12-Day Italy City Break in Siena With Itinerary

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Revel in the splendor of Siena on this exciting 12-day city break in Italy!

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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Itinerary summary

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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.

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 lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere.

This is the time to raise a toast for your 12-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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  • Loggia del Papa, Siena
  • Tower of Mangia
  • piazza del Campo
  • Pubblico Palace
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Get ready for another exciting day in Siena on day 2 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 10 nights ahead, make the most of your time and create unforgettable memories in Siena.

Get ready for a day filled with fun adventures, picturesque spots, and history-rich sites in the charming city of Siena. Your adventure starts at Loggia Del Papa, Siena, an intriguing local hot spot. Another notable attraction to explore is Tower Of Mangia. This underrated monument is known for its symbolic 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.

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 Ristorante Tar-Tufo, highly recommended for tonight's dining.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Maudit 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 3

Day 3

  • Siena
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  • Piccolomini Library
  • Piazza del Duomo
  • Siena Cathedral
  • Battistero di San Giovanni Battista
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Wake up to day 3 of your exciting city break in Siena. You still have 9 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!

A blend of family-friendly attractions, photo-friendly spots, and history-rich sites await you in Siena on today’s itinerary. First up is the beloved library, Piccolomini Library. Afterward, continue to Piazza Del Duomo, a public square every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Siena Cathedral. This interesting church is an essential stop. Following that, head to Battistero Di San Giovanni Battista, another must-visit site that will enhance your experience.

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 Antica Trattoria Papei, a highly-rated dining destination in Siena.

Explore the vibrant nightlife at Bar Impero Siena after your meal, a hub for lively evenings and memorable moments.

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

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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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As day 4 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.

Start by visiting Vista Panoramica De Siena, a prime spot to begin your journey. This visually striking observation deck is sure to impress. Next on your list is Basilica Of San Domenico, another must-visit landmark and underrated church renowned for its monumental features.

While exploring and sightseeing, take time to savor the ambiance of Siena by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Santuario Di Santa Caterina. This culturally significant church is a remarkable attraction that offers a unique experience. Fontebranda also adds charm to your journey.

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink.

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

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Day 5

Day 5

  • Siena
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  • Palazzo Salimbeni
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On day 5 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 7 nights in Siena and enjoy plenty of time for exploring.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Palazzo Salimbeni. This intriguing palace provides an insightful glimpse into the city's identity.

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 Fischi per Fiaschi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

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

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.

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 picture-perfect monument before continuing your journey.

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

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

Continue your lively evening at San Paolo Pub, 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 Siena, Italy. With each day comes new experiences to cherish and enjoy.

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Day 7

Day 7

  • Siena
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  • Porta Romana
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On day 7 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 5 nights left in Siena.

Porta Romana is must-visit monument and a great starting point for the day.

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

Enjoy a lovely dining experience at Ristorante San Desiderio, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.

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 8

Day 8

  • Siena
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  • Porta Tufi
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Rise and shine for day 8 of your city break in Siena! Today, 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 and uncover the heart of Siena.

Start your adventure at Porta Tufi. This frequently visited historical landmark is a must-visit for travelers looking for a unique holiday experience.

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.

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.

Raise your glass and relax after another 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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Get ready for another exciting day in Siena on day 9 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 3 nights ahead, make the most of your time and create unforgettable memories in Siena.

Siena is home to plenty of attractions that offer fun adventures, photo-friendly spots, and history-rich sites! Start at Musei Dell’accademia Dei Fisiocritici, a curiosity-inducing museum that is worthwhile a visit in the city. Nearby, you’ll find Pinacoteca Nazionale, enchanting visitors with its photogenic appeal.

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.

Dine in style at Ristorante Taverna Di Cecco, a top recommendation for dinner tonight.

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 10

Day 10

  • Siena
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  • Facciatone
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Wake up to day 10 of your exciting city break in Siena. You still have 2 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!

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

Don’t miss out on dining at Bar Pasticceria Nannini Toselli, a top-rated dining destination in Siena.

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

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Day 11

Day 11

  • Siena
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  • Фонтан контради Сельва
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As day 11 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.

When you’re ready, kick off your sightseeing adventure at Fontan Kontradi Sel'va. This frequently visited sightseeing destination is a must-visit for anyone seeking a unique vacation experience.

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.

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

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

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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, begin at Porta Pispini. This intriguing historical landmark is a popular place to see in the city.

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.

Dine in style at Bar osteria enea, a top recommendation for dinner tonight.

As you conclude your city break in Siena, treasure the memories you've made. May they accompany you on your journey homeward while carefully planned travel arrangements ensure your safe return. It's time to say, "See you later, Siena!" and travel onwards.

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