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9-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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Take a 9-day city break in Italy and explore Siena like a local. Immerse yourself in the charm of Siena, where every corner holds a new adventure.

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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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.

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

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists.

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

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 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.

Prepare for a day full of fun adventures, picturesque spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Palazzo Salimbeni. This curiosity-inducing palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Loggia Del Papa, Siena, one of the city’s best highlights.

Next, check out Tower Of Mangia, one of the most worthwhile places to see in Siena. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Campo. Wander around and soak in the enchanting atmosphere this public square offers. Then, head to Pubblico Palace, a top-rated palace that adds another dimension to your day.

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 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.

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

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

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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As day 3 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 6 nights left, the possibilities for discovery are endless.

Today’s route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Fontan Kontradi Sel'va. Continue your discovery at Piazza Del Duomo, an enchanting public square with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piccolomini Library. This worthwhile library offers an instagrammable encounter with Siena. Next, make your way to Battistero Di San Giovanni Battista to add another highlight to your day. After that, visit Siena Cathedral, a popular church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Facciatone, an increasingly popular observation deck in the city. 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.

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 Antica Trattoria Papei, a top recommendation for dinner tonight.

Continue your evening by exploring the vibrant nightlife scene at Bar Impero Siena, a prime destination for a thrilling night out.

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

Day 4

Siena
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Fortezza Medicea
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Get ready for another exciting day in Siena on day 4 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 Fortezza Medicea (siena). This culturally significant monument 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 delicious meal at Osteria Quattro Venti, a top-rated dining destination 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.

Wind down and recharge for tomorrow's escapades in Siena, Italy. With each day comes new experiences to cherish and enjoy.

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!

Savor the day by visiting some of the best places to see in Siena, including an observation deck, a church, and a historical landmark. Start your adventure at Vista Panoramica De Siena. This worthwhile observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of San Domenico located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Santuario Di Santa Caterina. Its culturally significant features will captivate you. After the church, continue your tour of the city with a visit to Fontebranda. Visitors usually appreciate the heritage-rich features of this historical landmark.

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

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Pinacoteca stands out as an excellent choice for a post-dinner cocktail.

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.

Day 6

Siena
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Porta Camollia, Siena
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On day 6 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.

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

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

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.

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

Day 7

Siena
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Porta Pispini
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Rise and shine for day 7 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.

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.

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

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

Day 8

Siena
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Musei dell’Accademia dei Fisiocritici
Pinacoteca Nazionale
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Wake up to day 8 of your vacation in Siena. With 1 night 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 fun adventures, picturesque spots, and history-rich sites. Start at Musei Dell’accademia Dei Fisiocritici, an underrated museum in the city. Then, head to Pinacoteca Nazionale and soak in the ambiance of this photogenic art gallery.

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

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, begin at Porta Tufi. This locally appreciated 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 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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With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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