Things to do in Siena
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Siena: Brunello di Montalcino Wine Tour & Tuscan LunchYou visit three wineries in the Montalcino region, walk through cellars and vineyards, taste Brunello at each stop, and sit down to a traditional Tuscan lunch at a family-run farm paired with their wines. You also explore the hilltop town of Montalcino and the Sant'Antimo Abbey. Transport, guide, and all tastings are included; the group stays under eight people so you get real attention from your guide.Is it for me?Book this if you want to taste Brunello di Montalcino in the cellars where it's made and eat lunch at the source, without arranging your own transport or winery appointments—the small group size and fixed itinerary are what make a full day of three tastings and a proper meal possible in one departure.
Siena: Duomo Skip-the-Line & Old Town Walking TourYou’ll wander Siena’s winding streets with a local guide who brings stories to life — from ancient banks to the drama of Palio horse races. Step quietly into sacred spaces at Basilica di San Domenico and skip the line into Siena Cathedral, where striped marble columns rise overhead. You’ll taste city rhythms and leave with more questions than answers (in a good way).
Siena: Organic Wine Tour & Tasting with Tuscan LunchYou’ll walk Siena’s countryside vineyards with a local guide who knows every vine by heart. Taste organic wines straight from the source in their cellar, then sit down to a light Tuscan lunch made from seasonal ingredients—all just minutes from medieval Siena. Expect real stories, real flavors, and maybe even a laugh or two you’ll remember later.
Tuscan Cooking Class Siena: Handmade pasta & wine dinnerYou'll spend three to four hours learning to make five traditional Tuscan dishes from scratch — fresh pasta, soup, a main course, sides, and dessert — under the guidance of Francesco, who's been teaching this since 1996. The class includes all ingredients, techniques, and a full dinner with local wine at the end. You'll leave with recipes written down and the muscle memory of how to make pici by hand.Is it for me?Book this if you want to actually cook, not watch — you're making five dishes with your hands, not observing from a stool. The small group size (max 15) and Francesco's focus on Tuscan family recipes mean you'll learn techniques you can use at home, not just follow a script for the day.
Siena: Pienza & Montepulciano Day Trip with Farm LunchYou meet your guide at San Domenico in Siena at 9:30am and travel south through the clay hills of the Crete Senesi to Pienza, a Renaissance town designed on paper by architects for Pope Pius II. After exploring the town and its cathedral, you head to a local farm for lunch with wine and a lesson in pecorino cheese-making. The afternoon takes you to Montepulciano, where you taste Vino Nobile in a winery carved underground, then have free time to walk the town before returning to Siena. The group stays under 8 people, so the pace is relaxed and the guide can answer questions.Is it for me?Book this if you want to see two of Tuscany's most distinctive towns and the Val d'Orcia landscape without renting a car or planning the route yourself — the small group size and fixed itinerary mean you spend the day looking around instead of navigating.
Montalcino: Brunello Cooking Class & Winery Tour with LunchYou’ll cook classic Tuscan dishes outdoors above Montalcino’s vineyards, guided by Chef Alexandra in her family’s ancient estate. Taste your handmade pasta paired with Brunello wines on a sunny terrace, then tour the castle cellars where these bottles are born. Expect laughter, floury hands, and views you’ll carry home long after lunch ends.
Florence / Tuscan Wine School: Tasting Class with Local PairingsStep into a cozy Florence classroom where you’ll taste classic Tuscan wines like Chianti and Brunello alongside local cheeses, meats, and olive oil. Learn pairing tips from a friendly local guide and hear stories behind each bottle. You’ll leave with new favorites—and maybe a few laughs—that stick with you long after you’ve left Tuscany.
Siena Walking Tour: Cathedral & Palio History with Local GuideYou walk Siena's medieval center with a licensed local guide who knows the stories behind the Palio horse race, the competing districts, and the art hidden in churches and palaces. You choose whether the tour lasts 2 or 3 hours and which sites matter most — the Cathedral, the Contrada museums, or the quiet corners most visitors miss. Your guide handles the route and the history; you just show up with comfortable shoes.Is it for me?Book this if you want to understand Siena through a local's eyes without arranging your own route or timing — the guide handles the history and logistics, leaving you free to ask questions and linger where something catches your interest.
Siena: Food Tour with Full Tuscan Meal & Local TastingsYou’ll taste Siena through its charcuterie and cheeses in Piazza del Campo, share stories over local wine with your guide, and sit down to a full Tuscan lunch near the cathedral. Expect laughter over coffee, new flavors in every bite, and moments where you forget you’re just visiting.
San Gimignano & Volterra Day Trip from Siena with Farm LunchYou’ll walk medieval streets in Monteriggioni and San Gimignano with a local guide, taste homemade Tuscan dishes (and Vernaccia wine) at a family farm lunch, watch alabaster artists at work in Volterra, and have time to explore each town’s corners your own way. Expect laughter over lunch and moments that stick with you long after you’re home.
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.
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.
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.
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: 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.
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.
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.
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.
