11-Day Italy City Break in Siena With Itinerary

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Photo of Siena cathedral against a bright blue sky in Italy.
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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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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Porta Romana
Loggia del Papa, SienaTower of Mangiapiazza del CampoPubblico Palace
Piccolomini LibraryPiazza del DuomoSiena CathedralBattistero di San Giovanni Battista
Fortezza MediceaPorta Camollia, Siena
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
Palazzo Salimbeni

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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 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.

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.

Enjoy a lovely dining experience at Enoteca I Terzi, 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, Meet Life Cafè offers a perfect venue to relax and savor a drink.

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!

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Day 2

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 9 nights left in Siena.

Today, you'll explore some of the most beautiful places in Siena, including a monument, a public square, and a palace. Start your day with a visit to Loggia Del Papa, Siena. This frequently visited monument is a must-visit in the city. When you’re ready for your next discovery, continue to Tower Of Mangia, which may be one of the most historic places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Del Campo, a top-rated public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pubblico Palace.

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 delicious meal at Ristorante Tar-Tufo, a highly-rated dining destination in Siena.

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.

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Day 3

Day 3

  • Siena
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  • Piccolomini Library
  • Piazza del Duomo
  • Siena Cathedral
  • Battistero di San Giovanni Battista
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Wake up to day 3 of your exciting city break in Siena. You still have 8 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!

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 locally appreciated places to visit in Siena. Next, head to Piazza Del Duomo, an intriguing public square, known for its visually striking 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 history-steeped 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.

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.

Dine in style at Antica Trattoria Papei, a top recommendation for dinner tonight.

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

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 4

Day 4

  • Siena
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  • Fortezza Medicea
  • Porta Camollia, Siena
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Wake up to day 4 of your vacation in Siena. With 7 nights left, you'll have ample time to explore and savor all Siena has to offer.

Siena is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Fortezza Medicea (siena), an intriguing monument that is worthwhile a visit in the city. Nearby, you’ll find Porta Camollia, Siena, enchanting visitors with its picture-perfect appeal.

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

Enjoy a delicious meal at Osteria Quattro Venti, a top-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, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail.

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 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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Get ready for another exciting day in Siena on day 5 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.

Today’s agenda in Siena includes an observation deck, a church, and a historical landmark. Vista Panoramica De Siena is must-visit observation deck and a great starting point for the day. Next, continue your journey to Basilica Of San Domenico, an underrated church, located just a leisurely stroll away. Next, head to Santuario Di Santa Caterina, a photogenic church, also available for your discovery today.

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 Fischi per Fiaschi, a top-rated dining destination in Siena.

After enjoying a fulfilling meal, continue your evening at Bar Pinacoteca, ideal for those looking to unwind with a drink in a comfortable setting.

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

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Day 6

Day 6

  • Siena
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  • Palazzo Salimbeni
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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 5 nights left, the possibilities for discovery are endless.

Prepare for a day full of fun adventures, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Palazzo Salimbeni. This up-and-coming palace is a must-visit for anyone seeking a unique vacation experience.

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

Savor the flavors at Osteria da Divo, a top pick for dinner tonight.

Continue the enjoyment post-dinner at San Paolo Pub, a cherished local gathering spot renowned for its welcoming atmosphere.

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 7

Day 7

  • Siena
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  • Porta Tufi
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Rise and shine for day 7 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.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most curiosity-inducing attractions included on the itinerary is Porta Tufi. This breathtaking historical landmark will help you start your sightseeing on top.

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 San Desiderio, highly recommended for tonight's dining.

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

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Day 8

Day 8

  • Siena
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  • Pinacoteca Nazionale
  • Musei dell’Accademia dei Fisiocritici
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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 3 nights in Siena and enjoy plenty of time for exploring.

Siena is brimming with adventures. Today’s wonderful stops include an art gallery and a museum. Begin your sightseeing adventure at the intriguing Pinacoteca Nazionale and allow yourself time to explore. Just a short distance away you'll find your next stop, Musei Dell’accademia Dei Fisiocritici, an instagrammable museum that draws visitors from far and near.

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 wonderful meal at Osteria Le Logge, a top-rated dining spot in Siena.

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

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Day 9

Day 9

  • Siena
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  • Facciatone
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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 2 nights left in Siena.

Begin your adventure at Facciatone. This is an intriguing observation deck you should not miss.

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.

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

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

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Day 10

Day 10

  • Siena
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  • Фонтан контради Сельва
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Wake up to day 10 of your exciting city break in Siena. You still have 1 night 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!

The first attraction of today is Fontan Kontradi Sel'va.

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.

Make sure to reserve a table at Bar Pasticceria Nannini Toselli, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

Raise your glass and relax after another amazing day in Siena, Italy.

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Day 11

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, we recommend visiting Porta Pispini, 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.

Dine in style at Ristorante Gallo Nero, 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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