Things to do in Siena
The unmissables
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Siena: Brunello di Montalcino Wine Tour & Tuscan Lunch★ 4.92 (1,024) · 9h
Top rated
Siena: Organic Wine Tour & Tasting with Tuscan Lunch★ 4.97 (398) · 3h
Best value
Siena: Duomo Skip-the-Line & Old Town Walking Tour★ 4.78 (790) · 2h
Recommended (7)
Tuscan Cooking Class Siena: Handmade pasta & wine dinner★ 4.85 (356) · 4h€ 130View ›
Siena: Pienza & Montepulciano Day Trip with Farm Lunch★ 4.91 (327) · 8h€ 190View ›
Montalcino: Brunello Cooking Class & Winery Tour with Lunch★ 4.99 (316) · 4h€ 259View ›
Florence / Tuscan Wine School: Tasting Class with Local Pairings★ 4.94 (266) · 2h€ 60View ›
Siena Walking Tour: Cathedral & Palio History with Local Guide★ 4.78 (263) · 2h–3h€ 155View ›
Siena: Food Tour with Full Tuscan Meal & Local Tastings★ 4.92 (243) · 3h€ 73View ›
San Gimignano & Volterra Day Trip from Siena with Farm Lunch★ 4.93 (201) · 8h€ 190View ›Top rated (9)
Siena: Private Walking Tour of Medieval Alleys & Quiet ChurchesYou’ll start in Siena’s famous main square with your private guide, then slip into quieter medieval alleys most visitors miss. Step inside peaceful churches and climb toward panoramic city views from an old basilica. Expect small surprises, gentle conversation, and moments where Siena feels like it belongs just to you.
Brunello di Montalcino Wine Tour: 2 Wineries with Pairing LunchA full-day wine tour in Montalcino takes you to two boutique Brunello wineries for tastings and a cellar tour, then to a pairing lunch at the second winery featuring local specialties. Hotel pickup and drop-off are included, along with an English-speaking driver-guide and a small group capped at 8 guests. The day also includes time to walk the medieval fortress and artisan shops of Montalcino itself.Is it for me?Hotel pickup means you don't need a car or a ride to the wineries—the driver collects you and handles the route, timing and navigation for the whole day, which settles the logistics if you're staying in town without transport or arriving by train.
Siena walking tour with lunch & Chianti wine tastingA 2.5-hour walking tour of Siena led by a licensed English-speaking guide, moving through medieval neighborhoods, historic piazzas and hidden streets to taste gelato, wine and a full lunch of homemade pici pasta, pecorino cheese and Chianti. The tour keeps to small groups of no more than 12 people and includes an awarded gelato shop, wine tasting near Piazza del Campo, and a meal at a traditional osteria.Is it for me?At 2.5 hours, this tour fits into a morning or afternoon without consuming your whole day, which means you can pair it with other Siena plans or simply move on to another town by evening. The small group size and licensed guide make it work for families with young children and for travelers who want actual conversation about the places you're walking through, rather than a rushed procession through checkpoints.
Siena: Tuscan Cooking Class & Wine Lunch from CountrysideYou spend four hours in a Siena farmhouse kitchen learning to make fresh pasta, bruschetta, sauce, and dessert from a professional chef who speaks English. You cook everything yourself, then sit down and eat it with local wine and the other people in your small group. The recipes and apron go home with you, along with the ability to actually make these dishes again.Is it for me?Book this if you want to actually learn how to make Tuscan pasta and bruschetta rather than just eat them, and you're willing to spend a morning in a kitchen with a small group—the hands-on format is what makes the recipes stick.
Hot Air Balloon Flight Over Tuscany from SienaA one-hour hot air balloon flight over Siena and the Tuscan countryside, piloted by an experienced captain with a safety briefing before takeoff. You rise to varying altitudes between 500 and 3,000 feet depending on wind conditions, then land to a toast and breakfast with local products and prosecco. Flights operate only in early morning hours; the exact time and launch spot are confirmed the day before based on weather and wind. Hotel pickup and return transfer can be arranged for an additional cost.Is it for me?Book this if you're flying from a hotel in the Siena area and want pickup included; choose a different operator if you prefer a private basket or a later departure time.
Montalcino Brunello Wine Tasting & Lunch in a CastleMontalcino wine tasting and lunch combines three local wines — including Brunello di Montalcino — with a three-course Tuscan meal served in a medieval castle. A professional sommelier leads you through the vineyard, explains the winemaking methods, and guides the tasting; the experience runs about 90 minutes and includes a tour of the property. English and Italian options are available, and vegetarian lunch is an option at checkout.Is it for me?Book this if you want to taste Brunello where it is made and understand how, rather than just sample wines in a tasting room — the sommelier's walk through the vineyard and the castle grounds is what sets this apart from a standard wine bar visit.
Siena: Pasta & Tiramisu Cooking Class with WineYou'll make fresh fettuccine and ravioli from scratch, then tiramisu, in a working Siena restaurant kitchen with a small group. Prosecco arrives when you do, and wine comes with the meal you've cooked. The class focuses on traditional recipes — if you have allergies or dietary restrictions, substitutes are available, though the instruction stays centered on the classic version.Is it for me?Book this if you want to learn pasta and tiramisu hands-on without spending a full day in a cooking school — the small group size and restaurant setting mean you're learning in a real kitchen, not a classroom, and you eat what you make the same afternoon.
Siena & San Gimignano: Medieval Towns, Chianti Wine & LunchYou visit four medieval towns—San Gimignano, Monteriggioni, Siena—and a Chianti winery, all in one day with transport, a three-course lunch, wine tasting, and an English-speaking guide included. The pace is set; you just show up at the Florence meeting point and let the coach and the escort handle the logistics.Is it for me?Choose this tour if you want the main Chianti and medieval Siena highlights in a single day without arranging transport, winery bookings, or timing yourself—the fixed schedule and English-speaking guide mean you arrive at Florence, get on the coach, and everything else is handled.
Val d'Orcia wine tour from Siena: Brunello and Nobile tastingsA full-day wine tour from Siena through Val d'Orcia visits three towns—Montepulciano, Pienza and Montalcino—with two wine tastings, lunch with cured meats and pasta, and free time to walk each town's historic streets. A multilingual guide leads the group by minivan, and wine tastings are held in English with translation support when needed. The tour runs 10 to 11 hours and departs from Siena Railway Station.Is it for me?Pick summer for warm weather and outdoor tastings, or winter for fewer crowds—both visit the same wineries and include tastings in Pienza and Montepulciano with lunch included.
Lowest price (10)
Siena Walking Tour: Self-guided monuments at your own paceA self-guided walking tour of Siena using a digital audio and text guide in five languages, covering Piazza del Campo, the Duomo, Basilica di San Domenico, and six other monuments. You move at your own pace, choose which stops matter to you, and get local recommendations for authentic restaurants and aperitivo spots alongside the history. The guide works on your smartphone with an internet connection; cathedral and museum tickets are separate.Is it for me?Choose this tour if you're traveling alone or with one or two others and want to explore Siena without waiting for a group to gather or keeping pace with a guide's itinerary. The self-guided format means you stop when something catches your eye, take a long lunch, or skip a site entirely — the city unfolds on your terms, not a fixed schedule.
Tuscany: Wine Tasting Near Siena with Local Foods & Terrace ViewsYou’ll taste three Tuscan wines on a quiet terrace near Siena, paired with local cheeses, honey, and homemade specialties. Share stories with your hosts as you relax under an old mulberry tree and soak up views of Chianti’s hills—a slow afternoon that lingers long after you leave.
Siena: Italian Opera Concert in Historic Church SettingYou’ll slip into Siena’s historic center for an evening surrounded by soaring opera voices inside a centuries-old church. Expect familiar arias from La Traviata and Madame Butterfly performed up close by local singers—sometimes with laughter mixed in. If you want to feel music echo through ancient walls and share a few unexpected moments with strangers, this is your night.
Siena: Underground Wine Tasting in Private Medieval CaveYou’ll step through an unmarked door near San Domenico into Siena’s oldest underworld for a private wine tasting led by a local sommelier. Taste Brunello di Montalcino, Chianti Classico, and Super Tuscan wines inside an Etruscan-era cave with only a handful of guests. Expect stories, laughter over local cheese, and that rare feeling of being let in on something secret.
Organic Wine Tasting in Siena: Vineyard, Cellar & 5 WinesA guided winery tour and tasting near Siena where you walk the organic vineyard, explore the cellar to understand winemaking at each stage, then taste five wines paired with seasonal Tuscan products and olive oil. The experience runs 2.5 hours and includes a light afternoon meal, parking and a guide in English or Italian. Minimum age is 18.Is it for me?The 2.5-hour length fits neatly into an afternoon without eating up your whole day in Siena, so you can combine it with time in the medieval town or other plans. If you want to understand wine beyond the taste—the soil, the process, the reasoning—this tour builds that knowledge as you go.
Brunello di Montalcino Wine Tour from Siena: 2 TastingsA wine tour from Siena to Montalcino with guided tastings of two Brunello di Montalcino wines at local estates, a professional multilingual guide, and free time to walk the medieval fortress town. The tour includes a scenic drive through Val d'Orcia vineyards, insight into Brunello aging traditions, and a light Tuscan snack with fresh bread and olive oil. Groups stay under eight in a minivan or up to thirty in a minibus, and the full day runs 5.5 hours from Siena Railway Station.Is it for me?Book this tour if you want to taste Brunello in the cellars where it's aged rather than in a hotel tasting room, and if you have a free afternoon from Siena — the 5.5-hour round trip leaves room for an early start or a late dinner back in the city. The small group size and English-speaking guide make it straightforward for first-time visitors to Montalcino, and the free time in the town means you're not locked into a schedule if you want to linger at a winery or explore on your own.
Siena Cathedral tour: Marbles, sculptures and the floorA guided tour of Siena Cathedral in Tuscany takes you through the building's internal decoration — marbles, statues carved by Donatello, Michelangelo and Bernini, and the Piccolomini Library — then down to the floor, an inlaid narrative of theology and philosophy spanning six centuries. A live guide in English or Italian leads the visit with radioguides so you hear clearly; the tour runs 90 minutes and suits all fitness levels.Is it for me?Small groups move through the Cathedral at a steady pace with a guide who knows the building's history and the stories carved into its floor — a good fit if you want to understand what you're looking at rather than simply pass through it.
Siena Private Walking Tour: Skip-the-Line Cathedral & ContradeA private walking tour of Siena with an expert local guide includes skip-the-line entry to Siena Cathedral, a guided visit inside, and a walk through the contrada neighborhoods where centuries-old traditions shape daily life. You choose between a 2-hour intro tour or a 3-hour extended version that adds the Crypt and Museum, and the tour runs in English, French, or German. The private format means the pace and stops are yours to shape with your guide.Is it for me?Book the 2-hour tour if you want the Cathedral, the main square, and a taste of the contrade in a morning or afternoon. Choose the 3-hour option if you want to see the Crypt's hidden frescoes and the Museum's original sculptures—the extra time lets you understand the Cathedral's full story and the ambition behind the unfinished Duomo Nuovo.
Siena Walking Tour: Medieval Streets with GuideA private walking tour of Siena's medieval center with a professional guide in your chosen language. You'll spend time at the Siena Cathedral, Palazzo Pubblico in Piazza del Campo, and the Basilica of San Domenico, moving at a pace that lets you absorb each one. The guide handles the route and the timing; you show up in covered shoulders and knees, ready to walk.Is it for me?Book this if you're in Siena without a car—your guide meets you at your chosen time and leads you through the medieval center on foot.
Chianti Castles & Wine Tasting Day Trip from SienaYou’ll walk castle paths above Chianti vineyards, taste wines poured by people who make them, share lunch at a Tuscan estate, and wander through medieval villages—all with a local guide who knows every shortcut and story. It’s not just tasting wine; you’ll feel part of this sun-baked landscape for a day.
