9-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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Explore Siena on a 9-day city break in Italy and experience a fusion of culture and excitement.

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 8 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 9-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
Фонтан контради СельваPiazza del DuomoPiccolomini LibraryBattistero di San Giovanni BattistaSiena CathedralFacciatone
Fortezza Medicea
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
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 8 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.

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.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area.

Celebrate the start of your 9-day city break in Siena with a toast!

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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 7 nights left in Siena.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most intriguing attractions included on the itinerary is Palazzo Salimbeni. This standout palace will help you start your sightseeing on top. Then, take a leisurely stroll to Loggia Del Papa, Siena and learn what makes this standout monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the up-and-coming Tower Of Mangia. After exploring the monument, head to Piazza Del Campo. This famous public square is a highlight in Siena. As your day continues, stop by Pubblico Palace, known for its awe-inspiring features.

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 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.

Continue the enjoyment post-dinner at Maudit Pub, a cherished local gathering spot renowned for its welcoming atmosphere.

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

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Day 3

Day 3

  • Siena
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  • Фонтан контради Сельва
  • Piazza del Duomo
  • Piccolomini Library
  • Battistero di San Giovanni Battista
  • Siena Cathedral
  • Facciatone
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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 6 nights ahead, make the most of your time and create unforgettable memories in Siena.

Fontan Kontradi Sel'va is must-visit sightseeing destination and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, an increasingly popular public square, located just a leisurely stroll away. Next, head to Piccolomini Library, a standout library, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the curiosity-inducing Battistero Di San Giovanni Battista. If you’re looking for more, Siena Cathedral is also a well-known attraction that is worthwhile a visit. Lastly, don’t miss Facciatone, a place of visually striking interest in the city.

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

Treat yourself to a delightful dinner at Antica Trattoria Papei, highly recommended for tonight's dining.

Let the evening flow smoothly from dinner to drinks at Bar Impero Siena, a top-rated bar in the area.

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

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Day 4

Day 4

  • Siena
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  • Fortezza Medicea
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Wake up to day 4 of your vacation in Siena. With 5 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 Fortezza Medicea (siena). This stunning monument is a highlight of any visit in the city.

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.

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena.

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

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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  • Vista Panoramica de Siena
  • Basilica of San Domenico
  • Santuario di Santa Caterina
  • Fontebranda
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Wake up to day 5 of your exciting city break in Siena. You still have 4 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, you'll explore some of the most beautiful places in Siena, including an observation deck, a church, and a historical landmark. Start your day with a visit to Vista Panoramica De Siena. This up-and-coming observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of San Domenico, which may be one of the most majestic 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 Santuario Di Santa Caterina, a worthwhile church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Fontebranda.

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

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

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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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 3 nights left, the possibilities for discovery are endless.

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

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.

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

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

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

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Day 7

Day 7

  • Siena
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  • Porta Pispini
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On day 7 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 2 nights in Siena and enjoy plenty of time for exploring.

Start your adventure at Porta Pispini. This frequently visited historical landmark is a place that is appreciated by travelers and locals alike.

These sights offer a fulfilling end to a perfect day.

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.

Dine in style at Ristorante San Desiderio, a top recommendation for dinner tonight.

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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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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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 1 night remaining, there's ample time to explore and uncover the heart of Siena.

Today’s route brings family-friendly attractions, picturesque spots, and history-rich sites. The first attraction of today is Musei Dell’accademia Dei Fisiocritici. This up-and-coming museum is a heritage-rich place to see in Siena. Continue your discovery at Pinacoteca Nazionale, a photogenic art gallery with stories to tell.

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.

Enjoy a lovely meal at Osteria Le Logge, a top-rated place to have dinner tonight.

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 - 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 breathtaking 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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