9-Day Italy City Break in Siena With Itinerary
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Embark on a memorable 9-day city break in Siena, 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 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!
Itinerary summary
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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.
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.
Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight.
Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink.
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.
Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Palazzo Salimbeni. This heritage-rich palace is a highlight of any visit in the city. Then, enjoy Loggia Del Papa, Siena, another symbolic attraction that never fails to captivate visitors. Next, head over to Tower Of Mangia, one of the city’s most worthwhile attractions, known for its UNESCO world heritage-listed features.
If you’re looking for more, spend time soaking in the atmosphere of Piazza Del Campo. This romantic public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Pubblico Palace, an often recommended palace, and take a stroll around the area.
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 Ristorante Tar-Tufo, 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 Maudit Pub, 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.
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.
Just a short distance away is Piazza Del Duomo, a romantic public square that draws visitors from far and near.
Continue your journey to Piccolomini Library, one of the city’s most up-and-coming spots that you shouldn’t miss. Another great site to visit is the curiosity-inducing Battistero Di San Giovanni Battista. Last up on today’s itinerary is a church. Make your way to Siena Cathedral for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Siena.
When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.
Enjoy a delicious meal at Antica Trattoria Papei, a highly-rated dining destination in Siena.
If you’re not ready to end the night just yet, Bar Impero Siena offers a perfect venue to relax and savor a drink.
Raise a toast and celebrate another memorable day in Siena, Italy!
Day 4
- Siena
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- Fortezza Medicea
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Wake up to day 4 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!
Start your adventure at Fortezza Medicea (siena). This worthwhile monument is a place that is appreciated by travelers and locals alike.
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.
Enjoy a lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.
Explore the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo after your meal, a hub for lively evenings and memorable moments.
Get some rest at your hotel in preparation for another wonderful day in Siena to come!
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 vacation in Siena. With 4 nights left, you'll have ample time to explore and savor all Siena has to offer.
Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Vista Panoramica De Siena is the first of them. Spend some time admiring this romantic observation deck before continuing your journey. Basilica Of San Domenico is your next stop. This often recommended church is one of the best-rated sights in Siena.
Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Santuario Di Santa Caterina. This heritage-rich church is a sight to behold. To round off your sightseeing experience, visit Fontebranda.
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 Fischi per Fiaschi, a top-rated dining destination in Siena.
Let the evening flow smoothly from dinner to drinks at Bar Pinacoteca, 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!
Day 6
- Siena
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- Porta Camollia, Siena
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Get ready for another exciting day in Siena on day 6 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 3 nights ahead, make the most of your time and create unforgettable memories in Siena.
Start by visiting Porta Camollia, Siena, a prime spot to begin your journey. This standout monument is sure to impress.
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 da Divo, a top-rated dining spot in Siena.
After enjoying a fulfilling meal, continue your evening at San Paolo Pub, ideal for those looking to unwind with a drink in a comfortable setting.
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 7
- Siena
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- Porta Pispini
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On day 7 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 2 nights left in Siena.
Begin your adventure at Porta Pispini. This is a beloved historical landmark 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.
Treat yourself to a delicious dinner at Ristorante San Desiderio, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.
Savor the memories of an amazing day in Siena, Italy!
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.
Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Musei Dell’accademia Dei Fisiocritici. This eye-catching museum is sure to ignite your curiosity. Next, dive into the standout features of Pinacoteca Nazionale, a must-visit art gallery in the city.
When it’s time to eat, Siena has restaurants and bars to suit all budgets.
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.
No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.
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 intriguing 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.
Dine in style at Ristorante Taverna Di Cecco, a top recommendation for dinner tonight.
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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