We’ll kick off the morning with a guided tour of the magnificent Santa Maria del Fiore, an elaborate basilica erected in the 13th century and finished nearly 150 years later. We’ll descend into a crypt, explore the iconic dome that tops the cathedral, and make our way to the top of Giotto’s Bell Tower, where we’ll enjoy sweeping views of the city below. In the afternoon, we’ll head to Biblioteca Riccardiana, a resplendent 17th-century library tucked away in the former palace of the Medici family. Alongside the library’s director, we’ll explore troves of centuries-old historical documents and baroque frescoes. We’ll enjoy a luxurious lunch at the neo-Gothic Ristorante Paoli, where we’ll dine in a room decked out in Art Nouveau frescoes. Later in the afternoon, we’ll head to the Uffizi Gallery for a private, one-hour tour of the esoteric and mystic messages hidden in Renaissance paintings. Once the tour concludes, you can explore the museum at your leisure and take the rest of the evening to explore the city’s many culinary delights on your own.

After a leisurely breakfast, we’ll head to the elaborately decorated Church of Santa Maria Novella, exploring its cloister, wandering the adjoining crypt, and taking a private tour of the historic Pharmacy of Santa Maria Novella—one of the oldest operating pharmacies in the world. Founded by monks in the 13th century, the pharmacy still stocks salves and ointments that hark back to its days of origin. (Consider Seven Thieves Vinegar, smelling salts used by grave robbers to ward off miasma, or Armenian Paper, a kind of incense that burns without a flame.) After lunch, we’ll visit the Museo Opificio delle Pietre Dure, an oft-overlooked museum showcasing an incredible array of pietre dure—intricate engravings in polished precious stones. Time permitting, we’ll visit the nearby Ospedale degli Innocenti, an orphanage dating back to the 15th century that once took in Florence’s overwhelming number of unwanted infants through a revolving door. After a packed day of exploration, enjoy the rest of the afternoon and evening at your own pace.

We’ll hit the road early and head to central Tuscany, stopping first in Pontassieve to wander the vineyards and olive groves of the sprawling Tenuta Bossi villa. The Gondi family, which owns the villa, was one of the most powerful families in Florence throughout the 15th and 16th centuries. Take in the magnificent landscape and, if you’d like, purchase a few delicious souvenirs to take back home. After lunch, we’ll head to Arezzo, a city steeped in history reaching as far back as the Iron Age. We’ll wander the city, admire its medieval architecture, and explore the frescoed Arezzo cathedral. Here, we’ll enjoy a tour and a private organ concert featuring the quick-fingered director of the illustrious Arezzo Organ Festival. Later, we’ll pay a short visit to the San Francis Basilica, with fabulous frescoes painted by Piero della Francesca, a Renaissance mastermind. We’ll enjoy some free time to wander (consider checking out Arezzo’s renowned antiques, wine, and olive oil), then regroup for an evening at the Theatrum Mundi Gallery. We’ll sip cocktails, share a light dinner, and join the gallery’s director for a private tour of its many curious collections, replete with artifacts such as the skull of a triceratops and a Soviet space suit.

We’ll begin today with a tour of the royal Palazzo Vecchio, the former seat of the Florentine government, led by an actor portraying Giorgio Vasari, a brilliant 16th-century architect, painter, and writer from Arezzo. Our personal polymath will guide us through the palace’s secret rooms, alchemy laboratory, and rooftop galleries. Then it’s off to Oltrarno where we’ll cross the famed medieval Ponte Vecchio bridge, visit the Santo Spirito Church, and stroll through the Palazzo Pitti square. In the afternoon, we’ll head to the Torrigiani gardens, which contain a neo-Gothic tower as well as artifacts inscribed with mysterious masonic and Egyptian symbology. We’ll enjoy lunch with the garden’s owner, who will treat us to a meal made with his family’s homegrown vegetables. Once satiated, we’ll head to the palatial home of Massimo Listri, a world-renowned architecture photographer and the official photographer of the Louvre and the Vatican Museums. Devoted to the study of universal beauty, this 16th-century palace now includes over 40,000 images, a sublime collection inspired by the Wunderkammer, Roman archeology, and artifacts from Asia. After taking in this dynamic collection, we’ll relax in Listri’s garden with a glass of local wine.

We’ll kick off the morning with a tour of the extraordinary and ever-mysterious Palazzo dei Visacci. Surrounded by an army of herms depicting particularly solemn-looking Florentine men, the 15th-century palace is an architectural wonder—and the current meeting spot for the Freemasons of Florence. With the help of our guide, we’ll unearth some of the hidden histories and well-kept secrets of this centuries-old society. After, take some time to wander the city and explore some of its most iconic sites at your own pace. We’ll visit Palazzo Gondi, one of the most spectacular private homes in the city—a palace designed by architect and sculptor Giuliano da Sangallo. Situated next to the city’s majestic central square, the home opens its doors to the occasional lucky guest. The resident marquis has extended this invitation to us, and we’ll have the opportunity to explore the residence and sip wine crafted by the family. If you need some air, ascend onto the roof for stunning panoramic views. Tonight, we’ll share a late, lavish dinner at Ristorante Frescobaldi, a restaurant owned by an aristocratic dynasty renowned for its wineries. Here in the lively heart of the Piazza della Signoria—the most famous square in the city—we’ll enjoy a final feast and toast to the adventures we’ve shared.

After nearly a week of exploring some of the world’s most intricate frescoes, hopping from palazzo to palazzo, and dining like royalty, it’s time to bid farewell to this enchanting region and the friends we’ve made along the way. Until our next adventure!