11-Day Italy City Break in Siena With Itinerary
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Embark on a memorable 11-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 10 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 11-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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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 10 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.
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 Enoteca I Terzi, a highly-rated dining destination in Siena.
After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere.
This is the time to raise a toast for your 11-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!
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 exciting city break in Siena. You still have 9 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!
Get ready to discover some of the most iconic wonders in Siena, including a monument, a public square, and a palace. Start your day at Loggia Del Papa, Siena. This symbolic monument is a worthwhile place to see in Siena. Then, wander over to Tower Of Mangia. If UNESCO world heritage-listed sites excite you, this monument will be right up your alley. Nearby, you’ll also find Piazza Del Campo. This visually striking public square is a favorite among visitors.
Siena offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Pubblico Palace is a locally appreciated spot in the city that will captivate you with its unique charm.
When it’s time to eat, Siena has restaurants and bars to suit all budgets.
Have a fantastic dining experience at Ristorante Tar-Tufo, a highly recommended choice for tonight's dinner.
After your meal, keep the night alive at a bar like Maudit Pub, known for its lively atmosphere.
Raise your glass and relax after another amazing day in Siena, Italy.
Day 3
- Siena
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- Piccolomini Library
- Piazza del Duomo
- Siena Cathedral
- Battistero di San Giovanni Battista
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On day 3 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 8 nights in Siena and enjoy plenty of time for exploring.
Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Piccolomini Library is the perfect place to start. This library is one of the most beloved places to visit in Siena. Next, head to Piazza Del Duomo, a worthwhile public square, known for its inviting features.
In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Siena Cathedral. This romantic church is a highly recommended experience. Nearby, you'll also find Battistero Di San Giovanni Battista. Visit these for an interesting touch to your journey.
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.
Let the evening flow smoothly from dinner to drinks at Bar Impero Siena, a top-rated bar in the area.
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 4
- Siena
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- Fortezza Medicea
- Porta Camollia, Siena
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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 7 nights left, the possibilities for discovery are endless.
Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most increasingly popular attractions included on the itinerary is Fortezza Medicea (siena). This culturally significant monument will help you start your sightseeing on top. Then, take a leisurely stroll to Porta Camollia, Siena and learn what makes this awe-inspiring monument unique.
Throughout the day, make sure to take breaks to appreciate the surroundings.
Before you know it, it’s time to head out for dinner. Treat yourself to a delicious meal at a nice restaurant in Siena.
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.
If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink.
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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On day 5 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.
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 locally appreciated 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 instagrammable features will captivate you. After the church, continue your tour of the city with a visit to Fontebranda. Visitors usually appreciate the symbolic features of this historical landmark.
When you’re ready for dinner, we recommend you try one of the best restaurants in Siena.
Savor the flavors at Fischi per Fiaschi, a top pick for dinner tonight.
Explore the vibrant nightlife at Bar Pinacoteca after your meal, a hub for lively evenings and memorable moments.
No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.
Day 6
- Siena
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- Palazzo Salimbeni
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Rise and shine for day 6 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 5 nights 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 Palazzo Salimbeni. This instagrammable palace is sure to ignite your curiosity.
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.
Don’t miss out on dining at Osteria da Divo, a top-rated dining destination in Siena.
Extend your evening after a delightful meal by visiting San Paolo Pub, 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.
Day 7
- Siena
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- Porta Tufi
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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 4 nights ahead, make the most of your time and create unforgettable memories in Siena.
Get ready for a day filled with fun adventures, breathtaking views, and picturesque spots in the charming city of Siena. Your adventure starts at Porta Tufi, an up-and-coming local hot spot.
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.
Make sure to reserve a table at Ristorante San Desiderio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.
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 8
- Siena
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- Pinacoteca Nazionale
- Musei dell’Accademia dei Fisiocritici
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Wake up to day 8 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.
A blend of fun adventures, photo-friendly spots, and history-rich sites await you in Siena on today’s itinerary. First up is the locally appreciated art gallery, Pinacoteca Nazionale. Afterward, continue to Musei Dell’accademia Dei Fisiocritici, a museum every traveler should visit.
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 delicious dinner at Osteria Le Logge, 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 9
- Siena
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- Facciatone
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Wake up to day 9 of your exciting city break in Siena. You still have 2 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!
Siena is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Facciatone, a worthwhile observation deck 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 Ristorante Taverna Di Cecco, highly recommended for tonight's dining.
Raise a toast and celebrate another memorable day in Siena, Italy!
Day 10
- Siena
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- Фонтан контради Сельва
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On day 10 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 1 night in Siena and enjoy plenty of time for exploring.
Begin your sightseeing with Fontan Kontradi Sel'va. This increasingly popular point of interest is one of the top attractions in the city.
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.
Enjoy a delicious meal at Bar Pasticceria Nannini Toselli, a top-rated dining destination in Siena.
Raise your glass and relax after another amazing day in Siena, Italy.
Day 11
- 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.
Enjoy a lovely meal at Ristorante Gallo Nero, a top-rated place to have dinner tonight.
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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