10-Day Italy City Break in Siena With Itinerary

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Discover the essence of Siena with a 10-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 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
piazza del Campo
Porta PispiniPorta Romana
Фонтан контради СельваPiazza del Duomo
Piccolomini LibraryBattistero di San Giovanni BattistaSiena CathedralFacciatone
Palazzo SalimbeniSantuario di Santa Caterina
Vista Panoramica de SienaBasilica of San DomenicoFontebranda

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Day 1

Day 1

  • Siena - Arrival day
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  • piazza del Campo
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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 Piazza Del Campo or 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.

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

This is the time to raise a toast for your 10-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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  • Porta Pispini
  • Porta Romana
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On day 2 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.

Siena is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at Porta Pispini, a frequently visited historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Porta Romana, enchanting visitors with its historic appeal.

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.

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.

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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  • Фонтан контради Сельва
  • Piazza del Duomo
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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 7 nights ahead, make the most of your time and create unforgettable memories in Siena.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Next, go to Piazza Del Duomo.

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 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.

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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  • Piccolomini Library
  • Battistero di San Giovanni Battista
  • Siena Cathedral
  • Facciatone
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Rise and shine for day 4 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 6 nights remaining, there's ample time to explore and uncover the heart of Siena.

Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and history-rich sites. 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. Piccolomini Library is the first of them. Spend some time admiring this history-steeped library before continuing your journey. Battistero Di San Giovanni Battista is your next stop. This underrated church is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Siena Cathedral. This romantic church is a sight to behold. To round off your sightseeing experience, visit Facciatone.

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.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight.

Explore the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo after your meal, a hub for lively evenings and memorable moments.

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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  • Palazzo Salimbeni
  • Santuario di Santa Caterina
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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.

Siena is brimming with adventures. Today’s wonderful stops include a palace and a church. Begin your sightseeing adventure at the frequently visited Palazzo Salimbeni. Just a short distance away is Santuario Di Santa Caterina, a photogenic church that draws visitors from far and near.

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.

Don’t miss out on dining at Fischi per Fiaschi, a top-rated dining destination in Siena.

Continue your evening by exploring the vibrant nightlife scene at Bar Pinacoteca, a prime destination for a thrilling night out.

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 6

Day 6

  • Siena
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  • Vista Panoramica de Siena
  • Basilica of San Domenico
  • Fontebranda
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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 4 nights left in Siena.

Today, you'll explore some of the most beautiful places in Siena, including an observation deck, a church, and a historical landmark. Start your day with a visit to Vista Panoramica De Siena. This beloved observation deck is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of San Domenico, which may be one of the most culturally significant 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 Fontebranda, one of the city’s most worthwhile historical landmark.

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.

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.

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.

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

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Day 7

Day 7

  • Siena
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  • Pubblico Palace
  • Tower of Mangia
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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!

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most locally appreciated attractions included on the itinerary is Pubblico Palace. This breathtaking palace will help you start your sightseeing on top. Then, take a leisurely stroll to Tower Of Mangia and learn what makes this culturally significant 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.

Treat yourself to a delightful dinner at Ristorante San Desiderio, highly recommended for tonight's dining.

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 8

Day 8

  • Siena
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  • Fortezza Medicea
  • Porta Camollia, Siena
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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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Fortezza Medicea (siena). This increasingly popular monument provides an insightful glimpse into the city's identity. Next, discover Porta Camollia, Siena, a breathtaking monument, promising a delightful encounter.

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

Enjoy a delicious meal at Osteria Le Logge, a highly-rated dining destination in Siena.

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

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Day 9

Day 9

  • Siena
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  • Porta Tufi
  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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On day 9 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.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a historical landmark, a museum, and an art gallery. Begin your adventure at Porta Tufi. This is an increasingly popular historical landmark you should not miss. Another must-see is Musei Dell’accademia Dei Fisiocritici, a locally appreciated museum in Siena.

When you’re ready for the next sight, head to Pinacoteca Nazionale.

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 wonderful meal at Ristorante Taverna Di Cecco, a top-rated dining spot in Siena.

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 - Departure day
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  • Loggia del Papa, Siena
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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.

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.

If you would rather go for some last-minute sightseeing, the remarkable Loggia Del Papa, Siena is an attraction you could visit today. This monument has an average rating of 4.5 out of 5 stars from 235 visitors.

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.

Savor the flavors at Bar Pasticceria Nannini Toselli, a top pick 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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