From the sun-drenched vineyards and medieval hill-towns of Tuscany to the art-filled streets and timeless grandeur of Florence, your days unfold with elegance, discovery, and delight.
You’ll stay four nights in a refined countryside hotel surrounded by olive groves and rolling hills, then four nights in a boutique city hotel in Florence—giving you the best of both worlds.
A selection of high-touch inclusions, designed to elevate every moment.
This journey is a refined immersion into the essence of Tuscany and Florence—authentic, personal, and deeply inspiring.
From wandering medieval streets in Siena and San Gimignano to savoring the flavors of freshly shaved truffles in the countryside, and from hands-on cooking in Florence to private guided tours of Renaissance masterpieces, every experience is thoughtfully curated. Expect a seamless blend of guided discovery, intimate culinary moments, and leisure to soak in the beauty of each setting.
You won’t just see Tuscany and Florence—you’ll live them.
Highlights:
Upon arrival at Florence Airport, your private driver will meet you and escort you to your elegant countryside hotel in the heart of Tuscany. Surrounded by olive groves, vineyards, and rolling hills, your hotel offers the perfect setting to unwind after your journey.
Take the rest of the day at leisure — settle into your room, stroll through the gardens, or relax by the pool as you soak in the golden Tuscan light. In the evening, perhaps toast your arrival with a glass of Chianti at the hotel restaurant, savoring your first taste of la dolce vita.
*Hotel Certosa di Maggiano with Breakfast *Private Transfer
After breakfast, set out for a full-day discovery of two of Tuscany’s most enchanting towns.
Your first stop is Siena, a UNESCO World Heritage treasure where history unfolds in the red-brick heart of Piazza del Campo, home of the famous Palio horse race. With your private guide, wander through narrow medieval streets, admire the magnificent Cathedral of Siena, and take in the city’s timeless beauty.
Continue to San Gimignano, known as “The Town of Fine Towers.” Its skyline of medieval towers rises above sun-drenched vineyards and cobblestone lanes filled with artisan boutiques and gelaterias.
Stop at a local family-run winery for a seated lunch and wine tasting, featuring saffron — San Gimignano’s prized spice — woven into a delicious Tuscan menu.
Return to your countryside hotel by late afternoon and enjoy an evening at leisure.
*Hotel Certosa di Maggiano with Breakfast *Private Transfer *Private guide *Saffron Lunch
This morning, experience an authentic slice of Tuscan life with a truffle hunting adventure led by an expert hunter and his trusty dogs. Walk through oak and chestnut woods, learn the secrets of finding these culinary treasures, and immerse yourself in the traditions of truffle hunting.
Afterwards, enjoy a gourmet truffle-themed lunch prepared with freshly discovered truffles, paired with fine local wines.
*Hotel Certosa di Maggiano with Breakfast *Private Transfer *Truffle Hunt with lunch
Today’s journey takes you through the rolling landscapes of the Val d’Orcia, one of Tuscany’s most photographed regions.
Begin in Pienza, a Renaissance gem and the birthplace of world-famous Pecorino cheese. Visit a local organic cheese farm for a guided tasting and tour, learning how this flavorful cheese is crafted — from fresh milk to aging cellars. Enjoy a light lunch featuring Pecorino paired with honey, chutneys, and local wines.
Continue to Montepulciano, a hilltop town celebrated for its elegant architecture and Vino Nobile wines. Enjoy some free time to stroll, shop, or relax in one of its panoramic cafés.
*Hotel Certosa di Maggiano with Breakfast *Private Transfer *Cheese tour & Tasting
After breakfast, check out and bid farewell to the countryside as you make your way toward Florence — but not before one final Tuscan treat. En route, stop at a boutique Chianti winery for a tour, tasting, and traditional lunch, where you’ll savor the flavors of Tuscany’s most famous wine region.
Arrive in Florence by afternoon and check into your centrally located hotel. Enjoy some time to settle in and take an evening stroll along the Arno River, perhaps stopping for dinner near Piazza Santo Spirito — a local favorite.
*Grand Hotel Cavour with Breakfast *Private Transfer *Chianti Wine tour with lunch
Begin your exploration of Florence with a private 3-hour walking tour led by an expert local guide.
Discover the Duomo, with Brunelleschi’s masterpiece dome; stroll through Piazza della Signoria, Florence’s open-air museum of sculptures; and cross the Ponte Vecchio, where jewelers still craft treasures by hand. End your visit at the Accademia Gallery, home to Michelangelo’s iconic David.
Enjoy the afternoon at leisure — shop for leather goods, visit hidden artisan workshops, or relax at a café with a view. Dinner is at leisure tonight in one of Florence’s traditional trattorie.
*Grand Hotel Cavour with Breakfast *Private Guide *Michelangelo’s David tour
This morning, discover Florence’s creative soul with a walking tour of local artisans. Visit workshops where leatherworkers, jewelers, and paper marblers keep ancient crafts alive — each telling the story of a tradition passed down through generations.
In the afternoon, step into the kitchen at MaMa Florence Cooking School for a private hands-on cooking class. Under the guidance of a professional chef, prepare a full Tuscan menu featuring seasonal ingredients, fresh pasta, and classic dishes.
Conclude with a convivial dinner where you’ll enjoy your creations paired with excellent regional wines.
*Grand Hotel Cavour with Breakfast *Private Artisan Tour *Hands-on Pasta Cooking Class with dinner
Your final full day invites you to savor Florence at your own pace. Sleep in, enjoy breakfast at the hotel, and perhaps revisit a favorite museum, shop for local crafts, or relax at the Mercato Centrale for gourmet treats and souvenirs.
In the afternoon, take in the sweeping views from Piazzale Michelangelo or simply enjoy an espresso in a sunlit piazza.
Tonight, gather for a farewell dinner at a traditional Florentine restaurant, raising a glass to your unforgettable Tuscan adventure.
*Grand Hotel Cavour with Breakfast *Dinner reservation in Florence Trattoria
After breakfast, your private driver will accompany you to Florence Airport for your departure. Though it’s time to say goodbye, you’ll leave with hearts full of memories — the taste of Pecorino, the scent of vineyards at dusk, and the timeless beauty of Tuscany and Florence.
*Private Transfer
