How to Spend ONE or TWO days in Siena, Italy: 1 or 2 Day Itinerary

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Planning a quick trip to Siena? This one or two-day itinerary hits all the highlights!

Siena is a city that blends medieval charm, mouthwatering food, and sweeping countryside views—all packed into walkable streets and vibrant piazzas. Whether you’ve got just 24 hours or a little more time to linger, having a clear plan helps you soak it all in without missing the highlights.

We’ve put together a flexible itinerary based on our own visits, complete with local tips, standout tours, and plenty of personal favorites. Follow it day by day or mix and match to suit your style. Either way, you’re in for an unforgettable experience in one of Italy’s most timeless cities!

Day 1

Breakfast – Torrefazione Fiorella

Start your morning with something simple and classic like a fresh croissant and a creamy cappuccino at Torrefazione Fiorella. This tiny, beloved café sits just a short walk from Piazza del Campo, and it serves some of the best coffee in town. No frills, no fuss, just great espresso in a lively local setting. Expect to stand at the bar alongside regulars who stop in for their daily dose of caffeine and cornetto.

It’s the kind of place where you’ll feel like you’ve instantly stepped into the rhythm of Italian life, and the perfect fuel before a full day of exploring.

Important note: On Sundays, this spot is closed, the Duomo only offers tours in the afternoon, and the cooking class also isn’t available—so if your Day 1 falls on a Sunday, you’ll need to swap this itinerary with Day 2 to keep everything running smoothly.

After breakfast, head straight to Torre del Mangia (about a 5-minute walk) to buy your climbing tickets for the afternoon. Tickets can only be bought in person, on the same day, and they do sell out, especially in high season. The ticket office opens at 10:00 am, so plan to arrive right when it opens or even a few minutes before. The walking tour starts at 10:30 am, and the ticket office is just a 10-minute walk from the meeting point, so you’ll have just enough time to get both done without rushing.

Morning – Take a walking tour of Siena and get skip-the-line entry to the Duomo

Some cities feel like they’ve been frozen in time, and walking through Siena with a guide made that clear right away. We joined this small-group walking tour that brought centuries of history to life, from age-old rivalries between neighborhoods to the famous Palio horse race that still fuels local pride.

We began at the Basilica of San Domenico, home to relics of Saint Catherine, Siena’s most legendary figure. With Georgia as our guide—sharing vivid stories at every stop—we wandered into the heart of the city, passing through Siena’s historic contrade, each one bursting with identity and tradition. Standing in Piazza del Campo, it was easy to imagine the thunder of hooves and the roar of the Palio crowds.

The tour ends with skip-the-line access to the Siena Duomo, where we explored masterpieces by Michelangelo and Bernini, plus the cathedral’s unbelievable marble mosaic floor.

We recommend booking the 10:30 am slot so you can follow the rest of this itinerary without shifting things around. On Sundays, this tour is only available at 3 pm, so if your Day 1 falls on a Sunday, you’ll want to swap the days in this itinerary.

This experience helped us understand just how unique Siena really is, and we loved every minute of it. And we’re not the only ones—check out hundreds of five-star reviews here to see why this is a top-rated tour in Siena!

Book this walking tour here and get FREE cancellation before you go!

Check out the rest of the Monument Complex of the Cathedral

After the walking tour ends inside the Duomo, don’t rush off just yet. Your ticket (the OPA Si Pass) gives you access to several other sites that are part of Siena’s stunning Cathedral Complex. 

Depending on how much you love art and history, you could easily spend another couple of hours here if you’re really diving deep, but in order to make it to lunch and your afternoon activities, you’ll need to pick just one or two. There’s still plenty left to explore in Siena!

• The Baptistery of San Giovanni – Located beneath the Duomo, the Baptistery is filled with vivid frescoes and features a beautifully carved baptismal font by Donatello. It’s a compact but impressive stop that doesn’t take long to visit. The art and architecture here feel grand, even in such an intimate space.

• The Cathedral Museum (Museo dell’Opera del Duomo) – This museum offers a deeper look at Siena’s artistic legacy, showcasing original sculptures from the Duomo along with paintings, stained glass, and religious artifacts. It’s a fascinating mix of art and architecture, and a must-visit for anyone wanting to explore the stories behind Siena’s most iconic monuments.

• The Piccolomini Library – Tucked inside the cathedral, this library stuns with colorful frescoes that tell the story of Pope Pius II. It’s small, but the artwork is some of the most vibrant in the city. The entire room feels like a hidden jewel box—brilliantly preserved and bursting with color from floor to ceiling.

• The Crypt – Only rediscovered in the 1990s, the crypt reveals centuries-old frescoes that predate the current cathedral and offer a glimpse into Siena’s medieval spiritual life. The faded yet powerful artwork, buried for centuries, gives this space an almost sacred stillness. It feels like stepping into a long-lost chapter of the city’s past.

Lunch – Il Bargello

After a morning steeped in art, history, and sweeping views, it’s time to recharge, and Il Bargello is just the spot. This cozy trattoria is only a few minutes’ walk from the Cathedral Complex, located just off Siena’s iconic Piazza del Campo, making it the perfect place to break for lunch without venturing far.

Il Bargello offers a classic Tuscan menu that’s big on flavor and tradition. Whether you’re in the mood for handmade pasta, wild boar ragu, or a refreshing caprese salad, the ingredients here are fresh and locally sourced. The atmosphere is relaxed but lively, especially if you grab a table outside where you can enjoy views of the Torre del Mangia while you eat.

If you’re visiting during the lunch rush or high season, it’s a good idea to make a reservation. This place fills up fast for a reason!

Afternoon – Find the best views of Siena

After a satisfying lunch and a morning of cathedral-hopping, it’s time to take in Siena from above. The city’s rooftop views are some of the most memorable in Tuscany—think red rooftops, rolling hills, and towers that stretch into the sky. There are two fantastic ways to soak it all in, depending on your energy level and whether you’re up for a bit of a climb.

Both viewpoints offer completely different perspectives, and either one is a great way to slow down and let the city’s beauty sink in. Here’s how to choose:

Option 1: Climb the Torre del Mangia

If you followed our tip this morning and bought your ticket early, you’re all set to climb Siena’s tallest tower: the Torre del Mangia. Just a couple of minutes from lunch, this slim, brick tower rises from the heart of Piazza del Campo and offers panoramic views of the entire city—and beyond.

But fair warning: there’s no elevator. You’ll need to tackle over 400 narrow steps, and the stairwell can feel a bit tight. That said, once you reach the top, you’re rewarded with 360-degree views that more than make up for the effort. It’s one of those experiences that truly feels like you’ve earned the view.

Allow about 30–45 minutes for the full climb and photo break at the top. If you’re good with heights and up for a workout, this is the most iconic way to see Siena from above.

Option 2: Panorama dal Facciatone

Prefer a slightly less intense climb? Take a 5-minute walk to the Cathedral Museum and enter the Panorama dal Facciatone, the viewing platform built on top of the unfinished 14th-century cathedral extension.

This option involves fewer stairs and should be included with your OPA Si Pass (check with the tour provider), but be prepared for a possible wait. Lines can take 20–30 minutes, especially in peak season, as only a few people are allowed up at a time. Still, the views from the top are stunning, framing Siena’s rooftops with the green Tuscan countryside in the background. It’s a bit quieter than Torre del Mangia and just as beautiful in its own way.

Evening – Take a cooking class

After soaking in Siena from above, wind down your day with an experience that’s full of flavor and tradition. This hands-on Tuscan cooking class is a great way to shift gears, from sightseeing to slow cooking, local drinks, and plenty of laughter.

The meeting point is just a 7-minute walk from Torre del Mangia, making it easy to head there straight after your afternoon viewpoint. The class runs from 4–8 pm and conveniently doubles as dinner.

We were welcomed into the kitchen like old friends by Francesco and Julia, whose warmth set the tone. The class kicked off with pappa al pomodoro, a humble tomato and bread soup that filled the room with comforting aromas. Then came the tricky art of hand-rolling pici pasta. Francesco made it look easy—ours had a bit more “character,” but tasted just as good.

For the main course, we made pici all’aglione, a garlicky tomato sauce brought to life with rosemary and rich local olive oil. We sat down to enjoy porchetta, roasted potatoes, pici, and plenty of bread to dip into our homemade soup.

Just when we thought we were done, Julia arrived with Siena’s signature sweets, including chewy ricciarelli and slices of panforte that somehow found room.

Whether you’re a home cook or just love Italian food, this class is a delicious way to end the day. 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!

Related Read: If you’re looking for even more things to do in Siena, have a look at our 5 favorite activities here!

Day 2

Full day Tuscany wine tasting

If you’re lucky enough to have two days to spend in Siena, set aside one for this unforgettable journey into the heart of Tuscan wine country. Running from 9:30 am to 6:30 pm, this small-group tour delivered everything we hoped for—rolling vineyards, rich reds, and long, leisurely meals. Just consider grabbing a quick bite at your hotel before heading out, as lunch won’t be served until later in the day.

Our guide, Giuliana, brought the region to life with her deep knowledge and easy charm. We started at a local winery near Montalcino, walking through sun-drenched vines before heading inside to taste Rosso and Brunello di Montalcino. Learning about the aging process and DOCG rules gave us a new appreciation and a few good reasons to take a bottle or two home.

After some free time to explore the town of Montalcino, we made our way to a family-run winery for lunch. Sitting down to bruschetta, homemade pasta, and generous pours of wine felt less like a tasting and more like a long lunch with friends. 

The afternoon stop at the Abbey of Sant’Antimo was a peaceful surprise. Surrounded by olive trees and quiet hills, the ancient stone church gave us a moment of calm, and if you’re lucky, you might even hear monks chanting inside.

By the time we wrapped up the final tasting, we weren’t just drinking wine—we understood it. With stunning views, incredible flavors, and thoughtful storytelling throughout, this tour was one of the best parts of our time in Tuscany.

Secure your spot on this unforgettable tasting experience here!

Related Read: Need help planning the rest of your Italy adventures? Check out the top 18 things to do in all of Italy for an epic trip!

Dinner – Compagnia dei Vinattieri

You’ll return from your countryside tour around 6:30 or 7 pm, just in time to unwind with a relaxed dinner at Compagnia dei Vinattieri. This cozy spot is tucked away on a quiet street near the center, making it the ideal place to decompress after a full day of sipping, swirling, and sightseeing.

Despite its elegant underground setting, the vibe is friendly and laid-back. The menu leans classic Tuscan, with options like wild boar pappardelle, grilled meats, and seasonal specials. The prices are moderate, and the drink list (unsurprisingly) is excellent. And if you’re still up for a glass, the staff can help you pick something local to round out your day.

Gelato stop – Venchi Cioccolato e Gelato

To cap off your time in Siena, head to Venchi Cioccolato e Gelato for something sweet. After a full day of tastings and vineyard views, a scoop of gelato felt like the perfect way to toast the end of our trip—just rich, creamy goodness.

Venchi’s flavors range from classic stracciatella to chocolate-hazelnut blends that taste straight from a dream. Whether you’re a dark chocolate devotee or a fruit gelato fan, there’s something here to make everyone happy. Grab a cone or a cup, take a slow stroll through the nearby piazzas, and let Siena say goodbye the best way it knows how—with one last taste of something unforgettable.

Related Read: Planning a trip to Sicily? Don’t miss our 3-day Catania itinerary here—packed with history, street food, and epic Mount Etna adventures.

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!

Grand Hotel Continental – $$$

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. 

Albergo Chiusarelli – $$

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.

Albergo Cannon d’Oro – $

Albergo Cannon d’Oro is a lovely stay without breaking the bank! Located in the historic center, this hotel is located in a 13th-century building, giving charming stone arches and stunning beams, cozy vibes, and panoramic city views. You can enjoy the daily Italian breakfast to fuel for the day, and easily access Siena’s top sights from its convenient location.

Prices average around €100 per night and can be booked here on Booking.com.

For more options, see all of the hotels in Siena here!

Related Read: Heading to Milan after? Check out our favorite areas and hotels in Milan to make your planning easier.

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!

Thanks for reading!

Whether you have one quick day in Siena or can stretch it to two days, you can still experience a lot! We loved the historic charm and slow-paced atmosphere of this town, it was such a change of pace from the other bustling cities we’d been in. Follow this itinerary and I know you will fall in love with Siena, just as we did!

Before you go, be sure to check out our other Italy blogs. We have more itineraries, city guides, recommended places to stay, and our favorite things to do that will help you plan an epic holiday. Here are a few related blogs to get you started – cheers!

5 Best Things to do in Siena, Italy

Where to Stay in Florence, Italy: 5 Best Areas & Hotels

How To Spend The Best TEN DAYS In Italy: 10-Day Itinerary

How to Spend THREE DAYS in Palermo, Italy: 3-Day Itinerary