Tuscany Tour of Charming Villages, Ancient Towns & Unforgettable Landscapes

A 8 day trip to Italy 
4.75 out of 5 stars
16 reviews

There are few greater moments than sitting on a hillside at a quiet café with a view overlooking the red-tiled roofs of a historic city. You can hear the bells of the cathedral chime at dusk. The aromas of freshly cooked pasta and rich locally grown wine add to the unforgettable ambiance. Images of Renaissance statues and oil paintings decorate the fantasy. Your custom tailored Tuscany tour to Florence, Sienna, Arezzo and Florence turns dreams into realities, taking you through the treasured hills and medieval towns of, where every moment is luxurious, illuminating, and unforgettable.

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General Information

Detailed Itinerary

Places Visited 

Florence, Siena, Monte dei Chianti, Arezzo, Vinci, Fiesole, Pisa

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Cradle of Art

Florence is a city that embraces its past and showcases inspiring artwork in the open for locals and visitors to see. The Old Bridge, known as the Ponte Vecchio, is a testament to the city’s Roman roots. The spectacular dome of the Florence Cathedral highlights Renaissance ingenuity. The pristine details of Michelangelo’s David connote the possible splendor of dedication and imagination. The city is emblematic of the surrounding region of Tuscany. Florence is filled with modern culture but deeply connected to its heritage, from the medieval buildings to a commitment to certain undeniable regional flavors.

Your private transfer meets you at Florence International Airport and escorts you into the heart of the historic city, where the red brick dome of the Cathedral helps create the skyline. You can trace your fingers over the stones of each building, refurbished but still maintaining their deep connection to the past. In the afternoons, locals fill into the Florence Rowing Club for an aperitivo, a pre-dinner drink ritual similar to happy hour. Locals sit on the banks of the Arno River enjoying the jovial conversation and simmering aromas of the restaurant Aqua Otto. The river shimmers in the fading sunlight and majesty is already prevalent, and you have just arrived.

What’s Included: transfer, accommodation

Day 2: Past and Present Florence

In the morning, you prefer the foamy and semi-sweet tastes of a cappuccino to the Italian favorite of an espresso. The scent of freshly brewed coffee beans emanates from cafes and bakeries. Mercato Centrale in San Lorenzo opens its doors and locals arrive in search of cheeses, crostini, chutneys, and local olive oils. After breakfast, your guide meets you at the hotel ready to take you on a private tour of the city, which will highlight the breathtaking art of the past and the inspiring flavors of the present. You stroll through Piazza della Signoria, passing the Loggia where Renaissance sculptures decorate the square with immaculate design and production.

Next, skip the line and visit the Uffizi Gallery. The opulence of the building dates back to the 16th-century when Cosimo de Medici commissioned the building. Marble floors and pillars decorate the halls. Large, open windows allow natural light to enter the building. The attention to detail has turned the edifice into as much of a piece of art as the works the building holds. The entire museum encompasses 139,000 square feet of space.

Your guide takes you through each room in the Uffizi, calling your attention to selected works across the museum, including the Adoration of the Magi by Leonardo da Vinci.  The painting dates back to the 15th-century and depicts Mary and child in the foreground with the Magi kneeling in adoration in front of ruins, possibly referencing the Basilica of Maxentius.

The discoveries of the city continue outside of the museums. Your guide leads you to Central Market, not only to see the adjacent Medici chapels, but also to indulge in the particular flavors of Tuscany that speak to the people of Florence and the surrounding areas, including a taste of savory Prosciutto Crudo.  

What’s Included: breakfast, tour, dinner, accommodation

Day 3: Starting in the Hills

Tuscany ranges from mountaintops to hilltops, and even stretches along the coastline with sensational beaches. After breakfast, you step out of Florence for the day and make your way into the iconic Tuscan hills, quickly reaching the quiet town of Fiesole. The small and elegant village sits atop a hill surrounded by olive groves. The cool air rushes through the streets brushing against Renaissance villas and the sweeping plain below. When you walk through town, it feels like a storybook village outside of time. The tranquil streets lead to the Zona Archeologica, situated behind the cathedral.

The Roman Theater was erected in the 1st-century BC along the natural sloping hill in a semi-circular formation. The stone seats and archways continue to help the acoustics flourish when in summer the theater is still utilized with concerts and performances. Farther along the archeological area of the city, you will find the remains of an Etruscan temple from the 3rd-century BC, highlighting the two ancient cultures that once supported the region.

At the edge of town lies the Villa Medici, one of the oldest Renaissance residences, complete with a garden. The quaint streets open up to a view of the emerald trees below. Beyond the trees, you have a quiet panorama of Florence bordered by the Tuscan hills. The red-tiled rooftops are unmistakable, with the circular dome of the Duomo at the center.

What’s Included: breakfast, tour, accommodation

Day 4: Medieval Delights

In the morning, Santa Croce stands tall over the public square, which often houses seasonal markets. The white marble exterior glints in the rising sunlight. A stoic statue of Dante flanks the stairs leading to the tripartite doors. In the serene early hours of the day, devout locals and interested visitors enter the cathedral for different reasons. The aroma of myrrh fills the nave. Some come to pray, others wish to see the tombs of Michelangelo and Galileo.

After breakfast, your private transfer meets you in the hotel lobby and escorts you out of the Renaissance city, taking you to the enchanting medieval streets of Siena’s historic center. The city of Siena has preserved its past in its iconic buildings and showcases its heritage twice a year with the Palio horse races. The prize is pride and the competitors are the 17 districts in the region, which act more like neighborhoods. The cobblestone streets meander along the hillside creating a labyrinth of charm. The Piazza del Campo has a sloped crescent shape in front of the Palazzo Pubblico and stands beneath the 13th-century Torre del Mangia. The earth-colored walls of the city stand out against the outer hills of the countryside.

Black and white marble decorate the façade of the Siena Cathedral, including the columns of the interior. Fifty-six mosaics decorate the cathedral floor depicting images from the Old Testament and myths of the city. Beyond the obvious beauty of the interior is the Piccolomini Library to the left of the cathedral’s midway point. Exquisite frescoes decorate the walls painted by Pinturicchio and Sanzio. The colors emanate joy, and the perspective showcases a master at work. The walls depict ten scenes representing the life of Pope Pius II. The ceiling is decorated with the family stem as the centerpiece of a larger, crescent moon motif.

What’s Included: breakfast, transfer, tour, accommodation

Day 5: Timeless Works  

In the morning, small bakeries set out decadent cakes and brioches in the display cases. Boutique stores open their windows to showcase their seasonal collection. The bells of the cathedral chime bringing the start of the day to many local residents. After breakfast, your guide meets you at your hotel and escorts you outside of the city to the charming village of Vinci. The name sounds familiar because it was the birthplace of the famous inventor, architect, and artist, Leonardo da Vinci. You can see the village peeking out of the treetops on a lush hillside overlooking the valley. The castle and church bell towers climb above the encircling buildings.

The city is an iconic picture of Tuscany.  The city’s exterior has not changed since the 15th-century. The narrow, cobbled streets meandering around the Palazzina Uzielli quickly enchant you. The palace now maintains the Leonardo Museum, which houses a collection of models, machines, drawings, and notes from Leonardo’s collection. Wooden replicas of his works decorate the interior galleries and are situated underneath lofted ceilings. An elegant arcade encircles the interior courtyard adding the grace of the castle and touching on the historic architecture around the village. You can even see the inventor’s designs and a replica of a historic bicycle. The aroma of rich cheese emanates from a nearby cheese shop close to Piazza Giusti. The village represents Tuscany at large, filled with charming villages hidden by the hillsides, holding treasure-troves of history.

What’s Included: breakfast, tour, accommodation

Day 6: Ancient and Contemporary

In the morning, you leave behind the high towers, and marble facades decorating Siena and make your way across Tuscany to the town of Arezzo. History unfolds quickly in Arezzo, from its roots as an important Etruscan trading post dating back to the 9th-century BC, to medieval churches, and even its placement at the center of a battle during the Second World War. When you arrive, you find the traditional red-tiled roofs atop cream-colored buildings in the foreground of lush mountains. The city stands at an elevation of more than 970 feet above sea level with a central square sloping down the hillside. Shops line the main street of Corso Italia. The atmosphere takes you back in time, filled with ruins, monuments, parks, and piazzas.

The central square looks familiar as it was seen as a main location in the 1998 Oscar winning film “Life is Beautiful.” The Romanesque church of Santa Maria della Pieve strikes a commanding pose. The 12th-century bell tower has vertical elements, from doors to windows, that make it seem more imposing. The exterior wall of the city leads to greenery dominated by a large statue honoring the famous poet Petrarch. The park has a view to the valley and sweeping vineyards below, including the succulent aroma of olive groves rising from the orchards.

What’s Included: breakfast, transfer, tour, accommodation

Day 7: Perfect Countryside Pictures

In the morning, you can look out over Arezzo and the valley beyond. The subtle layers of dew reflect the rising sunlight. The creamy stone around the city stands out from the lush surroundings. The city has a relaxed ambiance throughout the day, never wavering from its steady pace. After breakfast, your private transfer and guide meet you at the hotel. You leave behind the background of mountains and medieval churches venturing into the picturesque scenery of the Chianti Hills. Olive groves and chestnut trees make an organic skyline along the hills. Vineyards stretch along the foothills absorbing the unique properties of the soil.

Stop in Castellina, in Chianti, to see the massive castle known as Rocca. The castle was erected in the 14th-century and now houses an Etruscan archeological museum with four showcases holding artifacts dating back to the 7th-century BC. The powerful structure holds an imposing sway over the town, joined by the silos of Chianti Classico situated along the landscape encircling the area. An impressive tunnel winds underneath the city and was once used by local guards. Today, shops and restaurants line the tunnel adding rich character to the city leading to the main street of Via Ferruccio. The same family has owned the Enoteca Antiquaria for more than 100 years, archiving the history of wine in the region, and where you can gather a few samples of the Chianti’s traditions.   

What’s Included: breakfast, transfer, tour, accommodation

Day 8: Enlightened Departure

Florence has a certain undeniable quality to its streets. Once there, you can feel a particular draw to history and art based in the Duomo and the statues decorating the Loggia in Piazza della Signoria. Whether you stay in the city for one day or one week, you always leave knowing there was more to see and more to experience.

At breakfast, you sip your espresso and nibble on your fresh brioche thinking back on your time in Tuscany. Every day was a joy, enlightening and breathtaking in both natural landscape and artistic majesty. Your private transfer will soon meet you at your hotel ready to lead you to Florence International Airport. You can’t help but feel there is so much more to do and see in Tuscany and Italy. You can always extend your trip and continue to immerse yourself in the wonders around the cities and countryside. For trip extension ideas, browse the travel reviews for Italy on Zicasso.

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.