12-Day Italy City Break in Siena With Itinerary

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

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.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting 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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On day 2 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 10 nights left in Siena.

Today, you'll explore some of the most beautiful places in Siena, including a monument, a public square, and a palace. Start your day with a visit to Loggia Del Papa, Siena. This curiosity-inducing monument is a must-visit in the city. When you’re ready for your next discovery, continue to Tower Of Mangia, which may be one of the most historic places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Del Campo, a spectacular public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pubblico Palace.

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

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

To truly maximize your evening out, consider visiting Maudit Pub after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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 3

Day 3

  • Siena
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  • Piccolomini Library
  • Piazza del Duomo
  • Siena Cathedral
  • Battistero di San Giovanni Battista
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Get ready for another exciting day in Siena on day 3 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 9 nights ahead, make the most of your time and create unforgettable memories in Siena.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, photo-friendly spots, and history-rich sites. Start at Piccolomini Library, a beloved library in the city. Then, head to Piazza Del Duomo and soak in the ambiance of this history-steeped public square.

There are many interesting places to see in Siena, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most locally renowned visually striking spots of interest. After exploring the church, visit the underrated Battistero Di San Giovanni Battista.

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 Antica Trattoria Papei, highly recommended for tonight's dining.

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.

Savor the memories of an 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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Wake up to day 4 of your vacation in Siena. With 8 nights left, you'll have ample time to explore and savor all Siena has to offer.

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Siena. Your adventure starts at Vista Panoramica De Siena, an intriguing local hot spot. Another notable attraction to explore is Basilica Of San Domenico. This often recommended church is known for its visually striking 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 Santuario Di Santa Caterina. This culturally significant church offers a fascinating experience that many visitors find memorable. Fontebranda is also worth visiting.

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.

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

Continue the enjoyment post-dinner at Charlie Mixology Bar Di Aldinucci Riccardo, a cherished local gathering spot renowned for its welcoming atmosphere.

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 5

Day 5

  • Siena
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  • Palazzo Salimbeni
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Rise and shine for day 5 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 7 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 Palazzo Salimbeni. This often recommended palace provides an insightful glimpse into the city's identity.

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 lovely dining experience at Fischi per Fiaschi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.

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

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

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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 6 nights in Siena and enjoy plenty of time for exploring.

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

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

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

Round off your dining experience by visiting San Paolo Pub, a prime location for a drink.

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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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!

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Porta Romana. This frequently visited monument is a picture-perfect place to see in Siena.

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 for dinner, we recommend you try one of the best restaurants in Siena.

Treat yourself to a wonderful meal at Ristorante San Desiderio, 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 8

Day 8

  • Siena
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  • Porta Tufi
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As day 8 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 4 nights left, the possibilities for discovery are endless.

Siena is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Porta Tufi, an increasingly popular historical landmark that is worthwhile a visit in the city.

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.

Don’t miss out on dining at Osteria Le Logge, a top-rated dining destination 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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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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On day 9 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 3 nights left in Siena.

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 increasingly popular museum, Musei Dell’accademia Dei Fisiocritici. Afterward, continue to Pinacoteca Nazionale, an art gallery every traveler should visit.

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 Taverna Di Cecco, a highly recommended choice for tonight's dinner.

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

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Day 10

Day 10

  • Siena
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  • Facciatone
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Get ready for another exciting day in Siena on day 10 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 2 nights ahead, make the most of your time and create unforgettable memories in Siena.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Facciatone. This UNESCO world heritage-listed observation deck is sure to ignite your curiosity.

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 meal at Bar Pasticceria Nannini Toselli, a top-rated place to have 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 11

Day 11

  • Siena
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  • Фонтан контради Сельва
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Wake up to day 11 of your vacation in Siena. With 1 night left, you'll have ample time to explore and savor all Siena has to offer.

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

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.

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

Savor the memories of an 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 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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