Tuscany Tour for Lovers: Siena, Cortona, Volterra, San Gimignano and Certaldo

A 8 day trip to Italy 
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Medieval city walls and historic towers make each town in the Tuscan countryside feel like a fairytale, and you will feel like royalty. On your custom tailored Tuscany tour for lovers, each day takes you to the intimate villages and enchanting landscapes, from lush valleys to glistening seaside. Taste the traditions of elegant, regional cuisine and savor the treasured company of your partner. You will find the charms of history and the enchantment of sunsets over castle walls, sipping wine in a piazza, sharing gelato, and discovering all the different ways that Tuscany is for lovers. 

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General Information

Detailed Itinerary

Places Visited 

Siena, Cortona, Lucignano, San Gimignano, Certaldo, Volterra, Grosseto, Castiglione della Pescaia, Pisa

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: The Romance of Tuscany

Tuscany is the pinnacle of Italian beauty, set inside the lush, rolling hills and towering cypress trees. Vineyards wind up and down the landscape and medieval towers rise over the scenery with indelible elegance. When you arrive at the Florence International Airport, your private transfer is waiting. When traveling through the countryside, you find the aroma of the cypress trees fresh and herbaceous. The Tuscan landscape is everything you had imagined, bright with emerald colors and projecting picturesque beauty. At the edge of Siena’s old city center, you find a medieval town filled with magnificent buildings and an ornamental cathedral.

The cobblestone streets wind and twist along the historic buildings. In the Piazza del Duomo, the Gothic structure erected between the 11th and 13th-centuries provides a white and green marble sheen to the square. The city has a romantic ambiance set in its antique décor and slow pace. In the evening, street lamps dimly light the walkways, offering an ethereal glow. The aroma of fresh pici, traditional Tuscan pasta similar to thick spaghetti, cooked with herbaceous fennel seed and pork drifts through the doorways of a classic restaurant. Inside, the atmosphere is charming, allowing you to indulge in every bite, and savor the company.

What’s Included: transfer, dinner, accommodation at Castello Banfi

Day 2: A Private View

In the morning, you find the scent of fresh brioche drifting out of bakery doors. The city slowly comes to life with locals crowding into cafes and sipping fresh espresso. After breakfast, your guide meets you at your hotel and escorts you through the city. Today you’ll have the option to explore Siena's history and architecture or enjoy a unique experience wine tasting in Tuscany with the highly-regarded tour guides from Wine Tour in Tuscany.

In the Piazza del Campo, you find the Torre del Mangia, a 14th-century tower overlooking the sloping half-moon square. It takes 400 steps to reach the top of the tower. The view opens up to the expansive, shingled rooftops of the old city with a panorama of the countryside spreading across the horizon. In the quiet of the serene city, it feels like your own private view shared with the one you love. Your guide leads you to the lesser-visited areas of the city, where vineyards stretch across the 17 districts, with each district acting as a neighborhood.

At the steps of the 13th-century Church of San Domenico, you find where Saint Catherine of Siena took her vows, and legend says, performed miracles. Lofted ceilings create an immense sense of space. A painting by Mattia Preti shows the saint’s canonization. The scent of frankincense fills the church. Candles flicker against the marble columns of the Chapel of Saint Catherine. Your guide quietly leads you around the stunning examples of Renaissance art and masonry, alongside the large windows helping bathe the nave in light.

Wine connoisseurs have the option to spend their day tasting the finest wines of the Chianti region. Your local sommelier from Wine Tour in Tuscany will take you on an exploration of a lifetime. You’ll spend seven hours visiting three of the most spectacular wineries in the area. Relax under the Tuscan sun while you enjoy the taste of the bold-bodied wine. Enjoy a gourmet lunch before you purchase a bottle of your favorite wines, which historically came in a straw basket. You’ll never forget the taste, which has taken hundreds of years to perfect, and the knowledge of the guides from Wine Tour in Tuscany.

What’s Included: breakfast, tour, accommodation at Castello Banfi

Day 3: The Edge of Tuscany

When the morning light shines over the hillsides, you find a refreshing mist settling over the grasses. The morning dew soon fades, leaving behind a layer of moisture that reflects the sunlight. You notice that every moment in Tuscany is filled with majesty, and the countryside is filled with luxurious romance.

After breakfast, you set out to the city of Cortona, located on the Tuscan and Umbrian border. The town sits on a hilltop overlooking the valley below, filled with 14th-century extravagance and Etruscan roots. Antique walls made of stone and mortar encircles the cityscape. Houses and churches climb up the hillside. Charming cafes set out tables on the cobbled pathways shaded with umbrellas. The beauty of the city was captured in the film “Under the Tuscan Sun,” and that same radiance enchants you today.

Piazza Garibaldi is quiet but filled with charm. The Piazza is filled with locals sitting beneath the trees and enjoying a moment with the view of Lake Trasimeno. The 13th-century façade of Palazzo Casali decorates the 17th-century building, housing a grand display of Etruscan, Roman, and Renaissance marvels. The antiques found in the tombs around the city date back to the 7th-century BC offering insight into the metalwork and weapons of the Etruscans.

After you have soaked in the beauty of Cortona, get ready for an amazing Tuscan wine tour with your guides at Tuscan Magic. You will first set out to the spectacular medieval hilltop town of Montepulciano. As you stop here, you will learn about the art and craftsmanship of Tuscan wine production, which is known as some of the best wine in the world. Next, as you make your way to Montalcino, a small tuscan hilltop town famous for it Brunello di Montalcino wine, you will stop in Pienza for a taste of the town’s famous Pecorino cheese. As you make your way back to Cortona, you will notice how the stunning combination of landscape and history creates an unforgettable, luxurious view of the Italian countryside.

What’s Included: breakfast, tour with Tuscan Magic, accommodation at Villa Di Piazzano

Day 4: Cities in the Sky

The splendor of Tuscany is visible day and night, whether strolling through the sun-drenched piazzas of a small town or reveling in the passions of fresh dishes in a candlelit restaurant on a hidden, medieval street. After breakfast, you make your way through the Tuscan countryside once again, finding the sister cities of San Gimignano and Certaldo staring at one another on the hilltops overlooking the separating valley. San Gimignano continues to be known as “The City of 100 Towers.” On the outskirts of the city, you can see the tallest tower standing 177 feet tall.

On the opposite hillside, you arrive at the footsteps of Certaldo, where you have a view of San Gimignano some six miles away. At the bottom of the hills, the atmosphere of Certaldo comes to exuberant life before you have even stepped onto the streets. A funicular climbs the hillside taking you through the narrow streets and to Old Town, known as Certaldo Alto. Ivy wraps around ancient buildings adding greenery to the cityscape. Charming lamps dangle from the side of brick and mortar buildings. The tall buildings shade the narrow streets. People decorate their windowsills with fragrant and vivacious flowers.

Palazzo Pretorio was erected in the 12th-century and is decorated with coats of arms cast into the stone and terracotta façade. Restored medieval houses fill Castello Quarter. The town feels like a tranquil escape from the present, into a picture of the past, in a place few venture to experience.

For an alternative, hands-on Tuscan experience, you will make your way to Guardastelle in San Gimignano where you will partake in a cooking class with local Italian cooks. Their friendly and knowledgeable home-style cooks will teach you how to handcraft fresh antipasti, ragu, pasta, and much more all from local raw ingredients. As you cook, they will explain to you the significance and origin of the various types of pasta found throughout Italy. Once you finish creating your amazing culinary delights, have a taste and notice the rich, diverse flavors. Enjoy your tasty pasta with a perfectly paired glass of fine in-house Guardastelle wine as you relish in your spectacular creation. Make your way to the on-site wine shop and feel free to purchase a bottle of your favorite wine as they are exclusively sold at Guardastelle.

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

Day 5: Walls and Cobbled Streets

The walls of Volterra have been preserved to perfection, protecting the winding, cobbled streets of a settlement dating back to the Etruscans. After breakfast, it is a short journey to the township that was once the last city in the area to succumb to Rome in 260 BC. The current shape of the city emanates 12th-century magnetism, filled with alabaster artistry.

The Arco Etrusco, Etruscan Arch, frames Via Porta all’Arco and remains a gate to the ancient circuit of walls. The Etruscans positioned the dressed stones flanking the entryway and the weathered heads of the arch. The walls have an enchanting effect over you, covered in emerald hues of ivy and shaded by holm-oaks.

Small cypress trees rise over the ramparts. The walls rise to a height of 36 feet in some places, including near the Church of Santa Chiara. You can stroll around town hand in hand and enjoy the calm luxuries of the city, making it feel like a private excursion for you and the locals. Walk down to the Roman Theater situated north of the town walls and dated back to the 1st-century AD. The natural sloping hillside contained 19 visible rows of seating and an orchestra pit. The breeze sweeps across the surrounding grasses, and the scenery is perfect.

What’s Included: breakfast, tour, accommodation

Day 6: Turquoise Coast

The hexagonal shape of the town of Grosseto stands against the azure waters of the Mediterranean Sea. The city was once held under the protectorate of Siena before falling to the Medici’s in the 16th-century. Sailboats cast out from the marina near Castiglione della Pescaia, a town closely situated to Grosseto. A medieval castle watches over the coastline and encompasses 2,500 acres of land. The often-overlooked beaches are lined with resorts frequented by Italians, and other Europeans, creating a luxurious seaside community bordered by refreshing, welcoming waters.

The hilltop fortress has narrow lanes winding through the historic buildings, some dating back to the 9th-century. The walls around the city of Grosseto now lay claim to a public park, adding greenery to the forceful ramparts. The combination of sand and cobblestones creates a perfect combination for a romantic getaway, providing a historic atmosphere with beachside ambiance.

In town, you can visit a local artisan salumeria whose family has been in the business for generations. Grab a platter of boar prosciutto, a specialty of Tuscany, and some delicious cheeses, of which your new friend at the salumeria is happy to recommend, and revel in your romantic picnic on the beach. The sand is soft under your blanket. The breeze is cool against your skin. The waves lap against the shoreline. In the warmth of the afternoon, you could venture up the hillside to the fortress and take in the sweeping view of the water against the historic archways along the castle grounds.

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

Day 7: Leaning In

In the morning, the beauty of the medieval city continues to exude splendor and amorousness. With so many charming hidden villages and luxurious historic cities around Tuscany, there is an endless world of enchantment to discover. Today, you take a step back onto the footpaths of Tuscan landmarks, making your way to Pisa. The city is known for the unique and captivating Leaning Tower of Pisa.

When you reach the Campo dei Miracoli, you find the sensational edifice standing more than 183 feet tall and listing at almost four degrees. The marble glistens in the sunlight. The remarkable baptistery and cathedral also stand in the square, creating a tremendous piazza filled with the unique styles of Pisan Romanesque style. Beyond the tower and the square, you will find the grace of historic Borgo Stretto, the city’s most elegant street. Arches line an arcade filled with designer boutiques. You can sit for a moment at the street-side tables of the exquisite Pasticceria Salza.

The scents of fresh cakes and confections blend with the ground and brewed coffee beans. The colorful display case showcases the endless array of traditional sweets you can enjoy with your partner, watching the city move past you like a local before continuing onward to the Cittadella di Pisa, the Old Citadel, home to the Guelph Tower. This is an area of the city where you have the ease and beauty of the city’s past in unique seclusion. Climb the 300 steps to the top of the tower for a dazzling view of the cityscape, sweeping from the Leaning Tower to the pine trees of San Rossore Park touching the riverbanks. The neighborhood’s shipbuilding past adds to the prestige of the tower, helping the city accumulate its medieval wealth. If you want to extend your time in Pisa, see the reviews for Pisa travel agents.

Upon your return to Siena, you can dine in the city’s oldest restaurant founded in the 19th-century. The frescoes of the interior at Tre Cristi set the mood and the simple, yet flavorful cuisine does the rest.

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

Day 8: In Love in Tuscany 

After your days in Siena, you have found a favorite café where you prefer to sip your espresso and let the morning begin. The barista greets you gregariously, treating you like family after so many days in the city. The aroma of chocolate and buttery dough filter out of the display case. You and your partner relax with one another, looking out over the Piazza del Campo, and its unique sloped crescent shape. It is easy to lose yourselves in the history and ineffable beauty of Tuscany’s charm.

After breakfast, your private transfer meets you at the hotel and escorts you to the Florence International Airport for your flight home. In Tuscany, you found passion, pride, and enchantment across the landscape radiating from every step.

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.