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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Discover the essence of Siena with a 12-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 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 to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand.

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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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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring family-friendly attractions, picturesque spots, and history-rich sites. Start at Loggia Del Papa, Siena, an often recommended monument in the city. Then, head to Tower Of Mangia and soak in the ambiance of this breathtaking monument.

There are many interesting places to see in Siena, and when you are ready for more, go to Piazza Del Campo. This is one of the city’s most astonishing history-steeped spots of interest. After exploring the public square, visit the frequently visited Pubblico Palace.

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

Dine in style at Ristorante Tar-Tufo, a top recommendation for dinner tonight.

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

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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Rise and shine for day 3 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 9 nights remaining, there's ample time to explore and uncover the heart of Siena.

Today’s itinerary in Siena covers several incredible sights, including a library, a public square, and a church. Start your adventure at Piccolomini Library. This beloved library is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the majestic wonders of Piazza Del Duomo, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Siena Cathedral. This captivating church offers an enriching experience. For a change of pace, head to Battistero Di San Giovanni Battista, where you can take in culturally significant features. These sights offer a fulfilling end to a perfect day.

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

Don’t miss out on dining at Antica Trattoria Papei, a top-rated dining destination in Siena.

Round off your dining experience by visiting Bar Impero Siena, a prime location for a drink.

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 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.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Vista Panoramica De Siena. This up-and-coming observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Domenico, one of the city’s best highlights.

Next, check out Santuario Di Santa Caterina, one of the most intriguing places to see in Siena. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Fontebranda. Wander around and soak in the instagrammable atmosphere this historical landmark offers.

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

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

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

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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.

Palazzo Salimbeni is must-visit palace and a great starting point for the day.

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

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

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

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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Wake up to day 6 of your exciting city break in Siena. You still have 6 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!

Start your day at Porta Camollia, Siena. This historic monument is an intriguing place to see in Siena.

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 wonderful meal at Osteria da Divo, a top-rated dining spot in Siena.

Continue the enjoyment post-dinner at San Paolo Pub, a cherished local gathering spot renowned for its welcoming 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 Romana
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Get ready for another exciting day in Siena on day 7 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.

Start by visiting Porta Romana, a prime spot to begin your journey. This awe-inspiring monument is sure to impress.

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 Ristorante San Desiderio, a top pick for dinner tonight.

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

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Day 8

Day 8

  • Siena
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  • Porta Tufi
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On day 8 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 4 nights left in Siena.

Siena is home to plenty of attractions that offer family-friendly attractions, scenic views, and photo-friendly spots! Start at Porta Tufi, a frequently visited historical landmark that is worthwhile a visit in the city.

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

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

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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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.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Musei Dell’accademia Dei Fisiocritici is the perfect place to start. This museum is one of the most underrated places to visit in Siena. Next, head to Pinacoteca Nazionale, a locally appreciated art gallery, known for its photogenic features.

Visit these for an interesting touch to your journey.

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 Ristorante Taverna Di Cecco, 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 10

Day 10

  • Siena
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  • Facciatone
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Rise and shine for day 10 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 2 nights remaining, there's ample time to explore and uncover the heart of Siena.

Start your day with a visit to Facciatone. This often recommended observation deck is a must-visit in the city.

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 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.

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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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.

Begin your adventure at Fontan Kontradi Sel'va. This is an increasingly popular sightseeing destination you should not miss.

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.

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

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 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 underrated 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.

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

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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