With its exquisite food and drink, incomparable views and rich history and culture, it’s no surprise that Tuscany is one of Italy’s most visited regions. Just like the Renaissance geniuses of Tuscany’s past, our travel experts here at Plum Guide are (humble) geniuses of the modern age. We’ve used our in-depth knowledge of the region to put together this Tuscany itinerary for ten days so that all you have to do is pack. You’re welcome.
Day One and Two: Admire Renaissance delights in Florence
What better place to start a jaunt through Tuscany than in its beautiful Renaissance capital? Florence deserves multiple days to explore, so spend the first two of your itinerary discovering the city’s highlights.
A view of the dome of Cathedral Church Santa Maria del Fiore behind pink flowers, Florence, Italy
Get up early and head to Piazza del Duomo to see Santa Maria del Fiore, the city’s iconic cathedral. Start the day with a workout by climbing the 463 steps to the top of Brunelleschi’s famous dome to snap photos of the views (and catch your breath). For more Renaissance architecture, the Basilica di Santa Croce is home to magnificent frescoes and the tombs of geniuses like Galileo, Michelangelo, Rossini and Machiavelli. In the Uffizi Galleries, marvel over Michelangelo’s Doni Tondo and Botticelli’s Birth of Venus and Primavera, impossible to miss when in Florence.
The next day, pop into Accademia Gallery to see Michelangelo’s David before climbing the Torre di Arnolfo for a classic photo of the Duomo and the Campanile from above. If yesterday’s climb has killed your legs off, follow your stomach to Mercato Centrale instead. Set over two levels, this foodie heaven sells everything from meats and cheeses to pasta and olive oils—there’s even a food court upstairs. Belly full, head to Oltrarno to browse through the galleries and artisan workshops, or relax in the lush Boboli Gardens until sunset, where the best views are found at Piazzale Michelangelo.
Day Three: Experience the charm of Lucca
On day three, head to the nearby city of Lucca. Surrounded by huge Renaissance walls which you can walk or cycle around, the city is a friendly, laid-back place with plenty to see and do. Via Fillungo is the main pedestrian area where you’ll come across quaint shop fronts, opulent palaces and old churches.
Make your way to Piazza dell’Anfiteatro, built on the ruins of an ancient Roman amphitheatre. Grab some lunch here (Ristorante Trattoria L’ Angolo Tondo is a popular spot) before choosing between the Torre delle Ore (207 steps) or the tree-topped Guinigi Tower (233 steps). Whichever one you choose, both offer fantastic views of Lucca and the surrounding countryside. If you don’t fancy any climbing, we don’t blame you—the Orto Botanico Comunale is a large, shaded garden filled with beautiful plants and greenhouses, an arboretum, a herbarium and water features.
Day Four: Take (many) photos in Pisa
Leaning Tower of Pisa and Cathedral at sunset, Tuscany, Italy
A trip to Tuscany without visiting Pisa is like pasta without cheese—what’s the point? Home to the iconic leaning tower and one of Italy’s most famous sights, Pisa calls for you to lose your inhibitions and test out just how cheesy your photos with the tower can get. And before you ask, yes, you can climb the 294 steps to the top. Satisfied with your shots, visit the surrounding Campo dei Miracoli where you’ll find the Pisa Duomo, Baptistery, the Monumental Cemetery, the Duomo museum and the Museum of Sinopie.
From here, stroll along the River Arno to sightsee at a slower pace. With colourful buildings on either side and romantic bridges spanning the river, this is one of the most picturesque parts of Pisa. Come late afternoon, take a drive to Pisa’s nearby seaside towns (Tirrenia and Marina di Pisa are good options) for a sundowner on the beach.
Day Five: Seek beaches and art in Viareggio
Crowds watching the floats pass at the Viareggio Carnival, Tuscany
Halfway through your Tuscany itinerary for ten days, swap the cities for the seaside. Viareggio is one of Italy’s most beloved beach resorts, with endless stretches of sand and azure waters. But Viareggio is more than just a seaside destination—it also attracts lovers of the figurative arts. Along the Margherita Walk promenade, you can see magnificent examples of Liberty and Art Deco architecture from the early 20th century. Elsewhere in the city, the Villa Argentina is an Art Nouveau jewel with interiors to die for.
If you’re here in the spring, you can’t miss the Viareggio Carnival. The locals take it pretty seriously, with festivities lasting an entire month. This is one of Italy’s most famous carnivals, where costumed dancers and marching bands take to the streets, displaying spectacular floats, confetti and streamers. There’s no excuse not to join in with face paint and costumes.
Day Six and Seven: Find your favourite wine in Chianti and Monteriggioni
Spread between Florence and Siena, Chianti is one of Italy’s most renowned wine regions. As it’s a large area (and there are so many wineries to visit), we recommend spending two days here.
Vineyard in Chianti, Tuscany
On your first day, start your wine country explorations with a drive through the countryside, which is made up of vineyard-covered hills and olive groves which stretch into the distance. There are many scenic small towns to visit as you drive through, such as Greve in Chianti and its Wine Museum (and the nearby 16th century Castello di Querceto for a tasting), Panzano in Chianti with its ancient streets, Radda in Chianti for its many wine bars and medieval feel, and Castellina in Chianti with its majestic fortress.
Aerial view of Monteriggioni, Tuscany, Italy
The next day, continue your journey south to Monteriggioni. Once a medieval castle, this impressive walled town is perched on a hill with fantastic views of the countryside from atop its walls. The town still maintains that middle-aged feel with its cobbled streets and buildings, and walking around is like stepping back in time. Monteriggioni is celebrated for its red and white wines, so be sure to take a wine tour in the town’s vineyards and cellars.
Day Eight: Gaze at medieval architecture in Siena
View of Siena, Italy
For more medieval delights, the city of Siena has more than enough sights to satisfy the history nerd in you. Head straight for the 13th-century Piazza del Campo, the beating heart of the city. During the summer, the historic Il Palio horse race takes place in the piazza, a truly thrilling spectacle. When there’s no race, your eyes will be drawn instead to the white and greenish-black marble-striped Duomo di Siena, home to amazingly detailed frescoes and artwork by history’s greatest artists like Donatello, Pinturicchio, Baldassarre Peruzzi, Ghiberti, Pisano, Michelangelo and Bernini.
Because we can’t stop recommending climbing towers in our Tuscany itinerary for ten days, we’re going to suggest scaling the Torre del Mangia for far-reaching vistas of Siena and its surroundings. If we can’t convince you, then the Palazzo Pubblico next door is a worthy substitute where you can spend the rest of the day in Siena’s Civic Museum.
Day Nine and Ten: Live la dolce vita in Val d’Orcia
Farmhouse on a hill in Val d'Orcia, Siena, Tuscany, Italy
The final two days of your Tuscany adventure bring you to the picturesque Val d’Orcia. Just south of Siena, this is the Tuscan countryside that you see in films and photographs. Rolling green hills are separated by winding country lanes bordered by cypress trees; fields of sunflowers and bright red poppies add a splash of colour to the landscape; medieval towns rise out of the mist like a dream.
Spend day nine driving through the countryside, stopping at the quaint little towns that dot the landscape. The UNESCO World Heritage Pienza will enchant you with its stone architecture and pecorino cheese, the spa town of Bagno Vignoni is known for its Roman hot springs, and San Quirico d’Orcia is home to the romantic Horti Leonini Garden.
Tuscany seen from the walls of Montepulciano
On day ten, swing by the town of Montepulciano. Chock-full of lavish Renaissance palazzos, artisan workshops and sumptuous churches, Montepulciano is one of Italy’s (and quite possibly the world’s) finest winemaking regions. That being said, the most appropriate way to end your Tuscany trip is to raise a glass to your time here at one of the wineries—we recommend Boscarelli, De’ Ricci and La Braccesca. This won’t be the last time you visit Tuscany.