Beyond the Leaning Tower: An Insider’s Guide to the REAL Florence and Pisa

Not since Benito Mussolini has Italy seen so many arms raised in open-palmed salute.

Tourists line the southern edge of Pisa’s Piazza dei Miracoli in hordes, climbing barricades raised to protect the lawns of Tuscany’s most beloved acre.

As it happens, the mob is not engaged in any sort of political rally. It’s merely a small army of day-trippers posing for photos. You’ve seen the shot: a smiling tourist appears to prop up Pisa’s infamously off-kilter belltower. In the flesh, the scene is flabbergasting. Rows of people with their arms aloft, teeth and eyes shining brightly, their backs turned to the very attraction they came to see.

Modern-day tourism has a production-line intensity to it. Florence alone plays host to upwards of four million tourists a year. Most of them come to Florence hell-bent on seeing the essential sights: Michelangelo’s David, the Ponte Vecchio, the Duomo.

In Pisa, their itinerary is even more concentrated. Many see nothing beyond the tower… and the 100 yards of souvenir stalls between it and the parking lot.

In fact, the very word “tourist” derives partly from Tuscany. As early as the 17th century, the elite cadre of English society—on summer break from the quads of Oxford and Cambridge—would make their way through Florence and Pisa on their way to the classical antiquities of ancient Greece. They called it “The Grand Tour,” lending us the term we use today.

But, though the Italian oeuvres are everything they’re billed to be, it would be a shame to miss the living, breathing atmosphere of the cities in which they’re housed.

Watching the sun set over the Ponte Vecchio in Florence, or people-watching at a sidewalk trattoria in Pisa, is likely to linger in your memory longer than a crowded glimpse of a Botticelli canvas.

Just a few blocks from the tourist crowds of Florence and Pisa lies a wealth of gardens, parks, little-visited architectural masterpieces, historic experiences, and contemporary artworks that go unnoticed by the masses…

Florence: Cradle of the Renaissance and Ground Zero of Tuscan Tourism

The drop-hipped casual arrogance of Michelangelo’s David, the Duomo’s playful strata of pastel green and coral pink marble, the glow of the Ponte Vecchio at sunset… they each deserve their audience.

If you time your trip outside of the high season of June, July, August, and Easter Week (when thousands of Italian and international tourists witness a ritual at the Piazza de Duomo involving an exploding ox-cart), you’ll already go a long way toward having a local experience.

Timing: The Most Effective Hack

When native son of Tuscany Galileo Galilei proposed that the sun did not rotate around the earth, he triggered a landslide of doubt in the Church. If the Church could be wrong about something so fundamental, could it be wrong on other things? Chiefly, could the Franciscan virtues of chastity, obedience, and poverty, perhaps, be misguided, too? (Particularly that one about poverty?)

Trace a line of selfserving thought from Galileo forward, and it leads to everything you see in central Florence. The Medici dynasty of bankers, accumulating wealth on a scale alongside today’s Bezos, Musk, or Gates, made the city of Florence their showroom.

Indulgence, in Renaissance Florence, was the true religion.

But Florence’s greatest beauty—its sunset—isn’t honed by artists. It’s the best free show in Florence. Enjoy it from Ponte Santa Trinità bridge. With wide, flat walls, the bridge is comfortable for sitting (unoccupied seating in the city is extremely difficult to find, so take it where it comes) and it offers the best view in Florence of the Ponte Vecchio and Arno River reflecting the russet light of evening.

Cross the River Arno to Central Florence’s Most “Local” District

The Ponte Santa Trinità is the gateway to Oltrarno. Bohemian and artsy, Oltrarno is the residential neighborhood closest to the central quarter’s galleries, hotels, churches, museums, and retail outlets.

Ignore the popular gelato haunt Gelateria Santa Trinità and instead walk a block west along the river to Gelateria La Carraia. The lines of people waiting to enter might suggest a tourist trap, but if you listen closely, you’ll notice as many speaking Italian as there are foreigners.

That’s a good sign, and you’ll get as good a scoop of gelato here as you’ll find anywhere in Florence.

While you’re on the south side of the river, it may be worth backtracking to the Palazzo Pitti for leather goods designed by the highly-regarded Jennifer Tattanelli at Casini. While Casini may not be as affordable as the leather goods sold to tourists at the Mercato Centrale, you’re less likely to end up with something made in a Chinese sweatshop.

Wine Windows: A Curious, and Satisfying, Hospitality Holdover

Keep an eye out for decommissioned wine windows as you stroll through the Oltrarno district.

Back in the 1600s, the city fathers decreed that landowners could sell wine from their estates directly from their city properties. The families proceeded to do so with gusto, via eye-level portholes cut into the walls of their palatial homes.

Many have been bricked up, some have been converted to mailboxes, but they’re unmistakable once you learn to recognize them.

Some 120 wine windows exist in the city, but Babae Wine Window on Via Santa Spirito is one of only seven or so that still function, since the window is connected to the interior of the restaurant of the same name Get there between 7 p.m. and 8 p.m. for a chance to indulge in a Florentine tradition.

As well as red, white, and rosé, Babae also serves orange wine—made from white grapes left in contact with the grape skin long enough for the characteristic color to occur.

With more body than a typical rosé, the orange wine at Babae has a prominent rusty tickle of oxidation on the palate, along with a rounded, Chardonnay-style fruitiness.

Find the Restaurants Only Locals Know

The Oltrarno, Sant’Ambrogio, and Porta Romana districts in Florence are central, and historical, but still hidden from the gaze of mass tourism. They’re also home to abundant authentic eateries.

The historic district is simply too crowded for good dining. When you come across a long line of people, you can bet that the joint’s popularity owes more to its Instagrammable performance than to the quality of its food.

One trick is to search for restaurant recommendations in Italian. “Dove mangiare bene a Firenze” (Where can I eat well in Florence?) is a good starting point. You can Google Translate the results. It’s not a foolproof way to get under-the-radar recommendations—I couldn’t get a table at the now-tourist haven of I Brindellone on Piazza Piattellina, for example—but it can lead you in the direction of lesser-known districts with locally-sourced ingredients and regional specialities in their restaurants.

I suggest beginning in Porta Romana, a district at the southeast corner of the Boboli Gardens. Alla Vecchia Bettola on Viale Vasco Pratolini is best for traditional Florentine cuisine like ribollita bean soup, tagliatelle pasta with cream and black truffle sauce, or the house specialty, Florentine steak—a grilled T-bone cut from fat-marbled, dry-aged beef—but it gets jammed with locals very quickly.

If you can’t get a table, its sister restaurant across the street, Alla Bettolina, serves a limited version of the same menu in a less formal setting. House wine, for example, is served in an oversized Chianti bottle, and your wine bill is calculated by what’s left in the bottle after you’ve finished.

Alla Bettolina’s not exceptionally affordable—nowhere in Florence is—but you can expect two courses with wine to come in under €30 ($32). A similar meal in the historic district of the city might cost twice that.

The menu changes with the seasons, but it’s always authentic Tuscan cuisine—usually a first course of pasta in sauce, followed by a simple grilled meat or fish plate, and a choice of seasonal vegetables as a contorno (side plate).

All that is accompanied, traditionally, by a basket of unsalted bread. Because salt features prominently in Tuscan cuisine (think in terms of salamis and dry-cured hams), local bakers leave it out of the bread. Probably wise.

A Walk With a View

The Porta Romana is, as its name suggests, the site of Florence’s ancient Roman gate and walls.

That gate is worth seeing. It’s also the starting point for a rewarding—if challenging—walk up the grand boulevard of Viale Machiavelli, twisting past the Giardino del Bobolino (not to be confused with the larger Giardino del Boboli) and up into the cypress trees and olive groves of Florence’s hillside.

If you follow the highway upward to Viale Galileo, another 20 minutes’ walk is rewarded with views of the city from the candy-striped Duomo to the Arno valley.

From the viewpoint on Viale Galileo, it’s downhill to the throbbing melée of souvenir stalls and pounding music that is the Piazzale Michelangelo.

Michelangelo’s Other David

The Piazzale Michelangelo has wonderful city views, and at its center is a bronze cast of David that Michelangelo had a hand in producing. Somehow, the bronze version here in the open air, with its centuries of weathering, is actually more impressive than the marble original at Galleria dell’Accademia di Firenze. (Plus, it’s free to view.)

Directly downhill to the west is an often-overlooked gem: the terraced rose garden, with an inviting outdoor bar serving cold beers and Aperol Spritzes at a reasonable price (€5-€7).

The Via del Monte alle Croci winds along crumbling stone walls, handsome farmhouses, and medieval alleys before ending at the Roman walls in the eastern side of the Oltrarno district.

Family-Style Fare Where the Italians Eat

North of the exquisite—but-overcrowded—Basilica di Santa Croce, the Piazza Sant’Ambrogio is an oasis.

The Sant’Ambrogio quarter is a defiantly local district of traditional butchers, bakers, and even a food stall specializing in the definitive Florentine delicacy—lampredotto, or tripe. (Only true Florentines could be enthusiastic about a sandwich filled with the boiled linings of a cow’s stomach.)

Florence’s Humble Culinary Highlight

A culinary highlight of a trip to Florence: Trattoria da Rocco, inside the decidedly workaday Sant’Ambrogio produce market. (An antique/flea market takes place here each Sunday.)

Within its cast-iron and terracotta confines, Rocco and his family dish up hearty Tuscan dishes to a clientele who range from market workers to well-heeled gastronomes.

Think Tuscan classics such as peposo (slow-cooked beef in black pepper sauce) and perfectly executed pasta dishes. House wine is a quaffable Chianti, the panna cotta is delectable, and the menu comes with an English translation that makes it easier to avoid unexpected tripe dishes (always a risk in Florence). Expect to pay around €30 for three courses and a couple of glasses of wine.

Seating is at shared tables on polished wooden benches. I shared a booth with three Italian women celebrating a retirement, and our efforts to converse in any and every language we could muster was a highlight of my time in Florence.

Epic People-Watching, Generous Cocktails, and Free Art in Pisa

Compact, eclectic, and chatty, Pisa looks like an eccentric aunt’s kitchen and feels like a grandmother’s hug. Grand townhouses and palaces line the city’s riverbanks, 55 miles downriver of Florence.

Pisa’s beauty, less formal and imposing than Florence’s, is more approachable than its larger counterpart upriver.

That alone makes it worthy of your time, and the independent-minded traveler would do well to consider making the city a base for further explorations into the region, from the hikes of Cinque Terre to the vineyards of Chianti.

Bear in mind that this is not an either/or conundrum. Pisa is a mere 50 minutes away from Florence via train. It’s an easy day trip to see the Duomo, the Uffizi Gallery, the Michelangelo statues, or any of Florence’s magnificent sights.

In central Pisa, leafy piazzas and snug pedestrianized streets are a catwalk of locals dressed in eye-catching combinations of vintage, high street, and designer styles.

The soundtrack: exuberant Italian conversation, church bells, the crunch of ice in an Aperol glass, and the everpresent tink of spoon upon espresso cup. More impressive is the 13th-century Santa Maria della Spina chapel, just west of the Ponte Mezzo.

Built to house a thorn believed to be taken from Christ’s crown, the church is a masterpiece of the Pisan Gothic.

Hewn from multi-toned marble, adorned with carvings of Christ and the apostles, and almost entirely ignored by tourists, it’s arguably Italy’s finest building. When it was threatened by rising river levels, the whole building was moved brick-by-brick to its current, higher, position.

Just south of Santa Maria della Spina, the Parco Santi Cosma e Damiano is a postage-stamp of green in the patchwork of the city. It’s wonderful to rest on a bench, surrounded by banana plants, cacti, and calm.

Nearby Palazzo Blu is a well-regarded art gallery, with its current exhibition including 20th-century works by Chagall, Kandinsky, and Picasso showing until April 2024 (entry €14).

The Giardino Scotto is a leafy respite from the city, built in the courtyard of an imposing 15th-century fortress. It’s also a good point at which to head toward the Piazza Vittorio Emmanuele II: the unofficial center of Pisa.

Doing so brings you along Viale Francesco Bonaini, a wide thoroughfare lined with niche ethnic stores, family businesses, and affordable Asian, Arabic, and African cuisine like Ristorante Cinese Xin Zhon Guo and Ristorante Senegalese da Mari.

Lunch Without the Tourist Tax

The one thing you must do if you’re in Pisa: find the elusive menu giornale.

A set menu designed for workers on their lunch break, the menu giornale is a chance to eat hearty local fare at a reasonable price.

At L’Alba Rossa on Via Carlo Cattaneo, the chalkboard on the street offers set lunches for €14 or €16, depending on whether you choose a meat main course or the more expensive seafood option.

For that, you get a choice of first course (usually pasta and sauce), a choice of main courses, a side-plate of vegetables or salad, and a coffee to finish. House wine is €2 per glass.

Be warned, you’ll be charged extra for the basket of bread that’s placed on your table without warning. Also for water, if you ask for that. This is standard practice in Italian restaurants, and adds around €4–€5 to the total.

On the upside, a tip is not expected. (Leave a euro or two if you feel inspired.)

Walk it all off with a stroll to the Piazza Vittorio Emanuele I, then fill up on 20th-century pop art. Just on the northwest corner of the plaza, a side street is bookended by Keith Haring’s “Tuttomondo”—a mural painted by the visiting artist in 1989. It’s a complement to the more formal artistic and architectural works in the rest of the city.

Leonardo Café, a terrace bar just across the street, is a top choice for a €5 glass of Aperol spritz after 6 p.m. (In second place: Ars Café on Corso Italia.)

Their buffet of appetizers, which you can enjoy free of charge with every drink, is enough that you probably won’t need another meal that day. (Unless you count a gelato from Coltelli’s.)

Accommodation Tips for the Budget-Conscious Traveler

While neither city is particularly cheap to stay in, hotels in Pisa tend to cost less than their counterparts in Florence… enough to offset the price of the train between cities.

Savings can be made elsewhere, too. At La Bottega del Parco in Pisa, I enjoyed a grilled T-bone steak priced at €40 per kilo. The same dish at a traditional steakhouse in Florence, such as Trattoria da Marione, can cost upwards of €60 per kilo.

For longer-term rentals in both Pisa and Florence, the aggregator site Cozycozy.com lists properties from single rooms to independent villas. In Florence, local agency Pitcher & Flaccomio arranges medium- and long-term rentals in and around the city.

For rentals or hotels in Florence that are close enough to the major sights, but far enough away to be out of the melee, look to the Sant’Ambrogio and Oltrarno districts.

The city’s finest hotels line the northern bank of the Arno between the Ponte Vecchio and the Ponte Carraia, but prices drop in the area northwest of Sant’Ambrogio market, or around the Porta Romana.

Pisa is small enough that there isn’t much difference in prices around the city. The only rules of thumb are that the area immediately around the Leaning Tower is more expensive, and the district south of the river is a little more affordable. But there’s not much in it. As long as you’re north of the train station and south of the Tower, you’re within walking distance of the sights.

And even though they’re hardly an insider secret, online platforms such as Booking.com, Airbnb, or FlipKey list vacation rentals as well as hotels. If you’re staying for three weeks or more, especially outside of high season, don’t hesi-tate to ask for a discount on the published price. Nothing ventured…

Both cities are well served by Italy’s road and rail networks. Pisa’s air connections, though, are the clincher. Its airport serves almost twice as many international routes as Florence… and the terminal is a mere two miles from the center of Pisa, which you can reach by a monorail service for €5 each way.