Couple walking through Tuscan vineyard with harvest baskets

February 27, 2026

10 Things to Do in Tuscany for Wine Lovers

Senior Travel Designer

Tuscany has a way of getting under your skin. It’s not just the wine, although that alone would be reason enough to visit!

It’s the rhythm of long lunches, the winding roads lined with cypress trees, the way vineyards, villages and olive groves blur into one timeless landscape. For wine lovers, Tuscany isn’t about rushing from tasting to tasting. It’s about context, craft and taking the time to savour where you are.

If you’re planning a trip in 2026, these are the best things to do in Tuscany for wine lovers, blending iconic experiences with SmoothRed-led moments that reveal the region at its most authentic.

Our 10 Favourite Things to Do in Tuscany

1. Learn About Tuscan Winemaking with an Estate Stay

Imagine waking in a beautiful, centuries-old villa to the sound of birdsong. Throwing open the shutters to see rows of vines stretching before you, while rosemary, thyme and lavender scent the air.

One of the most immersive ways to understand Tuscan wine is to stay where it’s made. Tuscany is home to some of Italy’s most celebrated styles, from Brunello di Montalcino and Chianti Classico to Vino Nobile and the bold Super Tuscans. Vineyard hotels allow you to experience these wines in their natural setting, not just in a tasting room.

At Mastrojanni, near Montalcino, you’re surrounded by vines producing Brunello, with opportunities to join guided tastings, walk the vineyards and learn how vintage, altitude and soil shape the final wine.

SmoothRed tip: staying on an estate often means access to informal tastings or behind-the-scenes insights that day visitors don’t get. It’s not only idyllic, but an immersive experience for wine lovers.

2. Embark on a Vespa Tour Through the Tuscan Hills

Few experiences capture the romance of Tuscany quite like exploring it on a Vespa. With the wind in your hair and rolling hills unfolding ahead, it’s a joyful, unhurried way to move through the landscape.

Routes through Chianti and the Val d’Orcia are especially scenic, passing vineyards, stone farmhouses and medieval villages. Some luxury estates, including Borgo Santo Pietro, offer Vespas for guests, making it easy to head out for a half-day adventure.

SmoothRed tip: early morning or golden hour rides are quieter, cooler and far more atmospheric.

3. Take a Traditional Pasta-Making Class

Wine in Tuscany is inseparable from food, and a hands-on pasta-making class brings that connection to life. With our local partners, you’ll learn to make traditional pasta using simple, high-quality ingredients, guided by cooks who treat these recipes as living traditions. Classes often include a shared meal paired with Tuscan wines, helping you understand why certain shapes and sauces work so well with Sangiovese-based wines.

As well as pasta, you can learn to make sauces, risottos, hearty Tuscan stews and even your own gelato during Italian cookery classes. Enjoy the fruits of your labour while looking out over the rolling countryside and sipping a glass or two of wine.

SmoothRed insight: pay attention to texture. Tuscan cuisine is all about balance, and once you notice it on the plate, you’ll start spotting it in the wines too.

4. Cycle From Town to Town, Through Vineyards and Villages

Cycling is one of the most enjoyable ways to explore Tuscany’s countryside. Quiet roads, vineyard views and hilltop towns make every ride feel cinematic. Whether you opt for a single day or a longer cycling tour, the journey becomes just as important as the destination. E-bikes are particularly popular, making Tuscany’s hills accessible without taking away the pleasure of the ride.

Small medieval hamlets, perched upon rolling hills, are one of the defining features of the Tuscan landscape. Unchanged for centuries, wandering these ancient streets is like stepping back in time. These hilltop hamlets, such as San Gimignano, make for great pitstops during your cycle ride. Head to the highest point for mesmerising views over the terracotta roof tiles to the verdant landscape beyond.

SmoothRed tip: plan your route to include a long lunch stop in a small town. Cycling builds an appetite, and Tuscan food is best enjoyed slowly.

5. Unwind in the Thermal Hot Springs at Cascate del Mulino

After days of tastings and travel, Tuscany’s natural hot springs offer pure restoration. Cascate del Mulino, near Saturnia, is one of the most beautiful, with steaming, mineral-rich water cascading over natural limestone pools.

The springs are open year-round and especially inviting in cooler months.

SmoothRed tip: arrive early in the morning or just before sunset to avoid crowds and enjoy the springs at their most tranquil. It’s a perfect counterbalance to wine-focused activities.

6. Think Tastings Are Just for Wine? Try an Olive Oil Tasting

Tuscany produces some of Italy’s finest extra virgin olive oil, and tasting it properly is an education in itself. Structured olive oil tastings compare different cultivars, harvest times and regions, revealing flavours that range from peppery to buttery and green.

SmoothRed insight: olive oil tasting sharpens your palate. Learning to recognise bitterness, fruitiness and spice can actually improve how you taste wine. It’s one of the most overlooked yet enriching things to do in Tuscany.

7. Jump in the Saddle and Explore

The Tuscan landscape is simply idyllic. Rolling hills outlined with rows of cypress and poplar trees, vineyards stretching into the distance, sunburnt wheat fields and tiny hamlets. It’s a landscape begging to be explored – and there are plenty of opportunities to immerse yourself in beauty and adventure.

Horseback riding offers a slower, more traditional way to explore Tuscany’s countryside. Guided rides take you through vineyards, olive groves and woodland, revealing corners of wine estates you’d never reach by car.

SmoothRed tip: morning rides are cooler and quieter, with soft light that brings the landscape to life. Even if you’re not an experienced rider, gentle estate rides are designed to be accessible and deeply relaxing.

8. Enjoy an Unforgettable Vineyard Lunch

In Tuscany, lunch often steals the spotlight from dinner. A vineyard lunch, especially one enjoyed outdoors, captures everything the region does best: seasonal food, estate wines and views that seem to stretch forever.

At Castelfalfi, meals are rooted in local produce and paired with wines grown just beyond the table.

SmoothRed insight: lunch allows you to truly see the landscape you’re tasting. In daylight, the connection between vineyard, food and glass feels immediate and profound.

9. Stroll Through Eight Centuries of History at the Abbey of San Galgano

The Abbey of San Galgano is one of Tuscany’s most striking historic sites. This roofless Cistercian abbey, dating back to the 13th century, stands quietly in the countryside, open to the sky. Walking through its arches feels almost meditative.

SmoothRed tip: visit in the late afternoon when the light softens and the abbey feels especially atmospheric. It’s a picturesque reminder that Tuscany’s appeal isn’t only about indulgence, but depth and history too.

10. Take a Day Trip to the Etruscan Coast and Bolgheri

For a different side of Tuscany, head west to the Etruscan Coast. Here, vineyards meet the sea, creating a distinct microclimate that shapes some of Italy’s most famous Super Tuscan wines.

The village of Bolgheri is a highlight, known for its prestigious estates and iconic cypress-lined road.

SmoothRed insight: combine a morning tasting with an afternoon at the beach. The contrast between structured wines and coastal ease is part of what makes this area so special.

Where to Go in Tuscany

With everything from rolling vineyards and soft-sand beaches to Renaissance art and dinky hilltop towns, this iconic Italian region really packs a punch. You could spend entire months in the Tuscan region and still find new things to discover. Assuming you probably don’t have that long, here’s where to visit depending on what your dream trip looks like.

For wine lovers

Montepulciano & Montalcino: Renowned for their rich, red wines, these towns come alive during the autumn harvest, making this an ideal time to visit. Montepulciano is synonymous with Vino Nobile di Montepulciano, a prestigious red wine made primarily from Sangiovese. The town plays host to few underground cellars, with tastings and tours available. In Montalcino, Brunello di Montalcino is king and this powerhouse of a wine draws in oenophiles from far and wide.

Chianti Region: With picturesque vineyards and rolling hills, spring or early autumn offers a perfect balance of beauty and wine tasting opportunities. World-renowned for its wine of the same name, this delightfully hilly region stretching between Florence and Siena is a must-visit for any wine lover.

For art and history buffs

Florence: Rich with Renaissance treasures, Florence can be enjoyed year-round but it’s especially gorgeous during autumn and winter when the city is quieter. The city’s celebrated museums, including the Uffizi Gallery and the Accademia, can be enjoyed with fewer crowds between November and February.

Siena: Another medieval masterpiece, Siena is home to the iconic Piazza del Campo, the Torre del Mangia and the Duomo di Siena. Visit in spring or autumn to comfortably explore the historic streets, spectacular architecture and atmospheric piazzas.

Combine a trip to the medieval town of Siena with the blissful relaxation of the Chianti Hills on our 5-day Discovering Siena and Chianti wine tour.

For foodies

Tuscany is a gourmet destination par excellence. Renowned for its sensational slow food, Tuscan cuisine is simple, often rustic, with local, seasonal produce at its heart.

Pienza: Renowned as Tuscany’s ‘cheese capital’ for its Pecorino di Pienza (a rich, sharp sheep’s milk cheese).

Florence: The beating heart of Tuscan cuisine, sample Bistecca alla Fiorentina and Pici (hand-rolled pasta, often served with wild boar cinghiale ragù).

From bountiful fruit and veg to wild game and a coastline abundant with fish and seafood, Tuscan cuisine enhances the natural flavours and quality of the ingredients by doing as little to it as possible. From countryside trattorias to Michelin-starred restaurants, all our Tuscany wine tours give you the opportunity to savour the true tastes of the region.

For romantic escapes

Val d’Orcia: Extending from the hills south of Siena to Monte Amiata, Val d’Orcia is perfectly suited to romantic escapes. Famous for its rolling hills, cypress-lined roads and picturesque villages, we think it’s breathtaking in spring and autumn. You’ll find some of Tuscany’s most prestigious and sought-after red wines here, too.

Cortona: A charming hilltop town, perfect for couples looking to enjoy Tuscany’s beauty without the crowds. As one of the region’s oldest hill towns, you can expect winding cobblestone streets, charming trattorias and sweeping valley views.

For beach and sun seekers

Maremma Coast: This unspoiled stretch of southwestern Tuscany is ideal for sun seekers. Visit in June or September when the weather is ideal and the summer crowds have thinned out, where you can enjoy relaxing beach days and quaint coastal villages.

Elba Island: The largest island of the Tuscan archipelago, its renowned for its pristine beaches and Arcipelago Toscano National Park. A visit here can be combined with the Maremma Coast for history, nature and coastal relaxation.

For wellness and slow travel

Saturnia: This thermal spa towns offers luxurious relaxation, ideal for visits during the cooler months when a soak in warm waters is especially inviting.

Bagno Vignoni: Similarly to Saturnia, Bagno Vignoni is also home to natural hot springs. Both towns get busy during peak tourist seasons, so visiting in the winter is the way to go – the warming waters will counteract the cooler climes.

A few of our favourite wellness estates in Tuscany include Borgo Santo Pietro, Hotel Le Fontanelle and Borgo Pignano.

For active travellers

San Gimignano: Tuscany’s countryside lends itself to active adventures and the countryside surrounding San Gimignano is pretty spectacular. Hike between hilltop hamlets, cycle past vineyards and orchards, or saddle up for a horseback adventure through the hills. And if you love foraging for food, visit during autumn for truffle hunting.

Lucca: The city’s well-preserved Renaissance walls are wide enough to stroll or cycle along, for relaxed, active adventures. Visit during spring to see the surrounding countryside at its best, when Tuscany’s vineyards are at their most verdant and the landscapes are particularly lush.

Overview of Tuscany’s Must-Visit Towns and Cities

City/Town	Best known for	Things to do
Florence	Renaissance masterpieces and iconic landmarks	Visit the Uffizi Gallery, the Accademia and the Duomo. Seek out the city's historic 'Wine Windows'
Siena	Medieval architecture, rolling hills and historic charm	Visit the Duomo, climb Torre del Mangia, see the medieval Piazza del Campo
Pisa	Architectural icons and authentic Tuscan food	Snap the iconic Leaning Tower photo, stroll along the Arno River and wander through Borgo Stretto for local dining
San Gimignano	Nicknamed the 'Medieval Manhatten' for its iconic skyline	Climb the Torre Grossa, sip Vernaccia di San Gimignano and wander the cobblestone streets and sample award-winning gelato
Lucca	Its well-preserved Renaissance walls and foritifications	Visit the Piazza dell'Anfiteatro, cycle along the city walls, wander through the botanical gardens
Saturnia	An ancient spa town with hot springs and waterfalls	Soak in the thermal springs and visit the Terme di Saturnia spa
Elba	Coastal charm and beautiful beaches. The largest island in the Tuscan archipelago	Relax on the beaches, hike dramatic trails and explore the Medici fortresses
Montepulciano	Vino Nobile di Montepulciano and historic wine cellars	Taste Vino Nobile, visit the wine cellars and cycle through surrounding vineyards
Montalcino	Brunello di Montalcino and classic Tuscan landscapes	Tour La Fortezza, wander Piazza del Popolo and taste Brunello di Montalcino
Pienza	Renaissance architecture, sweeping valley views and Pecorino cheese	Indulge in cheese-heavy dishes, such as Pici Cacio e Pepe, visit local vineyards and wander through the historic centre
Volterra	Its rich Etruscan, Roman and medieval heritage	Visit the remarkably preserved 1st-century BC Roman Theatre, Volterra Cathedral and the Medici Fortress

Why Plan Your Tuscany Wine Escape With SmoothRed?

Tuscany is a region that rewards those who take their time. By blending vineyard stays, hands-on food experiences, cultural landmarks and moments of pure relaxation, you’ll discover a side of Tuscany that goes far beyond the postcard views.

Of course, one of the best things to do in Tuscany is simply taste the region’s iconic wines. From Sangiovese and Chianti Classicos to Super Tuscans and Vin Santo dessert wines, we can arrange fully chauffeured tastings of some of Tuscany’s finest wines. These experiences offer not just great bottles, but a deeper understanding of how wine fits into Tuscan life. Slow down, stay curious and let Tuscany unfold around you.

For example, our 6-day Florence to Chianti Wine Experience blends wine tours and gourmet dinners with hiking, biking and Italian cookery classes, giving you a flavour of everything Tuscany has to offer. All of our trips are completely bespoke, so whether you’re visiting for the vines or the views, our Travel Designers will tailor your itinerary accordingly.

Plan Your Bespoke Tuscany Escape

If Tuscany is calling, our travel designers at SmoothRed are here to help you experience it in a way that feels personal, seamless and deeply rewarding. Get in touch to start planning your tailored wine journey.

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FAQs about things to do in Tuscany

What is a must do in Tuscany?

In terms of ‘must do’ things in Tuscany, it’s tricky to pin down just one activity! As wine lovers, we recommend experiencing the region’s wine culture; tour the iconic Chianti Classico vineyards, take part in wine tastings in Montepulciano and stay in a vineyard hotel for an immersive experience. Florence and Siena are jam-packed with cultural attractions, while the Tuscan countryside is perfect for nature lovers and outdoor adventurers.

What is the prettiest town in Tuscany?

The ‘prettiest’ town in Tuscany is very dependent on what you’re looking for. For spectacular views of the countryside and its medieval skyline, San Gimignano is a must-visit. Montepulciano is a favourite among wine lovers, famed for its world-class Vino Nobile red wine. Lucca lends itself to leisurely bike rides along its city walls and boasts impressive Renaissance fortifications. Some of our other favourites include Pienza, Montalcino and Pitigliano. Speak to our expert Travel Designers who know Tuscany’s towns inside out and can help plan an itinerary featuring all of the must-see spots.

How many days do you need to spend in Tuscany?

We recommend spending five to seven days in Tuscany. This allows you to explore both the cities and countryside at a relaxed pace. Our Travel Designers can help plan the ideal Tuscany itinerary, which combines the best of the cities, towns and wine regions.

What is the best month to visit Tuscany?

The best month to visit Tuscany largely depends on what you’d like to do during your stay, as the region can be enjoyed year-round. For pleasant temperatures and fewer tourist crowds, May and September are the best months to visit Tuscany. We especially recommend September (and October) for wine lovers – the grape harvest takes place during these months and the vineyards will be bustling with activity.

Check out our full guide of when to visit Tuscany and speak to our Travel Designers for more advice on when to visit.

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