The Very Best 5 Day Tuscany Itinerary

Tuscany is blessed with everything you could want in an Italian getaway: undulating countryside, romantic villages, vibrant cities and exquisite food and wine. But with so much to see, how can you pack it all into just five days? Lucky for you, the travel gurus at Plum Guide are the real deal when it comes to itineraries. We've traversed the entire region, collating all the best things to see and do into this Tuscany itinerary for five days. This will enable you to make the very most of your time in Tuscany – all that's left to do is pack your stretchiest pasta-friendly pants.

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When travelling to Tuscany, you'll most likely arrive in Florence, so it makes sense to start your itinerary here. You could easily spend a whole week in Florence and not run out of things to do, but if you're pressed for time, one day in the city is doable to see its main sights. If entering museums and attractions, we highly recommend booking your tickets in advance to save time on the day.

Start the morning at the Piazza del Duomo, home to Santa Maria del Fiore, the city's famous cathedral. For far-reaching views over the city, climb (more like 'hike') the 463 steps to the top of Brunelleschi's famous dome. Back at street level, explore the inside of the cathedral and the baptistery before heading to Basilica di Santa Croce for its magnificent frescoes. This is also the final resting place of Galileo, Michelangelo, Rossini and Machiavelli. Of course, no visit to Florence would be complete without popping into the Uffizi Galleries to see its masterpieces, namely Michelangelo's Doni Tondo to Botticelli's Birth of Venus and Primavera.

After lunch, you can continue sightseeing at the Accademia Gallery to see Michelangelo's David or head to the Palazzo Vecchio for iconic photos of the Duomo and the Campanile from atop the Torre di Arnolfo. Alternatively, if you want to get a little retail therapy in, the streets of Via Roma and Via dei Calzaiuoli are the main shopping hubs. Mercato Centrale is heaven for foodies, complete with a food court upstairs. The surrounding streets of San Lorenzo Market are excellent for pottery, souvenirs and leather goods, and for artisan workshops, cross over the River Arno to the Oltrarno district.

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On day two, combine a trip to the cities of Lucca and Pisa. The two are just a 25-minute drive from each other and can easily be covered in a day. Start in Lucca, a lovely city surrounded by well-preserved Renaissance walls. Walk along these walls and admire the views before entering via the nearest gate. The crooked, medieval Via Fillungo is the main pedestrian area, where you'll come across charming shopfronts, ornate palaces and old churches. The bustling Piazza dell'Anfiteatro is the best place for a bite at one of the cafes around the perimeter of the plaza. If you loved climbing the domes and towers in Florence, you'll want to climb either the Torre delle Ore or the tree-topped Guinigi Tower (or both if you've had too much gelato).

Back on solid ground, and continue your journey to Pisa. It would be rude to visit Tuscany and not get at least one photo with the Leaning Tower of Pisa, no matter how cheesy. If your legs still work after climbing Lucca's towers, why not add Pisa's iconic column to your list? It's a mere 294 steps to the top. Surrounding the tower is the Campo dei Miracoli or Field of Miracles. Pisa is home to some of the country's most exquisite architecture. In this complex, you'll find a wonderful collection of Romanesque, Gothic and Early Renaissance architecture, including the Pisa Duomo, Baptistery, the Monumental Cemetery, the Duomo museum and the Museum of Sinopie. When you've finished exploring the Campo dei Miracoli, take a walk through the city and cross the Mezzo Bridge, which offers photogenic views of the River Arno.

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Did you think we wouldn't include wine tasting on our Tuscany itinerary for five days? Chianti is one of the world's most famous wine regions, where pretty farmhouses are dotted around vineyard-covered hills and olive groves. Wineries are spread across the region, and as you drive through, you'll spot them signposted along the roads—many of them set within grand castles dating back to medieval times. Our favourites include Castello Di Brolio, Castello Sonnino and Castello di Querceto. If you don't have a designated driver, a fun way to combine wine and sightseeing is to take a cycling tour of the Chianti region.

Just outside the region (there are no precise borders) is the impressive walled town of Monteriggioni. Perched on a hill, the town started as a castle during medieval times, its mighty towers visible for miles. The cobbled streets haven't changed much to this day, and visiting here is like stepping back in time. Walk around the city walls to see the town and the countryside from above before checking out the Armoury Museum for medieval and Renaissance weapons. If you happen to visit in July, don't miss the Medieval Festival, where the whole town dresses up in medieval finery to play games, watch falconry displays and eat to their heart's content.

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For more medieval discoveries, make your way to the picturesque city of Siena. Rich in history and art, it's no surprise that Siena is one of Tuscany's most visited places. Head straight into the heart of the city to the 13th-century Piazza del Campo. Lining the perimeter of the square (which is actually shell-shaped) are striking buildings like the Palazzo Pubblico (home to Siena's Civic Museum), the Torre del Mangia (yes, you can climb it, but there are over 400 steps), Palazzo Sansedoni, Palazzo Chigi-Zondadari, Cappella di Piazza, Loggia della Mercanzia and Palazzo d'Elci.

If you're visiting in the summer, you'll witness the legendary Il Palio horse race, which takes place twice a year in July and August. Contrade (different areas of the city) challenge one another to a thrilling horse race, each rider dressed in their unique contrade emblem and colours. It's a truly riveting spectacle and not to be missed. When there's no race, the white and greenish-black striped Duomo di Siena takes the limelight. It's one of Italy's finest cathedrals which boasts jaw-dropping frescoes and artwork by history's greatest artists like Michelangelo, Donatello, Pinturicchio, Ghiberti and Pisano. Inside the Duomo is the equally breathtaking Piccolomini Library, with its soaring frescoes full of bright colours and details.

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On the final day of your Tuscany itinerary for five days, take it easy and enjoy your surroundings with a drive through the scenic Val d'Orcia. You'll find it challenging to put your camera down as each bend in the road opens up to gentle green hills, fields carpeted with red poppies and towering cypress trees reaching up to the sky. Those who wake up early will be rewarded with epic photos of the sunrise bathing the mist-shrouded hilltowns in a warm glow.

Stop off at the various towns and villages along the way. Some of the most sought-after destinations in the Val d'Orcia include the UNESCO World Heritage town of Pienza, the spa town of Bagno Vignoni and the ancient Castiglione d'Orcia. Montalcino and Montepulciano are both famous for their excellent red wines, San Quirico d'Orcia is home to the romantic Horti Leonini Garden and Radicofani's imposing fortress offers mind-blowing views of the Val d'Orcia, Monte Amiata, the Apennines and the Trasimeno and Bolsena lakes.

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