10-Day Italy City Break in Siena With Itinerary

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Take a 10-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 9 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 10-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
Piazza del DuomoPiccolomini LibraryBattistero di San Giovanni BattistaSiena CathedralFacciatone
Fortezza Medicea
FontebrandaSantuario di Santa CaterinaBasilica of San DomenicoVista Panoramica de Siena
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 9 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 a long day of sightseeing, try one of the best restaurants in Siena.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area.

Celebrate the start of your 10-day city break in Siena with a toast!

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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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Rise and shine for day 2 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 8 nights remaining, there's ample time to explore and uncover the heart of Siena.

Today’s route brings family-friendly attractions, photo-friendly spots, and historic treasures. The first attraction of today is Palazzo Salimbeni. This underrated palace is a respected place to see in Siena. Continue your discovery at Loggia Del Papa, Siena, a photogenic monument 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 Tower Of Mangia. This beloved monument offers an UNESCO world heritage-listed encounter with Siena. Next, make your way to Piazza Del Campo to add another highlight to your day. After that, visit Pubblico Palace, an increasingly popular palace that’s sure to impress. 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 you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Dine in style at Ristorante Tar-Tufo, a top recommendation for dinner tonight.

Continue your lively evening at Maudit Pub, a perfect place for winding down or revving up the night, depending on which mood you’re in.

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 3

Day 3

  • Siena
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  • Piazza del Duomo
  • Piccolomini Library
  • Battistero di San Giovanni Battista
  • Siena Cathedral
  • Facciatone
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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 7 nights in Siena and enjoy plenty of time for exploring.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazza Del Duomo, an increasingly popular public square in the city. Then, head to Piccolomini Library and soak in the ambiance of this eye-catching library.

There are many interesting places to see in Siena and when you are ready for more, go to Battistero Di San Giovanni Battista. This is one of the city’s most underrated spots. After exploring the church, visit the popular Siena Cathedral. Before wrapping up your self-guided sightseeing tour, head to the frequently visited Facciatone, a frequently visited observation deck 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.

Don’t miss out on dining at Antica Trattoria Papei, a top-rated dining destination in Siena.

After savoring a delicious meal, step into the vibrant nightlife at Bar Impero Siena, where the evening is just getting started.

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

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Day 4

Day 4

  • Siena
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  • Fortezza Medicea
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On day 4 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.

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Fortezza Medicea (siena). This picture-perfect monument is a highlight of any visit in the city.

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Charlie Mixology Bar Di Aldinucci Riccardo, known for its inviting atmosphere.

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

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Day 5

Day 5

  • Siena
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  • Fontebranda
  • Santuario di Santa Caterina
  • Basilica of San Domenico
  • Vista Panoramica de Siena
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Wake up to day 5 of your vacation in Siena. With 5 nights left, you'll have ample time to explore and savor all Siena has to offer.

Get ready to discover some of the most iconic wonders in Siena, including a historical landmark, a church, and an observation deck. Start your day at Fontebranda. This eye-catching historical landmark is a beloved place to see in Siena. Then, wander over to Santuario Di Santa Caterina. If culturally significant sites excite you, this church will be right up your alley. Nearby, you’ll also find Basilica Of San Domenico. This stunning church 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, Vista Panoramica De Siena is a worthwhile spot in the city that will captivate you with its unique charm.

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 delicious meal at Fischi per Fiaschi, a highly-rated dining destination in Siena.

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.

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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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 4 nights ahead, make the most of your time and create unforgettable memories 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 beloved monument provides an insightful glimpse into the city's identity.

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 da Divo, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

To truly maximize your evening out, consider visiting San Paolo Pub after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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

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Day 7

Day 7

  • Siena
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  • Porta Pispini
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Wake up to day 7 of your exciting city break in Siena. You still have 3 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!

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

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

Raise your glass and relax after another amazing 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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As day 8 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.

Start by visiting Musei Dell’accademia Dei Fisiocritici, a prime spot to begin your journey. This standout museum is sure to impress. Next on your list is Pinacoteca Nazionale, another must-visit landmark and worthwhile art gallery renowned for its instagrammable features.

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.

Have a fantastic dining experience at Osteria Le Logge, a highly recommended choice for tonight's dinner.

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 9

Day 9

  • Siena
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  • Фонтан контради Сельва
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Rise and shine for day 9 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.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most beloved attractions included on the itinerary is Fontan Kontradi Sel'va.

Throughout the day, make sure to take breaks to appreciate the surroundings.

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

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

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

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Day 10

Day 10

  • 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 culturally significant 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.

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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