10-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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Discover the essence of Siena with a 10-day city break in Italy, blending cultural richness with exhilarating adventures.

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 9 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 10-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
Porta Romana
Palazzo SalimbeniLoggia del Papa, SienaTower of Mangiapiazza del CampoPubblico Palace
Piazza del DuomoPiccolomini LibraryBattistero di San Giovanni BattistaSiena CathedralFacciatone
Fortezza Medicea
FontebrandaSantuario di Santa CaterinaBasilica of San DomenicoVista Panoramica de Siena
Porta Camollia, Siena

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Day 1

Day 1

  • Siena - Arrival day
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  • Porta Romana
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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 9 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 Porta Romana, 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 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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink.

This is the time to raise a toast for your 10-day city break in Siena! Savor the moment and look forward to immersing yourself in the vibrant culture, stunning sights, and local delicacies of the city for the next few days to come!

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Day 2

Day 2

  • Siena
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  • Palazzo Salimbeni
  • 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 8 nights left, the possibilities for discovery are endless.

Siena is brimming with adventures. Today’s wonderful stops include a palace, a monument, and a public square. Begin your sightseeing adventure at the up-and-coming Palazzo Salimbeni and allow yourself time to explore. Just a short distance away you'll find your next stop, Loggia Del Papa, Siena, an eye-catching monument that draws visitors from far and near.

Continue your journey to Tower Of Mangia, one of the city’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the extraordinary Piazza Del Campo. When you're finished at the public square, Pubblico Palace awaits your visit. This palace is a breathtaking highlight on today's itinerary.

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

Treat yourself to a wonderful meal at Ristorante Tar-Tufo, a top-rated dining spot in Siena.

After enjoying a fulfilling meal, continue your evening at Maudit Pub, ideal for those looking to unwind with a drink in a comfortable setting.

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 3

Day 3

  • Siena
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  • Piazza del Duomo
  • Piccolomini Library
  • Battistero di San Giovanni Battista
  • Siena Cathedral
  • Facciatone
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Wake up to day 3 of your exciting city break in Siena. You still have 7 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!

Savor the day by visiting some of the best places to see in Siena, including a public square, a library, a church, an observation deck and much more! Start your adventure at Piazza Del Duomo. This frequently visited public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Piccolomini Library located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Battistero Di San Giovanni Battista. Its photogenic features will captivate you. After the church, continue your tour of the city with a visit to Siena Cathedral. Visitors usually appreciate the majestic features of this church. Next up is Facciatone, a highly recommended observation deck.

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 Antica Trattoria Papei, a top-rated place to have dinner tonight.

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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  • Fortezza Medicea
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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 6 nights left in Siena.

Start your adventure at Fortezza Medicea (siena). This worthwhile monument is a place that is appreciated by travelers and locals alike.

These sights offer a fulfilling end to a perfect day.

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.

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

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out.

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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  • Fontebranda
  • Santuario di Santa Caterina
  • Basilica of San Domenico
  • Vista Panoramica de Siena
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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 5 nights ahead, make the most of your time and create unforgettable memories in Siena.

Discover a day packed with fun adventures, photo-friendly spots, and historic treasures in Siena. Begin your sightseeing with Fontebranda. This often recommended historical landmark is one of the top attractions in the city. Proceed to Santuario Di Santa Caterina, 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 Basilica Of San Domenico. This increasingly popular church is a traveler-favorite. Not far away, you’ll find Vista Panoramica De Siena, another key site on your sightseeing itinerary.

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 Fischi per Fiaschi, a highly-rated dining destination in Siena.

After savoring a delicious meal, step into the vibrant nightlife at Bar Pinacoteca, where the evening is just getting started.

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 6

Day 6

  • Siena
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  • Porta Camollia, Siena
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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 4 nights in Siena and enjoy plenty of time for exploring.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. 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. Porta Camollia, Siena is the first of them. Spend some time admiring this standout monument before continuing your journey.

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

Enjoy a delicious meal at Osteria da Divo, a top-rated dining destination in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to San Paolo Pub, known for its inviting atmosphere.

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

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Day 7

Day 7

  • Siena
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  • Porta Pispini
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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 3 nights remaining, there's ample time to explore and uncover the heart of Siena.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Porta Pispini. This up-and-coming historical landmark provides an insightful glimpse into the city's identity.

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

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

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

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Day 8

Day 8

  • Siena
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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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Wake up to day 8 of your vacation in Siena. With 2 nights left, you'll have ample time to explore and savor all Siena has to offer.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Musei Dell’accademia Dei Fisiocritici. This heritage-rich museum is a highlight of any visit in the city. Then, enjoy Pinacoteca Nazionale, another eye-catching attraction that never fails to captivate visitors.

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.

Treat yourself to a delicious dinner at Osteria Le Logge, 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 9

Day 9

  • Siena
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  • Фонтан контради Сельва
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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 1 night left, the possibilities for discovery are endless.

Your adventure starts at Fontan Kontradi Sel'va, a beloved 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.

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

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

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Day 10

Day 10

  • Siena - Departure day
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  • Porta Tufi
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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 Tufi, 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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