Best Tuscany Sites and Towns To Discover on Your Next Visit to Italy

When thinking about top Tuscany sights, the infamous Leaning Tower in Pisa, the magnificent Ponte Vecchio bridge (also home to a spellbinding Michelangelo statue), the gracious Uffizi Gallery that hosts Botticelli masterpieces, the iconic Accademia Gallery at Piazza Pignoria in Florence where a far more spectacular original of David is on display, and delicious award-winning wine are among the first things to pop in mind.

However, there is so much more to see and do in Tuscany than just that! Winding roads snaking through hilly countryside and cypress alleys, chains of medieval villages, ruins of still glorious castellos, patchwork fields and immense waves of green lined with olive trees and vineyards, ancient churches, impressive Renaissance art, heart-stopping sunset views, and imposing cathedrals are a few more features of a Tuscany journey that can transform a quick escape here into a milestone moment in every traveller’s life. In fact, Tuscany is definitely worth visiting for countless more reasons. Below is just an illustrative guide with the best Tuscany sights to add on your must-visit list!

Siena – Where  natural allure meets local culture and history

Yet another of Tuscany’s UNESCO World Heritage Sites, Siena’s historic town centre bewilders with its mediaeval architecture and iconic landmarks. Considered a welcoming option in the heart of Tuscany, Siena is also seducing visitors with both its outstanding natural beauty and the annual Palio Di Siena horse race (the biggest local spectacle held every July or August) that has been taking place at Piazza del Ciampo for several centuries.

As for those appreciating chicness and creativity, Siena is a dream land for Tuscan sights like the cathedral (at Piazza del Duomo), a 12th-century gem with a striking facade in black and white tones and a wonderful collection of sculptures and paintings by local artists who put Siena on the cultural map way before Florence became a pole of attraction with Da Vinci and Michelangelo. Besides the architectural details that certainly surprise, strolling along Piazza del Duomo will also provide you with a lovely contrast of colours as it strikes uniquely against the warm yellows and oranges of the Siena buildings.

Want to inject some adventure into your overall experience? Torre del Mangia and its 300 steps are definitely a challenge worth taking up (you will find it at Piazza del Ciampo). The trade-off for this quite tedious endeavour? The amazing panoramas of the city and countryside and the fantastic details of the palaces from the top!

Apart from that, though, Siena is also a modern city with lots of bars, pubs, street art, and quirky shops for a fun leisure time.

San Gimignano – Unique Tuscan sights and flavours

Admittedly one of the most fetching Tuscany sights, San Gimignano is a charming hill town some 50 kilometres from Florence with wonderful limestone houses, narrow alleys lined with art, jewellery, and wine shops, and stone towers tucked in a vineyard-filled countryside that produces Vernaccia wine, one of the most famous Tuscany wines. Most people come all the way to San Gimignano, though, for its 14 tall towers and original city walls and, of course, to sample the local cuisine.

Indeed, San Gimignano’s gastronomy pleases every taste bud with delicious local cheeses and breads, yummy sweets (the creamiest gelato in Italy is probably served here), wine-tasting experiences, and pizza places that ensure your palate is fulfilled in every aspect. Ending up here is a fantastic way to close a day full of sightseeing, after climbing up the Torre Grossa and soaking up the 360-degree views of the countryside (you may also want to admire the masterworks housed there by infamous Lippo Memmi, Filippino, and more), wandering Piazza della Cisterna, and visiting the Tuscan farmer’s market from where you can pic up top-quality Italian bread, olives, wine, cheese, and local produce, right before sunset!

The Lucca and the Lucca Walls – Medieval allure at its finest

Not far from sublime Florence lies Lucca, one of the most historical Tuscany cities with admirable architecture and a hypnotising natural terrain. What is even more stirring about it, which makes it one of the best sights to see in Tuscany, is its 12-metre high, 4-kilometre-long city walls! Featuring six stately gates that enable visitors to enter and exit the city (and needing a special permit to pass through the gates with your car), what you see now is the fourth restoration of the original Roman wall.

Hands down, one of the best sights to see in Tuscany is Lucca’s historic centre that is nestled in 20-metre-thick, beautifully preserved stone walls whose construction differs significantly from any other walled city in Tuscany. Dating back to the Roman Age, the city of Lucca offers numerous opportunities for outdoor experiences, including jogging, cycling, and walking through the maze-like alleys that welcome visitors with dining gems, street markets, little pastry shops, pizza pasta joints, lovely music venues, delightful coffee bars serving delicious espresso, and fashion boutiques.

As for the captivating picnic-perfect and biking-ideal green spaces around them, these are the doings of Napoleon’s sister (and Princess of Lucca), Elisa Baciocchi, which also offer beautiful views of the enchanting Apuan Alps.

Besides the wonderful vistas and the many outdoor activities available, though, you may want to visit Lucca walls for one (or more) of the many events that take place here and attract thousands of tourists and locals, including the Comics & Games Festival every October, the Summer Festival in July, the Winter Festival in October, the Blues Festival in April, the Jazz Donna Festival in October, the Holly Cross Celebration in September, and the Marcia delle Ville running race!

For the most jaw-dropping views of the countryside, do dare to climb the original 13th-century wooden stairs to the top of Torre Guinigi (around 200 in total) and give yourself a pat on the back for making the effort. Expect sweeping vistas not often seen elsewhere in the world. After all, this is Tuscany…!

Val d’Orcia – Immersing in a spa-like venture

The entire area of Val d’Orcia is now declared a UNESCO World Heritage Site and provides perhaps the most idealised image of Tuscany for being one of the most representative Tuscan sights when thinking about Tuscany and visualising cascading hills and lush patches of green fields, cypress trees, olive trees, and vineyards.

However, apart from the natural charms surrounding this area, Val d’Orcia is also an inviting place to recharge your batteries and rejuvenate your senses by indulging in a refreshing bath at one of the many natural hot springs located here. Of the most visited ones are Vivo d’Orcia, Bagni San Filippo, and Bagno Vignoni.

Tip: You may even combine this natural spa-like experience with a wine-tasting tour, given that Val d’Orcia is the land that gives birth to the most internationally acclaimed local wines produced at regions like Montalcino and Monticchiello. Making a stop at the hot springs can also be a great option when touring the small villages in the Val d’Orcia region, although you will need to prepare yourself somehow for the wonderful peculiarities and special appeal of each one!