9-Day Italy City Break in Siena With Itinerary

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Discover the essence of Siena with a 9-day city break in Italy, blending cultural richness with exhilarating adventures.

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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Itinerary summary

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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.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes.

This is the time to raise a toast for your 9-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!

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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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Wake up to day 2 of your vacation in Siena. With 7 nights left, you'll have ample time to explore and savor all Siena has to offer.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Palazzo Salimbeni. This increasingly popular palace provides an insightful glimpse into the city's identity. Next, discover Loggia Del Papa, Siena, a symbolic monument, promising a delightful encounter.

Continue your sightseeing with a visit to Tower Of Mangia, a curiosity-inducing monument. When you’re done, don’t forget to make a stop at the widely recognized Piazza Del Campo. Round off your day at Pubblico Palace, another gem in Siena with breathtaking features to discover.

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.

Enjoy a lovely dining experience at Ristorante Tar-Tufo, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.

If you’re not ready to end the night just yet, Maudit Pub 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!

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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.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most underrated attractions included on the itinerary is Fontan Kontradi Sel'va. Then, take a leisurely stroll to Piazza Del Duomo and learn what makes this majestic public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Piccolomini Library. After exploring the library, head to Battistero Di San Giovanni Battista. This frequently visited church is a highlight in Siena. As your day continues, stop by Siena Cathedral, known for its visually striking features. Lastly, don’t forget to check out the curiosity-inducing Facciatone. Enjoy exploring this incredible observation deck at your own pace.

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.

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

Following your dinner, dive into the local bar culture at Bar Impero Siena. Enjoy this evening's relaxed ambiance with delightful drinks.

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

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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 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!

Siena is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Fortezza Medicea (siena), an increasingly popular monument that is worthwhile a visit 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.

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.

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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Rise and shine for day 5 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.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Vista Panoramica De Siena is the perfect place to start. This observation deck is one of the most locally appreciated places to visit in Siena. Next, head to Basilica Of San Domenico, a beloved church, known for its breathtaking 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 Santuario Di Santa Caterina. This photogenic church is a highly recommended experience. Nearby, you'll also find Fontebranda. Visit these for an interesting touch to your journey.

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

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.

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

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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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.

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

Enjoy a delicious meal at Osteria da Divo, a top-rated dining destination in Siena.

Cap off your dinner by heading to San Paolo Pub, ideal for a leisurely evening with a drink in hand.

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 7

Day 7

  • Siena
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  • Porta Pispini
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As day 7 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 2 nights left, the possibilities for discovery are endless.

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Porta Pispini. This frequently visited historical landmark is a picture-perfect 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.

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 Ristorante San Desiderio, a highly-rated dining destination in Siena.

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

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Day 8

Day 8

  • Siena
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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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On day 8 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, picturesque spots, and historic treasures. 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 historic art gallery.

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 Le Logge, a top-rated dining spot in Siena.

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

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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 historic 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.

Treat yourself to a delightful dinner at Ristorante Taverna Di Cecco, highly recommended for tonight's dining.

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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