The Ultimate Guide to Tuscany

By Jessica Russo

Yes, Tuscany does look just like the movies and postcards. Drive through hilly green vineyards speckled with terracotta-roofed villas, travel back in time as you walk through winding stone streets of medieval villages, and see the iconic landmarks of Florence and Pisa – all while slurping up some creamy gelato, of course!

Tuscany is jam-packed with so much culture, art, cuisine, and natural scenery that it can seem a bit overwhelming. Relax! Take a look at this expert guide that outlines the must-sees, must-dos, and must-eats in order to make your Tuscan vacation a dream come true.

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Ponte Vecchio (and its surrounding bridges) – Florence

The Ponte Vecchio is much more than “just” the oldest bridge in Florence. It’s a bustling pedestrian walkway that’s filled with fine jewelry stores, leather shops, live music, and picturesque views. At the center city base of the bridge, you’ll find the famous Uffizi Gallery, and at the south end of the bridge, you’ll find the beautiful Boboli Gardens. Also on the south side of the bridge, you’ll become immersed in a more relaxed feel of residential streets and authentic trattorias. Your stomach and your wallet will both be happy – the restaurants on the south side of the bridge are less touristy, delicious, and a bit less expensive than popular center-city spots.

Hint: Though the surrounding bridges to the east and west of Ponte Vecchio are not as famous, they offer some of the best views of the city – how would you take photos of the Ponte Vecchio from the Ponte Vecchio?! Just before sunset, head to the Ponte alle Grazie and feast your eyes on an amazing spectacle as oranges and yellows illuminate the famous Ponte Vecchio.

Leaning Tower – Pisa

This historic, and visually mesmerizing, 14th-century tower is a must-see in Tuscany. Go ahead, take one of the iconic “holding up the leaning tower” photos in-front of the tower, then check out the Piazza dei Miracoli, which is home to the Pisa Baptistery and Pisa Cathedral.

Hint: Make Pisa a quick pit-stop on the way to another destination. While it boasts some incredible landmarks that should definitely be seen, you’ll want to spend your time walking around a city with a bit more – let’s say - charm and pizazz. In short, go to Pisa, take some photos, then keep it movin’.

Siena Cathedral and Piazza del Campo – Siena

Take a step into medieval times! Siena’s brick buildings, hilly stone streets, and picturesque architecture will make you fall in love. Be sure to visit Siena Cathedral, a breathtakingly ornate Romanesque-Gothic cathedral, adorned with mosaics, vibrant colors, and incredible sculptures. If you get the chance, go inside! Then, head to the fan-shaped Piazza del Campo, famous for hosting the Palio horse race. Sip on a cappuccino at one of the piazza’s many cafes and take in the view of the impressive Torre del Mangia.

Hint: Siena is known for its sweets! Be sure to try traditional Panforte and some scrumptious Ricciarelli (soft almond cookies).

The Vineyards – Chianti Classico, Brunello di Montalcino, Nobile di Montepulciano

Driving through the Tuscan wine region is like driving through a postcard. You’ll be “oohing” and “awing” at stunning views as you weave through the hilly landscape. Take a long drive, stop for some photo-ops, and treat yourself to a wine tasting at any of the area’s vineyards!

Hint: Try the prototypical Tuscan wine, Chianti, then, try a “Super Tuscan” wine! Super Tuscan is a term used to describe red wines from Tuscany that are often blended with non-indigenous grapes, like Merlot and Cabernet Sauvingnon, which are generally from France. Pair these wines with some pecorino cheese, salame toscano, crostini, and olive oil – hungry yet?

Santa Maria del Fiore - Florence

As you wander through the streets of Florence, you’ll often see the red-orange Duomo peeking out over the buildings. You may even start using it as your “north star,” for sense of direction, as many Florentines do. This grand structure, and the entire Santa Maria del Fiore complex, is absolutely jaw-dropping from afar, and from up-close. These amazingly ornate landmarks hold so much history, and are the works of famous artists Brunelleschi, Giotto, and more. Walk around the surrounding piazza, gawk at the doors of the Baptistery, and hear the “ding-dong” of the church bells.

Hint: Yes, you can actually go inside the Cathedral, Giotto’s Bell Tower, Duomo, and Museum. In order to purchase tickets, head to the Museo dell’Opera del Duomo, located right behind the Duomo. There, you’ll be able to snag tickets and reserve visit times (yay – short lines)! The views from the top of the Dome and Bell Tower are absolute must-sees. Keep in mind, there are no elevators or escalators. The walks involve some narrow staircases and some spiral staircases – so wear sneakers and bring some water. Don’t be nervous – even travelers who are afraid of heights would do it again in a heartbeat. The views are worth it!

Medieval Towers/Rocca di Montestaffoli – San Gimignano

Ah, the magical hilltop town of San Gimignano. Nicknamed “medieval Manhattan,” San Gimignano boasts a picturesque “skyline” of 14 medieval towers or “skyscrapers” that dominate the Tuscan sky. Stroll along postcard-worthy stone streets, walk around the Piazza della Cisterna, admire the castle-like buildings that surround you, and weave in and out of quaint shops selling local goods, like saffron, wine, lavender, and ceramics. Head up to Rocca di Montestaffoli and feast your eyes on breathtaking views of the Tuscan countryside – vineyards, olive trees, and all! Don’t forget to try gelato in San Gimignano – it’s known to be some of the best in the world.

Hint: Unwind with a glass of local Vernaccia wine, a crisp white wine born right in San Gimignano!

Roman Amphitheatre/Piazza del Anfiteatro – Lucca

Feel the victorious spirit of ancient gladiatorial games as you walk through the gladiator’s entrance of the Roman Amphitheatre, nestled right in the heart of charming Lucca! The remains of this amazing structure are well-preserved, and have become the exterior of bustling Piazza dell’Anfiteatro. You’ll immediately be able to make out the arched walls of this ancient, elliptically-shaped arena – think: a smaller, discreet Colosseum that’s now filled with quaint shops and cafes.

Hint: The beautiful city of Lucca is also known for its well-preserved Renaissance walls that encircle its historic city center of cobblestone streets, tree-lined pathways, jaw-dropping churches, and adorable shops and restaurants. Stand on top of the walls and breathe in the history!

There’s something magical about seeing famous artwork in person. You may have seen the renowned works of Botticelli, Giotto, Raphael, da Vinci, Michelangelo, and Caravaggio on TV or in art history books, but seeing “the real thing” right before your eyes evokes a special feeling of awe. Get lost in the wonder of this breathtaking building, which boasts amazing views, ornate décor, intricate architecture, and – oh yeah – The Birth of Venus, Primavera, Annunciation, and tons of other eye-widening paintings and sculptures.

Hint: Not a fan of long lines? Who is!? Buy your Uffizi ticket in advance! Like the Duomo, you can choose to reserve a visiting time. At that specific time, head to the Uffizi and mosey right on in. In order to lessen crowds and noise, the Uffizi only lets a certain number of visitors in at a time. You’ll thank them once you’re inside – tons of room to take photos and gawk at the masterpieces!

Piazzale Michelangelo – Florence

Feel yourself gasp as you gaze out at the stunning view of Florence from this large, hilltop square. Best view of the city? Most would say so. In the center of this 19th-century piazzale (which simply means ‘large piazza’), you’ll find a large, green statue of David – okay, it may not be the real statue of David (which is located in the Accademia Gallery), but it’s still pretty cool. Take a new profile picture, gaze out at the terracotta-colored rooftops, and spot the iconic Duomo and Ponte Vecchio in the distance. Feel a moment of pure wonder as you stare at the city which gave birth to incredible artists and enthralling history. The square is speckled with cafes and gelato stands – what better way to spend an evening than sipping on a glass of Tuscan wine and watching the sun set over the city?

Hint: It’s no secret that if you’re seeing the city from a bird’s eye view, you must be pretty high up. Honestly, the walk – or should I say ‘hike’ - to Piazzale Michelangelo is no “walk in the park.” Although there are stone steps and ramps, it’s an uphill walk that may leave you a bit out of breath. Just below the Piazzale Michelangelo, you’ll find a wonderful rose garden, which makes the perfect pit-stop! The views will absolutely be worth it, just wear comfortable shoe and bring a bottle of water. Think about it this way – a little workout means you can eat more pasta!

Mangia, mangia!



One of the most popular, and most cozy, dishes in Tuscany! This heavy soup contains cabbage, white beans, onions, carrots, and soft bread, and is a delicious way to get through the chilly season.

Bistecca Fiorentina

Usually served rare, this iconic T-bone steak is every meat lovers’ favorite! The Tuscan steak comes from a special cow breed, the Chianina, and is often served alongside roasted potatoes, arugula or “rocket” salad, and/or beans.

Pappa al Pomodoro

A simple, yet scrumptious soup made from the basics: fresh tomatoes, bread, olive oil, garlic, and basil.


What's better than a smorgasbord? A smorgasbord of deliciously fresh Italian food! Order an antipasto and devour a tasty plate of crostini ("little crusts"), pecorino cheeses, salame toscano, prosciutto, and other cured meats. More often than not, the crostini will be topped with traditional chicken liver pate, white bean spread, fresh olive oil, or salty and creamy colonnata lard.

Pappardelle al cinghiale or al lepre

A pasta lover’s dream – thick ribbons of fresh pasta covered in a hearty tomato-filled wild boar or hare sauce. Some of these sauces are also made with a splash of Chianti, Tuscany’s most noteworthy vino! This meaty, noodley masterpiece can be thought of as a lighter, less-cheesey lasagna. Sprinkle some grated cheese on top and enjoy!

Olive oil

I repeat: dip everything in olive oil. As you drive around Tuscany, you'll see endless fields of olive groves. Taste the freshly-picked, sun-ripened olives in Italy's favorite form. Famous for its pungent, fruity flavor, Tuscan extra virgin olive oil is unlike any other. Drizzle it on top of a caprese salad or on a tasty crostini!


Souvenirs you'll want to take home

Ceramics and pottery
Watch sculptors and artists create one-of-a-kind pieces of all different shapes, sizes, and colors! From traditional bright blue and yellow plates to ceramic lemons and flowers, Italian pottery is some of the very best.

Tip: Don't let your beautiful pottery break during your travels! Ask the salesperson for bubble-wrap, or wrap them up in shirts and sweaters in your suitcase.


Keep your eyes out for tons of little purple shops hidden around many corners of Tuscany! Step inside and become bathed in the soothing, floral aroma of lavender. Find dried local plants, hand-made soaps, and more!


This one should be obvious. Come on, you're in Tuscany! Take the flavor of this beautiful wine capital home with you.

Tip: Be sure to check travel restrictions/regulations on alcohol before you happily zip up your bags! Bottles of wine can also add some serious pounds to your luggage, so plan accordingly.

Gold Jewelry

Whether it's from a tiny shop on the Ponte Vecchio or a posh store in Lucca, Italy's gold jewelry is in a league of its own. Find a striking piece to cherish forever!


Who doesn't want Italian leather? Walking the streets of Florence, you'll find endless leather shops and markets - you'll actually be able to recognize the smell of leather in the air! Find an amazing jacket, wallet, purse, or pair of shoes. Every time you wear them, you'll feel like you're walking in Italy!

Carrara Marble

Nestled between Florence and Pisa, you'll come across beautiful mountainous Carrara, known for its stunning, sparkling white and blue-grey marble. Find a beautiful piece that's small enough to pack! Whether it's a soap dish, a bowl, or a figurine, you'll know that it's made of the most authentic Carrara marble that exists!

Keep reading for more unusual things to do in Florence.

Buon Viaggio!

What to Pack

Good sneakers

Leave your fancy heels at home. Of course, everybody wants to look stylish in Italy, but you'll regret not wearing comfortable shoes when you realize that even the walk to the restaurant consists of hilly, cobblestone streets. You'll be doing tons of walking - whether it's on a rocky hiking path or the steps of Brunelleschi's Duomo! If you're traveling in the summer, add on a nice of light sandals for leisurely days.

A zippered purse or backpack

Aside from general comfort and convenience, you'll want to keep your belongings zipped tightly in a purse or backpack to prevent any theives from the thought of pickpocketing. While it's rare, Italy is notorious for petty theft, so by zipping up your stuff, you won't give the bad guys a chance!

A shawl or cardigan

Especially important for women, always keep a shawl or cardigan in your bag if you're interested in visiting churches and other religious sites. To enter the majority of Italy's churches, you must cover your shoulders and your knees - yes, even in the sweltering heat of summer.

Your appetite

Buon appetito! When visiting this foodie fantasyland, you better be ready to eat! Not only will you want to try everything you lay your eyes on, but sit-down Italian meals are generally larger and consist of more courses than American ones. Dinners usually start with a soup or salad, continue with a pasta, then a meat or fish, and then dessert. Just when you thought spaghetti on it's own was dinner, think again!

PS: always save room for gelato.

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