come. With buildings that shine along the coast, the natural harbor glows in the sunlight. Doria Castle was built in the 15th century and the lookout tower still stands high along the coastline. The water sparkles like crystals, and the sounds of the town are soft and soothing. People lay on the rocks of the harbor soaking in the heat of the sun with their feet dangling in the cool of the water.   If you hike, don’t forget to take one last look at Vernazza from the top of the mountain. The panoramic view is one of the most dynamic and all encompassing of any of the towns. One look back at Vernazza will sum up your entire journey through Cinque Terre: breathtaking. To recharge, try an earthy and meaty pesto lasagna at Taverna del Capitano di Basso Paolo e Barbara.

For a different experience, try traversing the hiking route from Monterosso back to Riomaggiore, plunging down into Vernazza and climbing up into Corniglia. This route makes for an exciting hike.  

The last town is Monterosso al Mare. Monterosso has the largest and nicest beach of all five towns. Treat yourself to a cabana and a refreshing fresca on the waterfront. In some parts of the town, the narrow streets dig high and deep into the mountain. With a stunning granite church and castle remains, Monterosso does not lack for things to see. It even has its own giant built into the mountain. Fragmented during WWII, the Giant of Monterosso al Mare still stands against the mountain holding Villa Pastine. The Giant is a 14 meter high statue of Neptune meant to depict him holding back the waves. A perfect image to end your journey through Tuscany, Neptune on the rocks and the Italian Coast, one last remnant of Italy’s past in its beautiful present. 

What's Included: breakfast, accommodation

Day 13 – Art is Never Far Behind

After a delicious breakfast by the sea, transfer to the airport. Although the trip might be over, know that the beauty of Tuscany and Cinque Terre is never far behind.

What's Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
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.