Arrival in Florence, Transfer to Chianti

Your Tuscan tennis adventure begins with arrival at Florence Amerigo Vespucci Airport, where you'll be greeted by our local host and transported by luxury van to the heart of Chianti. We'll enjoy lunch at a beautiful hilltop location with stunning views—your first opportunity to taste Chianti wine among the vineyards where the grapes are grown. After arriving at our villa homebase, we'll head to the courts to "kick the jetlag" with your first tennis session. As the golden hour sets over the Tuscan hills, we'll gather with an expert mixologist for a demonstration and tasting of iconic Italian cocktails, followed by dinner at one of Italy's most acclaimed pizzerias in a tiny medieval fortress town.

Tuscan Villa
Lunch (L) Dinner (D)

Panzano Market, Vineyard Visit & Monteriggione

After breakfast and morning tennis, we’ll visit a boutique family-owned winery outside Panzano, where owner Francesco will guide us through his 20-acre vineyards and cellar, followed by a wine tasting and lunch featuring local specialties. In the afternoon, we’ll discover the medieval walled town of Monteriggione, returning to Tavarnelle for dinner and sharing memories of the day over regional cuisine.

Tuscan Villa
Breakfast (B), Lunch (L), Dinner (D)

San Gimignano 

Following breakfast and morning tennis, we'll enjoy a multi-course farm-to-table lunch at a local farm before exploring San Gimignano, the "Manhattan of Tuscany." This UNESCO World Heritage jewel box features 14 remaining medieval towers. After lunch you'll have time to shop, try the world-famous gelato, and soak in the ambience of the triangular piazza–a picture-perfect Tuscan day. We’ll return to Tavarnelle for dinner.

Tuscan Villa
Breakfast (B), Lunch (L), Dinner (D)

Florence 

After breakfast we'll take a short journey to Florence, the cultural capital of Renaissance Italy, for leisure time—perfect for sampling artisan gelato or discovering a local café, and if you signed up for the leather jacket fitting, you’ll come home with a chic Italian treasure. After lunch at your leisure we’ll gather for a guided walking tour through Florence. Our local guide will introduce you to this fabulous city, home to the cultural rebirth that pulled Europe out of the Middle Ages, including a visit to L’Accademia, home to Michelangelo‘s infamous David. Afterwards we’ll return to Tavarnelle for dinner.

Tuscan Villa
Breakfast (B), Dinner (D)

Truffle Hunt & Tuscan Cooking Class

Today brings one of our most memorable experiences! After breakfast and morning tennis, we'll embark on a traditional truffle hunt through the woods near our villa, learning to recognize the ideal truffle habitat while our guides share local legends and techniques. When the dog starts wagging and digging furiously, treasure has been discovered! After lunch in Tavarnelle, we'll master the Italian art of creating delicious cuisine with simple ingredients in an afternoon cooking class, possibly incorporating our morning truffle finds. Dinner tonight will be a feast of our own preparation!

Tuscan Villa

Breakfast (B), Lunch (L), Dinner (D)

E-Bike Tour & Artisan Visit

Following breakfast and morning tennis, we'll explore the heart of Chianti on pedal-assisted e-bikes, a comfortable but adventurous way to explore our surroundings regardless of prior biking experience. Glide through countryside that unfolds like a Renaissance painting—vineyards stretching across sun-drenched slopes, olive groves glistening with morning dew, and cypress trees lining winding roads. After lunch at an authentic trattoria in a charming medieval village recognized as one of Italy's most beautiful, we'll partake in the annual olive harvest, witnessing the fruits of our labor being rendered into oil and tasting the delicious final product. Evening dinner will be in Tavarnelle.

Tuscan Villa

Breakfast (B), Lunch (L), Dinner (D)

Siena 

After breakfast and morning tennis, we'll journey to Siena for lunch beneath the famous Torre del Mangia, where we'll taste the delightful pici—the traditional hand-rolled pasta of Siena dating back to ancient Etruscan times. Our afternoon private tour will give you an insider’s look at the storied city of the legendary Palio horse race and the magnificent Piazza Il Campo. We'll explore the stunning Cathedral and learn about Siena's importance as a stop along the Via Francigena pilgrimage route to Rome. Our farewell dinner will be held at the 12th Century estate and 5 star COMO property, Costello Del Nero, or “the black castle”, very appropriate for Halloween. 😉

Tuscan Villa
Breakfast (B), Lunch (L), Dinner (D)

Departure

After a final breakfast at the villa, we'll transfer you to Florence Amerigo Vespucci Airport in time for your departure, taking with you unforgettable memories of Tuscany's tennis courts, rolling hills, fascinating history, and timeless culture.

Breakfast (B)

Duomo Tour, Fashion District

This morning, we'll experience the magnificence of Milan's stunning Duomo with a skip-the-line tour, exploring its intricate Gothic architecture and breathtaking views from the rooftop terraces. Lunch will be at your leisure in this stylish city, allowing you to discover Milan's vibrant café culture or sophisticated restaurants. This afternoon, we'll step into Milan's dazzling fashion world as our expert guide reveals the stories behind legendary houses like Prada, Versace, Armani, and Dolce & Gabbana during our Milan Fashion Tour. Tonight, we'll savor exceptional cuisine at one of Milan’s most celebrated restaurants.

Rocco Forte House
Breakfast (B), Dinner (D)

Bespoke Perfume Workshop, Cooking Class

This morning, we'll create our own signature scent during a bespoke perfume workshop, learning the art of fragrance blending from master perfumers in this city renowned for luxury and craftsmanship. Lunch will be at your own pace, allowing you to explore Milan's culinary scene or relax at your elegant accommodations. This afternoon, we'll participate in a hands-on cooking class, mastering the techniques of authentic Italian cuisine. Tonight, we'll gather for our farewell dinner, celebrating an unforgettable journey through Italy's most stylish destinations.

Rocco Forte House
Breakfast (B), Dinner (D)

Departure

After breakfast, luxury transfers will be provided to Milan's airports for your flights home, taking with you memories of Italy's timeless elegance and the special moments that made this journey truly extraordinary.

Breakfast (B)