12-Day Italy City Break in Siena With Itinerary

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Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
photo of view of Stylish woman walks on background of cityscape of Siena old town. Concept of travel famous cities in Tosacny region of Italy
photo of view of  Aerial view of Montepulciano, a medieval and Renaissance hill town in the Italian province of Siena in southern Tuscany, Italy
photo of view of Facade decoration of the cathedral of Siena, Italy.
photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
photo of view of Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
photo of view of Beautiful traveler girl exploring the historic city of Siena in Tuscany. Young tourist woman smiling at camera in Siena Cathedral square, Tuscany, Italy.
photo of view ofYoung woman having lunch with pizza and wine, sitting with dog at outdoor restaurant with beautiful view on the old town of Siena. Concept of italian cuisine and travel
photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view ofBeautiful view of campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Siena province, Italy
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Immerse yourself in the charm of Siena on this 12-day city break in Italy, where cultural delights and exciting experiences await!

In the heart of 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.

With this perfectly planned holiday package, you will experience the ultimate Siena city break. This trip includes 11 nights in Siena at one of the best hotels in the city. Let us take care of the details so you can fully enjoy all the attractions and activities the city has to offer. Whether you're seeking to discover the rich cultural heritage of Siena or indulge in its delicious culinary scene, this holiday package has got you covered.

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. Piazza Del Campo, Siena Cathedral, and Fortezza Medicea (siena) are only a few of the many spectacular attractions and sights you’ll find on your carefully planned travel itinerary.

Maximize your holiday experience in Siena by customizing each day with exciting tours and tickets. Whether you're tracing the footsteps of history through iconic landmarks, savoring the rich flavors of Italy's traditional cuisine, or uncovering the city's best-kept secrets on guided tours, Siena promises an adventure tailored to every traveler's passion. With a diverse selection of immersive experiences to choose from, 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, so it's advisable to book your holiday package in advance. Select a date and start planning your city break in Siena as early as today. Join us and discover the enchanting beauty of Siena, Italy!

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Fortezza Medicea
Loggia del Papa, SienaTower of Mangiapiazza del CampoPubblico Palace
Piccolomini LibraryPiazza del DuomoSiena CathedralBattistero di San Giovanni Battista
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
Palazzo Salimbeni
Porta Camollia, Siena

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Day 1

Day 1

  • Siena - Arrival day
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  • Fortezza Medicea
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Your exciting city break begins as soon as you arrive in the beautiful city of Siena. You’ll stay in Siena for 11 nights.

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), or just taking a stroll in the city center. 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.

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner.

After savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started.

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

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Day 2

Day 2

  • Siena
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  • Loggia del Papa, Siena
  • Tower of Mangia
  • piazza del Campo
  • Pubblico Palace
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As day 2 dawns in Siena, embark on another day of exploration and adventure. Discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 10 nights left, the possibilities for discovery are endless.

Get ready for a day filled with fun adventures, photo-friendly spots, and historic treasures in the charming city of Siena. Your adventure starts at Loggia Del Papa, Siena, a locally appreciated local hot spot. Another notable attraction to explore is Tower Of Mangia. This frequently visited monument is known for its photogenic appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Del Campo. This visually striking public square offers a fascinating experience that many visitors find memorable. Pubblico Palace is also worth visiting.

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 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 culinary experience with a visit to some of the most celebrated bars in the area. For instance, Maudit Pub stands out as an excellent choice for a post-dinner cocktail.

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

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Day 3

Day 3

  • Siena
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  • Piccolomini Library
  • Piazza del Duomo
  • Siena Cathedral
  • Battistero di San Giovanni Battista
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On day 3 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 9 nights in Siena and enjoy plenty of time for exploring.

Discover a day packed with family-friendly attractions, picturesque spots, and historic treasures in Siena. Begin your sightseeing with Piccolomini Library. This worthwhile library is one of the top attractions in the city. Proceed to Piazza Del Duomo, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Siena Cathedral. This well-known church is a traveler-favorite. Not far away, you’ll find Battistero Di San Giovanni Battista, another key site on your sightseeing itinerary.

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

Enjoy a delicious meal at Antica Trattoria Papei, a highly-rated dining destination in Siena.

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

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

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Day 4

Day 4

  • Siena
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  • Vista Panoramica de Siena
  • Basilica of San Domenico
  • Santuario di Santa Caterina
  • Fontebranda
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On day 4 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 8 nights left in Siena.

Today’s agenda in Siena includes an observation deck, a church, and a historical landmark. Vista Panoramica De Siena is must-visit observation deck and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, an increasingly popular church, located just a leisurely stroll away. Next, head to Santuario Di Santa Caterina, a heritage-rich church, also available for your discovery today.

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.

Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start.

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow holds new possibilities and discoveries!

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Day 5

Day 5

  • Siena
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  • Palazzo Salimbeni
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Get ready for another exciting day in Siena on day 5 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 7 nights ahead, make the most of your time and create unforgettable memories in Siena.

Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and history-rich sites. 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. Palazzo Salimbeni is the first of them. Spend some time admiring this symbolic palace before continuing your journey.

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

Don’t miss out on dining at Fischi per Fiaschi, a top-rated dining destination in Siena.

Let the evening flow smoothly from dinner to drinks at Bar Pinacoteca, a top-rated bar in the area.

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

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Day 6

Day 6

  • Siena
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  • Porta Camollia, Siena
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Wake up to day 6 of your vacation in Siena. With 6 nights left, you'll have ample time to explore and savor all Siena has to offer.

Begin your adventure at Porta Camollia, Siena. This is an underrated monument you should not miss.

After or in between exploring, treat yourself to a delicious meal at a nice restaurant in the city. Unwind and enjoy the local flavors and culinary delights while reflecting on the day's adventures.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at San Paolo Pub, a well-loved spot among locals and tourists.

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

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Day 7

Day 7

  • Siena
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  • Porta Romana
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Rise and shine for day 7 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 5 nights remaining, there's ample time to explore and uncover the heart of Siena.

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

Treat yourself to a delightful dinner at Ristorante San Desiderio, highly recommended for tonight's dining.

Wind down and recharge for tomorrow's escapades in Siena, Italy. With each day comes new experiences to cherish and enjoy.

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Day 8

Day 8

  • Siena
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  • Porta Tufi
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Wake up to day 8 of your exciting city break in Siena. You still have 4 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!

Prepare for a day full of family-friendly attractions, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Porta Tufi. This often recommended historical landmark is a must-visit for anyone seeking a unique vacation experience.

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.

Enjoy a lovely meal at Osteria Le Logge, a top-rated place to have dinner tonight.

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

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Day 9

Day 9

  • Siena
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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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As day 9 dawns in Siena, embark on another day of exploration and adventure. Discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 3 nights left, the possibilities for discovery are endless.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most intriguing attractions included on the itinerary is Musei Dell’accademia Dei Fisiocritici. This photogenic museum will help you start your sightseeing on top. Then, take a leisurely stroll to Pinacoteca Nazionale and learn what makes this heritage-rich art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings.

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.

Treat yourself to a wonderful meal at Ristorante Taverna Di Cecco, a top-rated dining spot in Siena.

As the day draws to a close, bask in the tranquility of Siena by night. With memories made and adventures ahead, rest well and embrace the journey anew tomorrow.

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Day 10

Day 10

  • Siena
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  • Facciatone
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On day 10 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 2 nights in Siena and enjoy plenty of time for exploring.

Start your day at Facciatone. This history-steeped observation deck is an intriguing place to see in Siena.

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

Treat yourself to a delicious dinner at Bar Pasticceria Nannini Toselli, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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

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Day 11

Day 11

  • Siena
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  • Фонтан контради Сельва
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On day 11 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 1 night left in Siena.

The first attraction of today is Fontan Kontradi Sel'va.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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

Have a fantastic dining experience at Ristorante Gallo Nero, a highly recommended choice for tonight's dinner.

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

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Day 12

Day 12

  • Siena - Departure day
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  • Porta Pispini
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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 culturally significant 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 or sightseeing. Downtown Siena offers excellent shopping opportunities and is the perfect place to browse for souvenirs and gifts to bring home. Take a walk and discover unique items you can purchase to remind you of your city break in Siena.

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 vibrant atmosphere over a delicious meal.

As your city break in Siena draws to a close, cherish the memories you've made. With your travel plans in place, you're all set for a safe journey home. Until next time, take care and safe travels!

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