Travel packages in Italy

City breaks in Italy

12-Day Italy City Break in Siena With Itinerary

1 / 15

Photo of Siena cathedral against a bright blue sky in Italy.

12-Day Italy City Break in Siena With Itinerary

Perfect travel plans

Everything included

Fully customizable

Description

Included

Flights

Select dates

Hotel

Select dates

Car rental

Select dates

Tours & tickets

Select dates

Travel plan

From A to Z

Travel agent

24/7 fast service

Description

Explore Siena on this 12-day city break in Italy and experience a fusion of culture and excitement.

In Tuscany, Siena stands as a medieval masterpiece. Discover the historic Palio horse race, the stunning Piazza del Campo, and the magnificent Siena Cathedral in this magnificent city. Stroll through its charming alleys and immerse yourself in this classic Italian city's timeless traditions and artistic treasures. Siena promises an unforgettable journey into Italy's rich heritage.

With this perfectly planned holiday package, you will experience 11 nights in Siena. It's the the ultimate 12-day Siena city break.

The home for your 12-day holiday in Siena will be one of the city’s best hotels. You’ll choose from a great selection of places to stay, all conveniently located in downtown Siena, close to many of the top attractions and best restaurants in the city.

Siena offers excellent hotels for every budget, ensuring travelers a fantastic city break. You can rest assured that we will always recommend the best available places to stay in the city.

During your vacation in Siena, you'll get the chance to experience some of the best things to see and do in the city.

Maximize your holiday experience in Siena by customizing each day with exciting tours and tickets. Whether you're tracing history on guided tours or savoring the rich flavors of Italy's traditional cuisine, the city offers a range of immersive experiences. Your time in Siena is sure to be anything but ordinary!

Between sightseeing and activities, you will enjoy plenty of time to wander through Siena's best shopping streets and markets. Let the unique souvenirs you find serve as fond reminders of your city break in Italy.

This travel plan is designed to include everything you need to experience the best of Siena. By booking this vacation package, you can avoid spending hours researching and planning your city break and jump straight to enjoying it. Let the experts take care of the details so you can relax and make the most of your time in Italy.

To make sure the city break is fully tailored to your interests and preferences, you can easily customize each day of your journey. Our intuitive trip planning puts you in control, ensuring that every moment in Siena reflects your unique travel style.

Book with us to get an expertly curated step-by-step travel itinerary and access to 24/7 personal travel support before, during, and after your city break in Siena.

The best hotels, flights, activities, and tours in Siena fill up quickly. Select a date and start planning your city break in Siena as early as today!

Travel details

Set your travel details to find the best price

Flights

Compare and choose from the best flights to Siena, landing in Florence

Include flights

Car

Choose from the best car rental deals or see all options

Include car

Personalize your itinerary

Customize tours under each day and destination

Day1

Day 1

Siena - Arrival day
More

Fortezza Medicea
More

Your exciting city break begins as soon as you arrive in the beautiful city of Siena. You’ll stay here for 11 nights and take time to discover what to see in Siena, along with enjoying the city’s best dining and cultural experiences.

Siena is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Fortezza Medicea (siena). Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When the afternoon arrives, make your way to the hotel of your choice in downtown Siena. Check-in at hotels in Italy normally starts around 2 to 3 PM. Each accommodation option in Siena offers a unique blend of comfort and style in addition to prime access to the city’s top attractions.

You have plenty of options for restaurants and bars in Siena. So when you’re hungry or need a break from exploring, all you have to do is take your pick.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail.

Celebrate the start of your 12-day city break in Siena with a toast!

Day2

Day 2

Siena
More

Loggia del Papa, Siena
Tower of Mangia
piazza del Campo
Pubblico Palace
More

Wake up to day 2 of your vacation in Siena. With 10 nights left, you'll have ample time to explore and savor all Siena has to offer.

Loggia Del Papa, Siena brings Siena's character to life. This culturally significant monument is a highlight of any visit in the city. Then, enjoy Tower Of Mangia, another culturally significant attraction that never fails to captivate visitors. Next, head over to Piazza Del Campo, one of the city’s most impressive attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Pubblico Palace. This historic palace is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

After a full day of exploring, we recommend you try one of the best places to eat in Siena. Enjoy the local flavors, unwind, and reflect on the day's adventures.

Make sure to reserve a table at Ristorante Tar-Tufo, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

Cap off your dinner by heading to Maudit Pub, ideal for a leisurely evening with a drink in hand.

No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.

Day3

Day 3

Siena
More

Piccolomini Library
Piazza del Duomo
Siena Cathedral
Battistero di San Giovanni Battista
More

On day 3 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 9 nights left in Siena.

Whatever your travel style is, Piccolomini Library is an essential stop in Siena. This frequently visited library provides an insightful glimpse into the city's identity. Next, discover Piazza Del Duomo, a visually striking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, an interesting church. When you’re done, don’t forget to make a stop at the up-and-coming Battistero Di San Giovanni Battista.

When it’s time to eat, Siena has restaurants and bars to suit all budgets.

Treat yourself to a delicious dinner at Antica Trattoria Papei, an excellent option for tonight's dining.

Keep the excitement of the evening going by visiting a bar or two. Bar Impero Siena is an excellent place to start.

Raise your glass and relax after another amazing day in Siena, Italy.

Day4

Day 4

Siena
More

Vista Panoramica de Siena
Basilica of San Domenico
Santuario di Santa Caterina
Fontebranda
More

Get ready for another exciting day in Siena on day 4 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 8 nights ahead, make the most of your time and create unforgettable memories in Siena.

Look forward to a unique sightseeing adventure at the underrated Vista Panoramica De Siena and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of San Domenico, a monumental church that draws visitors from far and near.

Continue your journey to Santuario Di Santa Caterina, one of the city’s most increasingly popular spots that you shouldn’t miss. Another great site to visit is the curiosity-inducing Fontebranda.

You have plenty of options for restaurants and bars in Siena. So when you’re hungry or need a break from exploring, all you have to do is take your pick.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink.

Savor the memories of an amazing day in Siena, Italy!

Day5

Day 5

Siena
More

Palazzo Salimbeni
More

As day 5 dawns in Siena, discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 7 nights left, the possibilities for discovery are endless.

Visiting Palazzo Salimbeni is always a good idea. This curiosity-inducing palace is a place that is appreciated by travelers and locals alike.

When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Enjoy a lovely meal at Fischi per Fiaschi, a top-rated place to have dinner tonight.

Continue your lively evening at Bar Pinacoteca, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Wind down and recharge for tomorrow's escapades in Italy.

Day6

Day 6

Siena
More

Porta Camollia, Siena
More

On day 6 of your city break, you will set out to discover Siena, including some of the most amazing things to see and do in the city. You’ll stay 6 nights in Siena and enjoy plenty of time for exploring.

Siena is brimming with adventures.

Awaiting your discovery is the curiosity-inducing Porta Camollia, Siena, a picture-perfect monument in Siena.

When you’re ready for dinner, we recommend you try one of the best restaurants in Siena.

Have a fantastic dining experience at Osteria da Divo, a highly recommended choice for tonight's dinner.

Extend your evening after a delightful meal by visiting San Paolo Pub, which offers the perfect atmosphere for a night out.

Raise a toast and celebrate another memorable day in Siena, Italy!

Day7

Day 7

Siena
More

Porta Romana
More

Wake up to day 7 of your exciting city break in Siena. You still have 5 nights left in Siena, and we recommend that you spend this day relaxing, sightseeing, and dining at the most wonderful places the city has to offer. Here's how you can make the most of today!

Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Your adventure in Siena is only getting started when you visit Porta Romana, a locally appreciated local hot spot.

Before you know it, it’s time to head out for dinner. Treat yourself to a delicious meal at a nice restaurant in Siena.

Enjoy a delicious meal at Ristorante San Desiderio, a top-rated dining destination in Siena.

Get some rest at your hotel in preparation for another wonderful day of your vacation to come!

Day8

Day 8

Siena
More

Porta Tufi
More

Rise and shine for day 8 of your city break in Siena! Delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 4 nights remaining, there's ample time to explore.

Porta Tufi leaves a lasting impression. This historical landmark is one of the most intriguing places to visit in Siena.

Exploring the most popular attractions in Italy can make you lose track of time. Be sure to grab something to eat at one of the best restaurants in Siena.

Make sure to reserve a table at Osteria Le Logge, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

As the day draws to a close, enjoy Siena at night. Rest well for more adventures tomorrow.

Day9

Day 9

Siena
More

Musei dell’Accademia dei Fisiocritici
Pinacoteca Nazionale
More

Wake up to day 9 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Experience Musei Dell’accademia Dei Fisiocritici, a beloved museum in the city. Then, head to Pinacoteca Nazionale and soak in the ambiance of this historic art gallery.

Exploring can easily make you lose track of time. Make sure to grab something to eat and use this opportunity to learn more about Siena's food culture.

Savor the flavors at Ristorante Taverna Di Cecco, a top pick for dinner tonight.

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow is a new day!

Day10

Day 10

Siena
More

Facciatone
More

On day 10 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 2 nights left in Siena.

Make a stop at Facciatone. This increasingly popular observation deck is a must-visit for travelers looking for a unique holiday experience.

When it’s time for dinner, try one of the most popular restaurants in Siena. Make sure to reserve a table in advance, as the best restaurants fill up quickly.

Enjoy a delicious meal at Bar Pasticceria Nannini Toselli, a highly-rated dining destination in Siena.

No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.

Day11

Day 11

Siena
More

Фонтан контради Сельва
More

Get ready for another exciting day in Siena on day 11 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 1 night ahead, make the most of your time and create unforgettable memories in Siena.

Catch Fontan Kontradi Sel'va before the crowds roll in.

After a long day of sightseeing, try one of the best restaurants in Siena.

Dine in style at Ristorante Gallo Nero, a top recommendation for dinner tonight.

Raise your glass and relax after another amazing day in Siena, Italy.

Day12

Day 12

Siena - Departure day
More

Porta Pispini
More

Your city break in Siena is coming to an end, and it's soon time to say goodbye to the city. Before you leave, make sure to capture a few last moments to cherish your rejuvenating vacation in Italy.

If you're up for some more sightseeing, we recommend visiting Porta Pispini, a picture-perfect historical landmark before you head out.

Depending on how much time you have to spare on your departure day, you may want to do some last-minute shopping at downtown Siena. It's the perfect place for browsing souvenirs and gifts to bring back home with you.

Before you conclude your city break in Siena, drop by a top-rated restaurant for your last chance at a memorable dining experience in the city. Savor the destination's local atmosphere over a delicious meal.

Treat yourself to a delicious dinner at Bar osteria enea, an excellent option for tonight's dining.

As you conclude your city break in Siena, treasure the memories you've made. May they accompany you on your journey homeward!

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

Similar travel packages

Discover other popular vacations in Italy

From 0

Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.