Best of Tuscany in a Week Itinerary: Lucca, Pisa, San Gimignano, Siena & Florence

A 8 day trip to Italy 
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The treasured hills of Tuscany are filled with verdant grasses and vast vineyards. Sprouting out of the hillsides, you can find exceptional medieval towns practically frozen in time. Walls encircle the historic city centers, and Renaissance statues remain in public squares to inspire locals and visitors alike. Marble cathedrals exemplify grandeur on the exterior and interior. Your custom tailored one week Tuscany tour itinerary to Lucca, Pisa, San Gimignano, Siena, and Florence guides you through the picturesque cities and famous landscape of the Tuscan countryside, where the cobbled lanes are as historic and gripping as the artifacts in the museums. 

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General Information

Bike through Tuscan Vinyards. Photo Credit: Bike Florence&Tuscany
Sunset with Smile & Ride. Photo Credit: Smile & Ride
Pierotucci Leather Factory
More than Miracle Square Bike Tour. Photo Credit: Smile & Ride
Pierotucci Leather Factory
Sunflorwer Groves in Tuscany.  Photo Credit: Bike Florence&Tuscany
Marina di Pisa. Photo Credit: Smile & Ride
Lavender Steps. Photo Credit: Bike Florence&Tuscany
Detailed Itinerary

Places Visited 

Lucca, Pisa, San Gimignano, Siena, Florence

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Florence – Arrive in the Enchanting Renaissance City of Florence

The historic streets and churches around Florence have lent the city to be dubbed the “Cradle of the Renaissance.” Stunning marble sculptures decorate the public square of Piazza della Signoria. The Loggia della Signoria decorates the southern border of the square, filled with images of the Renaissance set beneath the large, open arches and date back to the 14th century. Medici lions look out to Palazzo Vecchio. Perseus holds the head of Medusa, cast in shimmering bronze. The Arno River floats past in the nearby canal. The lush Tuscan hills encompass the outer reaches of the city, emphasized with thin towering cypress trees.

Our Italy travel agent will arrange a private transfer to meet you at the airport. Your private transfer leads you into Florence helping you settle into the beauty and romance of the historic city. Piazzale Michelangelo watches over the historic city center on the Otra Arno, known as the other side of the Arno River. The terrace provides a spectacular view of the entire city, stretching from the banks of the river, past the dramatic dome of the Florence Cathedral, all the way to the hills beyond the ancient city walls. The scent of fresh pasta fills the evening air.

Every evening the monks at the Abbey of San Miniato al Monte, just behind the piazza, perform mass. Their Gregorian chants echo in the gilded church gallery. The scent of frankincense filters out the doors of the church and into the countryside. It is a perfect introduction to Tuscany.

What’s Included: airport transfer, accommodation

Day 2: Pisa – Journey to Pisa and Discover the Leaning Tower and the City Beyond

In the morning, the soft light washes over the brick dome of the Florence Cathedral. The gold plated Gates of Paradise on the baptistery shimmer in the sunlight, with the images of the Old Testament, showcased on the east doors. The morning is yours to discover more of the majesty of Florence, savoring the quality of the city that resembles an open-air museum, with historic palaces, a marble cathedral, and priceless artistry for public viewing. In the early afternoon, you leave the Tuscan capital and make your way into the verdant hillsides, covered in emerald grass and jade cypress trees. Villas speckle the countryside en route to Pisa.

When you arrive, you find a principality with a historic Navy that once surpassed that of its northern neighbor of Genoa. Once you have checked into your hotel, your guide will accompany you to your “More than Miracle Square” bike tour. As your guide at Smile & Ride takes you on your Pisa bicycle tour you find a vibrant, youthful energy stemming from the student population. The university has been a staple in the city since the 14th century and remains a prized institution across Italy. At the Piazza dei Miracoli, you find the expansive square home to the renowned Leaning Tower, but also the sensational Pisa Cathedral. The medieval structure was erected in the 11th century with five naves and a Romanesque style. The pointed arches in the interior and the mosaics show a heavy Byzantine influence. The gray marble façade contrasts the white stone and marble disks enveloping the main doors made of bronze. The grandeur of the structure heightens the atmosphere around the Leaning Tower, showing the historic power and wealth of the city.

What’s Included: accommodation, transfer, bike tour with Smile & Ride, breakfast

Day 3: Lucca – Venture to the Medieval City and Explore the Historic Walled Town

In the morning, the remnants of the city’s opulent past blossoms out of the quiet streets, surrounding the Piazza dei Miracoli and emerging from the grounds of the Sacred Field made legendary by the Archbishop Ubaldo dei Lanfranchi. After breakfast, you pass the Piazza dei Cavelieri and the 16th-century palace of the same name, leaving Pisa behind for the sensational medieval walled city of Lucca. After you are settled in, you will meet with your guide at Lucca Tours for your Lucca half-day historical and educational tour.

Your guide will tell you all about the circuit of walls that are almost two and a half miles long bordering the historic city center. Eleven bastions and three gates have fortified the 35-foot tall walls since the 16th century. Today, a public park surrounds the walls providing lush space for locals to walk, run, and bike. As you pass through the wonders of San Paolino Street you will make your way to the church of San Michele. Notice the churches beautiful wedding-cake façade as it sits stoically in the center of the city. Flowers blossom and trees glow in the gentle Tuscan breeze, bringing a verdant scent to the city. The massive Guinigi Tower stands at the center of the old walled town adorned with holm oaks. The tower stands more than 145 feet tall and was erected to connect a complex of two mansions belonging to the Guingigi household, a family that brought the city an era of prosperity and peace in the 1400s. The city has an ineffable charm emanating from the Roman Amphitheater, whose oval outline remains in the design of the bordering homes. As you finish your tour you will view the city with an entirely new perspective and appreciation.

What’s Included: accommodation, transfer, tour with Lucca Tours, breakfast

Day 4: Lucca – Relish Tuscan Flavors with a Gourmet Cooking Class in an Antique Palace

The walls of Lucca practically blend into the scenery, embraced by the organic greenery of the park. In the morning, you savor the aroma of espresso drifting from the cafes along the main streets of the city amidst the images of  Renaissance structures enlivening the cityscape. The scent of fresh brioche fills the dining room at breakfast before you venture to Il Cuore, a gourmet shop offering delicious salumi, cheeses, and delicacies specific to Tuscany. Your professional chef from Extra Virgin Cooking Classes will greet you with a warm welcome introducing you to the alluring flavors of Tuscany by sampling the different tastes of the city, including tender salametto, which is similar to a gourmet pepperoni, as well as crumbly goat cheese, or a selection of produce steeped in marvelous marinades for vegetarian or vegan options.

Your guide will lead you on a small food tour of the city familiarizing you with the aromas and flavors of the organic fruits and vegetables, in addition to the flaky and buttery taste of fresh focaccia bread hinted with rosemary. The food leads the rhythm of Lucca’s life, and is shaped by the seasons. You will arrive at a historic palace hosting your private cooking class. Before you start the class, you will sip a glass of prosecco and enjoy a tour of the gorgeous courtyard. The villa was designed with clean lines typical of aristocratic homes of late-16th century Lucca. A noble family commissioned the villa for their son after his betrothal to a Frenchwoman. Descendants of the family continue residing in the apartments along the top floor. You enter the modern kitchen perfect for hosting a small cooking party.

You reawaken your sense of taste with an olive oil sampling, finding the lush textures and layered flavors of the different oils cultivated around Italy. The oil is ubiquitous in Tuscan cuisine, used in nearly every recipe defining the basic flavor of each dish. You will prepare a four-course meal consisting of a traditional Tuscan appetizer, two different pastas, and a desert focusing on seasonal ingredients. As you prepare the first pasta, your chef will offer a history of the various pastas, each with its own backstory, in the Tuscan region and the smaller municipality around Lucca.

You use flour and eggs to form a dough with a rich yellow color, implying the wealth of the city’s past due to a history of banking and the silk trade. The pasta is similar to a meat ravioli traditionally stuffed with beef and pork under a hearty helping of ragu. The aroma of the flour fades beneath the simmering meat and vegetables as you feed the dough into the pasta maker thinning the sheets until ready to stuff, fold, and cook.

What’s Included: accommodation, breakfast, cooking class with Extra Virgin Cooking Class

Day 5: San Gimignano – Explore the Historic Towers on the Hillside City

Today, you leave behind the Lombard region of Tuscany and make your way south to the Chianti region, known for the sweeping vineyards, tasty wine, and the dramatic towers of San Gimignano. Before you even reach the city, you can see the medieval edifices and strongholds standing atop the hillside like a picture in a storybook. Once in the city, you can stroll up the inclined walkway, through the city gates, and enter the historic streets.

In the center of the city, you can see the top of numerous square towers peeking through the top of the buildings and creating the unique skyline. The two Torri Salvucci Towers were erected in the 13th century and overlooking the Piazza del Duomo. Each tower in the city was erected to show a family’s wealth and prominence in the city, which is shown dramatically in the Torri Salvucci. Legend says the two towers were constructed to bypass a city ordinance defining a tower’s height, therefore when the height of towers is combined it would prove taller, and, therefore, prove the family’s wealth is greater than another rival family. The antique city is marvelously preserved and fills with the aroma of delicious gelato in the afternoon. The city walls have protected the town since the 13th century and continue to offer tremendous views to the exemplary Tuscan countryside.

Once you have properly acquainted yourself with the picturesque hill town of San Gimignano, you return to your charming accommodation for the evening, La Canonica di Cortine. Located in the heart of Tuscany, this upscale accommodation has a collection of luxury villas, with its premier selection, the Villa Castrum, possessing a history dating back to 1037 AD. Residing on the summit of a hill that is 310 meters above sea level, La Canonica di Cortine provides stunning views of the verdant Tuscan countryside and breathtaking sunsets. With 12 unique villas, each independent from the other, the beautifully restored luxury villas can accommodate up to 14 guests for private use and enjoyment.

You can also take the opportunity to embark on an unforgettable adventure by spending a day biking from San Gimignano to Siena with your local guides at Bike Florence&Tuscany. Stop along the way and discover three of the most beautiful medieval villages in Tuscany. Enjoy the breathtaking Tuscan scenery while you indulge yourself with a satisfying snack and taste the finest Tuscan wine grown and harvested in the region.

What’s Included: accommodation at La Canonica di Cortine, transfer, San Gimignano to Siena bike tour, breakfast

Day 6: Siena – Revel in the Charm of the Medieval City’s Cobblestone Streets

The picturesque Tuscan town of Siena stands on the hilltops 28 miles south of San Gimignano. The city was a seat of power and wealth in the 12th to 14th centuries competing with Florence for supremacy. The historic city center looks like a medieval city frozen in time. Colorful stone houses line the cobbled streets. The Gothic tower of Torre del Mangia, connected to Palazzo Pubblico, stands 318 feet and is visible from the rolling hills encircling the city, especially its marble crown atop the red brick turret. The scent of fresh pasta filters out of charming restaurants and cafes. Locals and visitors linger under the shady umbrellas decorating the entryways to cafes in the Piazza del Campo, the city’s main square.

The Cathedral of Santa Maria Assunta is a perfect example of Italian Gothic architecture. Dark stripes along the façade create a dramatic contrast with the shimmering white marble and pink hued tripartite entry arches. The cathedral was erected in the 13th century and is filled with the continuation of the black and white marbled motif. Your eyes are drawn to the mosaics on the floor. Fifty-six inlaid marble panels depict various Biblical scenes and popular mythologies, including a representation of Romulus and Remus found in the wild by a mother wolf. 

While you're heading south, you may want to visit one of the famous wineries located in close proximity to your luxury accommodation. The famed region of Chianti Classico is world-renowned for its red wines and extra-virgin olive oil, with wineries and estates offering guided tours and wine tastings. 

In the afternoon, you once again return to your private villa at La Canonica di Cortine. Indulge in the authentic flavors of a traditional Tuscan dinner, which uses the freshest local and regionally sourced ingredients. The meal is accompanied by a glass of Chianti Classico, the wine of choice in this world-famous region. If you are interested in furthering your culinary skills and cultivating the skills necessary to prepare a delicious Tuscan meal, La Canonica di Cortine provides cooking classes with one of their chefs, who will share their culinary secrets and techniques to prepare the quintessential dishes of Tuscan cuisine. Afterward, relax in the outdoor swimming pool or the lush gardens found just outside of your luxury villa. Exclusive massages and beauty treatments are also available upon request, allowing you to fully relax your body and mind in the heart of Tuscany. 

What’s Included: accommodation at La Canonica di Cortine, transfer, tour, breakfast

Day 7: Florence – Traverse the Beauty of Florence’s Public Squares and Museums

The morning light shines through the rose window of the Siena Cathedral, washing over the radiant marble panels you witnessed the previous day. After breakfast, you travel across the verdant Tuscan hills once more and return to the vibrant and enchanting city of Florence. Once in the city, the remainder of the day is yours to savor the beauty of the city and its treasured works.

The Galleria dell’Accademia was established in the 18th century and acts as a school for inspiring artists, along with a museum housing Renaissance paintings and sculptures. When you enter the museum, you find a pristine gallery. The sheer white walls around the main hall allow the art to burst from their canvases. A doorway to the left of the entrance leads you into a long hall. Crowning the hall is the original and breathtaking sculpture of Michelangelo’s David. The statue has stood in the gallery since 1873 and stands beneath a single dome framing the 17-foot tall marble masterpiece. What separates the statue from others you have seen is not just the size, but the remarkable detail connoting every muscle to create a divine structure of the body. Even David’s hair has heft and movement in its added curls. The cool air of the museum adds to the atmosphere surrounding the statue. The wonderment of the artwork created during the Renaissance never ceases.

On the way back to La Canonica di Cortine from Florence, consider making a stop at the world famous Pierotucci Leather Factory. As you arrive at this institution, the smell of ripened leather gently encompasses you as you explore some of the finest leather goods in the world, which are produced right on the premises into handcrafted jackets, handbags, belts, wallets, and accessories. Piero Tucci created the business in the early 1970's by gathering the finest group of leather artisans who were highly skilled in the timeless art of handcrafted leatherwork. Although Pierotucci has paved its own award-winning designs over the decades from its humble beginnings, the company has also gone on to design works for other famous international and Italian brands, such as Cole Haan, Hugo Boss, Valentino, as well as Toscanella, Pierotucci's own flagship label.

In 1985, the Tucci family expanded the workshop so that their master artisans could have the proper spacious environment they need to create their magic. The Pierotucci workspace can be accessed with a behind-the-scenes tour of their leather production, from prepping the raw letter to buffing its detailed finish. In May 1999, they grew even further to include an exclusive Art and Jewelry Corner, to showcase the legendary craftsmanship of Italian artists and jewelers. Partnering with the finest expert artisans and craftsmen from Rome, Florence, and Naples, they began to showcase selective displays of 18K gold jewelry, exquisitely detailed cameos, and glass and stone mosaics. Furthermore, Pierotucci especially prides itself on sourcing all of their materials locally in Italy, bearing a traditional brand of "Made in Italy" and the brand has become internationally acclaimed and synonymous with quality.

What’s Included: accommodation at La Canonica di Cortine, transfer, tour, breakfast

Day 8: Florence – Depart for Home

The chirping of the birds gradually crescendoes as life sleepily awakens in the dreamy countryside of Tuscany, a region that appreciates a slower pace of life. You glance outside of your luxury villa at La Canonica di Cortine, taking in the views of the verdurous vineyards and olive groves. However, for your final morning, you have one surprise left; you take to the skies in a hot air balloon to gain a newfound perspective of the iconic rolling hills of Tuscany. The panoramic angle is a Located a mere 10 minutes from La Canonica di Cortine, and the exhilarating experience is followed by a Champagne breakfast. 

After you have had the chance to fully take in the tranquil beauty of the landscape one last time, your private transfer will meet you at the hotel to escort you to Florence Airport Peretola. For now though, you can enjoy the morning and watch the countryside come to life around you.

What’s Included: airport transfer, breakfast



Your custom trip package will include accommodations, transportation within the country, guided tours and activities, unique experiences, trip planning, and 24X7 support during your trip. 

Please inquire for a custom trip quote based on your travel preferences and travel dates!