Tuscan Tapestry

Departure Date:
10 May – 14 May 2025

from USD $2,499/pp

Italy’s quintessential ‘la dolce vita’ unfolds in Tuscany and Umbria, where the scent of fresh basil mingles with the aroma of espresso, and church bells serenade locals over leisurely lunches. Based at a family-owned and operated villa in the Chianti region of Val di Pesa, our journey follows the Tuscan sun through a region dotted with magical sites. From San Gimignano’s towers to Florence’s Duomo, poetic Siena to its lesser-known hilltop villages, our days in Tuscany unveil art, culture, and timeless landscapes. Amid Chianti’s vineyards, we sip world-class wines, stroll Certaldo Alto’s silent alleys and savor Tuscan treats, and sunset vistas from our villa’s private terrace.

Join us on this magical small group, fully guided journey through the wonders of Tuscany.


  • Immerse yourself in the rich culture of Chianti with a wine tasting at a centuries-old winery indulging in local delicacies amidst picturesque vineyards
  • Explore the medieval allure of Certaldo Alto, home to the Boccaccio Museum and Praetorian Palace
  • Delve into Florence’s artistic treasures, with a locally guided tour of renowned landmarks like the Uffizi Gallery and the Medici Chapels, displaying masterpieces by Michelangelo, Da Vinci, Botticelli, and Raphael, and uncover the legacy of the Renaissance.
  • Stay at an authentic family-owned villa amidst the scenic landscapes of Tuscany, offering a true taste of quality Italian hospitality
  • Enjoy the vibrant cultural scene and historic charm of Tuscany’s most picturesque hilltop towns

Itinerary Overview

Day 1:    Arrive in Rome

Day 2:    Orvieto – Chianti – Val di Pesa

Day 3:    Certaldo Alto, San Gimignano, and San Cristiano

Day 4:    Florence

Day 5:    Siena – Rome


Day 1 – Rome

Make your way to the Starhotels Metropole Rome. Chosen for its convenient location, the hotel is situated within walking distance of Romes Termini station, which has a direct link to Rome International Airport. This region is scattered with trattorias offering local fare at reasonable prices and a downhill walk to the Coliseum. Your day is at leisure.

Metropole Hotel
Situated within the cobblestone streets and ancient marvels of Rome lies the charming Metropole Hotel. Nestled in the beating heart of Rome’s vibrant Repubblica district, the Metropole Hotel stands as a beacon of convenience and accessibility. Just a stone’s throw away from the famed Opera House, a leisurely 10 to 15-minute stroll will take you to the Coliseum and Trevi Fountain, and just a 5-minute walk away, you’ll find yourself at Roma Termini, the city’s main metro and railway station. A dedicated non-stop express train will take you just 32 minutes between the airport and Roma Termini, departing every 15 minutes. With the entirety of Rome at your fingertips, the possibilities are endless.

Awaken your senses with the aroma of freshly brewed coffee and Italian delicacies drifting from the hotel’s restaurant. Indulge in a culinary journey that mirrors the richness of Roman cuisine, from traditional classics to innovative creations that ignite the palate. After a day of exploration, retreat from the hustle and bustle to your room, designed to make you feel at home while immersing you in the timeless charm of Rome offering a blend of comfort and style. In the evening, retreat to the bar and sip on a cocktail crafted with care, as you share tales of your day’s escapades with fellow travelers from around the globe.

Accommodation: Starhotel Metropole Rome (or similar)

Day 2 – Orvieto – Chianti – Val di Pesa

We meet our Tour Leader and fellow travelers and bid ‘arrivederci’ to Rome as we head for the hills – the Tuscan hills that is. Where every hill tells a tale of ancient civilizations, Renaissance masters and former feudal kingdoms. Surrounded by the vibrant hues of lush paddocks, fields of sunflowers, and rows of grapevines, our first stop is Orvieto. Perched high above the Rome-Florence highway, Orvieto offers a timeless appeal with its Gothic Duomo and underground tunnels narrating centuries of history. We enjoy a locally guided tour, and a scrumptious lunch in this enchanting town. 

Your journey continues to Chianti, where rolling hills and medieval villages frame vineyards dating back to the 13th century. A wine tasting immerses us in Chianti’s culture, highlighting the region’s dedication to tradition. Our vintner introduces us to the region’s unique production method using hand-harvested Sangiovese grapes. After fermentation, the wine ages, typically in oak barrels, to develop its characteristic flavors and textures. Like Champagne in Champagne, adherence to tradition, gives Chianti its unique lightness, embodying the rich heritage and passion of Italian winemaking.  Upon your arrival, you will enjoy a guided tour of the vineyards and winery including the fermentation room, ageing cellars and cellar of sparkling wines before sitting down for a wine tasting session with cold cuts.

Late afternoon we find the Villa II Poggiale nestled amongst the wines and olive groves on this family estate. Our base near San Casciano in the Val di Pesa promises a traditional ambience amidst Tuscan landscapes. Dinner is at the villa’s restaurant, where we indulge in local delicacies over a glass or two of regional wines.

Villa Il Poggiale
Reminiscent of landscapes viewed in Tuscan Renaissance paintings, the estate of Villa Il Poggiale hosts pencil-pine cypress trees, a lush olive grove and rows of working vines. Located in the famous wine growing region of Chianti, and at the apex of towns such as Florence and San Gimignano, the villa is a perfect base for our exploration of Tuscany. Villa Il Poggiale’s classic ensuite rooms ooze Tuscany, with each room’s antique furniture and fabrics coming from Tuscan artisan weaving factories. Meals are a highlight at this family owned and operated villa, with breakfast produced using only local ingredients, and dinners often based on family favorites handed down by generations of ‘mamas’. Returning “home” to Il Poggiale each afternoon, there’s time to relax with a dip in the pool or a drink in the rose garden before being treated to a candlelight dinner of local specialties in the restaurant. 

Accommodation: Villa Il Poggiale – San Casciano, Val di Pesa (or similar)

Meals: Breakfast, lunch and dinner

Day 3 – Certaldo Alto, San Gimignano, and San Cristiano

Today is spent at two of the true gems of the valley of Pesa when we visit one of its much-admired villages and wander the cobblestone paths of Tuscany’s ‘tower village’; San Gimignano.  We will also explore nearby Certaldo Alto, with its medieval allure and Tuscan warmth. Despite its ancient origins, Certaldo Alto embraces 21st century Italy with a vibrant cultural scene, including art exhibitions, music festivals, and traditional markets. Yet, amidst the hustle and bustle, there is a sense that time has stood still at these hilltop towns, which makes them a traveler’s dream.

Our one-hour panoramic drive takes us to scenic San Gimignano, where our local guide walks us through this beautiful town, viewing the “Manhattan of Tuscany” skyline, bristling with many towers dating back to the 11th and 13th centuries.

When film makers look to Italy for locations, they need look no further than the Tuscan gem of San Gimignano. Tea with Mussolini, A Portrait of a Woman, Gladiator, Life is Beautiful, The English Patient and Under the Tuscan Sun all shot scenes here. San Gimignano itself is a work of art. The town’s medieval architecture serves as a backdrop for everything Tuscan, with artisan shopfronts displaying everything that is superb about Italian food and cafes offering everything that is wonderous about Italian cuisine. Even its streets and cobbled stone alleys wind in a way that makes every corner worthy of exploration. And did we mention its towers? For it is the town’s 14 remaining Medieval towers which proudly rise above its skyline as palaces preserving the towns feudal appearance which confirm San Gimignano as the supermodel of Tuscan towns. We explore this fascinating town and try a few of its treats as we explore its laneways, cobbled streets and eclectic treasures.

After the visit we enjoy a typical local meal in a nearby farmhouse. Sitting amongst the vines of Tuscany, we enjoy traditional snacks, whilst tasting a selection of local wines, before continuing to Certaldo.

Certaldo Alta is a Tuscan town with a big heart. Here is the home of the Boccaccio Museum, where the great Italian poet and scholar is presumed to be born in 1313 and lived until his death. Our visit offers us an insight into Tuscan life in the Middle Ages, a period leading up to the Renaissance for which the region is so well known. We also visit the Praetorian Palace, the symbol of this medieval town, which portrays the struggles of the town’s peoples against it dominant neighbor.

Late afternoon, return to our home village of San Casciano. This picturesque place is a popular spot to sip local wine and soak up the village ambience in its charming piazza. Its surrounding vineyards produce the acclaimed Chianti Classico, while the town’s medieval architecture, including the imposing walls of the Rocca del Cassero and the elegant Church of Santa Maria del Gesù, provide a tangible link to its storied past.  Later we return to the Villa for a delectable dinner.

Accommodation: Villa Il Poggiale – San Casciano, Val di Pesa (or similar)

Meals: Breakfast and dinner

Day 4 – Florence

Today we are off to a highlight of any visit to Italy – Florence. Rising from the ruins of the Roman Empire, Florence flourished into a wealthy trading and banking center, becoming Europe’s first capitalist state. The Duchy’s ruling family, the Medici’s, sponsored its artistic scene with fervor. Artists transitioned from tradespeople to celebrities overnight, with Da Vinci playing lute at their private parties and Michelangelo befriended by men who would become Popes.  The ruling classes commissioned works of art such as Donatello’s Penitent Magdalene, Cellini’s Medusa, Botticelli’s Birth of Venus and Raphael’s Maddona del Cardellino. Throughout the Duchy art was showcased in piazzas, scattered throughout the streets and placed at the town hall steps. A form of propaganda and sign of power for all to see.

Accessible to all those who visit, Florence’s works of art are scattered throughout its streets as statues, fountains, chapels and bell towers and all looked down upon by Brunelleschi’s magnificent domed cathedral. Even the gelato is sculpted in Florence. Carved from a single slab of marble, Michelangelo’s David is the ultimate Renaissance man, commissioned as the centerpiece for the city’s main square. Today it sits in its own gallery, but a replica at its original location tells its story almost as well. Our locally guided tour walks us through a day in the life of Renaissance man as we tread the streets where the early artists plied their trade, sought wealthy patrons and huddled in backstreet studios to learn from the masters.

Our exploration unveils Florence’s true treasures, including time spent in the renowned Uffizi Gallery, home to works by Michelangelo, Da Vinci, Titian, Botticelli, Raphael, and Caravaggio. Delving deeper, we discover Michelangelo’s profound passion, evident in every stroke of his marble statues housed within the Medici Chapels, a testament to the enduring bond between art and patronage. Our final dinner is at Villa Poggiale as a farewell treat.

Accommodation: Villa Il Poggiale – San Casciano, Val di Pesa (or similar)

Meals: Breakfast and dinner

Day 5 – Rome

Siena enchants us today with its timeless allure and wealth of historical treasures. Dating back to the Etruscan era, Siena flourished during the Middle Ages as a bustling hub of commerce and culture, rivalling even Florence in its heyday. We tour the center of town, with the city’s crown jewel, the magnificent Duomo di Siena standing as a testament to Siena’s architectural prowess and religious devotion. Its intricately carved facade and stunning interior, featuring works by renowned artists like Donatello and Pisano.

Siena’s medieval streets are steeped in history, with each winding alleyway leading to its fan-shaped piazza, famous for the running of the Palio. The city’s 17 contrade, or neighborhoods, each boast their own unique identity and fiercely compete in the annual Palio di Siena, a thrilling horse race held in the iconic Piazza del Campo twice annually.

Leaving Siena we continue to Rome, bidding farewell to Tuscany. Tonight, we commence our pre-voyage Rome experience, with time at leisure. Our team will greet you at the hospitality desk in the hotel lobby, where they will run through the details of your time in Rome, prior to your voyage and answer any questions you may have about your sailing.

Meal: Breakfast

Tour Inclusions

  • 1 nights’ accommodation pre-tour at Starhotel Metropole Rome with breakfast
  • 3 nights’ accommodation at the privately owned Villa Poggiale, San Casciano – Run of House
  • Breakfast daily at the villa
  • 2 x lunches
  • 3 x dinners hosted by Villa Poggiale
  • Services of an English speaking, qualified tour leader who will travel with the group throughout your tour (Day 2- Day 5)
  • Services of local guides in Florence, Orvieto, San Gimignano, Certaldo, and Siena
  • Transport daily on private coach
  • All parking fees
  • Wine tasting at a Chianti winery and San Gimignano winery
  • Entrance fees:  Orvieto Duomo, Orvieto Funicular, Uffizi Gallery Florence, Medici Chapels Florence, Certaldo return Funicular, Boccaccio Museum and Pretorian Palace, Certaldo, Duomo and Piccolomini library Siena
  • VAT and city taxes
  • Porterage for 1 piece of luggage at each property
  • Gratuities for city guides, drivers and restaurants for included meals

Tour Exclusions

  • International or domestic flights
  • Transfers not mentioned in the itinerary
  • Airport arrival or departure taxes
  • Passport, visa, reciprocity fees and vaccination charges
  • Hotels and meals not listed
  • Optional excursions not included in the itinerary
  • Optional activity surcharges
  • Gratuities for Villa Poggiale and tour leader are at your own discretion
  • All items of a personal nature including but not limited to alcoholic beverages and soft drinks, laundry services, personal clothing, medical expenses, additional gratuities, Wi-Fi, email or phone charges