The Best Things to Do in Tuscany, Italy

The best things to do in Tuscany Italy start here. I live part-time in Florence, and Tuscany is the region I send clients to when they want the version of Italy that everyone pictures in their head: cypress trees, rolling hills, a Brunello cellar at sunset, a long lunch at an agriturismo that turns into the afternoon. The trick is knowing which Tuscany you actually want. Chianti is the easy postcard Tuscany. Val d'Orcia is the more cinematic, hilltop-town Tuscany. The Maremma coast is the secret one Italians keep to themselves.

I have spent months in Tuscany over the past three years, both as a part-time Florence resident and as a FORA travel advisor scouting hotels, wineries, and cooking classes for clients. I have driven the Val d'Orcia at sunset more times than I can count. I have soaked at Terme di Saturnia. I have eaten lunch at agriturismi with the same family running them for four generations. This is the post I wish I had handed my first clients before they went, an honest list of what to do, what is worth your time, and what to skip.

Below are the 12 best things to do in Tuscany ranked by what I would actually do first, with my framework for picking the right sub-region, the hotels I book for clients, and how to time the trip so you catch vendemmia or the olive harvest. If you only have time to read one Tuscany post before booking, this is the one.

The Quick Picks: Tuscany at a Glance

If you are skimming, here is the shortlist of what is actually worth your time in Tuscany. The full ranked list with my honest takes is below.

Tuscany by Sub-Region: The Framework I Use

The single biggest mistake first-time visitors make is treating Tuscany as one place. It is enormous, and the regions inside it feel completely different. Here is the framework I use with every client before we pick a base.

My short answer for first-timers: spend two to three nights in Florence, then base in Chianti or the Val d'Orcia for three to four nights and use that as your launchpad for everything else. If you have a full week and have already been to Italy, swap Chianti for the Val d'Orcia and add two nights in the Maremma.

The 12 Best Things to Do in Tuscany

Ranked by what I would actually do first, second, third on a Tuscany trip. Each entry tells you who the experience is for, what the honest tradeoff is, and where my advisor opinion lands. Number one is the thing you build the trip around.

1. 01
   Drive Through the Val d'Orcia. Who it is for: every traveler, especially anyone visiting Tuscany for the first time. The Val d'Orcia is the UNESCO-protected stretch south of Siena that contains every cypress, hilltop town, and rolling vineyard you have ever seen on a Tuscany Pinterest board. Drive the SR2 and the smaller country roads between San Quirico d'Orcia, Pienza, Montalcino, and Bagno Vignoni in the late afternoon. The light at 5pm in October is what people mean when they talk about Tuscan light. Allow at least one full day. The famous lone cypress on the road to San Quirico is worth pulling over for. Park, do not block traffic.
2. 02
   Brunello Tasting in Montalcino. Who it is for: anyone who likes wine and is staying more than three nights. Montalcino is the hilltop town in the Val d'Orcia that produces Brunello, arguably the most serious red wine in Italy. The producers I send clients to range from cult to welcoming: Biondi-Santi (the original Brunello estate, book months ahead), Casanova di Neri, Fattoria dei Barbi, Poggio Antico, and Argiano. Book one or two cellars with lunch in between. Tastings run 35 to 120 euros depending on the producer and whether you taste a Riserva. Hire a driver. The hill roads are tight and the pours are generous.
3. 03
   Visit Florence: Uffizi, Duomo, Oltrarno. Who it is for: every traveler, ideally on the first two or three nights of the trip. Book the Uffizi for the 8:15am entry through the official Florence museum website, not a third-party reseller. Two and a half hours inside is the right amount. After lunch, climb to the top of the Duomo (book Brunelleschi's dome tickets a month ahead) or walk across the Ponte Vecchio into the Oltrarno for an afternoon that locals actually have. The Oltrarno is where I live when I am in Florence, full insider detail in my Florence travel guide.
4. 04
   Wine Tasting in Chianti Classico. Who it is for: every wine drinker, especially first-time Tuscany travelers. Chianti Classico is the rolling vineyard country between Florence and Siena, with Greve in Chianti as the main hub. Drive the SR222 (the Chiantigiana) between Greve and Castellina, stopping at family estates for tastings. Producers I send clients to: Antinori nel Chianti Classico (architectural icon, restaurant on site), Castello di Ama, Felsina, Volpaia, and Castello di Brolio. A half-day tour with two cellars and a lunch is the sweet spot.
5. 05
   Cooking Class with a Local Nonna. Who it is for: every traveler, especially couples and families. The single best thing I have ever done in Tuscany is a half-day cooking class at an agriturismo with the family's grandmother running the kitchen. You go to the market with her, you come back, you make pasta by hand, you sit down at her table and eat what you cooked with a bottle of the family's wine. Most agriturismi run them. The Tuscan Wine School in Florence runs in-city versions. Cost runs 90 to 180 euros per person. Worth more than three museum tickets put together.
6. 06
   Climb the Towers of San Gimignano. Who it is for: first-time Tuscany visitors, families with kids, history travelers. San Gimignano is the medieval skyscraper town between Florence and Siena, with 14 stone towers still standing out of the 72 it had at its peak. Go early (before 10am) or late (after 5pm) to skip the day-tripper buses. Climb the Torre Grossa for the view across the Tuscan countryside. Honest tradeoff: midday it is the most touristed town in Tuscany. Time it right and it is one of the great Italian skylines. Pair with a Vernaccia di San Gimignano tasting at Cantina di Fulignano or Tenuta Torciano.
7. 07
   Visit Siena: Piazza del Campo and the Duomo. Who it is for: every traveler. Siena is the medieval Gothic counterpoint to Renaissance Florence, and the city most travelers underrate. Sit on the brick fan of Piazza del Campo with a coffee mid-morning. Visit the Duomo, where the marble floor inlays are the most extraordinary in Italy (some panels only uncover late June through October). Climb the Torre del Mangia for the view. If you are visiting around July 2 or August 16, the Palio horse race takes over the Piazza del Campo. It is one of the great Italian spectacles, book a hotel with a window view six to nine months ahead.
8. 08
   Truffle Hunting in San Miniato or the Crete Senesi. Who it is for: food travelers, couples, families with curious kids. Tuscan truffle hunting is genuine, not a tourist trick. You head into the woods with a local truffle hunter (un tartufaio) and his trained dog, then sit down to a meal where the truffles you found are shaved over fresh pasta. The best season for white truffle is October through December, around San Miniato in particular. Black truffle is available year-round. Expect three to four hours plus the meal, around 150 to 250 euros per person. Book through your hotel concierge or an agriturismo.
9. 09
   Soak at Terme di Saturnia (Maremma Hot Springs). Who it is for: every traveler with three or more nights, especially couples. The Terme di Saturnia cascade is the natural sulphur hot spring in the Maremma where the warm water tumbles over travertine pools at 37 degrees Celsius year-round. The free public cascate (Cascate del Mulino) sit just outside the village of Saturnia and are open 24 hours. Go at sunrise to have them almost to yourself. The five-star Terme di Saturnia resort next door has the same thermal water in private pools with a serious spa. Either works. Bring a dark swimsuit, the sulphur stains light fabrics.
10. 10
    See Pisa (Quick Stop Only). Here is my honest advisor call: the Leaning Tower is genuinely interesting for 20 minutes and the Piazza dei Miracoli is one of the great medieval squares in Italy. The rest of Pisa is a working university city you will not remember. If you are driving between Florence and the coast, build in a two-hour stop, climb the tower if you booked ahead, photograph the Duomo and Baptistery, then keep going. Do not spend the night. Do not book it as a day trip from Florence over Siena or San Gimignano. It is the most overrated thing on a Tuscany Top 10.
11. 11
    Tuscan Olive Oil Tasting (Autumn Harvest). Who it is for: food travelers, anyone visiting between mid-October and late November. Olive harvest (la raccolta) is the second wine harvest in Tuscany, and frantoi (olive mills) across Chianti and the Val d'Orcia open their doors to visitors. You walk the groves, watch the just-picked olives press into bright green oil, then taste it on toasted Tuscan bread (fettunta) with salt. Mills I send clients to include Frantoio Pruneti in Chianti and Frantoio Franci near Montalcino. Pair with a Brunello tasting for the best food and wine day of your trip.
12. 12
    Stay at a Working Agriturismo. Who it is for: every traveler. An agriturismo is a working farm that takes guests, and a real one (not a five-star hotel calling itself an agriturismo) is one of the great Italian experiences. You eat dinner at a communal table, the wine on the table is from the vines you can see, the pasta was made that morning, and the bedrooms are simple and beautiful. Tenuta di Capezzana, Castello di Ama (also a winery), Fattoria San Donato near San Gimignano, and Agriturismo Il Rigo in the Val d'Orcia are four I send clients to. Two nights minimum. One night barely counts.

Where to Stay in Tuscany

Tuscany is one of those regions where the hotel is part of the experience. You are not staying in a city, you are staying on the land. The right property gives you a pool with a Val d'Orcia view, a restaurant pouring the wine from down the hill, and a base you do not want to leave for half of your trip. Here are the six I keep returning to for clients.

Best Time to Visit Tuscany

Tuscany is a year-round region, but each window has a different character and the harvest months are the ones to plan around. Here is how the calendar actually breaks down for travelers.

My honest call: late September into mid-October is the absolute best window for Tuscany. Vendemmia is winding down, olive harvest begins around October 15, the countryside is still warm enough for pool time at five-star properties, and the light over the Val d'Orcia is at its best. The next best window is mid-May into early June. If you can only travel in summer, build the trip around early mornings and pool afternoons, and dinners later in the evening as the sun is setting to beat the heat. For broader timing logic across the country, my 14-day fall Italy itinerary shows how Tuscany sits inside a longer trip.

How to Get Around Tuscany

Tuscany is the only region of Italy where I tell almost every client to rent a car. The vineyards, the agriturismi, the Val d'Orcia, the Maremma, none of it is reachable by train. The trains work well for Florence, Siena, and Pisa, and that is roughly the limit.

Browse the best tours and experiences in Tuscany, from half-day Chianti wine drives to small-group Brunello tastings and cooking classes in a Florentine kitchen. Use code TRAVELINGBALANCED5 for 5% off any booking.

Insider Tuscany Tips

Tuscany on the Map

The interactive map below shows hotels across Tuscany, from Florence down through Chianti, the Val d'Orcia, and the Maremma. Use it to plan your routing and check availability for your dates.

Final Thoughts: Planning Your Tuscany Trip

Tuscany is the region I send clients to when they want the version of Italy that everyone has in their head before they go. It is also the region where the wrong itinerary will leave you exhausted and wondering what the fuss was about. The version that disappoints people is the seven-day blur of Florence, Pisa, Lucca, Cinque Terre, Siena, and the Val d'Orcia in one trip. The version that changes your sense of Italy is two or three nights in Florence, then a slow base in Chianti or the Val d'Orcia where you do one beautiful thing a day and leave room for nothing.

Build it that way, pick the sub-region that matches what you actually want, book the Brunello cellars and the agriturismo cooking class months ahead, and Tuscany will give you the slow, generous, unhurried week that taught me what dolce far niente actually means. For a longer Italy trip that includes Tuscany alongside Rome and the Amalfi Coast, my Italy honeymoon itinerary shows how the regions fit together. For the same routing without the honeymoon angle, my Italy honeymoon guide is the broader pick.