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Planning a trip to Siena? You’ve come to the right place!
This medieval Tuscan city is packed with history, culture, and incredible food. From the moment we arrived, we were drawn in by its charm. Whether you’re wandering winding streets, stepping inside breathtaking cathedrals, or indulging in local wine, Siena has plenty to offer.
After exploring firsthand, we put together this list of the best things to do in Siena, including our favorite tours and experiences. With a mix of history, adventure, and food, this guide will help you make the most of your time in this unforgettable city. Get ready to plan the perfect adventure!
Don’t Miss Out On Our Top Choice!
The tour we loved the most and suggest booking ASAP is this one!
Our personal FAVORITE thing we did in Siena was this small-group wine tasting tour! We strolled through vineyards, had lunch at a winery, and tried one of Italy’s most famous wines, Brunello di Montalcino. It was a highlight of our trip!
Things to do in Siena, Italy
1. See Siena with a guide and get skip-the-line entry to the Duomo
- Duration: 2 hours
- Time: 10:30 am and 3 pm (dates vary)
- Highlights: Visit Siena’s UNESCO World Heritage-listed Old Town, see the Basilica of San Domenico and Piazza del Campo, enjoy skip-the-line entrance to the Siena Duomo, see works of art by Donatello, Bernini, and Michelangelo
- Inclusions: Walking tour of Siena and Siena Duomo with an expert guide, Siena Duomo admission ticket
- Rating: 4.8 stars (check 500+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Some cities feel like they belong to another era, and this walking tour of Siena proved it firsthand. Exploring this UNESCO-listed town with a guide brought its history to life, from medieval rivalries to the Palio horse race that still defines the city today.
Our guide, Georgia, made the tour more than just a history lesson. Her storytelling kept us hooked!
We started at the Basilica of San Domenico, where we saw relics of Saint Catherine, one of Siena’s most famous figures. It was incredible to learn how she became one of medieval Europe’s most influential women!
Wandering through Siena’s narrow streets, we explored the city’s contrade (neighborhoods), each with its own colors, traditions, and fierce pride (especially during the Palio). Standing in Piazza del Campo, it was easy to imagine the roar of the crowd during the legendary race.
Skipping the long lines at the Siena Duomo was a huge bonus! We went right inside, where Georgia pointed out artwork by Michelangelo, Donatello, and Bernini. But the real showstopper was the intricate marble floor—each panel telling a different biblical story.
Walking these historic streets with an expert guide made Siena’s past feel vivid, and we left with a deeper appreciation for this remarkable city. This tour was the best way to uncover layers of Siena’s history!
Book this walking tour here and see Siena in a whole new way!
2. Taste the famous Brunello di Montalcino wine (and more) on a wine-tasting tour
- Duration: 9 hours
- Time: 9:30 am (dates vary)
- Highlights: Small-group wine-tasting tour to Montalcino from Siena, visit three wineries to taste Brunello di Montalcino and other wines, savor a generous Tuscan lunch
- Inclusions: Local Guide, visit to wine cellars and wine tasting, lunch at a family-run winery, air-conditioned vehicle
- Rating: 4.9 stars (check 800+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Tuscany and wine go hand in hand, but this small-group wine-tasting tour from Siena took it to another level! From strolling through vineyards to lunch at a winery, every stop felt like a dream.
Our guide, Giuliana, made the day even better with her deep knowledge and fun personality! At the first winery, we walked through the vines before heading inside to sip Rosso and Brunello di Montalcino. Learning about the strict aging process and certification rules gave us a new respect for these wines—and an excuse to bring home a bottle (or two)!
After some free time in Montalcino, we made our way to a family-run winery for a classic Tuscan lunch. From the moment we sat down, it felt like we were eating at a friend’s home.
First came bruschetta with fresh tomatoes and local olive oil, followed by steaming bowls of homemade pasta that tasted like a recipe perfected over generations. Each dish was paired with a new wine, and with every sip, we could taste the passion behind it!
The ancient stone walls and rolling hills surrounding the Abbey of Sant’Antimo gave us a peaceful break before our final tasting. If you’re lucky, you might even hear monks chanting inside. It was the perfect moment of calm before one last round of wine!
By the end of the day, we weren’t just enjoying the wine—we understood it! Between the tastings, breathtaking countryside, and expert guidance, this tour was an absolute highlight of our trip.
Secure your spot on this unforgettable wine-tasting tour here!
Related Read: If you’re doing some more traveling through Italy, have a look at our all-time favorite things to do in Italy here!
3. Learn how to cook authentic Tuscan food
- Duration: 4 hours
- Time: 4 pm (dates vary)
- Highlights: Cook traditional Italian dishes, transform local ingredients into a delicious meal, enjoy your dishes paired with an excellent wine
- Inclusions: Small group cooking class preparing a traditional Tuscan meal from starter to dessert, professional chef, fresh hand-made pasta, vegetarian option available, large and well-equipped cooking school, Tuscan IGT wine
- Rating: 4.9 stars (check 200+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Rolling out fresh pasta by hand and sipping Tuscan wine? Now that’s our kind of evening! This Tuscan cooking class isn’t just about following recipes—it’s about stepping into tradition, where food is made with patience, passion, and great company.
From the moment we arrived, Francesco and Julia welcomed us like old friends. We started by making pappa al pomodoro, a simple yet delicious tomato and bread soup that smelled like pure comfort. Next came the real challenge of hand-rolling pici pasta. Francesco made it look easy, but our lopsided noodles had a bit more… character!
For the main course, we prepared Pici with Aglione sauce, a classic Tuscan pasta dish. The sauce was made with local olive oil, fresh tomato, garlic, and rosemary. It was an absolute delight!
The best part was sharing the meal with our small group! Porchetta, roasted potatoes, pici in aglione sauce, and pappa al pomodoro, which we shamelessly used for bread-dipping. With a glass of St. Giorgio Toscana IGT wine in hand, it was a true Tuscan feast!
Just when we thought we couldn’t eat another bite, Julia arrived with traditional Siena sweets. One bite of chewy ricciarelli almond cookies and flaky panforte was all it took to find room!
Whether you’re a home cook or just love Italian food, this class is unforgettable. But don’t just take our word for it—read glowing reviews here and see why travelers love this experience!
Check out reviews here and book this top-rated cooking class!
Why We Book Tours with Viator
Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:
- Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
- Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
- Lowest price guarantee – If you happen to find the same tour at a lower price elsewhere, Viator will refund you the price difference.
- Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
- Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.
Check out the Viator website here! Or, for more info, read our detailed review about Viator here.
4. Take a hot air balloon flight over Tuscany
- Duration: 3 hours
- Time: 6 am or 6:30 am
- Highlights: Hot air balloon ride over Tuscany from Siena, enjoy aerial views of the countryside, float over rolling hills with villas, castles, vineyards, and olive groves, enjoy a glass of sparkling wine upon landing
- Inclusions: Shared one-hour balloon flight, expert captain and crew, transfer from landing site back to launch spot, one glass of sparkling wine, picnic style breakfast with croissant and local products, round-trip hotel transport (if option selected), small group tour
- Rating: 4.7 stars (check 100+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
We absolutely loved this hot air balloon ride over Tuscany! Drifting over rolling hills, ancient villages, and vineyards stretching as far as the eye can see was the best way to take in the landscape.
Our adventure began early in the morning when the air was crisp, and the fields glowed with golden light. After a safety briefing, we even got to help inflate the balloon, which made everything even more exciting! Before we knew it, we were gently lifting off, rising higher and higher as the view stretched endlessly in every direction.
From above, Tuscany looked like a real-life painting! Stone villas perched on rolling hills, cypress-lined roads cut through the countryside, and vineyards and olive groves formed a perfect patchwork of green.
The only sounds were the occasional whoosh of the burner and our guide pointing out landmarks like San Casciano in Val di Pesa, a charming wine town near Florence. Up there, time seemed to stand still—it was just so peaceful!
After an hour of floating, the balloon made a gentle descent into a field, where a welcoming crew awaited us with a glass of sparkling wine and a picnic-style breakfast. It was a truly unforgettable way to start the day!
If you’re looking for a bucket-list-worthy way to experience Tuscany, this is it! It’s an experience we’ll never forget.
Check availability and book this incredible aerial experience here!
5. Go wine tasting right near Siena
- Duration: 3 hours
- Time: 11:30 am
- Highlights: Escape the city and explore the vineyards surrounding Siena, educate your palate to recognize subtle flavors with the help of a sommelier, sample at least four local wines, enjoy a light Tuscan lunch
- Inclusions: Guided visit to the organic vineyards and wine cellar, sensorial tasting of four organic wines, fresh, seasonal light Tuscan lunch, bottled water, alcoholic beverages, small group tour
- Rating: 5 stars (check 290+ reviews here)
- Free cancellation: Yes
- Price: Check price here!
Wine tasting in Tuscany is a must, but nothing beats getting a true insider’s look at the winemaking process. This wine tour at Azienda Agricola La Lastra wasn’t just about sipping wine—it was about experiencing the journey from vine to bottle in one of the most beautiful settings near Siena.
We started in the vineyards, learning about organic grape-growing techniques while standing among the rows of vines. It was incredible to see how much work goes into producing a single bottle of wine!
Inside the cellar, we got a behind-the-scenes look at the winemaking process, from fermentation to bottling. This is where our guide, Maya, really shined! She had a wealth of knowledge, explaining each step with enthusiasm and making even the science behind fermentation engaging. It was clear she wasn’t just leading a tour—she was sharing something she truly loved!
Then came our favorite part—the wine tasting! With Maya’s guidance, we sampled four organic wines, training our senses to pick up subtle flavors we never would have noticed.
We didn’t think we’d be able to tell the difference between a wine’s acidity and tannins, but by the third sip, we actually could! Paired with a light Tuscan lunch featuring fresh seasonal ingredients and their organic olive oil, it was the perfect way to end the experience.
This small-group tour fills up fast, so make sure to book it early. Check out the 5-star reviews here and see why this tour is a must-do!
Don’t miss this amazing wine tour, reserve your spot here for FREE cancellation!
Related Read: Need some help planning the perfect Siena trip? We’ve got you covered! Just follow our detailed Siena itinerary to make sure you don’t miss out on any of the best spots and hidden gems.
Where to Stay in Siena, Italy
Now that your Siena adventure is planned out, it’s time to choose where to stay! With so many charming options, finding the perfect spot can feel like a challenge. To make it easier, I’ve rounded up the best centrally located stays for every budget—so you can focus on enjoying the city’s medieval magic!
Luxury – $$$
The Grand Hotel Continental Siena is a top choice for a luxurious stay in the heart of the city. Set in a stunning 17th-century palace, this 5-star hotel blends history with elegance, featuring beautifully decorated rooms with frescoed ceilings and antique furnishings. Located just steps from Piazza del Campo, it’s the perfect place to immerse yourself in Siena’s charm while enjoying top-tier service, an on-site restaurant, and even a refined wine bar!
Prices vary depending on the time of year but usually range from €400 to €600 per night. You can check prices and book this stay on Booking.com.
Mid-range – $$
Albergo Chiusarelli is a fantastic mid-range option in Siena, housed in a beautiful 19th-century building. The rooms feature classic decor with modern touches, offering a comfortable stay just a short walk from Piazza del Campo and Siena’s historic center. Guests can start their day with a complimentary buffet breakfast or enjoy traditional Tuscan cuisine at the on-site restaurant.
Prices are usually around €120- €150 per night, and you can book this stay on Booking.com.
Budget – $
Albergo Bernini is a budget-friendly stay in the heart of Siena, offering an incredible panoramic terrace with breathtaking views of the city’s rooftops. The rooms are simple but comfortable, with private or shared bathrooms, depending on your choice. Plus, the central location means you’re just a short walk from Siena’s top sights, cafés, and restaurants!
Rooms can start as low as €70 per night. You can reserve your room here on Booking.com!
For more options, see all of the hotels in Siena here!
Renting a Car in Italy
Renting a car in Italy is one of the best ways to explore the country beyond the cities—think charming Tuscan villages, dramatic Amalfi Coast drives, and hidden gems in the countryside. While Italy’s roads can be a little chaotic (especially in cities), with the right preparation, renting a car here can be an unforgettable and rewarding experience!
We always use Discover Cars when booking our rentals, and highly recommend them. They compare dozens of providers to find you the best rates, include important filters like “automatic transmission,” and offer affordable full insurance coverage. For more info, you can read our in-depth Discover Cars review here.
Tips for Renting a Car in Italy
- Drive on the right: Italians drive on the right-hand side of the road and overtake on the left. Right turns on red are illegal, and you must often yield to vehicles coming from the right at intersections.
- Stay alert and confident: Italian driving can feel aggressive in cities—expect assertive drivers, scooters weaving through traffic, and liberal horn use (often just a form of communication). Stay calm and practice defensive driving.
- Insurance is a must: We highly recommend adding full coverage insurance when booking. Minor damage like scratches and dents is common, especially in cities, and Discover Cars’ full protection gives you peace of mind at a low cost!
- Mind the ZTL zones: Many city centers have restricted traffic zones called ZTLs. Entering without a permit can result in a fine. Check with your hotel and use GPS with ZTL alerts.
- Choose the right vehicle: Roads in Italy can be narrow and parking tight, so a compact car is usually best. Most rentals are manual, but if you need an automatic, you can easily filter for one when booking with Discover Cars.
What You Need to Rent a Car in Italy
- A valid driver’s license from your home country.
- If you’re from outside the EU, you’ll likely need an International Driving Permit (IDP).
- A credit card in the driver’s name is typically required for the security deposit.
- You must be at least 18 years old, but renters under 25 may incur a young driver surcharge.
Ready to hit the road? Book your car with Discover Cars here and discover the freedom of exploring Italy on your own terms!
Don’t Forget Travel Insurance!
If you’re looking to save money on travel insurance, we currently use and recommend SafetyWing. We’ve been using their coverage since 2018 and they’ve had our backs when we needed emergency flights and got sick overseas.
SafetyWing is one of the cheapest providers out there and covers everything from medical costs to lost luggage, travel delays, and emergency flights. A huge difference we’ve found between them and other companies is that they let you take out a policy AFTER leaving your home country. We’ve also found it handy that it’s a monthly payment rather than a lump sum, and you can get a refund for unused time.
SafetyWing has helped us out in some scary situations before and their affordable coverage has given us peace of mind. You can read our honest review of SafetyWing for all the pros and cons.
Thanks for reading!
I hope our guide on the best things in Siena has you ready to explore this amazing part of Italy! Of course, the wine is outstanding, but we also enjoyed learning more about the city with these experiences. It made us want to return as soon as we can!
If this is only one of your stops in Europe, keep exploring by checking out our full travel blog here. We’ve been all over the world and have lots of itineraries, travel guides, and tour recommendations. Here are a few Italy guides that might come in handy!
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