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Widely considered the birthplace of the Renaissance, Tuscany boasts centuries of extraordinary art and architecture—not to mention ample mystery. Beginning in the historic capital of Florence, our journey will usher us through elaborately frescoed cathedrals, sprawling palaces steeped in history, and museums full of artwork and mysterious curios. While we’ll delve into the majesty and mythos surrounding some of the region’s most iconic royal residences, we’ll also take the time to trace its lesser-known history through secret society meeting spots, ancient villages, and centuries-old pharmacies. We’ll pepper our journey with Tuscany’s equally exquisite food and drink—tucking into lavish meals, sipping wine from local estates, and sampling some of the region’s finest olive oil as we go.
Welcome to Florence! After taking some time to settle into our historic hotel, we’ll gather for a walking tour of the city. We’ll learn about the medieval past of Florence, its Roman roots, and the myriad myths, mysteries, and supernatural legends that haunt the city. As the sun begins to set, we’ll head to Buca San Giovanni, a beloved Tuscan restaurant that served as a clandestine gathering spot for the Rosicrucian Secret Society in the 20th century. We’ll begin to get to know each other over a hearty dinner and toast to the dazzling palaces, cathedrals, artists—and even a 16th-century polymath—that await us.
Hotel Pendini, Florence
Welcome Dinner
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 Alongside the library’s director, we’ll explore troves of centuries-old historical documents and baroque frescoes.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.
Hotel Pendini, Florence
Breakfast, Lunch
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.
Hotel Pendini, Florence
Breakfast, Lunch
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.
Hotel Pendini, Florence
Breakfast, Lunch, Dinner
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.
Hotel Pendini, Florence
Breakfast, Lunch
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. Tonight 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, sip wine crafted by the family, and enjoy a baroque opera concert. 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.
Hotel Pendini, Florence
Breakfast, Dinner
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!
The cost of this trip is $2,925, based on double occupancy.
Travelers should feel comfortable walking anywhere between two and four miles over the course of each day. You should be comfortable staying on your feet for long stretches at a time, as we’ll be out and about most of each day with time to rest at lunch and dinner, both of which will take place on the later side.
You’re in good company. Solo travelers typically make up about half of our small groups. With curiosity at the center of our experiences, there’s a natural camaraderie that develops over the course of a trip. We have two options for you:
Shared Room (subject to the latest Covid-19 guidelines): You'll be matched with another solo traveler of the same gender.
Private Room: Have your own room, subject to availability, for a supplemental cost of $520. After booking your trip, please request a single room when you fill out your traveler information form and we’ll send a separate invoice for the cost.
You should aim to arrive in Florence on Day 1 by 3 p.m. and depart any time on Day 7. If you decide to extend your stay, your guides would be more than happy to suggest things to do and see on your own!
Most dietary restrictions can be accommodated. Please let us know in advance, and we'll do our best to arrange alternatives.
This trip presents an extraordinary opportunity to explore and support oft-overlooked sites within Florence and throughout Tuscany. Our local partners and collaborators are devoted to the preservation of the region's rich cultural and heritage and ecology. We'll eat at restaurants that support local agriculture and products—and two of them, Buca San Giovanni and Paoli, contribute to local historical businesses, most of them under danger due to increasing gentrification. By visiting small museums such as the Opificio delle Pietre Dure and meeting with local artists, musicians, and artisans, we'll be supporting the preservation of local arts that date back to the Renaissance period.