Discover Tuscany Tour 2019-2020

A 8 day trip to Italy 
4.96 out of 5 stars
390 reviews

Tuscany overflows with extraordinary vistas, flavors, and artwork that you will discover, explore, and experience on this 8-day vacation, redesigned for 2019-2020, in the most famous region of Italy. From renowned Renaissance artists to charming seaside towns and medieval villages, you will be guided through the vineyards and the museums filled with masterworks. You will stroll through ancient streets and delight on local cuisine. From fabulous wines to marvelous accommodation, you will find the picturesque landscapes in the charm of Tuscany are endlessly present. 

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General Information

Detailed Itinerary

Places Visited 

Florence, Siena, Chianti, Castellina in Chianti, Greve in Chianti, Val d'Orcia, Pienza, Montalcino, Montepulciano, San Gimignano, Pisa, Pietrasanta, Le Cinque Terre, Riomaggiore, Manarola, Vernazza

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Florence - Super Beginnings

Florence is a city steeped in marvelous history, from the local legends to the Renaissance, and reaching into the modern allure of its beautiful streets and enthusiastic museums. Arrive at the airport and be met by a private transfer who will take you into the historic city center near the unfathomable luster of the Ponte Vecchio and Duomo. It is hard to consider the city anything less than captivating; its streets continue to look as though they have come straight from the 15th century. At the top of Piazzale Michelangelo you will be able to view Florence’s panorama. The famous Duomo, a cathedral with the largest brick dome in history, towers with imposing wonder at the heart of the city. The elegant spires of Santa Croce’s marbled façade stand close by in the skyline’s scale as the vista pushes its way towards the mountains.

Follow your guide on an introductory tour of the streets, through the mesmerizing aroma of fresh baked pizza surrounding Piazza Signoria. A creamy gelato will soon drift by as well, ranging in flavors from fragola, strawberry, to stracciatella, chocolate chip.  The buildings block the skyline but offer more historical grandeur. Small plaques adorn certain stretches of buildings that connote their inclusion within Dante Alighieri’s Divine Comedy, letting passersby know the book, chapter, and passage in which you can find the reference.

Standing before the Duomo, Santa Maria del Fiore, you will feel dwarfed by the immensity of the structure, not only in height but in total magnitude, every inch decorated of the façade is covered in detail, from color to saintly statues. It took almost 80 years to complete, not including the almost 40 extra years it took to finish the dome. In the cavernous interior there is a subdued glow that shines along the colorful images that encircle the cupola. Vasari and Zuccari painted the fresco over a seven-year span; the depiction of Last Judgment ranges from the unfavorable depths to the heavenly sky.

In the afternoon you will find yourself within the open halls of the Galleria dell’Accademia, known for centuries of teaching artists and also housing one of the most famous sculptures of all time, Michelangelo’s David. View the lofted ceilings and immaculate hallways graced with vibrant paintings, stunning musical instruments, and inspiring sculptures, none more notable than the David.  Through a long stretch of hallway you can see the figure standing in its own domed gallery, lit by a natural glow from the relief of stained glass above. As you venture closer to the iconic image you notice its scale, standing over 14 feet tall, with a stoic gaze and storied sling hung over his shoulder. The detail is in the mythology; the inspiration for the piece stemmed from the original biblical telling and resulted in the representation standing before you.

What’s Included: transfer, walking tour, dinner, accommodation

Day 2: Florence - Flavors of All Varieties

The diverse flavors of Florence come from its varied artistry, from literature to paintings, sculptures to food. Today you will discover the depths of the city’s fabulous flavors, tasting its variety with all your senses. The morning begins with your arrival at the Uffizi Gallery. From the façade you know that this building has not always been a museum. Located adjacent to the Old Palace and Piazza Signoria, the cobblestone walkway is surrounded by a pillared portico with sunken stairs leading up to the Via Lungarno Archibusieri. The palace was originally constructed for the Medici’s in the 16th century and was filled with artistry patronized by the legendary family as well. The opulent halls are brimming with masterwork from Botticelli to da Vinci, even the windows have a gilded edge as they look out over the square. The Hall of Tiziano, a newer location labeled Hall 83, displays the unique beauty of Venus of Urbino, a piece coveted for its sensuality and sophistication, painted by Titian in 1538.     

In the early afternoon you will be guided through the Florence Farmer’s Market located inside Mercato Centrale, where local cheese shops can also be found. The multi-tiered market has been the center of Florentine shopping for centuries, offering colorful fresh produce, meats, and more. Soon you will be outside of Florence in the charming Tuscan hills within the Chianti countryside. Taste the Prosecco wine, a bubbly sweetness filled with crisp citrus, before following your guide turned chef to create and taste typical Tuscan cuisine, including a starter of crostini di funghi, a canapé of crunchy bread with rich mushrooms.

What’s Included: breakfast, tour, cooking class, accommodation

Day 3: Florence - Into the Gardens

The excitement of the day takes you from bed to explore the persistent wonder of Florence however you desire. Whether sitting in a café full of character while overlooking the Arno River or sitting on the hills of the village of Fiesole that overlooks Florence’s vastness, you can find the natural and the inspired splendor. Across the Arno River is the Pitti Palace where the Boboli Gardens stretch along a large expanse of the land. The palace became the primary residence for the Medici in the mid 16th century and now houses a collection of silver objects once commissioned by the ducal family.

Once in the gardens you will be engulfed by the remarkable, manicured area that dates back centuries. Buontalenti’s Grotto was constructed in 1583 and presents its sensational façade like a fairytale image. Dual statues flank the two central pillars that sit beneath an arch covered with artistic dangling leaves. The exterior luster brings the opulent image of stalactites and stalagmites to the forefront while the interior chambers hold statues that look to celebrate nature and the metamorphosis of its power. In the evening you can enjoy a delectable taste of Tuscany at the Quattro Leoni near Palazzo Pitti, letting their creamy pear and cheese tortellini give you a proper taste of unparalleled flavor.

What’s Included: breakfast, accommodation

Day 4: Siena - Sweets and Cathedrals

The day takes you through the sweeping hills of Tuscany, beginning with the famous medieval city of Siena. Siena is known for its renowned horse races in July and August, along with its cameo in the James Bond film Quantum of Solace. The Duomo is a masterpiece inside and out, showcasing pristine white and black marble on the façade. When you enter the building there is an immediate soft echoing of footsteps accompanied by the herbaceous scent of myrrh. As you step through the opulently constructed cathedral you will notice the elegant designs on the pavement, 59 etched marbled panels in all depicting sibyls and biblical scenes. There is no end to the mosaics and frescoes, gilded cornices and polished pillars within the basilica. 

Enjoy a lunch in the hillsides of Chianti, known for its lavish landscape and wine that is graced with a hint of spice. In the medieval town of San Gimignano you will come to the rising hills known for their remaining towers that overlook the valley. Once the towers were built by the wealthy families of the city, the taller the tower the wealthier the family, but after centuries only 14 remain. The sensual air of the town is due to its quaint size, mixed with the local Verna Sangiovese, wine that blossoms from the rugged terrain. Stay for the sunset or for a small delicate taste of  limoncello as the day passes by. 

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

Day 5: Siena - The Noble Hills

The hills of Tuscany are known to be flush with green and endlessly rolling; however, you will also come across vibrant sunflowers and elegant poppies as you travel through the countryside en route to Val d’Orcia. Situated along the gently winding roads you will find the Strada del Vino, the Street of Wine, leading to the town of Montepulciano. The stone coloration of the city contrasts with the lush hillside, almost absorbed by the trees and overlooking the stunning valley. The areas of Montepulciano and Montalcino, both located on the Street of Wine and separated by less than an hour’s drive, are similar in their city walls and medieval structure; however, it is in their culture and vastly different wines that the cities are distinct.

A tasting of the Vino Nobile di Montepulciano will give you your first inkling. The noble red is considered a rustic cousin of Chianti with a robust flavor and scent of oaky, dark fruits. The Brunello di Montalcino has ripe fruit and wild cherry flavors with an elegant body. From one sip to the next you will find beauty, not just in the flavors but also in the moment. You will revel in the sensational landscape beyond the vineyards where you can look out over the countryside and watch the vines rise and fall.

What’s Included: breakfast, lunch, tour, wine tasting, accommodation

Day 6: Pietrasanta - The Quiet Hills

The pleasant greenery of the rolling hills never appears to diminish, morning, noon, or night. After breakfast you will leave behind Siena, waving goodbye to the medieval city walls, and come to the Field of Miracles in Pisa. The city is known for its iconic tower that has leaned for centuries, causing a mixture of curiosity and delight in everyone who visits. Once you arrive at the Campo dei Miracoli, you notice the many structures beyond the tower, filling the square with opulent architecture and devoted spirituality. The Baptistery was completed in 1363 after constant construction and alterations beginning in the 12th century. The rotunda stands over 155 feet tall, with over a .5 degree tilt due to the soft ground and the structure’s weight. When you enter the pristine marble building you can hear the perfect acoustics, as if every step you take or noise you make is a choired concert that echoes through the dome. Look up and see the archways and pillars condense into the cylindrical shape that adds to the musical reverberations.

With the stunning basilica standing beside the Baptistery there is no mistaking the ornate design that also decorates the circular tiers of the Leaning Tower of Pisa. The 294 steps that ascend to the top of the tower bring people over 183 feet above the ground at an almost four-degree angle. Whether you want to hold the tower in the palm of your hand or sit back and study the architectural marvel that has defied the odds, you will eventually come to the charming town of Pietrasanta, a medieval city of artists and marble. 

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

Day 7: Cinque Terre - Along the Coastline

Just beyond the western boarders of Tuscany is the marvelous coastline of the Italian Riviera. The charm of Cinque Terre, five villages that were once only connected by a single trail or by boat, continue to captivate people. Arrive in the first town of Riomaggiore which looks to be carved brightly into the mountainside. The marina sways in the gentle wake of the village as the intoxicating aromas of herbaceous pesto and fresh seafood linger in the air. From close up the water is transparent, giving a glassy ripple to the rocky floor. Follow the pathway which will take you between villages to the tiny town of Manarola, rising along the cliff that overlooks the marina below. Taste the pleasant variety of wines produced in the region such as the Sciacchetrá, a sweet, white wine with scents of candied orange and dried apricots.

The view overlooking the marina is simple and elegant, with rippling sapphire water that you will soon find yourself traveling through en route to the Vernazza, just around the rocky bend. The village is the perfect imagined picture of the five towns, complete with a rising tower that overlooks the entire area, situated on the outcrop and defending itself from an onslaught of pirates in the 15th century. In the evening you will return to Pietrasanta for your delectable dinner within the quintessential Tuscan Hills; however, for now you can venture up to the lookout point along the trail and gaze at the magnificent colors of Vernazza pressed against the shining sea.

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

Day 8: Depart Home - Super Goodbyes

There is a timelessness to the mornings and evenings along the Tuscan Hills, a place where you can imagine the past residents of the countryside waking up to the same view overlooking the trundling grass that reaches the horizon. The aromas of breakfast have made themselves known, filled with freshly brewed cappuccino and the promise of flaky pastries. After your meal you will have a private transfer to the airport where you will embark on your journey home, saying goodbye to Italy. From the hills to the town, the museums to the cuisine, you have found the superb in the everyday reaches of Tuscany.

What’s Included: breakfast, transfer

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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.