Things to do in Siena
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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: 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.
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.
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.
Montalcino wine tasting tour: Private guide, Brunello estatesA private guided wine tour in Montalcino takes you through Brunello estates and cellars with tastings, lunch and snacks over eight hours. Your guide speaks English, Spanish, Italian or German and handles all transport from your hotel in Siena or Arezzo province. The Abbey of Sant'Antimo is an optional stop on the route.Is it for me?Book this private tour if you want a guide who knows the producers and can adjust the day to what interests you most—the winemaking process, the history, the landscape, or simply more time at one estate. A shared group tour moves faster and costs less; this one gives you the guide's full attention and the flexibility to linger.
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: 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.
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.
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.
Private Cheese and Wine Tour from Siena: Pienza, MontalcinoA private full-day tour from Siena takes you south through the Val d'Orcia to an organic dairy farm for cheese and olive oil tasting, then to the Renaissance town of Pienza for lunch at your own pace, and finally to Montalcino for a winery tour and tasting of Rosso and Brunello di Montalcino wines. Your English-speaking guide picks you up from your hotel and handles all driving; the route covers eight hours and includes all tastings and farm access.Is it for me?Book this tour if you want to taste food and wine where it is made rather than in a restaurant, and you prefer traveling as a private group instead of joining others. The eight-hour day is built around the farm and winery visits, so the tastings and cellar tour are the focus, not a quick stop between other sights.
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 Walking Tour: Palazzo Pubblico & City CenterYou walk Siena's medieval center with a local guide starting from Palazzo Pubblico, covering the main attractions without the usual tourist rush. The two-hour loop is compact and accessible, leaving you time to explore on your own afterward or sit down for lunch knowing you've seen what matters.Is it for me?Book this if you want the essential Siena without spending half the day figuring out where to go — a guide who knows the city and a fixed two-hour loop means you see what matters and still have the afternoon free.
Siena: Val d'Orcia Wine & Gourmet Food Tour PrivateYou taste Brunello wine in a working cellar, then sit down to a homemade lunch in a Tuscan farmhouse overlooking the Val d'Orcia, with Pecorino cheese, olive oil, and handmade pasta included. The tour adds a panoramic drive through the landscape with photo stops wherever you choose. Hotel pickup and private transport are included; the meal cost is separate.Is it for me?Book this if you want to taste real Brunello and eat in a Tuscan home without arranging transport, finding a winery, or navigating the Val d'Orcia yourself — the private format means you move at your own pace and stop for photos whenever something catches your eye.
Private Brunello di Montalcino Wine Tour with Local SommelierIf you want to taste real Brunello wines right where they’re made—and see what makes this part of Tuscany so special—this tour’s got it all: local stories, small-batch wineries, and plenty of time to soak up Montalcino’s charm.
Siena Walking Tour & Cathedral: Guided Historic CenterA guided walking tour of Siena's historic center with entry to the Cathedral, led by a local guide in English, Spanish or Italian. You'll see Piazza del Campo, the Palazzo Pubblico and its civic tower, the Gaia Fountain, and the palazzos of Siena's great noble families before stepping inside the Cathedral to view works by Renaissance masters. The tour runs about an hour; note that the Cathedral closes on Sundays and certain dates (2 July and 16 August), when you'll visit a museum instead. A minimum of 4 participants is required for the tour to run.Is it for me?Book this tour if you want the Cathedral and the major squares of Siena's center explained by someone who lives there, all in one morning without piecing together separate tickets and routes. The guide ties the noble families, the Palio tradition and the pilgrimage stories to the places you're standing in, so the city makes sense as you walk it.
