The Piazzale Michelangelo offers an unmatched view of Florence, so we begin here, then make our way into town. A walk through winding streets takes us to the Uffizi Gallery, where we’re astonished by renowned works of art by Renaissance masters: The Birth of Venus by Botticelli, The Holy Family by Michelangelo, Bacchus by Caravaggio, Adoration of the Magi by Leonardo da Vinci, and more. Art also inspires our ensembles as we explore Florence, a city that calls for the effortless elegance of the Jillian Top, London Pants, and Selena Necklace. 

The hustle and bustle around the Duomo is fitting for Tuscany’s largest and most fashionable city—just around the corner, we find a lively leather market with some of the region's most sought-after shoes, bags, and other handcrafted leather accessories. A stroll over the Ponte Vecchio (“The Old Bridge”) offers amazing views of the Arno River and leads us to the Oltr’Arno, or south bank. Here, the artisans of Florence truly flourish, and artisanal jewelry and woodworking shops are bustling with activity. 

We make time for a day trip to a vineyard or tasting room near one of these villages, coupled with leisurely walks in town and punctuated by an espresso (ask for “caffe”) amidst the energy of a local piazza. We end the evening at dinner in a local trattoria, where pasta, pizza, and wine dazzle the senses at a sensible price. For breathtaking Tuscan views and incredible hospitality, we wind our way up to the quaint village called Cortona.

A meandering stroll through the back streets of Cortona leads up to Santa Margherita, a beautiful basilica with magnificent views of the Valdichiana. We continue up the hill past the church to the Fortezza di Girifalco, wander the grounds, and enjoy a glass of local wine on the terraces where another great lookout is nestled. From casual to fancy, there are plenty of great dinner options in Cortona. We start the evening with aperitivi at a sidewalk wine bar, where it’s customary for complimentary snacks to come with a drink purchase.