Meet your private English-speaking assistant outside of airport customs. Waiting with a sign with your name on it, they will direct you to your awaiting private transfer, and accompany you to your hotel for check-in.

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

Explore Florence on a privately guided walk through its UNESCO-listed historic center, where your guide weaves stories and local insight into the city’s squares, bridges, and everyday streets. Move through Cathedral Square, Piazza della Signoria, and across the Ponte Vecchio as your guide draws attention to details and viewpoints many visitors miss, before entering the Accademia Gallery with included tickets. The experience concludes before Michelangelo’s original David, completed in 1504 and unforgettable up close.

Experience Florence’s culinary heritage through insider dining spots that blend timeless tradition with local character. Near Santa Maria Novella, Trattoria 13 Gobbi is beloved by locals for its hearty Florentine fare and nostalgic, vintage charm. In the Sant’Ambrogio district, Cibreo Ristorante & Teatro del Sale offers a multi-sensory dining experience that fuses Tuscan flavors with creative flair and live performance. In the elegant Palazzo Antinori near Via Tornabuoni, Cantinetta Antinori invites guests to dine beneath vaulted ceilings, pairing refined Tuscan dishes with the family’s acclaimed wines. And just steps from the Duomo, Osteria di Giovanni delivers warm hospitality and authentic flavors, with its perfectly grilled bistecca alla Fiorentina standing out as a true local favorite. If you would like assistance arranging reservations at any of these restaurants, your Destination Expert will be pleased to help.

Step into the timeless charm of Tuscany with a journey from Florence to Lucca, a perfectly preserved medieval gem encircled by Renaissance walls and alive with history, artistry, and atmosphere. Your private driver will take you west across the Tuscan countryside to the banks of the River Serchio, where you’ll meet your local guide for a two-hour exploration. Stroll along Lucca’s famed Renaissance Walls, a 2.5-mile circle of ramparts transformed into tree-lined promenades beloved by locals. Admire the striking faÇade and bell tower of Lucca Cathedral, said to house the legendary Volto Santo relic, before continuing into the elliptical Amphitheater Square, built on the foundations of an ancient Roman arena. As you wander, uncover layers of history at sites like the Baptistery of Saints Giovanni and Reparata and soak in the city’s graceful piazzas and palaces. Conclude with an hour at leisure before returning to Florence.

Meet your private driver and vehicle for a transfer to Montepulciano. Approximate travel time is two hours.

Taste Tuscany from pasture to cellar on a gourmet day with your private guide and driver. Begin at a family pecorino producer, where heritage methods shape every wheel. Enjoy a flight of six pecorini paired with a glass of Rosso di Montepulciano. Continue into the Val di Chiana to a working farmhouse that raises Chianina cattle and Cinta Senese pigs. Sit down to a three-course lunch built from the farm’s own products, then tour the property, meet the family, and see the salumi room where their meats are crafted. Finish at an organic winery committed to a light footprint, including select wines made without added sulfites. Join a small-group walk through the vines and cellar, followed by a guided tasting of five estate wines. On the way back to your hotel, stop for a gelato so the day ends on a sweet local note.

Go beneath Montepulciano’s streets with your private guide into a hidden world of Etruscan-carved cellars, silent chapels, and barrels of Nobile quietly aging. Stroll the historic center, then slip through a discreet wine shop and descend about 40 feet into sandstone tunnels that open into a main gallery, vaults and passageways shaped by 16th-century winemakers and used for centuries since. Explore chapels where Nobile di Montepulciano still rests, view a private family collection, and step into a cave that preserves an authentic Etruscan tomb. Your visit culminates with a guided tasting that brings the stories to the glass. Continue to a second historic cellar for another atmospheric tasting, comparing styles and techniques. Emerge to the sunlit lanes with a deeper feel for Montepulciano, its ancient roots below ground and its living wine culture above.

Meet your private driver and vehicle for a transfer to Siena. Approximate travel time is 1 hour and 15 minutes.

Explore Siena’s hilltop charm with a private guide, where everyday life and medieval masterpieces share the same streets. Slip into medieval lanes that open onto Piazza del Campo, the fan-shaped heart of the city. Take in the graceful Palazzo Pubblico and the slender Torre del Mangia, then pause by Palazzo Sansedoni and the sparkling Fonte Gaia. Continue to the Duomo and Baptistery, a Gothic masterwork adorned with treasures by artists such as Pisano, Donatello, and Michelangelo. Along the way, hear how the Palio and the contrade give Siena its spirit. The tour concludes in the historic center with time to wander, shop, or linger over a coffee as you savor the city’s easy charm.

Indulge in a day of culinary enchantment as you depart your hotel to the 12th-century hillside haven of Castello di Volpaia. Unlike others, this is a terra murata, a walled village, preserving its medieval charm. The well-preserved layout within unveils a culinary treasure trove. Engage in an intimate cooking class, unraveling the secrets of crafting perfect Italian dishes with a private chef. This immersive experience blends centuries-old traditions with contemporary flair. After crafting your lunch, savor it in a relaxed setting, expertly paired with Castello di Volpaia wines. Bid adieu to the chef and journey to the captivating village of Radda in Chianti. Enjoy a leisurely stroll before your return drive to Siena. This exclusive culinary escapade seamlessly weaves history, gastronomy, and the scenic beauty of Tuscany for an unforgettable experience.

Follow the scent of crushed olives into Umbria’s hills on a private estate visit near Assisi. Arrive at a stone farmhouse surrounded by nine hectares of silvery trees and meet a local expert for a gentle walk through the groves. Learn how the land is tended, when olives are harvested, and how extra virgin olive oil is produced from fruit to mill. Settle in for a private tasting led by a professional taster, comparing aromas and flavors while learning how to spot top-quality EVOO by its fruitiness, balanced bitterness, and peppery finish. Enjoy a light farm lunch built from estate products, then relax on the scenic drive back to Siena with the flavors of Umbria still fresh on your palate.

Meet your private driver and vehicle for a transfer to Florence Airport. Approximate travel time is 1 hour and 15 minutes.

The Hotel Brunelleschi is located in the historical center of Florence, a stone’s throw from the Uffizi Gallery, the Piazza della Signoria, and one of the world’s most famous shopping streets. The Brunelleschi was included as one of Travel & Leisure’s 500 Best Hotels as selected by their readers and offers rooms and suites, spectacular views of the Duomo, a restaurant, and a gym. The hotel was created within a circular Byzantine tower and a medieval church, entirely reconstructed, but keeping the original characteristics of the buildings. Inside you can find a private museum that has conserved the architectural ruins discovered during the restoration of the buildings. This hotel is also featured at the end of Dan Brown’s The Da Vinci Code.

Villa Cicolina is an enchanting hideaway that was once home to a noble family of Montepulciano. Originally built in the late 16th century, secret gardens, romantic characteristics and sun-kissed hues fill every corner of this charming villa. Guestrooms feature classic style and antique furnishings, boasting fantastic views of the Tuscan countryside and onsite gardens. The Villa's charming onsite restaurant offers cuisine which stays true to Tuscan culinary traditions. Set between century-old olive trees and overlooking the Tuscan landscape around Montepulciano, the travertine infinity pool and the jacuzzi are the gems of Villa Cicolina. During the spring and the summer seasons, the infinity pool and the jacuzzi are open every day until sunset.

Surrounded by great ancient walls and breathtaking panoramic views of Tuscany lies Hotel Athena. Located in the heart of Siena, Duomo and Piazza del Campo are just walking distance away. The Hotel Athena provides rooms fitted with all the comforts you require for a relaxing stay. Visit Il Mangia Restaurant to savor deliciously prepared traditional Tuscan food, all featuring natural and organic ingredients. Ideal for an appetizer at sunset, the San Marco Terrace Bar happily serves guests until late in the evening, featuring all kinds of drinks and snacks. Admire the breathtaking landscape of green hills and the ancient city walls of Siena from the panoramic terrace, a spacious yet intimate environment that is ideal for enjoying an appetizer at sunset or a drink in total relaxation.