Finest Wines of Tuscany & Central Italy Tour

A 10 day trip to Italy 
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On this 10-day tour of Tuscany and Central Italy, immerse yourself in the encompassing culture of Italy and enjoy the sumptuous luxuries that the country has to offer. Taste wine from boutique wineries that have mastered the craft over centuries. The authentic Tuscan culture, the appetizing food, and the delectable wine are all within arms reach in this luxury Tuscany vacation. 

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General Information

Detailed Itinerary

Places Visited 

Italy, Tuscany, Rome, Umbria, Pisa, Lucca, Bolgheri, Siena, San Gimignano, Montalcino, Monepulciano, Assisi, Spello, Orvieto

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: The Cradle of the West

Arrive in Rome and be transferred to your fabulous hotel. Settle into the lifestyle with a strong caffe, letting the smooth, earthy coffee revitalize you. Take advantage of your time in Rome. From the Etruscans to the people, the Vatican to Mussolini, Fellini to Berlusconi, you will be able to feel the pulse of the city’s history and beauty from the moment the plane touches down.

Ease into the Italian lifestyle, the pace of life and the food, and the opulent history displayed on almost every corner. If you choose to walk around the city, the smells of fresh pasta and zesty oranges are hard to miss. The city is boisterous with the conversations of the locals as they spend their afternoons in the sun with a glass of white wine and a plate of pasta.

Wander down the Spanish Steps, where the locals spend their nights playing guitar and drinking wine. Located between Piazza Trinità dei Monti at the top and Piazza di Spagna at the bottom, the Spanish Steps are a nice space to sit, relax, and watch the lovers stroll by. If you are in a mood to stroll, the neighborhood at the base of the Spanish Steps has often been referred to as the “Beverly Hills of Rome, ” boasting luxurious shops and restaurants; look through the lavish window displays of the stores before going inside.

What’s Included: transfer, accommodation

Day 2: Open Up to Rome

Enjoy a luxurious breakfast at the hotel before journeying through a tour of ancient Rome. Today you will walk through the antiquity of the Western World, beginning with the Colosseum, a relic of Rome’s past, and ending with the romantic glow of the Trevi Fountain. The grand edifice of the Colosseum stands proudly in the open grounds, as electrifying now as it was to the crowds that once filled the arena. Outside of the walls, you can smell the ice cream from the surrounding vendors, but once inside the structure, the aromas shift into the scent of gravel and sand from the ancient floors. You can almost see the remnants of the battles that took place during the Empire’s peak.

Across the square are the Forums, the centers of the Roman Republic and Empire. Built over one and a half centuries, the large space impresses the most unimpressed, the same ground which once held Caesar and Marcus Aurelius. The foundations of the structures have survived centuries of decomposition, both from the elements and from man. Continue the tour to Capital Hill; the avenue was elaborated upon by Mussolini to connect Rome’s proud history with its bright future. The grand open space in the piazza allows you to stand in Michelangelo’s beauty, as he designed the square and the facades of the palaces that surround it.

With the sights and smells of Rome around every corner, satisfy your hunger with a delicious Roman lunch; indulge in the artichoke, crunchy fried or semi-sweet, and sautéed with mint and garlic, or the decadent fried zucchini flowers stuffed with mozzarella cheese.

Enjoy the incredible Pantheon, the beautiful Piazza Navona, and the stunning Trevi Fountain. The Pantheon is the most preserved ancient building in all of Rome. Surrounded by government buildings and quaint shops, it is a lovely area to purchase authentic Italian stationary. Piazza Navona is a public space where the city market has been located for centuries. The smells of fresh produce and the tastes of mozzarella and fresh bread have accompanied it throughout the passage of time. The square is mentioned in Dan Brown’s Angels and Demons, specifically the Fontana dei Quattro Fiumi, “The Fountain of the Four Rivers.” The Trevi Fountain has been showcased in movies throughout cinematic history, including Fellini’s La Dolce Vita, and Audrey Hepburn’s Roman Holiday. The fountain depicts an opulent collection of Roman gods. Take part in the tradition, and throw a coin into the water. With your back to the fountain, throw a coin over your left shoulder using your right hand.

As the day winds into night, you’ve earned an indulgent dinner at one of Rome’s finest dining establishments. The friendly, exuberant owner can be seen walking through the city during the day, inviting locals and foreigners alike into his restaurant for the evening. The buttery quality of the lobster fettuccini will have you wanting more, not just of dinner, but of all of Italy.

What’s Included: breakfast, tour, accommodation

Day 3: Open Up to Italy

Have an early breakfast at the hotel and be on your way to the gorgeous rolling hills of Tuscany, as you make your way to Pietrasanta, a beautiful beachside town full of golden sand, located near Lucca.

While in Pietrasanta, you will be taken to Pisa to experience all that the town has to offer. The Leaning Tower is an architectural wonder as it stands tall over the open square with an incredible tilt toward the ground; however, it is not the only wonder in Pisa. Maneuver through the tourists taking photos of themselves holding the tower in their hands and make your way to the cathedral. Consider learning more about your Pisa travel agents who strive to produce a trip for you as memorable as the Leaning Tower. The cathedral is an unbelievable presence in the square; its vastness comes not just in its size, but also from its quality. The pillars of the façade and the immaculate marble inside are to be marveled at, as is the entirety of the structures in the piazza.

Lunch in Tuscany can mean many things: a collection of cured meats and cheeses, a glass of wine or risotto in a red-wine sauce. Enjoy the variety and the savory tastes of Tuscany before heading to Lucca for the latter part of the day. Lucca is a beautiful medieval city known for its medieval walls that continue to surround it. Stroll along the walls and you will also see the beautiful Tuscan hills in the distance. Walk the streets of the city, and let yourself get lost amongst the architecture and inside the museums. The Basilica of San Michele in Foro displays tremendous arches, each adorned with gargoyles baring their teeth at birds and invaders.

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

Day 4: Settling In

Settle into the day with a light breakfast followed by a visit to Bolgheri. Located in the beautiful commune of Castagneto Carducci, Bolgheri is known for its delectable and delicious wines. The white wine opens up with the characteristics of citrus, followed by floral aromas with creamy oak and a clean finish. The reds tend to have a spicy side, with mineral notes and a tannic taste, leaving a balanced finish.

Follow up your time in Bolgheri with opportunity to learn from an acclaimed local chef. Take part in a private cooking class where you will learn and, better yet, taste the culinary traditions of Tuscany. The art of Pici, a long egg noodle that wraps around the plate, smothered in a citrusy, rich tomato sauce, will linger on your fingertips as the taste remains on your tongue. Cooking in Tuscany is not just an art form, it’s a time-honored tradition. The smells of garlic and the sweet tomatoes will have you pampering yourself in each flavor, separately and together.

What’s Included: breakfast, accommodation

Day 5: Reach Out

Say goodbye to Lucca and enjoy the ride through the heart of Tuscany on your way to the charming hillside city of Siena. The city’s cobblestone streets wind through the hilly, age-old city until you come upon the main piazza, the Piazza del Campo. The large piazza is shaped like a shell, flanked by the peach walls of Palazzo Pubblico. Piazza del Campo is where the city holds the Palio, bareback horse races where the usual quiet neighborhoods of the city erupt from their sleepiness and cheer on their rider for neighborhood supremacy.

Trips to Tuscany aren't complete until you visit the Siena Cathedral, where the detail of the façade is magnificent, in each statue that climbs the spires, and in the stunning marble-white color. The grand circular window shines light into the cathedral and the stunning fresco above it. The cathedral smells like cinnamon and candlewax. The black and white marble stripes in the cathedral’s interior are striking, but the main attraction is the mosaics that decorate the floor. The She-Wolf of Siena, with its emblems of the allied cities, is considered to be one of the oldest mosaics in the cathedral.

Relish in a delicious Tuscan lunch and taste the beauty of a traditional Chianti Classico. With cherry notes and minty, herbaceous spice, mellow tannins and medium acidity, Chianti can compliment most Tuscan foods.

It is a quick and exquisite ride to San Gimignano, a medieval Tuscan town known for its standing towers and white wine. Three walls encircle the city; fourteen towers stand tall over the architecture both old and new. The towers were originally a sign of wealth, with the higher the tower, the wealthier the family. Stroll through the city, enjoying the architecture and the Vernaccia, a lovely white wine that Dante Alighieri claimed was so good, it led to Pope Martin IV’s gluttony.

As the night sinks over the Tuscan hills, return to Siena and discover a tiny, exquisite restaurant that is famed as one of the region’s best. The smell of fresh bread and a succulent wild boar sauce atop fresh pasta awaits.

What’s Included: breakfast, lunch, dinner, transfer, accommodation

Day 6: Grab Hold

Start the day with a fresh caffe and a brioche in the main piazza, watching the sleepy city of Siena come to life. After breakfast, you will be taken to Montepulciano, a Medieval and Renaissance town near Siena. The main road through Montepulciano stretches from the bottom of the hillside, through the historical Renaissance buildings, and up to Piazza Grande at the top of the hill. The Palazzo Comunale was built in the tradition of the Old Palace in Florence, in its size, structure, and color. The city is known for its car-free streets and its delicious wine. While in Montepulciano, you will luxuriate in the wines of the area. The intense and fine bouquet of blackberries, violet, plum, and black pepper gives the Nobile di Montepulciano a well-balanced structure. Rosso di Montepulciano has a full-bodied, vanilla spice. Enjoy a typical Tuscan lunch before heading to Montalcino.

The fortress in Montalcino perches over the city at its highest point and looks down upon the roofs and trees, where you can see the quintessential Tuscan hills rolling in the distance. A quiet town with incredible wine, you will be happy that you didn’t miss the delicacies of Montalcino. The Rosso di Montalcino has wild-berry fruit and subtle oak revealed in a hint of spice and vanilla. The Brunello di Montepulciano has an intense ruby red color, dark fruit, vanilla, and is blended with tobacco; a variety of flavors packed into one specialty.  

What’s Included: breakfast, transfer, accommodation

Day 7: Pull Italy in Close

After breakfast, you head to the Maremma area of Tuscany, where the beautiful green of the hills meets the gorgeous blue of the sea. The upper hillside towns trickle down into the heart of Maremma, where the ocean pulls gently at the sands. A mixture of the Medieval brick and modern seaside, Maremma smells like the ocean and cedar, where all your dreams of fresh seafood, medieval architecture, and lounging in the sun come together in one place.

In the evening, you will experience a gourmet dinner at a refined estate near Badia a Passignano. Known for its wine, the estate also offers a selection of delectable food, grown and picked fresh to maximize the flavor of every ingredient that’s placed on the table. The cannelloni with lamb and asparagus is topped with a lemon zabaglione, a traditional fluffy Italian custard, and thyme salt. Or perhaps try the bistecca alla Fiorentina, a grilled T-bone steak seasoned with sea-salt and pepper; simple and incredibly delicious.

What’s Included: breakfast, accommodation

Day 8: Opening Up to Umbria

After breakfast, you depart for Torgiano in Umbria, where you leave behind the lush green of the Tuscan hills for the incredible gold of the Umbrian countryside. Torgiano is known for its medieval walls that still surround the city, including the large tower that looks over the Umbrian valley below it, guarding the old, main road into the city. Torgiano also boasts delicious wines like the delicate, yet bold Torgiano Rosso Riserva. 

Montefalco is a beautiful medieval city that looks over the Umbrian valley, a city that has lived under subsequent conquerors since its inception. Walk through the peaceful town and enjoy the hanging gardens that soften the strong buildings which enclose the narrow streets. Reach the piazza that opens the city up to the sky. You will have the treat of a tasting the Sagrantino di Montefalco and the Montefalco Rosso. The Sagrantino di Montefalco develops earthy and warm spice aromas; it features rich dark cherries with some heat on the finish. The Montefalco Rosso is a bit intense, with notes of ripe red fruit and delicate hints of vanilla, full-bodied, with a long dry finish. To finish the wonderful day, try dining at Ristorante Coccorone. The black truffle pasta fills the restaurant with a buttery, earthy aroma and tastes as good as it smells.

What’s Included: breakfast, accommodation

Day 9: Hold onto Umbria

Start the day with a delicious breakfast, before sightseeing around the incredible city of Assisi. The birthplace of Saint Francis, Assisi is built up the Monte Subasio and looks out over the Umbrian plain. On a clear day, you can see Perugia in the distance. The Basilica of San Francesco di Assisi is so large that it is separated between the monastery, and the lower and upper church. The lower church displays incredible Frescoes, some by Giotto, and candles and frankincense fill the room. The upper church exhibits frescos from the life of Saint Francis, highlighting his piety.

Assisi climbs Monte Subasio and tops the mountain with an open and inviting square, along with two medieval castles that watch over the city streets. The smaller castle is a remnant of the Romans while the larger castle is known as Rocca Maggiore. Its massive presence was meant to demand respect from the townspeople. There is plenty to indulge in Assisi, including delicious olive oil and native balsamic vinegar.

A short drive will take you to Spello, an ancient town that has as much character as it does history. Remains of Roman and medieval gates surround the city, helping to maintain the quaint and historic feel. Visit Santa Maria Maggiore, a lovely church with a Romanesque façade. Next, indulge the sense in a fine dining experience. Start with a selection of cheeses accompanied with honey. The richness of the cheese mixed with the sweetness of the honey is an enticing combination. The Pasta Pomodoro is a simple dish with fresh pasta and a light tomato sauce; Umbria knows how to do simple, which makes every ingredient pop.

What’s Included: breakfast, accommodation

Day 10: Open Up and Let Go

Your final day in Italy takes you from Torgiano to Orvieto, an ancient city built on an impregnable rock. The city’s origins date back to the Etruscans. The cathedral showcases an elegant Gothic façade with spires that tower over the square, decorated with sophisticated gold-leafed frescos, and a rose window at the center.

A wine tasting in Orvieto brings about the delicious wines of Decugnano, Bianco, and Rosso. Decugnano Bianco has delicate ripe fruit and is slightly spicy with a well-balanced finish. Decugnano Rosso has notes of raspberry jam, reminiscent of licorice and juniper berries; the taste is rich, bodied, and generous. A light lunch at Al Saltapicchio is a great way to finish your time in Orvieto. The antipasto possesses a lovely selection of jams, cheeses, and fresh bread, wonderful flavors to add to the wine still lingering on the palate.

A ride through the Umbrian valleys will take you back to Rome for your return flight home. The tastes of Tuscany and Umbria may have come and gone, but the memories of your trip will stay forever. Italy has opened itself to you and you have embraced it all.

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.