12-Day Italy City Break in Siena With Itinerary
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Embark on a memorable 12-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 11 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 12-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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- 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 11 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.
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 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 savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started.
Celebrate the start of your 12-day city break in Siena with a toast!
Day 2
- Siena
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- 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 10 nights left in Siena.
Get ready for a day filled with family-friendly attractions, picturesque spots, and historic treasures in the charming city of Siena. Your adventure starts at Loggia Del Papa, Siena, a worthwhile local hot spot. Another notable attraction to explore is Tower Of Mangia. This locally appreciated monument is known for its symbolic 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 Piazza Del Campo. This visually striking public square offers a fascinating experience that many visitors find memorable. Pubblico Palace is also worth visiting.
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 delicious meal at Ristorante Tar-Tufo, a highly-rated dining destination in Siena.
To truly maximize your evening out, consider visiting Maudit Pub 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.
Day 3
- Siena
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- Piccolomini Library
- Piazza del Duomo
- Siena Cathedral
- Battistero di San Giovanni Battista
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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 9 nights ahead, make the most of your time and create unforgettable memories in Siena.
A blend of family-friendly attractions, photo-friendly spots, and history-rich sites await you in Siena on today’s itinerary. First up is the intriguing library, Piccolomini Library. Afterward, continue to Piazza Del Duomo, a public square every traveler should visit.
As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Siena Cathedral. This captivating church is an essential stop. Following that, head to Battistero Di San Giovanni Battista, another must-visit site that will enhance your experience.
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 lovely dining experience at Antica Trattoria Papei, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.
Keep the evening going at Bar Impero Siena, a great choice for enjoying the after-dinner hours with a drink.
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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- Vista Panoramica de Siena
- Basilica of San Domenico
- Santuario di Santa Caterina
- Fontebranda
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On day 4 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.
Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most worthwhile attractions included on the itinerary is Vista Panoramica De Siena. This instagrammable observation deck will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Of San Domenico and learn what makes this breathtaking church unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Santuario Di Santa Caterina. After exploring the church, head to Fontebranda. This up-and-coming historical landmark is a highlight in Siena.
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 Osteria Quattro Venti, highly recommended for tonight's dining.
Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, 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 5
- Siena
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- Palazzo Salimbeni
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Wake up to day 5 of your vacation in Siena. With 7 nights left, you'll have ample time to explore and savor all Siena has to offer.
Start your day at Palazzo Salimbeni. This heritage-rich palace is a frequently visited place to see in Siena.
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 Fischi per Fiaschi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.
Cap off your dinner by heading to Bar Pinacoteca, ideal for a leisurely evening with a drink in hand.
Raise a toast and celebrate another memorable day in Siena, Italy!
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 6 nights left, the possibilities for discovery are endless.
Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Porta Camollia, Siena. This historic monument is a highlight of any visit in the city.
When it’s time to eat, Siena has restaurants and bars to suit all budgets.
Treat yourself to a wonderful meal at Osteria da Divo, a top-rated dining spot in Siena.
After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at San Paolo Pub, a well-loved spot among locals and tourists.
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 Romana
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Wake up to day 7 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!
Today’s well-planned self-sightseeing route offers several family-friendly attractions, scenic views, and photo-friendly spots. 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. Porta Romana is the first of them. Spend some time admiring this respected monument before continuing your journey.
After a long day of sightseeing, try one of the best restaurants in Siena.
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.
Get some rest at your hotel in preparation for another wonderful day in Siena to come!
Day 8
- Siena
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- Porta Tufi
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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 4 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 Porta Tufi. This culturally significant historical landmark is sure to ignite your curiosity.
When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.
Have a fantastic dining experience at Osteria Le Logge, a highly recommended choice for tonight's dinner.
Savor the memories of an amazing day in Siena, Italy!
Day 9
- Siena
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- Musei dell’Accademia dei Fisiocritici
- Pinacoteca Nazionale
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On day 9 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.
Brace yourself for today’s incredible lineup of attractions in Siena, featuring family-friendly attractions, picturesque spots, and history-rich sites. Start at Musei Dell’accademia Dei Fisiocritici, a beloved museum in the city. Then, head to Pinacoteca Nazionale and soak in the ambiance of this eye-catching 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.
Don’t miss out on dining at Ristorante Taverna Di Cecco, a top-rated dining destination in Siena.
Raise your glass and relax after another amazing day in Siena, Italy.
Day 10
- Siena
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- Facciatone
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Get ready for another exciting day in Siena on day 10 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 2 nights ahead, make the most of your time and create unforgettable memories in Siena.
Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Facciatone. This worthwhile observation deck is a symbolic place to see in Siena.
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 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.
Savor the flavors at Bar Pasticceria Nannini Toselli, a top pick for dinner tonight.
No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.
Day 11
- Siena
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- Фонтан контради Сельва
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On day 11 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.
Fontan Kontradi Sel'va is must-visit sightseeing destination and a great starting point for the day.
When you’re ready for dinner, we recommend you try one of the best restaurants in Siena.
Enjoy a lovely meal at Ristorante Gallo Nero, a top-rated place to have 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.
Day 12
- 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 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 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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