One-Week 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 8-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 7 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 8-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
Palazzo SalimbeniLoggia del Papa, SienaTower of Mangiapiazza del CampoPubblico Palace
Musei dell’Accademia dei FisiocriticiPinacoteca NazionalePiazza del DuomoSiena CathedralBattistero di San Giovanni BattistaPiccolomini Library
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
Porta Camollia, Siena
Porta Romana
Porta Tufi
Porta Pispini

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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 7 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.

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.

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

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink.

This is the time to raise a toast for your 8-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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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 6 nights left in Siena.

Get ready for a day filled with family-friendly attractions, picturesque spots, and history-rich sites in the charming city of Siena. Your adventure starts at Palazzo Salimbeni, a beloved local hot spot. Another notable attraction to explore is Loggia Del Papa, Siena. This curiosity-inducing monument is known for its standout 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 Tower Of Mangia. This culturally significant monument offers a fascinating experience that many visitors find memorable. Piazza Del Campo is also worth visiting, along with Pubblico Palace. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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 Ristorante Tar-Tufo, a highly-rated dining destination in Siena.

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

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

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Day 3

Day 3

  • Siena
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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
  • Piazza del Duomo
  • Siena Cathedral
  • Battistero di San Giovanni Battista
  • Piccolomini Library
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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 5 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 Musei Dell’accademia Dei Fisiocritici. This standout museum is sure to ignite your curiosity. Next, dive into the photogenic features of Pinacoteca Nazionale, a must-visit art gallery in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Piazza Del Duomo, a beloved public square. For a change of scene, check out Siena Cathedral, known for its romantic features. We also recommend visiting Battistero Di San Giovanni Battista. This church is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piccolomini Library, yet another increasingly popular attraction in Siena.

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 Antica Trattoria Papei, a top pick for dinner tonight.

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

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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Rise and shine for day 4 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, romantic experiences, and scenic views. Start at Vista Panoramica De Siena, an often recommended observation deck in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this breathtaking church.

There are many interesting places to see in Siena, and when you are ready for more, go to Santuario Di Santa Caterina. This is one of the city’s most often recommended culturally significant spots of interest. After exploring the church, visit the frequently visited Fontebranda.

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 Quattro Venti, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out.

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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  • Porta Camollia, Siena
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Wake up to day 5 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Start your day with a visit to Porta Camollia, Siena. This increasingly popular monument is a must-visit in the city.

When you’re ready for dinner, we recommend you 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.

After your meal, keep the night alive at a bar like Bar Pinacoteca, known for its lively atmosphere.

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

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Day 6

Day 6

  • Siena
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  • Porta Romana
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As day 6 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 2 nights left, the possibilities for discovery are endless.

Prepare for a day full of family-friendly attractions, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Porta Romana. This beloved monument is a must-visit for anyone seeking a unique vacation experience.

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 Osteria da Divo, a highly recommended choice for tonight's dinner.

After savoring a delicious meal, step into the vibrant nightlife at San Paolo Pub, where the evening is just getting started.

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

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Day 7

Day 7

  • Siena
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  • Porta Tufi
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Wake up to day 7 of your exciting city break in Siena. You still have 1 night 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!

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.

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 8

Day 8

  • 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 beloved 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.

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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