Only shop on Via Tornabuoni.
Florence has some great shopping, but head to Via Tornabuoni or any of the shops that line the Piazza del Duomo and you’re sure to pay extra for the location.
Locals don’t like paying for designer labels, so take a cue from them and do your shopping at the markets. The best one is the Ciompi Market in Piazza dei Ciompi. Unlike most of the markets that are only open on certain days, Ciompi is open Monday through Saturday, 9am to 7pm, as well as the last Sunday of the month.
Come in the summer.
It’s not worth it. With scorching hot days, swarms of mosquitoes, and even bigger swarms of tourists, sightseeing in summer is almost a surefire way to ruin your day. The locals who know better escape to the hills or seaside instead.
Springtime is perfect because you can enjoy the city’s gardens and a more moderate temperature, or come for the winter holidays to see the Christmas lights and the famous Santa Croce Christmas Market. In any season besides summer, you’re sure to have less crowds and more peace.
Order the wrong food.
Each region in Italy has its own unique cuisine. Florence is home to Tuscan food, which is definitely different from what you’d eat in Rome. Don’t screw up your trip by ordering basic tourist dishes like pasta al pomodoro, or worse, a salad.
Most classic Florentine meals are simple dishes with a rustic flavor. Try an antipasto of crostini di fegato, thin slices of lightly toasted bread spread with a chicken liver pate. For a primo, try the ragù al cinghiale (pasta with wild boar sauce) or tagliatelle al tartufo (pasta covered in a truffle sauce), a specialty found nearly exclusively in Tuscany.
Afterward, split a bistecca fiorentina with a friend. This mammoth T-bone steak is so thick it’s cooked on its front, back, and side and usually weighs three to four pounds. For the best fiorentina, head to the Trattoria Bordino in Oltrarno.
Use the Ponte Vecchio to actually cross the river.
The Ponte Vecchio is beautiful, a historic landmark, and filled with interesting people, but that doesn’t make it a particularly useful bridge. Connecting the city center with Oltrarno, the bridge also houses the Vasari Corridor, connecting the ancient Pitti Palace with the Uffizi Gallery and Palazzo Vecchio so that the nobles wouldn’t have to walk among the common folk. But even today, you won’t find an Italian on the overcrowded bridge.
Go at least once around sunset to check out the jewelry shops and the beautiful view of the Arno, then stick around to listen to the live music that starts after nightfall. After that, use one of the nearby parallel bridges if you actually need to get somewhere.
Wait in line to climb the Duomo.
If you don’t have a lot of time in the city, climbing the 463 steps to the top of the Duomo’s cupola is definitely not worth it. The Duomo is magnificent, and the view from the top is mesmerizing, but it’s not the only place to catch an awesome view of the city. Skip hours of waiting in the sun, and use the time to hike up to Piazzale Michelangelo for a more relaxed, definitely more satisfying, and free view of Florence. Or, if you have a longer day, take the #7 bus from the train station to Fiesole, a city that sits in the hills above Florence, for a more romantic view.
If you’re still dead set on climbing the Duomo, you’ll likely be able to skip the line if it’s November and you get there at least half an hour before it opens at 8:30am.
Oltrarno, or “the other side of the Arno,” is the neighborhood located across the Arno River, away from the city center. Home to the Boboli Gardens, Palazzo Pitti, and Piazzale Michelangelo, it’s also a vibrant neighborhood with some great shopping. Once the artisan quarter of Florence, it’s still home to dozens of workshops and studios.
You can spend hours talking with the artisans, or shopping for real products from Florence (instead of the mass-produced ones at San Lorenzo Market). The Sarubbi Brothers on Sdrucciolo dei Pitti create handmade prints and hand-drawn maps, or visit Monaco Metropolitana on Via Ramaglianti to learn what it takes to make leather shoes and purses.