Top 25 best things to do in Tuscany

Tuscany, with its rolling hills, historic towns, and world-class wines, is an idyllic destination for discerning travelers. From private vineyard tours to exclusive spa experiences, this region offers unparalleled opportunities for indulgence. Whether you’re an art enthusiast, a culinary connoisseur, or someone seeking the ultimate in relaxation, Tuscany has something extraordinary for you.

Here’s your guide to the top 25 best things to do in Tuscany, filled with rich experiences that capture the essence of this enchanting region.

Explore Florence: the cradle of the renaissance

Unveil masterpieces at the Uffizi Gallery

Step into the artistic heart of the Renaissance with a visit to the Uffizi Gallery. Avoid the crowds by booking a private, early-access tour with an expert guide who can reveal the hidden stories behind Botticelli’s The Birth of Venus, Michelangelo’s sketches, and Caravaggio’s dramatic canvases. Afterward, enjoy a glass of Chianti on a rooftop terrace with views of the Ponte Vecchio.

The Duomo: a marvel of architecture

Florence’s skyline is defined by Brunelleschi’s Dome, a masterpiece of engineering and artistry. Ascend the 463 steps to marvel at breathtaking views of Florence. Enhance your experience with a behind-the-scenes tour that delves into the history and challenges of constructing this iconic landmark.

High-end shopping and gastronomy

For a dose of luxury, stroll along Via de’ Tornabuoni, where fashion houses like Gucci and Ferragamo line the streets. End your day with a decadent meal at a Michelin-starred restaurant, such as Enoteca Pinchiorri, where Tuscan ingredients meet avant-garde culinary techniques.

Savor the flavors of Chianti wine country

The vineyards of Chianti

Chianti’s rolling vineyards produce some of the world’s most celebrated wines. Opt for a private guided tour at estates such as Castello di Ama or Antinori nel Chianti Classico. These vineyards not only offer tastings but also tours of their ancient cellars, art installations, and insights into the winemaking process.

Exclusive wine tasting experiences

Elevate your wine experience with helicopter tours that whisk you to prestigious vineyards. Indulge in a sommelier-led tasting session that includes rare vintages paired with gourmet Tuscan dishes.

Immerse yourself in Siena’s medieval splendor

Piazza del Campo: where history comes alive

Siena’s historic centre is anchored by the Piazza del Campo, one of Europe’s most beautiful squares. Sit at a café with an aperitivo and watch as the golden sunlight illuminates the square’s medieval architecture. If you’re visiting in July or August, don’t miss the Palio, a thrilling horse race with centuries-old traditions.

The magnificence of Siena Cathedral

Siena’s Duomo is a Gothic masterpiece with intricate marble floors, sculptures by Michelangelo, and frescoes by Pinturicchio. Book a private tour to access hidden chapels and admire the Piccolomini Library’s vibrant frescoes up close.

Visit the leaning tower of Pisa and beyond

The piazza dei miracoli

The Leaning Tower of Pisa is an essential stop, but the entire Piazza dei Miracoli is a treasure trove of architectural marvels. Visit the Cathedral and Baptistery to admire their intricate designs. Opt for a private tour that offers evening access to enjoy these landmarks under a serene, starlit sky.

Stroll through San Gimignano: Tuscany’s Manhattan

The towering beauty of San Gimignano

San Gimignano’s medieval towers offer a glimpse into its affluent past. Climb Torre Grossa for panoramic views of the surrounding countryside. Wander through the town’s cobblestone streets and discover artisan shops selling handcrafted ceramics, olive oils, and local wines.

A gelato lover’s paradise

Don’t miss Gelateria Dondoli, famous for its innovative gelato flavors. Try creations like saffron and pine nuts or Vernaccia wine sorbet—each bite is a celebration of Tuscany’s culinary heritage.

Experience Tuscany from above: hot air balloon rides

Imagine gliding silently over Tuscany’s iconic landscapes at sunrise, with golden light bathing the vineyards, olive groves, and cypress-lined roads. A hot air balloon ride offers an unparalleled perspective of the region’s beauty. After landing, enjoy a champagne breakfast with local delicacies prepared exclusively for your party.

Indulge in thermal spa escapes

The healing waters of Bagno Vignoni

Nestled in Val d’Orcia, Bagno Vignoni is a spa village like no other. Relax in thermal pools that have been soothing visitors since Roman times. For the ultimate indulgence, book a private spa suite at Adler Thermae, where treatments incorporate local ingredients like olive oil and wine extracts.

Discover Val d’Orcia: a UNESCO world heritage site

Scenic drives through rolling hills

The Val d’Orcia is the epitome of Tuscan landscapes. Drive through its winding roads, dotted with cypress trees and rustic farmhouses. Stop at iconic photo spots, including the chapel of Vitaleta and the winding road near Monticchiello.

Explore Pienza: the Ideal renaissance town

Pienza is celebrated for its harmonious design and rich flavors. Wander its charming streets, sample artisanal Pecorino cheese, and enjoy panoramic views of the valley from its fortified walls.

Go truffle hunting in San Miniato

The hunt for culinary gold

Embark on a private truffle hunting excursion in the forests of San Miniato. Guided by expert hunters and their dogs, uncover these prized fungi. Afterward, indulge in a gourmet lunch featuring truffle-inspired dishes, paired with the region’s finest wines.

Enjoy the coastal beauty of Maremma

Beaches and seaside elegance

Maremma’s pristine coastline offers secluded beaches and turquoise waters. For an exclusive experience, rent a private beach cabana or charter a yacht to explore hidden coves and offshore islands.

Tuscan Cowboys

For a unique cultural experience, visit Maremma’s cowboys, known as butteri. Witness their horsemanship during a private ranch tour, complete with a traditional Tuscan barbecue.

Immerse yourself in Montepulciano’s heritage

Vino Nobile and historic cellars

Montepulciano, perched high on a hill, is famous for its Vino Nobile wine. Visit historic wine cellars like Cantina Contucci, carved into the ancient town’s foundations. Arrange a private tasting experience where sommeliers guide you through vintages paired with artisanal cheeses and cured meats.

The splendor of Palazzo Comunale

The town’s Renaissance-era Palazzo Comunale offers breathtaking views from its tower. After exploring, take a leisurely walk through Montepulciano’s charming streets, where local artisans sell handcrafted leather goods and ceramics.

Sail the Azure waters of Monte Argentario

Charter a Yacht along the Tuscan coast

Monte Argentario, a coastal jewel, is best explored by sea. Charter a luxury yacht to uncover hidden coves and pristine beaches, accessible only by boat. Stop for a swim in crystal-clear waters before indulging in a seafood lunch prepared on board by a private chef.

Explore Porto Ercole

Back on land, visit the picturesque town of Porto Ercole. Wander its harbor filled with luxury yachts, enjoy gelato at a waterfront café, or dine at Il Pellicano, one of Tuscany’s most exclusive restaurants.

Cycle along Lucca’s Renaissance walls

Discovering Lucca’s charm

Lucca is a city of elegance and tranquility, best experienced from its perfectly preserved Renaissance walls. Rent a bicycle and take a leisurely ride around the perimeter, stopping at charming cafés and lush gardens along the way.

Opera and history

Lucca is also the birthplace of composer Giacomo Puccini. Visit his home-turned-museum, then enjoy an intimate opera performance at San Giovanni Church for an unforgettable evening.

Indulge in Bolgheri’s super Tuscan wines

The road of cypresses

Bolgheri’s iconic Cypress Avenue sets the stage for a day of indulgence. Visit prestigious wineries such as Tenuta San Guido, the birthplace of Sassicaia, for a private tasting of Super Tuscan wines.

Culinary delights

Pair your wine with a gourmet meal at Osteria Magona, where the region’s celebrated vintages are complemented by dishes featuring locally sourced ingredients like wild boar and seasonal truffles.

Explore Arezzo: Tuscany’s artistic gem

The art of Piero della Francesca

Arezzo boasts one of Italy’s most significant artistic treasures: The Legend of the True Cross, a fresco cycle by Piero della Francesca. Book a private guided tour to fully appreciate the narrative and symbolism of this masterpiece.

Antiques and artisans

On the first weekend of every month, Arezzo hosts a renowned antiques fair. Stroll through the stalls and discover unique treasures, from vintage jewelry to Renaissance-era furniture, while soaking up the vibrant atmosphere.

Witness the drama of the Palio di Siena

A tradition like no other

The Palio di Siena is more than a horse race; it’s a deeply rooted tradition that captures the spirit of Tuscany. Secure a private balcony overlooking the Piazza del Campo for an unparalleled view of the action. A knowledgeable guide can provide context on the rivalries and history behind this thrilling event.

Delve into Cortona’s tranquility

A hilltop haven

Cortona is a picturesque hilltop town with panoramic views of the Valdichiana. Wander through its medieval streets, browse boutique shops, and visit the Museo dell’Accademia Etrusca to learn about the region’s ancient past.

Culinary experiences

For a taste of Tuscan cuisine, dine at Relais La Corte dei Papi, where traditional recipes are elevated to fine dining. Alternatively, take a private cooking class with a local chef to master the art of handmade pasta.

Discover Volterra’s etruscan soul

Ancient history

Volterra is a treasure trove of history, from its Etruscan roots to its medieval and Roman influences. Visit the Etruscan Museum and the ancient Roman theater for a journey through time.

Alabaster craftsmanship

Volterra is famous for its alabaster artisans. Tour a local workshop to see how this luminous stone is transformed into exquisite sculptures and decorative pieces, and perhaps commission your own bespoke creation.

Attend the Puccini Festival in Torre del Lago

Opera under the stars

Every summer, Torre del Lago hosts the Puccini Festival, an open-air opera experience set against the backdrop of Lake Massaciuccoli. Reserve VIP seating for the best acoustics and views, and enjoy a pre-show dinner at a nearby lakeside restaurant.

Relax at Lake Trasimeno

Private sailing adventures

Although technically in Umbria, Lake Trasimeno is a serene escape near Tuscany’s border. Charter a private boat to explore the lake’s tranquil waters and visit its charming islands, such as Isola Maggiore, known for its historic charm and lace-making tradition.

Marvel at San Galgano’s mystical abbey

An enchanting ruin

The Abbey of San Galgano is a striking, roofless Gothic church surrounded by rolling hills. Nearby, you’ll find the Sword in the Stone, a legendary relic that inspired the tales of King Arthur. Visit at sunset for a truly magical atmosphere.

Savor Montalcino’s Brunello wines

Exclusive winery tours

Montalcino is synonymous with Brunello, one of Italy’s most prestigious wines. Arrange a private tour of renowned estates like Biondi-Santi or Casanova di Neri to sample these exceptional vintages paired with locally sourced dishes.

The fortress of Montalcino

Climb the fortress walls for panoramic views of the vineyards and valleys, then stroll through the town’s charming streets to discover artisanal shops and cafés.

Attend a Tuscan cooking workshop

Master Tuscan Cuisine

Join a private cooking workshop hosted in a historic villa or farmhouse. Learn to prepare classics like pici pasta, Tuscan bean soup, and cantucci biscuits. The best part? Savoring your creations paired with handpicked wines in a beautiful outdoor setting.

Photograph Tuscany’s iconic landscapes

Capture picture-perfect moments

Tuscany is a photographer’s dream. Hire a professional photographer to guide you to the most photogenic spots, from cypress-lined roads in Val d’Orcia to golden sunflower fields near Arezzo. Whether you’re a seasoned photographer or a casual enthusiast, the region offers endless inspiration.

Stay in a Luxury Villa with The Thinking Traveller

Experience Tuscany like never before with The Thinking Traveller’s exclusive portfolio of luxury villas. From infinity pools and private vineyards to panoramic terraces, our properties offer unparalleled comfort and style.

Enhance your stay with bespoke experiences, including private chefs, chauffeurs, and tailored excursions like truffle hunting or wine tours. With unique villas you won’t find anywhere else and our expert planning, we ensure your holiday is effortless and unforgettable.

Speak to one of our villa specialists today to begin your journey to Tuscany.

Conclusion

Tuscany offers a tapestry of experiences that blend luxury, culture, and natural beauty. From exploring medieval towns to savoring fine wines, every moment invites you to embrace la dolce vita.

At The Thinking Traveller, we specialize in transforming dreams into reality. Our exclusive collection of handpicked luxury villas, combined with our insider knowledge and bespoke services, ensures your Tuscan holiday is nothing short of extraordinary. Whether it’s organizing private vineyard tours, arranging a personal chef, or curating unique local experiences, we handle every detail to make your getaway seamless and unforgettable.

Let us craft your perfect Tuscan escape. Speak to one of our villa experts today, and start planning a holiday like no other.