Experience The Best Of Tuscany With This Seven Day Itinerary

Ah, Tuscany. A magical land of Renaissance cities, romantic medieval towns and verdant countryside. If you’re planning a trip to this region, you’ve come to the right place. Our travel experts at Plum Guide know Tuscany like the back of their hands, from where to go, what to do and where to stay. We’ve put together this Tuscany itinerary for seven days so you won’t miss out on any of the region’s best sights.

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Kick off your trip in Florence, the beautiful capital of Tuscany. You’re going to want to spend at least two days here, which will give you just enough time to see all its highlights. As the birthplace of the Renaissance, Florence is incomparable when it comes to Renaissance art and history.

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Start day one at the Piazza del Duomo, where you’ll find Santa Maria del Fiore, the city’s famous cathedral. Be sure to book a reservation to climb the 463 steps to the top of Brunelleschi’s famous dome for incredible views over the city. Not up to the challenge? Next door’s Giotto’s bell tower is (only) 414 steps. Back at street level, explore the inside of the cathedral and the baptistery before checking out Ghiberti’s Gates of Paradise and Michelangelo’s Florentine Pietà in the Opera di Santa Maria del Fiore museum. If you can’t get enough of Renaissance buildings, the Basilica di Santa Croce is also worth a visit to see its magnificent frescoes and view the final resting place of many geniuses, including Galileo, Michelangelo, Rossini and Machiavelli.

Come late afternoon (the best time to avoid the crowds) and head to the Uffizi Galleries to view masterpieces such as Michelangelo’s Doni Tondo, Botticelli’s Birth of Venus and Primavera. Surrounded by such extravagance, it only makes sense to want to treat yourself to the finest meal in the city—and why shouldn’t you? The three Michelin-starred Enoteca Pinchiorri is a wonderful choice, offering artfully plated dishes inspired by Tuscan tradition.

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The next day, get in early at the Accademia Gallery to see Michelangelo’s David without tourists bumping into you. Next, stroll to the Palazzo Vecchio (Florence’s town hall) to climb the Torre di Arnolfo for that iconic photo of the Duomo and the Campanile. The palazzo is worth exploring in itself, boasting extravagant interiors and ancient Roman ruins down in the basement.

If you’re all building-ed out, take a moment to relax and watch street artists perform in the Piazza della Repubblica. Follow your stomach to Mercato Centrale, heaven for gourmands. Set over two levels, the ground floor market offers stalls selling meats, fresh produce, cheeses, pasta and olive oils—fill your bags with souvenirs before heading upstairs to eat your way around the food court. Outside the market is the San Lorenzo Market, where you’ll find pottery, clothing, souvenirs and various leather goods like bags, belts, wallets and jackets.

In the afternoon, cross over the Ponte Vecchio bridge (more shopping to be had here) to Oltrarno, the ‘newer’ part of the city. Spend some time in this vibrant neighbourhood, popping into the various galleries and artisan workshops, or relaxing in the elegant Boboli Gardens. End the day at Piazzale Michelangelo, the best spot to watch the sunset over the city.

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On day three of your Tuscany trip, head to the cities of Lucca and Pisa. The two are just a 25-minute drive from each other and can be covered in a day. In Lucca, get a feel for the place by walking around the Renaissance walls which encircle the city. Head into the town via the nearest gate and wander down Via Fillungo, the main pedestrian drag, to explore the sights of Lucca’s laid-back town centre. Grab some lunch at one of the cafes around the Piazza dell’Anfiteatro—you’ll need the energy—before climbing Torre delle Ore or the tree-topped Guinigi Tower for incredible views of the city.

Photos snapped, head back down and drive to Pisa. No trip would be complete without seeing the iconic leaning tower in real life, and if you still have the energy, you can even climb the 294 steps to the tilting top. The surrounding complex of Campo dei Miracoli, or Field of Miracles, is a wonderful collection of Romanesque, Gothic and Early Renaissance architecture. These monuments include the Pisa Duomo, Baptistery, the Monumental Cemetery, the Duomo museum and the Museum of Sinopie. It doesn’t take too long to see Pisa’s top sights, so we recommend ending the day at one of Pisa’s nearby beaches (Tirrenia and Marina di Pisa are good options) for sunset.

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On your fourth day, head to the medieval towns of Volterra and San Gimignano. Porta all’Arco is Volterra’s ancient gateway and main landmark, dating back to the 3rd century. Zig-zag your way upwards to the Piazza dei Priori in the heart of the Volterra. This is where you’ll find the Palazzo Pretoria as well as the cathedral of Santa Maria Assunta, the Etruscan Museum, and the Etruscan walls and gates. Be sure to check out Volterra’s Roman ruins, including its impressive amphitheatre from the 1st century.

Next, journey on to San Gimignano, one of the most visited places in Tuscany. Once home to 72 towers built by the town’s wealthiest families, only 14 remain today—you can either attempt to climb them or admire them from street level. There’s plenty to do in San Gimignano, but first, drop by Gelateria Dondoli for a scoop (or three) of their famous gelato. The Piazza del Duomo is the central square where you’ll find most of the town’s attractions, such as the Civic Museum located inside the Palazzo del Popolo. The Duomo itself is worth popping into, housing stunning frescoes from Early Renaissance luminaries. At night, the town transforms into a magical place with the monuments and towers all lit up, and the winding streets glow under warm street lights.

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It wouldn’t be a real Tuscany itinerary for seven days without including Chianti. This area between Florence and Siena is one of the world’s most renowned wine regions. Each bend in the road opens up to vineyard-covered hills and olive groves stretching as far as the eye can see. Of course, it would be rude to visit Chianti and not sample its finest offerings. As you drive along, you’ll pass signs signalling wineries which you can visit for a tasting. This is the Chianti region, so you can’t go wrong—just be sure to have a designated driver.

We also recommend stopping by various small towns in the area, such as Greve to visit the Wine Museum (and the nearby 16th century Castello di Querceto for a tasting), Panzano in Chianti to walk its ancient streets, and Castellina in Chianti with its impressive fortress. With all that wine in you, it’ll be the best sleep you’ve ever had.

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In search of medieval charm? The picturesque city of Siena is your best bet. The city centre is perched on a hill, so expect to do some climbing, but it’s quite compact, and its main attractions are close to each other. The 13th-century Piazza del Campo is the beating heart of the city, home to the legendary Il Palio horse race, which takes place twice a year during the summer. During the rest of the year, the white and greenish-black marble-striped Duomo di Siena is the showstopper. This is one of the finest cathedrals in all of Italy, with jaw-dropping frescoes and artwork by history’s greatest artists like Donatello, Pinturicchio, Baldassarre Peruzzi, Ghiberti, Pisano, Michelangelo and Bernini.

If you’re up for another climb (a repeating pattern in this Tuscany itinerary for seven days), the Torre del Mangia offers epic vistas across the whole town. Skipping the workout? We don’t blame you. Next door is the Palazzo Pubblico—home to Siena’s Civic Museum, which is a lovely place to spend a couple of hours before dinner at La Taverna di San Giuseppe, set inside an original Etruscan house dug into the earth.

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On the last day of your trip, take a drive through the breathtaking Val d’Orcia just south of Siena. This is one of the most scenic areas of Tuscany, the kind you see on postcards. Rolling green hills are dotted with medieval hilltop towns; cypress trees line the winding country lanes, and fields of sunflowers dazzle in the sunshine. Pull over at the many romantic towns such as the UNESCO World Heritage town of Pienza, the spa town of Bagno Vignoni and the ancient Castiglione d’Orcia.

Montepulciano is another must-visit town in the region, filled with Renaissance palazzos, artisan workshops and ornate churches which are equally as beautiful inside as they are on the outside. The town is considered to be one of the finest winemaking regions not just in Italy but the world and is a magnet for oenophiles. To test this claim to fame, don’t miss a visit to one of its many wineries, such as Boscarelli, De’ Ricci and La Braccesca.

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