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.

The sunlight spreads across the Val d’Orcia and brings the sea of emerald to glistening life. The main boulevard of Montepulciano highlights the beautiful stone lion that adorns a column, which was built to show the town’s allegiance to Florence. The original construction stands in the Museo Civico. After breakfast, traverse the Val d’Orcia, the picturesque valley below Montepulciano, to visit the town of Pienza. In the mid 15th-century, Pope Pius II transformed his sleepy home village into a thriving Renaissance town, complete with papal palace and magnificent town hall. Piazza Pio II contains a symmetrical design surrounded by the rosy travertine stone structures.

The Palazzo Piccolomini stands to the right of the Cathedral, and it was known for its hanging gardens that offer stunning views of the surrounding valley. The narrow streets of the town make you feel as though you have stepped into a painting to observe the work of a creative master as opposed to a true Tuscan town. The savory aroma of Pecorino cheese emanates from the outdoor markets, whose vendors favor the cheese crafted near the city. The cheese monger eagerly slices a piece of the Pecorino of Pienza for you to sample. The delicate, tang comes from the sheep’s milk and the certain way that the cheese-makers age each cheese.

Leave Pienza for the town of Arezzo, which was once a Roman military settlement erected atop an Etruscan trading post. The town sits on a hilltop at the crossroads of the four encircling valleys. The Italian poet Petrarch worked along the cobbled streets of Arezzo, which is nearly 50 miles south of Florence. The main square was featured in Roberto Benigni’s academy award-winning film Life is Beautiful. The unique slope of the piazza leads to the graceful colonnade of the Palazzo delle Logge and the 14th-century façade of Palazzo della Fraternita dei Laici.

The pristine medieval town of San Gimignano soars above the hills of Tuscany with preserved grandeur as if time forgot the walls and towers of the town altogether. After breakfast, your private transfer will meet you at your villa and escort you to the base of San Gimignano, which stood along the Via Francigena, the main route the pilgrims used when traveling to Rome. The town also stood along the traditional saffron trade route, which allowed the noble families of San Gimignano to grow even wealthier.

The first thing visitors notice they arrive at the central towers, symbols of the rivaling families that built them. The scent of antique stone rises from the cobbled streets, historical walls, and preserved medieval structures. Many stores continue to work in leather-goods, which adds the aroma of polished and woven leather to the air. The main triangular square contains a cluster of the remaining towers, which once added up to 72 in total. After exploring the city walls and culture of the “Town of Fine Towers,” visit a local Tuscan farm for a private introduction into the spirit of the cuisine.

Sheep and cows graze on the verdant plain as a church bell tower rises in the distance to imitate the trees. Your guide will welcome you into the rustic kitchen with a view of the entire farm out the window. The scent of fresh herbs drifts from the garden alongside the farmhouse as your instructor leads you through the garden to pick fresh herbs, tomatoes, and the majority of the vegetables you will use while you make the special dishes passed down through generations on the farm. Follow your instructor in making pici, traditional regional pasta similar to spaghetti but thicker and richer.

In the morning, locals linger around the Piazza del Campo in the center of Siena. The sunlight turns the city rose colored from the stone, surrounded by the waves of the rolling Tuscan hills. The scent of freshly-brewed espresso drifts along the cobblestone streets and emanates from the cafes. After breakfast, leave Siena for the overlooked gems of Pisa, the once maritime powerhouse. The university has brought some of the greatest minds of Italy to the city since its opening in the 14th-century, which contributes to the youthful ambiance in the streets and bohemian atmosphere of the cafes.

Your guide will lead you to Piazza dei Miracoli to view the famous Leaning Tower and the gorgeous Gothic cathedral before you arrive at the Campo Santo, the Sacred Field. The legend of the field states that Archbishop Ubaldo dei Lanfranchi returned from the Fourth Crusade with mounds of earth from the Holy Land. The rectangular cloister contains Gothic arches that lead into the courtyard as 14th and 15th-century frescoes decorate the walls.

To experience the pleasures of Pisa beyond the surface beauty is thrilling and makes you feel as though you have uncovered a secret that others may never know. In La Spezia, board a local train to pass through a tunnel carved into the Apennines, and arrive along the Ligurian coastline at Cinque Terre. Disembark in the center town of Corniglia as a collection of 300 steps leads you to the best view along the coast. The town itself stands high above the tranquil Mediterranean Sea by nearly 600 feet and from the plateau, you can see the pastel homes of each of the five villages nestled into the cliffs.

In the morning, the fishing boats will return from an early cast-off as their nets are filled with seafood ready for the market. The daily farmers market contains bright produce and displays a wide array of fresh fish, from anchovies to clams. Take the train to Vernazza, the second northernmost town connected by the famous mountain trails. The pastel homes look carved into the cleft between the cliffs, edged by the natural harbor as the main street splits the heart of town with every side street leading to a small piazza.

Board a small boat in the harbor, and set out onto the Mediterranean Sea for a private cruise. The turquoise water glistens in the sunlight as the refreshing breeze carries the scent of the slightly briny sea. Water crashes against the rocky promontory beneath the town as your captain takes you along the coastline to show you the rugged elegance of the natural landscape. A round tower and stone walls stand on the outcrop above Vernazza with a view of the water. The walls act as a reminder of the 12th-century conflict between Genoa and Pisa, which catapulted Genoa into the regional maritime power.

The tower was erected in the 16th-century to protect Vernazza from the roaming pirates. In the serene scenery of the Mediterranean, cast out your line and relax in the sunlight. Mackerel, eel, sturgeon, and swordfish offer a complete array of fish to bait for while you relish in the pristine view. Return to shore and your captain will lead you to a restaurant willing to cook the fish you caught in the regional flavors of Liguria, taking advantage of the olive oil produced in the mills and cultivated from the olive groves located in the hills above the town.

The day is yours to indulge in the pleasures of Cinque Terre at your leisure as you stroll along the footpaths that connect each town and relax on the smooth pebbled beach of Monterosso.  The train from La Spezia takes you on a short ride to Riomaggiore as the housing that seems carved into the cliffs merge over the narrow beach. Poets and artists have sought inspiration on through the vistas and along the cobbled streets of Riomaggiore since the 19th-century.

The marble pulpit of the 14th-century church of San Giovanni embodies the beauty of Cinque Terre as the soft-spoken beauty rises from the rocks in the secluded landscape. Take the Lover’s Trail that connects Riomaggiore to Manarola as the rock-face opens above the water to provide an easy and accessible walkway. The breeze brushes over the cliff-side, and you can hear the water splash against the rocks below. Once you arrive in Manarola, find the aroma of farinata wafting from the local bakeries and pizzerias as olive groves and vineyards spread across the hills that lead back to mainland Italy.

Today you will leave behind the gem-like coastline of Liguria and return to the emerald trees and hills of Tuscany. Your private transfer will lead you along the scenic road to Carrara, famous for its marble quarries. Sculptors like Michelangelo visited the quarries to choose personally their perfect slabs from which to carve their masterpieces. The Cathedral of Sant’Andrea was erected between the 11th and 14th-centuries, which accounts for the variety of architectural styles, including the Romanesque and Gothic features of the façade. The stone contains an almost translucent hue, which adds an extra sheen to the surface of structures and sculptures.

The marble quarry makes the mountain look capped with snow, which encompasses nearly 5,000 acres. Outside of the old city walls, find the Accademia Carrara, a sculpture’s school founded in the 18th century. The school contains works by Italian masters, including Botticelli and Titian. The scent of marbled dust fills the workrooms. In the Arco Arte Marble Sculpture School, meet a private instructor ready to teach you the tools of the trade. The goal of the course is to learn how to mold a block of shimmering marble into a piece of breathtaking art. Before you travel to Florence, visit the historical city of Lucca to explore the fortified walls.

Cafes set out their umbrellas and chairs along the cobblestone streets of the Renaissance city of Florence as the scent of frothy cappuccinos, and strong espresso fills the city. Beneath the massive dome of the Cathedral stands the hidden Museo dell’Opera del Duomo, the museum dedicated to the Cathedral. Priceless works of art have been created for the Duomo over the centuries, from gold and silverwork to embroidery. The museum was opened in the late 19th-century to protect the works more vulnerable to the elements, including the great bronze panels of Ghiberti’s Baptistery doors, known as the Gates of Paradise.

Florence embodies the pleasures of Tuscany and brims with a Renaissance atmosphere that lays over the city’s original Roman grid. After breakfast, your private transfer will meet you in the lobby of your opulent hotel to escort you to the Florence airport for your flight home. You could extend your time in Italy with more days in Florence, followed by time spent near the stunning canals of Venice or with the ancient history of Pompeii.