24 Best Things to Do in Tuscany, Italy: Cities, Hill Towns & Hidden Gems

From world-famous cities like Florence and Siena to quiet hill towns and scenic drives through vineyard-covered hills, Tuscany offers a wide range of experiences, but deciding what to do (and what to skip) can be overwhelming.

We’ve explored Tuscany on two very different trips: a one-week highlights tour with our kids and a longer 10-day visit focused on the countryside and smaller towns. Based on both experiences, this guide covers the best things to do in Tuscany, with a mix of must-see landmarks, scenic spots, and hidden gems to help you plan your trip.

Planning your own trip? Start with our Tuscany Itinerary for 3-day, 5-day, and one-week options, or browse our full Italy Travel Guide if Tuscany is part of a longer trip.

Tuscany At a Glance

BEST THINGS TO DO | Florence, Siena, Val d’Orcia road trip, hill towns (San Gimignano, Montepulciano, Pienza), food & wine experiences

DON’T MISS | Florence + one hill town + a scenic drive through the countryside

IDEAL TRIP LENGTH | 3 to 5 days (highlights) | 7 to 10 days (deeper exploration)

WHEN TO GO | April to June and September to October

GETTING AROUND | Rent a car for countryside and hill towns; trains work well for major cities

WHERE TO STAY | Florence (no car needed) or countryside towns for a quieter experience

April 2026 Update: Added new photos, new links to our Italy content, updated information about truffle hunting, additional food tours and hot air balloon tours, plus new sections on how to plan your time and the best way to get around Tuscany.

Start Here: The Best of Tuscany

If it’s your first time in Tuscany, or you’re short on time, these are the experiences we recommend prioritizing.

First-Time Visit to Tuscany

Don’t miss Florence, Siena, and a drive through the Tuscan countryside (Val d’Orcia or Chianti). This gives you a perfect mix of cities, hill towns, and scenery.

Food & Wine Lovers

Go wine tasting in Chianti or Montepulciano and consider taking a cooking class. Tuscany is one of the best places in Italy for food-focused travel.

Scenic Views & Hill Towns

Visit Pienza, San Gimignano, and the rolling hills of the Val d’Orcia. This is the Tuscany you see in photos.

Short on Time (2 to 3 Days)

Base yourself in Florence and take day trips to Siena and nearby hill towns.

Slower, Off-the-Beaten-Path Trip

Add places like Arezzo, Monteriggioni, or San Quirico d’Orcia for a quieter, less touristy experience.

Want help turning this into a full itinerary? See our Italy itinerary or browse our Italy Travel Guide for more ideas.

Italy Itinerary

10 Day Italy Itinerary: Rome, Florence, Cinque Terre & Venice

On this itinerary, visit Rome, Venice, and the Cinque Terre, and spend 3 days in Florence and Tuscany.

Here is a map of the best places to visit in Tuscany.

What is Tuscany?

Tuscany (Toscana) is a region in central Italy. Florence is the capital of Tuscany and the largest city in the region.

Tuscany is famous for being the birthplace of the Italian Renaissance, for its wine, and for its long list of UNESCO World Heritage Sites.

Famous artists such as Michelangelo, Leonardo da Vinci, Donatello, Cimabue, Giotto, Brunelleschi, Ghiberti, and Andrea Pisano left their mark throughout Tuscany (and Italy), on the cathedrals, baptisteries, and palaces in the cities throughout Tuscany.

This one region is home to multiple wines, including Chianti, Brunello di Montalcino, Vernaccia di San Gimignano, and Vino Nobile di Montepulciano. Visiting the hilltop towns to go wine tasting is one of the best things to do in Tuscany.

Map of Tuscany

Best Things to Do in Tuscany

After two trips to Tuscany, we’ve learned that this region rewards every kind of traveler: the art lover, the foodie, the wine enthusiast, and the one who just wants to drive slowly through beautiful countryside. We’ve organized our list into five sections to help you find what best fits your trip.

Best Cities to Visit in Tuscany

Visit the Historic Center of Florence

Florence is the cultural heart of Tuscany and one of the most iconic cities in Italy, home to masterpieces like Michelangelo’s David, the Duomo, and the Uffizi Gallery. We’ve visited Florence on multiple trips to Italy, and it’s a place that always feels worth the time, especially if it’s your first visit to Tuscany.

Plan to spend at least one to two days exploring the historic center, museums, and viewpoints. Florence also makes an excellent base for day trips to Siena, Pisa, and nearby hill towns.

Sunset at Piazzale Michelangelo

The Florence Cathedral

Plan Your Visit

👉 Add this to your itinerary if it’s your first time in Tuscany or you want easy access to top sights without renting a car.

For the full list, see our 30 Best Things to Do in Florence or our One Day in Florence Itinerary if you’re short on time. Or take a look at our 2 Day Florence Itinerary ↓

Florence Itinerary

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Spend Some Time in Siena

Siena is one of our favorite towns in Tuscany, with a compact medieval center, stunning architecture, and a slower, more relaxed feel than Florence. At its heart is the shell-shaped Piazza del Campo, one of Italy’s most unique squares and home to the famous Palio horse race.

If you only have time to visit one hill town in Tuscany, Siena is our top pick. It offers the perfect mix of history, walkability, and iconic sights, including the Siena Cathedral, one of the most impressive churches in Italy.

Plan to spend at least half a day here, although one full day in Siena gives you time to climb the Torre del Mangia, visit the cathedral complex, and wander the quiet side streets.

Siena

Siena Cathedral

Piazza del Campo

Plan Your Visit

👉 Add this to your itinerary if you want a classic Tuscan hill town experience with iconic sights but fewer crowds than Florence.

Best of Siena

10 Amazing Things to Do in Siena (+Map & Photos)

Here are the best things to do in Siena, with tips we’ve learned from our visits.

See the Leaning Tower of Pisa

Pisa is best known for its iconic Leaning Tower, but there’s more to see here than just the famous photo spot. The Piazza dei Miracoli is home to the tower, cathedral, and baptistery, an impressive collection of white marble buildings and one of the most recognizable landmarks in Italy.

That said, for most travelers, Pisa works best as a quick stop rather than a full-day destination. We saw the highlights in just a few hours, visiting Pisa while traveling from Florence to the Cinque Terre. We share exactly how to do this in our guide to visiting Pisa on a day trip from Florence.

Leaning Tower of Pisa

👉 Add this to your itinerary if it’s your first time in Italy or you want to see one of the country’s most famous landmarks, but plan to spend just a few hours here.

Pisa

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Walk the Lucca City Walls

Lucca is one of Tuscany’s most charming small cities, known for its intact Renaissance walls that completely encircle the historic center. Unlike many Tuscan towns, you can walk or bike along these tree-lined walls for views over the rooftops, one of the most unique experiences in the region.

Plan to spend a few hours to half a day here, often as a stop between Florence and Pisa or as a day trip from either city.

Lunch in Lucca

Lucca

👉 Add this to your itinerary if you want a relaxed, less touristy alternative to Pisa or a charming stop between major cities.

Lucca, Italy

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Best Tuscan Hill Towns to Visit

Climb the Towers in San Gimignano

San Gimignano is one of the most iconic hill towns in Tuscany, famous for its skyline of medieval stone towers that rise above the surrounding countryside. Often called the “Medieval Manhattan,” it offers a very different feel from Siena, with its compact historic center, sweeping views, and unmistakable silhouette.

If you want sweeping panoramic views over the Tuscan hillside, this is our top pick. We’ve been here twice, and climbing the towers for the views never gets old.

This is one of the easiest hill towns to visit from Florence and is a popular stop on day trips through Tuscany. While it can get crowded midday, it’s absolutely worth visiting, especially if you arrive early or later in the afternoon.

San Gimignano

San Gimignano

👉 Add this to your itinerary if you want a classic Tuscan hill town with iconic views and an easy day trip from Florence. We cover what there is to see, do, and eat in our post Best Things to Do in San Gimignano.

Go Wine Tasting in Montalcino

Montalcino is a small hill town in southern Tuscany best known for producing Brunello di Montalcino, one of Italy’s most prestigious red wines. Set on a hilltop overlooking the Val d’Orcia, it combines beautiful views with a more refined, wine-focused experience than many other Tuscan towns.

Compared to places like San Gimignano or Siena, Montalcino feels quieter and less crowded, making it a great place to slow down, enjoy a long lunch, and sample local wines.

Plan to spend a few hours here or pair it with nearby towns like Pienza or Montepulciano as part of a day exploring the Val d’Orcia.

Montalcino

👉 Add this to your itinerary if you’re interested in wine, want a quieter hill town experience, or are exploring the Val d’Orcia. For more ideas, see our guide to the best things to do in Montalcino.

Visit the Wine Cellars in Montepulciano

Montepulciano is a beautiful hill town in southern Tuscany known for its Renaissance architecture, sweeping views over the Val d’Orcia, and its famous wine, Vino Nobile di Montepulciano. Perched on a ridge, the town’s steep streets lead to elegant squares, historic buildings, and viewpoints that are some of the best in the region.

Compared to Montalcino, Montepulciano feels a bit livelier and more visually dramatic, with grander architecture and more to see within the town itself. For us, the highlight was touring the wine cellars beneath the city streets.

Plan to spend a few hours to half a day here, often paired with nearby towns like Pienza or Montalcino as part of a day exploring the Val d’Orcia.

Montepulciano

👉 Add this to your itinerary if you want a classic Tuscan hill town with great views, wine experiences, and more to explore than smaller villages.

Montepulciano

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Explore Lovely Pienza

Pienza is a small hill town in the Val d’Orcia known for its beautiful views, Renaissance architecture, and pecorino cheese. Perched above the rolling hills of southern Tuscany, it offers some of the most iconic scenery in the region, with panoramic viewpoints just steps from the historic center.

Unlike larger towns like Siena or Montepulciano, Pienza is compact and easy to explore in just a few hours, making it a perfect stop on a scenic drive through the Val d’Orcia. It’s also a great place to slow down, enjoy a relaxed meal, and sample local cheeses.

PRO TRAVEL TIP: Pienza, Montepulciano, and Montalcino are all located near each other, so these three towns can be visited in one busy day.

Pienza

👉 Add this to your itinerary if you want classic Tuscan views, a quick but memorable stop, and a relaxed food-focused experience. Get the full list in our guide Things to Do in Pienza.

Spend a Few Hours in San Quirico d’Orcia

San Quirico d’Orcia is one of the most underrated towns in Tuscany, set right in the heart of the Val d’Orcia and surrounded by some of the region’s most iconic landscapes. While it’s smaller and quieter than nearby towns like Pienza or Montepulciano, it offers a more authentic, less crowded experience. For a small town, San Quirico is also home to a surprisingly long list of highly rated restaurants, including a few with Michelin stars.

This is also one of the best places to see Tuscany’s famous cypress-lined roads and rolling hills, some of the most photographed views in the region are just outside of town.

Lunch in San Quirico d’Orcia

San Quirico d’Orcia

👉 Add this to your itinerary if you want a quieter, off-the-beaten-path experience with some of the most iconic scenery in Tuscany.

San Quirico d’Orcia

San Quirico d’Orcia: An Underrated Gem in Tuscany

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Visit Cortona

Cortona is a picturesque hill town in eastern Tuscany, best known as the setting for Under the Tuscan Sun. Perched high above the Val di Chiana, it offers sweeping views, quiet streets, and a more local, laid-back feel compared to some of Tuscany’s more visited towns.

With its stone streets, charming piazzas, and scenic viewpoints, Cortona is a great place to wander without a set plan. It’s especially appealing if you’re looking for a slower-paced experience away from the busier towns in central Tuscany.

Plan to spend a few hours to half a day here, often as a stop when exploring eastern Tuscany or traveling between Tuscany and Umbria.

Cortona

Shopping in Cortona

👉 Add this to your itinerary if you want a quieter, romantic hill town with great views and fewer crowds. We cover what to see and do in our Guide to Cortona.

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Spend Some Time in Arezzo

Arezzo is one of Tuscany’s most underrated cities, offering a quieter, more local experience than places like Florence or Siena. With its sloping streets, historic piazzas, and fewer crowds, it feels more authentic and less polished than Tuscany’s more famous destinations.

We spent time here on our second trip to Tuscany, focusing on smaller towns and the countryside, and found Arezzo to be a refreshing change of pace. It’s a great place to wander, enjoy the architecture, and experience a different side of Tuscany without the crowds.

Plan to spend a few hours to half a day here, often as part of a trip through eastern Tuscany or combined with nearby towns like Cortona.

Piazza Grande, Arezzo

Arezzo antique market

Corso Italia

👉 Add this to your itinerary if you want a less touristy, more authentic Tuscan experience or are exploring eastern Tuscany. Find out what to do, where to eat, and how to plan your one day itinerary in our Arezzo Guide.

Visit Volterra

Volterra is one of Tuscany’s oldest and most atmospheric towns, known for its Etruscan roots, medieval architecture, and quieter, more rugged feel. Perched on a hilltop between Florence and Siena, it offers sweeping views and a much less touristy experience than nearby San Gimignano.

Unlike many Tuscan towns, Volterra feels a bit more raw and historic, with ancient city walls, Roman ruins, and a long tradition of alabaster craftsmanship that you can still see in local shops.

Plan to spend a few hours to half a day here, often paired with San Gimignano or as part of a scenic drive through central Tuscany.

Volterra

Roman theater in Volterra

👉 Add this to your itinerary if you’re interested in history, want a less crowded alternative to San Gimignano, or enjoy towns with a more authentic, slightly rugged feel. Learn how to add this to your Italy itinerary with our post Things to Do in Volterra.

Walk the Walls at Monteriggioni

Monteriggioni is a tiny, walled medieval village that feels like stepping back in time. Completely enclosed by its original stone walls and towers, it’s one of the most unique and well-preserved fortified towns in Tuscany.

Because of its small size, Monteriggioni is best visited as a quick stop rather than a standalone destination. You can walk the entire village in under an hour, but the experience of strolling its quiet streets and climbing the walls for views makes it well worth the visit.

Monteriggioni

👉 Add this to your itinerary if you’re driving between Florence and Siena or want a short, memorable stop that feels very different from larger Tuscan towns.

Best Wine and Food Experiences in Tuscany

Go Wine Tasting in the Chianti Wine Region

Chianti is a wine region that sits to the south of Florence. This wine region, also called Monti del Chianti, includes the provinces of Florence and Siena and extends towards Arezzo, Val d’Orcia, and Pisa.

This wine region is further divided into smaller appellations, including Chianti Classico, Chianti Montalbano, Colli Senesi, and Chianti Rufina, just to name a few.

You can day trip into the Chianti wine region by visiting the towns in this area (such as Siena, Arezzo, Volterra, and San Gimignano) or join a tour that has wine tastings in the vineyards in this area.

One of the best ways to visit the Chianti wine region is on a tour.

This highly rated tour includes a visit to two wineries in the Chianti Classico region with food and wine pairings.

On this half day tour from Florence, visit two wineries in the Chianti wine region. And this tour from Florence includes lunch at a winery plus visits to Siena, Pisa, and San Gimignano.

👉 Add this to your itinerary if you’re a wine lover, foodie, or want to learn more about this region’s wine.

Go Truffle Hunting in Tuscany

Truffle hunting is one of the most unique and memorable experiences you can have in Tuscany. Join a local guide and trained dog to search for truffles in the forest, then enjoy a meal or tasting featuring your finds.

This experience is especially popular in the fall (September through November), when truffle season is in full swing, but it’s offered year-round in several areas of Tuscany. It’s a great way to experience the region beyond its cities and hill towns and get a behind-the-scenes look at Tuscan food culture.

Most tours include a guided walk through the woods followed by a tasting or full meal, often paired with local wines.

This highly-rated tour takes just a few hours and also includes a wine and olive oil tasting.

👉 Add this to your itinerary if you’re a food lover or want a unique, hands-on experience that goes beyond sightseeing.

Go Olive Oil Tasting

Olive oil tasting is one of the most underrated experiences in Tuscany, and one of the best ways to understand the region’s food culture. Tuscany produces some of Italy’s highest-quality extra virgin olive oil, known for its rich flavor, peppery finish, and deep green color.

Many farms and agriturismos offer tastings where you can sample freshly pressed olive oil, often paired with bread, local cheeses, and wine. You’ll also learn how olive oil is produced and what makes high-quality olive oil different from what you find at home.

The best time for this experience is during the harvest season (typically October through November), when you can taste newly pressed oil, but tastings are available year-round throughout Tuscany.

This e-bike tour plus olive oil tasting starts in Florence, so it’s easy to add to most itineraries. On this tour, visit three wineries, tour an olive mill, and have a traditional Tuscan lunch.

👉 Add this to your itinerary if you’re a food lover or want a relaxed, authentic experience that goes beyond sightseeing.

Take a Cooking Class or Food Tour

One of the best ways to experience Tuscany is through its food, whether that means learning to cook traditional dishes or sampling local specialties on a guided tour.

Cooking classes are widely available throughout Tuscany, from countryside villas to city kitchens in Florence and Siena. These typically include hands-on instruction, followed by a meal paired with local wines. This pasta cooking class in Florence gets nothing but stellar reviews (plus it includes unlimited wine 🍷) or you can visit a Tuscan farm and learn how to make pizza or pasta.

Food tours, on the other hand, are a great way to discover regional dishes without doing the cooking. In cities like Florence, you can visit local markets, bakeries, and wine bars while learning about Tuscan cuisine from a knowledgeable guide, as on this street food tour.

Both experiences offer a deeper connection to the region’s culture and are especially memorable if it’s your first time in Tuscany.

Outdoor & Scenic Experiences in Tuscany

Road Trip through Val d’Orcia

Val d’Orcia is one of the most beautiful landscapes in all of Italy and one of the most beautiful we have ever seen. Rolling hills dotted with lone farmhouses, long avenues of cypress trees, and golden fields that seem to glow in the afternoon light. It’s no surprise that this valley inspired the Renaissance painters, or that it’s now a UNESCO World Heritage Site.

The best way to experience Val d’Orcia is by car, driving the winding country roads at your own pace.

Some of the most photographed spots in Tuscany are here, including the famous cypress-lined road leading to Agriturismo Baccoleno and the Cappella della Madonna di Vitaleta, a small chapel sitting alone on a hilltop surrounded by fields. Both are worth going out of your way for, especially in the golden hour before sunset.

The hilltop towns of Montalcino, Pienza, and San Quirico d’Orcia are all located within Val d’Orcia and can be combined into one long day. This is also the heart of Brunello di Montalcino and Vino Nobile di Montepulciano wine country, so wine tasting is never far away.

PRO TRAVEL TIP: Val d’Orcia looks its most dramatic in late April and May, when the fields are a vivid green, and again in early June when they turn golden just before harvest. By midsummer, the fields are plowed, and those iconic rolling hills give way to bare, brown earth, which is still beautiful, but a very different look. If photographing Tuscany at its most lush and vibrant is a priority, late spring is your window.

In September, some fields are plowed, giving this appearance

But not all of the fields are plowed. This photo was also taken in September.

The Gladiator Viewpoint (near San Quirico d’Orcia)

👉 Add this to your itinerary if you want classic Tuscany views, a slower-paced experience, and the freedom to explore beyond the cities.

Take a Hot Air Balloon Ride Over Tuscany

A hot air balloon ride over Tuscany is one of the most unforgettable ways to experience the region. Floating above rolling vineyards, hill towns, and cypress-lined roads at sunrise gives you a completely different perspective of the Tuscan countryside.

Most balloon rides take place early in the morning, when the air is calm and the light is at its best. Flights typically last about an hour and are often followed by a light breakfast or a glass of wine after landing.

This is one of the more expensive experiences in Tuscany, but for many travelers, it’s a once-in-a-lifetime splurge and a highlight of their trip.

Hike in the Apuan Alps

The Apuan Alps are one of Tuscany’s best-kept secrets, offering rugged mountain scenery that feels completely different from the rolling hills of the Val d’Orcia. Located in northern Tuscany, near the coast, this area is known for its dramatic peaks, marble quarries, and sweeping views that stretch all the way to the sea.

This is one of the best places in Tuscany for hiking, with trails ranging from short walks to more challenging climbs. It’s a great option if you want to add some adventure to your trip or see a less-visited side of the region.

👉 Add this to your itinerary if you enjoy hiking or want to experience a completely different side of Tuscany beyond the hill towns and countryside.

Relax in a Hot Spring

Tuscany is home to several natural hot springs, where you can soak in warm, mineral-rich waters surrounded by beautiful countryside. The most famous is Saturnia, known for its cascading limestone pools that create one of the most unique landscapes in Italy.

These thermal waters stay warm year-round and are completely free to visit, making this one of the most relaxing, and memorable, experiences in Tuscany. Arrive early or later in the day for fewer crowds and the best light for photos.

In addition to Saturnia, you can also visit smaller hot springs and spa towns throughout Tuscany, many of which offer a more peaceful, less crowded experience.

Cascate del Mulino | shutterstock.com/travelwild

👉 Add this to your itinerary if you want a unique, relaxing experience or are exploring southern Tuscany.

Unique Things to Do in Tuscany

Stay in a Villa

One of the best decisions you can make in Tuscany is to get out of the cities and spend at least a few nights in the countryside, either in a villa or an agriturismo. Both offer something that no hotel in Florence or Siena can: waking up surrounded by vineyards, olive groves, and the unhurried pace of rural Tuscany.

Villas are the classic Tuscany splurge. From your room, gaze across the vineyard, have a sunset dinner surrounded by vines, and enjoy a private wine tasting. The best villas offer gourmet dinners, private tours of the estate, a pool, and sometimes a spa.

We spent three nights at Villa le Prata, a short drive from Montalcino and a perfect base for exploring Val d’Orcia. Each evening we had dinner on the property, followed by sunset wine tastings and tours of the vineyard. In 2024, Villa le Prata received one Michelin key, a new award recognizing extraordinary hotels.

Agriturismos are farm stays, typically a working farm that also accommodates guests in apartments, cottages, or private rooms on the property. They range from simple and rustic to surprisingly luxurious, and many produce their own wine, olive oil, and food.

Staying at an agriturismo gives you an authentic slice of Tuscan rural life that most visitors never experience. Some offer cooking classes, farm tours, and meals made almost entirely from what’s grown on the property.

PRO TRAVEL TIP: Both options are best booked through Booking.com, where you can filter by location and amenities. If you plan to stay in either, you will need a rental car.

Villa le Prata

Visit Elba Island

Elba is a beautiful island off the Tuscan coast, known for its clear turquoise water, beaches, and relaxed Mediterranean feel. It’s a completely different side of Tuscany, offering a mix of seaside towns, hiking trails, and scenic coastal views.

While Elba is best known as the place where Napoleon Bonaparte was exiled, most visitors come for the beaches, swimming, and laid-back atmosphere. It’s a great escape from the crowds of Florence and the hill towns, especially in the warmer months.

Visiting Elba requires a bit more planning, including a ferry ride from the mainland (typically from Piombino), so it’s best suited for travelers with extra time in Tuscany.

Elba | shutterstock.com/essevu

👉 Add this to your itinerary if you have extra time, enjoy beach destinations, or want to experience a completely different side of Tuscany.

Visit Montecatini Terme

Montecatini Terme is a historic spa town in northern Tuscany, known for its thermal baths, elegant architecture, and relaxed atmosphere. Once a popular destination for European royalty and celebrities, it still retains a classic, old-world charm.

The town is split into two parts: the lower town, home to the famous spa complexes, and Montecatini Alto, a small hilltop village reached by a scenic funicular. From the top, you get nice views over the surrounding countryside. We did this, and weren’t all that impressed with the view.

While Montecatini isn’t a must-see for first-time visitors to Tuscany, it’s a great place to visit if you like the idea of visiting its thermal baths.

Montecatini Terme

👉 Add this to your itinerary if you’re interested in spa experiences or want a relaxing stop between Florence and the Tuscan countryside.

How to Get Around Tuscany

Getting around Tuscany depends on what you want to see—and whether you plan to visit mostly cities or explore the countryside.

By Car (Best for Most Travelers)

Renting a car is the best way to explore Tuscany, especially if you plan to visit hill towns, the Val d’Orcia, or smaller villages. This is our preferred way to get around Tuscany.

Public transportation is limited outside of major cities, and having a car gives you the flexibility to stop at scenic viewpoints, wineries, and lesser-known towns along the way.

Pros:

• Easy access to hill towns and rural areas
• Flexibility to explore at your own pace
• Essential for scenic drives like the Val d’Orcia

Cons:

• Parking can be limited in historic centers
• ZTL zones (restricted traffic areas) in cities

Best for: Val d’Orcia, Chianti, smaller towns, road trips

By Train (Best for Cities)

Trains connect Tuscany’s major cities, including Florence, Pisa, and Siena (via nearby stations), making this a good option if you’re focusing on urban destinations.

Trains are fast, affordable, and easy to use—but they won’t take you to many of Tuscany’s most scenic areas.

Pros:

• Fast and convenient between major cities
• No need to worry about parking or driving

Cons:

• Limited access to hill towns and countryside
• You’ll still need taxis or buses for some destinations

Best for: Florence, Pisa, Lucca

By Bus (Limited but Useful)

Buses can reach some towns that trains don’t, including Siena and San Gimignano, but schedules can be limited and travel times are longer.

This is a workable option if you don’t want to rent a car, but it requires more planning and flexibility.

Best for: Reaching select towns without a car

By Tour (Easiest Option)

If you prefer not to drive, guided tours are an easy way to visit multiple destinations in one day, especially from Florence.

Many tours include stops in Siena, San Gimignano, and the Tuscan countryside, often with wine tastings included.

Best for: First-time visitors or short stays

What We Recommend

• First-time visitors (short trip): Base yourself in Florence and take day trips (train or tour)
• Classic Tuscany experience: Rent a car for at least part of your trip
• Deeper exploration: Combine trains (for cities) + car rental (for countryside)

Wine tasting in Montalcino

What Not to Miss in Tuscany

If it’s your first time in Tuscany or you’re short on time, these are the experiences we recommend prioritizing.

Florence – The cultural heart of Tuscany, with world-class art, architecture, and iconic landmarks like the Duomo and Michelangelo’s David.

Siena – Our top pick for a hill town, with its beautiful historic center and the stunning Piazza del Campo.

Val d’Orcia – The most scenic part of Tuscany, known for its rolling hills, cypress-lined roads, and postcard-perfect views.

One Classic Hill Town – San Gimignano, Montepulciano, or Pienza; choose at least one to experience Tuscany’s iconic villages.

A Food or Wine Experience – Whether it’s wine tasting in Chianti, a cooking class, or truffle hunting, this is one of the best ways to experience the region.

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How Many Days Do You Need in Tuscany?

Tuscany rewards however much time you can give it, but here’s a practical breakdown based on our own experience.

3 days is the minimum worth considering. Spend two days in Florence and use the third for a day trip to one or two hill towns. You’ll get a taste of Tuscany, but you won’t have time to slow down or explore the countryside.

5 days is where Tuscany starts to open up. Add Siena and a day in Val d’Orcia, and you’ll begin to feel the rhythm of the place, the winding roads, the hilltop towns, the long lunches.

7 days gives you time for Florence, Siena, several hill towns, a wine tasting or two, and at least one night in the countryside. This is enough time to feel like you’ve actually been to Tuscany, not just passed through it.

10 days or more is ideal if you want to go deeper. Spend time in lesser-known towns like Volterra, Cortona, and Arezzo, relax in the hot springs, day-trip to Elba, or simply sit in a vineyard with nowhere to be.

We have visited Tuscany twice, once for a week with our kids, and again for ten days focused almost entirely on the hill towns and countryside.

For a detailed day-by-day breakdown, visit our Tuscany Itinerary guide, which covers 3-day, 5-day, and one-week options with specific recommendations on where to go and where to stay.

Tuscany Itinerary

The Perfect Tuscany Itinerary for 3 Days, 5 Days & One Week

When is the Best Time to Visit Tuscany?

The best time to visit Tuscany is April through June and September through October, when the weather is pleasant, the countryside is at its most beautiful, and crowds are more manageable than peak summer.

Each season offers something different, so the best time for your trip depends on what you want to experience.

Spring (April to June) — Best Overall

Spring is one of the best times to visit Tuscany. The weather is mild, wildflowers are in bloom, and the countryside is lush and green.

This is a great time for sightseeing, scenic drives, and exploring hill towns before the peak summer crowds arrive.

Summer (July to August) — Busy & Hot

Summer is the most popular time to visit Tuscany, but it also comes with high temperatures and larger crowds, especially in Florence and popular towns.

That said, this is a great time for festivals, long evenings, and visiting the coast or islands like Elba.

Fall (September to October) — Food & Wine Season

Fall is another fantastic time to visit Tuscany, with warm temperatures, fewer crowds, and the grape and olive harvest in full swing.

This is the best time for wine tasting, truffle hunting, and food-focused experiences.

Winter (November to March) — Quiet & Low-Key

Winter is the quietest time to visit Tuscany, with fewer tourists and lower prices. While the countryside is less vibrant and some attractions have reduced hours, cities like Florence remain lively.

What We Did: Our first visit was in July. The weather was warm, and Florence and the hill towns were a bit crowded. During that visit, thunderstorms rolled in at 3 pm almost every day like clockwork. But overall, it was a great time to visit Tuscany, with good weather and long days for sightseeing. Our second trip was at the end of September into October. We had fewer crowds, cooler days, and a mix of sunny and cloudy, rainy days. If you don’t mind the chance of wet weather, late summer into early fall is a great time to visit Tuscany. We haven’t visited in May yet, but we’re hoping to do so soon.

Below are weather graphs so you can get an idea of average temperatures and rainfall.

Where to Stay in Tuscany

For a quick visit to Tuscany (3 days or less) pick one location. Florence is your best option, since you will spend a day or two visiting the sites in Florence. The next best choice is Siena, a large town that is well connected to many places in Tuscany by public transportation.

With more time, I recommend spending two to three nights in Florence and then picking a location outside of Florence, either Siena, a Tuscan villa, or a centrally located Tuscan hill town.

On our most recent trip, we spent ten days in Tuscany, dividing our time between Villa Le Prata (in Val d’Orcia), Siena, and Florence.

Frequently Asked Questions

How many days should I spend in Tuscany?

If you want to explore several hilltop towns, go wine tasting, road trip through the beautiful landscapes of Val d’Orcia, plan on spending at least three days in Tuscany, with another day or two for Florence. You could easily spend a week in Tuscany and never run out of things to do.

What is the best month to visit Tuscany?

If you want to see Tuscany with the lush, green landscapes that make it look like a Renaissance painting, plan your visit for the month of May. By mid-summer, the landscapes turn a golden yellow and in late summer, some of the fields are tilled.

Do you need a car in Tuscany?

Many of the larger towns, such as Siena, San Gimignano, Pisa, and Lucca, are very easy to get to using public transportation. But if you want to visit the smaller towns or spend time photographing the landscapes, you will need to rent a car, because some smaller towns are very difficult or time consuming to get to using public transportation.

Plan Your Trip to Tuscany

Tuscany pairs beautifully with the rest of Italy. Whether you’re building a first-time Italy itinerary or coming back for a deeper look at one region, here are some resources to help you plan:

• Tuscany Itinerary — 3-day, 5-day, and one-week options with day-by-day recommendations
• Italy Travel Guide — our complete guide to planning a trip to Italy, covering every major region
• 10 Days in Italy: Rome, Florence, Cinque Terre & Venice — the classic first-timer itinerary that includes two days in Florence and a day trip into Tuscany
• Two Weeks in Italy — if you have 14 days, this itinerary gives you more time in Tuscany alongside Rome, Venice, and the Amalfi Coast

If you have any questions about the best things to do in Tuscany, let us know in the comment section below.

More Information for Your Trip to Italy

We have TONS more information about Italy in our Italy Travel Guide, including Rome, Florence, Venice, Tuscany, the Dolomites, the Amalfi Coast, the Cinque Terre, Sicily, and Puglia.

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Header photo credit: shutterstock.com/Gaspar Janos