Meet your private driver and vehicle for an airport transfer.

An English-speaking assistant will meet you upon arrival to Florence, ensure you are checked-in to your hotel and walk-through your Welcome Package documents. They will be on hand to answer any questions you have related to your itinerary and your time in Italy.

A Welcome Package will be provided upon arrival and will include any relevant documents or tickets required for your trip.

Tonight, indulge in an authentic Italian dinner at local trattoria. Located in Oltrarno, the neighborhood directly across the River Arno and less-frequented by tourists, Ristorante Trattoria Angiolino AI 13 Arrosti welcomes you to a traditional, rustic atmosphere as you indulge your palate on an unforgettable taste of place with a 3-course menu.

Walk through a living museum where every street tells a story and every statue has a soul. With your private guide, explore Florence’s historic heart, beginning with the soaring Cathedral and Giotto’s Bell Tower. Wind through narrow alleys to Piazza della Signoria, where the mighty Palazzo Vecchio and Neptune Fountain reveal tales of power and myth. Discover hidden gems like Orsanmichele’s ornate faÇade and the beloved porcellino fountain. At the Accademia, stand before Michelangelo’s David and his raw, unfinished Prigioni. Throughout the walk, your guide weaves together history and legend, revealing the soul of the Renaissance in every step.

Set out on a scenic drive through vine-covered hills to a charming medieval villa, where the scent of herbs and sun-warmed stone sets the tone for an unforgettable culinary experience. Inside a welcoming, fully equipped kitchen, join your instructor to craft a traditional three-course Tuscan meal from scratch, guided by time-honored techniques and the freshest local ingredients. As aromas build and flavors come to life, settle in to savor your creations, whether in the cozy warmth of the villa or al fresco in the lush garden, surrounded by the beauty of the countryside. Please note: dietary restrictions must be communicated at time of booking.

Awaken your senses in the birthplace of Renaissance fragrance with a private, two-hour workshop at a historic Florentine perfume house. Guided by a master perfumer, step behind the scenes to discover the artistry and traditions of perfume making, from ancient alchemists and apothecaries to today’s refined techniques. Explore raw materials and their origins before crafting your own signature scent, learning each step from essence selection and olfactory analysis to blending, dilution, and bottling. Conclude your experience with a personalized perfume to take home, an enduring reminder of Florence captured in a bottle.

This afternoon, make your way to the Oltrarno neighborhood on the other side of the Arno for a delectable wine tasting at Le Volpi e l'Uva. Named after Aesop's fairytale The Fox and the Grapes, the interior is quaint and sophisticated with a touch of whimsy. While the story ends with the grapes being too sour for the fox, the result for you will be much more pleasant. Expect to sample some of the region's top-quality organic and biodynamic wines, accompanied by a lavish charcuterie board with cheese and Tuscan bread.

Follow the scent of Tuscany’s “edible gold” on an unforgettable truffle hunt through rolling woodlands with a master tartufaio and his loyal dogs. Begin your adventure with an introduction to the prized varieties that thrive in harmony with the roots of ancient oaks and chestnuts. Then step into the forest, savoring the crisp air and earthy aromas as you watch the dogs’ remarkable instincts at work and share in the thrill of unearthing these rare treasures. After the hunt, return to the warmth of the kitchen for an aperitif and a lesson in cleaning and storing truffles. The experience culminates with a sumptuous multi-course meal, where each dish is infused with the rich, distinctive flavor of freshly harvested truffles, paired perfectly with rustic Tuscan ingredients.

This morning, enjoy time at leisure to explore at your own pace, or simply unwind at your hotel and recharge for what is next.

Depart Florence with your private driver and transfer to Castelnuovo Berardenga. Approximate travel time is one hour and 30 minutes.

Savor an unhurried day in the Chianti countryside with time to enjoy Castel Monastero’s resort amenities. Drift through the spa’s serene water area with two indoor pools, including a high-salinity hydromassage pool, then reset in the Finnish and bio saunas, Hammam, Kneipp path, whirlpool, and multisensory experience showers. Linger outdoors by the pool surrounded by gardens and vineyards, or stretch out with a gentle yoga session. Break for Tuscan flavors at La Cantina, set in the medieval wine cellar with a lovely terrace, or plan a refined dinner at Contrada’s gourmet restaurant. If the mood strikes, choose from optional on-site activities such as cooking classes, wine and olive-oil tastings, tennis, cycling, truffle hunting, and even a hot-air balloon flight over the rolling hills.

Indulge in Tuscan vineyards and medieval grandeur on a journey from wine country to Siena’s storied streets. Begin with a stop at a wine estate, where an open-air jeep carries you through rolling vineyards before a guided cellar tour and a tasting of fine wines paired with artisanal cheeses and cured meats. Continue to Siena, a UNESCO World Heritage city where history lives in every stone. With your local guide, stroll cobbled lanes to the graceful Piazza del Campo, famed for its unique architecture and the centuries-old Palio horse race that embodies the city’s passion and pride. Step inside the Duomo, one of Italy’s most magnificent cathedrals, celebrated for its dazzling marble mosaic floor, revealed to visitors only on select summer and autumn weeks. On religious holidays, when the cathedral is closed, the visit shifts to the Palazzo Pubblico, Siena’s grand Gothic town hall, a striking testament to the city’s golden age as a powerful republic.

Soar above the patchwork landscapes of Chianti at sunrise on a private hot air balloon flight, then touch down for a countryside picnic breakfast with regional delicacies and chilled Prosecco. This early morning experience begins with a transfer to the launch site near Castiglione in Val di Pesa, a charming medieval town nestled in the heart of the Chianti region known for its rolling vineyards and historic charm. Watch as your private hot air balloon is brought to life in the soft morning light, then rise gently into the sky with just your party and pilot. Drift peacefully over vineyards, olive groves, and hilltop villages as the first golden rays of sunlight illuminate the Tuscan landscape. After approximately one hour in the air, touch down for a relaxed, open-air breakfast in the countryside before concluding with a private transfer back to your accommodation.

This afternoon, enjoy time at leisure to explore at your own pace, or relax at your hotel.

Depart Castelnuovo Berardenga with your private driver and transfer to Rome. Approximate travel time is two hours and 30 minutes.

When the sun sets, Rome transforms into pure magic, its monuments bathed in golden light and its streets alive with laughter and clinking glasses. Glide through the Eternal City’s most breathtaking sights after dark with your private English-speaking driver, uncovering the city’s nocturnal charm and romantic glow. Admire the Colosseum and Arch of Constantine illuminated against the night sky, the quiet majesty of St. Peter’s Square, and the timeless beauty of Piazza Navona, Campo de’ Fiori, and Trastevere. Pause to enjoy a drink in one of the locals’ favorite haunts, soaking in the vibrant energy that defines Roman nightlife.

Discover one of Italy’s most dazzling Renaissance treasures on a half-day journey to Tivoli’s UNESCO-listed Villa d’Este. This 16th-century masterpiece combines a Renaissance palazzo with some of Europe’s most enchanting gardens, famed for their romantic terraces, ingenious water features, and the spectacular Hundred Fountains. Wander through its celebrated gardens, where romantic terraces, ingenious water features, and the famed Hundred Fountains create a breathtaking outdoor spectacle. Then step inside the 16th-century palazzo to admire grand reception halls and frescoed apartments showcasing the artistry of the Renaissance. Your day concludes with a return transfer back to Rome.

Tucked away on Rome’s historic Tiber Island, an intimate culinary experience awaits within an elegant private residence. Once frequented by celebrities such as Marlon Brando and featured as a filming location for director Michelangelo Antonioni, this distinctive venue offers an atmospheric setting far removed from a traditional restaurant. Arrive by private transfer and enjoy exclusive use of the space, where a chef prepares a four-course Italian dinner featuring seasonal, locally sourced ingredients, introducing each dish along the way. A welcome glass of Prosecco sets the tone for a memorable evening of Italian hospitality in the heart of Rome.

The magnificent Hotel Lungarno is conveniently located on the Arno River in Florence, just a stone’s throw away from the Ponte Vecchio. Imagine the most wonderful rooms and luxury suites, softened by the beautiful light and surrounded by the reflections of the Arno River and the inspirational atmosphere of the medieval quarters of Florence. This luxurious accommodation has been included as one of Travel & Leisure’s 500 Best Hotels, as selected by their readers. The hotel invites you to sample its delightful interpretations of authentic Italian cuisine over lunch or dinner in the unforgettable Michelin Star restaurant, the Borgo San Jacopo. The Picteau Bar in the lounge of this luxury hotel is the perfect place to enjoy a coffee or a cocktail among original art by Picasso and Cocteau.

Amid the enchanting Chianti vineyards lies Castel Monastero, a beautifully restored 13th-century monastery offering a harmonious blend of history and modern luxury. This Tuscan haven features 70 elegantly designed rooms and suites, centered around the monastery’s picturesque piazza and hamlet. Culinary excellence shines at the Michelin-starred restaurant and Cantina, nestled within a historic wine cellar. Savor Tuscan-inspired dishes crafted with creative finesse, or relax with a cocktail and light bites in a serene setting. The spa is a sanctuary of tranquility, combining time-honored techniques with modern therapies drawn from natural ingredients. Whether indulging in a soothing treatment or unwinding by the pool, every moment is tailored to restore balance and vitality. Castel Monastero embodies the Italian lifestyle, offering stillness, connection, and a deep sense of well-being, creating an unforgettable retreat in Tuscany’s timeless beauty.

Imagine stepping into the heart of Rome's iconic Via Veneto, where the charm of "La Dolce Vita" comes alive. At Baglioni Hotel Regina, you're not just booking a stay; you're immersing yourself in a piece of Italian history. This distinguished hotel, once the residence of Queen Margherita of Savoy, offers 95 elegantly appointed rooms, including 23 luxurious suites, each reflecting a harmonious blend of Art Deco sophistication and classic Italian design. Your culinary journey begins at the hotel's restaurant, where traditional Italian and Roman dishes are reimagined with a contemporary flair. The ambiance seamlessly fuses modern design with timeless elegance, setting the stage for unforgettable dining experiences. After a day exploring nearby landmarks like the Spanish Steps and Villa Borghese, retreat to the Baglioni Spa—a serene oasis offering a range of treatments designed to rejuvenate both body and mind. The spa features massage rooms, a beauty room, fitness center, sauna, Turkish bath, and Jacuzzi, ensuring a comprehensive wellness experience. At Baglioni Hotel Regina, every detail is curated to offer you an authentic Roman experience, blending historical grandeur with contemporary luxury.