Wine Connoisseur's Dream Tour of Tuscany

In the morning, the aroma of fresh baked, chocolate stuffed, sugar-dusted brioche emanates through the doors of the city’s hidden bakeries. Gorgeous cakes and pastries fill the display cases of the cafes as they open their doors for the day. The sunlight washes over the mixture of marble and bronze figures adorning Neptune’s Fountain, a celebratory gift for the marriage of Francesco de’ Medici in the mid-16th century. After breakfast, your private transfer meets you in the lobby of the remodeled palazzo and escorts you into the famous hills of Tuscany to explore the Chianti wine region.

Cypress trees line the roadways while oak and walnut trees shade the verdant knolls. Vines growing Sangiovese grapes roll over the landscape leading to olive orchards; the groves and vineyards around the region date back 600 years and grow on private estates or in historical monasteries. You stop at your first of several wineries for the day to embark on a private tour of the grounds. An 11th-century monastery continues to watch over the estate, and roses grow bright yellow and rich ruby against the lush grass in the botanic gardens.

You follow your guide through the vineyard and touch the waxy peel of the plump grapes, and notice the dry soil which allows the flavor of the grape to fortify in its struggle. The estate has produced wine across its nearly 125 acres since the mid-19th century and continues to follow the profiles of tradition, allowing the wine to age in small oak barrels. You swirl your sample of the Chianti Classico, finding hints of dark tea leaves and lavender drifting from the glass.

At breakfast, you sip a cup of fresh espresso and recall the engaging tour you had in the preserved medieval streets of Siena. The images of mosaic tiles on the floor of the cathedral flash through your mind, retaining artistic interpretations of biblical history and the legends on which the city was founded. After breakfast, you continue your exploration of the Tuscan countryside around the town of Montalcino, a county known for wines of elegance and prestige.

You will discover the quaint town of Montalcino, dotted with endurable wine bars opening to the medieval cobbled lanes. Locals continue in their traditions of loyalty and precision, a reputation the city gained after holding out against Florence even after Siena had fallen. The orange-tiled rooftops slope above the emerald forest framing the hilltop town. The 14th-century fortress continues to look over the remnants of the ancient road of Via Francigena that once traveled between Rome and France.

You meet the vintner who takes pride in the winery located along a hillside at 820 feet above sea level and spread across 7,000 acres. Oak and cypress trees shade the lanes away from the sea of vines. The floral breeze adds to the herbaceous qualities of the grapes. The scent of fermenting peels emanates from the stainless steel tanks in the cellar. You touch the smooth exterior of the new oak barrels where the wine ages for several years in order to reach its maximum potential of depth and character. Your guide pours you a taste of the Brunello di Montalcino, known as one of the noble vines of Tuscany, and you notice the earthy aromatics that carry hints of tobacco and peanut butter, accentuated by the slight tartness of blackberry. The rich, ruby hue gives way to a velvety texture with mature notes of cooking spices and roasted coffee.

The morning carries the musky scent of nearby olive groves fading beneath the decadent fragrance of freshly brewed espresso. The sunlight washes over the greenery of the hillsides, which roll like waves across the horizon. After your morning meal, a private transfer greets you in the hotel lobby and escorts you across Tuscany to the hidden charms of Maremma. Medieval villages rise out of the marshland; Etruscan tombs disguise themselves as knolls in the distance; and woodlands open to isolated coves, untamed beaches where wild pigs and storks roam. Yachts speckle the harbor at Porto Argentario, and cowboys continue to travel through the meadows on the back of gorgeous colts.

You arrive at the medieval village of Montemerano, which embodies the traditional charm of Tuscany, including its cuisine and folklore. The homes shimmer with white and gold in the sunlight around the 12th-century heart of town. You discover the ancient walls that continue to protect the town center as you step through the three doors of the main gateway. The 12th-century parish church of the Pieve of San Lorenzo is the oldest building in town. Vines climb over the homes along the hidden alleyways guiding your eye to the flower pots adorning the upper windowsills. You continue to the town of Pitigliano, often referred to as “Little Jerusalem,” where a Jewish community has thrived since the 17th century when many communities around Italy fled Roman persecution. The stone homes gleam with golden hues atop a plateau overlooking three rivers.

Uncovering the gem of undiscovered Tuscany is like finding a diamond amongst precious stones, allowing you to experience the beauty of wholesome culture, landscape, and life in one of Italy’s most popular regions. You return to the countryside outside of your lavish villa to explore the stunning Super Tuscans, wines celebrating the tradition of flavors in the region while offering boutique selections. You begin your tour at a fabulous winery embracing the forests, vineyards, and olive groves for which Tuscany is known.

The rich soil plays a big role in the flavors the grape absorbs, from the pine notes of the surrounding trees to hints of the sea breeze.  The winery opened in the 1990s and has since risen to fame with its magnificent balance spread across the nearly 750 acres that reach the edges of the Tyrrhenian Sea. The hills glow a slight red from the mineral-rich soil and help accentuate the flavors in the segmented grapes of Merlot, Cabernet Sauvignon, Sangiovese, and Cabernet Franc. The main building subverts the traditional villas of the region with a modernist style reaching 500 feet into the landscape to create an artistic and state-of-the-art cellar.

You sample a Tuscan red blending Merlot, Syrah, and Petit Verdot, finding elements of the sunbaked earth and red berries. The complex structure leaves spiced notes and the sweetness of strawberries on your palate. After your first boutique winery, you make your way to lunch at a traditional restaurant that takes pride in each ingredient used, down to the olive oil. The owner is an expert in wine and oil, and offers to teach you the delicate differences between the varieties of olive oil.

The wild meadows of Maremma give way to the iconic rolling hills and vineyards of the historic Chianti region, and the rich scent of the grasses fades beneath the familiar aroma of oak and olive groves. Your private transfer escorts you back to the vibrant city of Florence, stopping en route in the town of San Gimignano. Fourteen of the original 72 medieval towers continue to create the fascinating skyline. The town grew to prominence in the 12th century due to its proximity to the Via Francigena. You enter the pedestrian lanes through the preserved main gate. The sense of history is palpable along the protective walls and textured stone facades.

The undulating streets lead to sporadic views over the rolling hills and vineyards of Tuscany. The triangular Piazza della Cisterna sits at the heart of town amidst the cluster of towers, including the stump of Casa Razzi. Echoes of conversations bounce off the surrounding stone and brick, and two Salvucci towers rise beside Piazza del Duomo. Legend states that the towers were erected simultaneously for the family in order to circumvent a mid-13th-century statute which limited the height of family towers. The galleries in Santa Maria Assunta contain hints of frankincense. The Romanesque features date back to the 12th century, and the vaulted ceilings frame the magnificent fresco cycles.

The scent of cappuccino drifts out of the corner bar and central cafes of Florence in the morning. The bakeries place elegant displays of cakes, pastries, and marzipan in their windows, and the sunlight washes over the colorful shops along the historic Ponte Vecchio covered bridge. After breakfast, you venture into the countryside outside of the city to find the hills of Ponte a Cappiano. Vineyards and olive groves spread across the hillsides of the historic hamlet near the antique bridge arching over the Arno River.

The gentle breeze rustles through the leaves and olives of the orchard as you arrive on the family-owned estate. The grounds overlook the 16th-century bridge and fertile riverbanks from the summit of Cappiano Hill. Your guide leads you through the nursery to learn about the importance of seeds, bushes, and forestry to the cultivation of the orchard.  In the nursery, young acorns blossom alongside the fully matured nuts which are harvested for the pig farms in the area.

Wander beneath the canopy of the orchard and over the nets meant to catch dropping olives before touring the mill. The olives are harvested after ripening and pressed using a cold method within 36 hours of being picked. In the tasting room, your guide offers you a sample of regular olive oil, virgin olive oil, and extra virgin olive oil and you discover the distinct differences. When you reach extra virgin olive oil, you notice floral notes similar to lilac and a light, creamy texture coating your palate.

The memory of your home-cooked meal from the previous afternoon remains rich and fresh in your mind. You can recall the scent of ribollita, a hardy soup of cannellini beans and tomatoes. The citrus and spice of panzanella bring back details of bright tomatoes, red onion, fresh basil, and crusty bread. At breakfast, you nibble on a sweet brioche stuffed with cream and balance the saccharine flavor with the blend of richness and bitterness of your coffee. The jewelers on The Ponte Vecchio open their doors to passersby, the stalls in San Lorenzo display lavish leather jackets, shoes, and purses, and the regal statue of Dante Alighieri stares down from his perch in front of the Basilica of Santa Croce. When you are ready, your private transfer greets you at the hotel before escorting you to Florence-Peretola Airport for your flight home.