One-Week Italy City Break in Siena With Itinerary

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Revel in the splendor of Siena on this exciting 8-day city break in 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 7 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 8-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 Tufi
Pubblico Palacepiazza del CampoTower of Mangia
Porta Camollia, SienaPalazzo Salimbeni
Basilica of San DomenicoSantuario di Santa CaterinaFontebranda
FacciatoneSiena CathedralBattistero di San Giovanni BattistaPiccolomini Library
Musei dell’Accademia dei FisiocriticiPinacoteca Nazionale
Porta PispiniPorta Romana
Fortezza Medicea

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Day 1

Day 1

  • Siena - Arrival day
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  • Porta Tufi
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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 7 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 Tufi 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 a long day of sightseeing, try one of the best restaurants in Siena.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink.

Celebrate the start of your 8-day city break in Siena with a toast!

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Day 2

Day 2

  • Siena
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  • Pubblico Palace
  • piazza del Campo
  • Tower of Mangia
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As day 2 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 itinerary in Siena covers several incredible sights, including a palace, a public square, and a monument. Start your adventure at Pubblico Palace. This beloved palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Piazza Del Campo, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Tower Of Mangia. This intriguing monument offers an enriching experience.

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

Treat yourself to a wonderful meal at Ristorante Tar-Tufo, a top-rated dining spot in Siena.

After your meal, keep the night alive at a bar like Maudit Pub, known for its lively atmosphere.

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

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Day 3

Day 3

  • Siena
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  • Porta Camollia, Siena
  • Palazzo Salimbeni
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Wake up to day 3 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!

Discover a day packed with fun adventures, scenic views, and picturesque spots in Siena. Begin your sightseeing with Porta Camollia, Siena. This intriguing monument is one of the top attractions in the city. Proceed to Palazzo Salimbeni, another must-visit attraction that enhances the city’s allure.

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 Antica Trattoria Papei, 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 Impero Siena, a top-rated bar in the area.

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

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Day 4

Day 4

  • Siena
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  • 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 4 nights in Siena and enjoy plenty of time for exploring.

Get ready to discover some of the most iconic wonders in Siena, including a church and a historical landmark. Start your day at Basilica Of San Domenico. This picture-perfect church is a beloved place to see in Siena. Then, wander over to Santuario Di Santa Caterina. If photogenic sites excite you, this church will be right up your alley. Nearby, you’ll also find Fontebranda. This symbolic historical landmark is a favorite among visitors.

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.

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink.

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 5

Day 5

  • Siena
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  • Facciatone
  • Siena Cathedral
  • Battistero di San Giovanni Battista
  • Piccolomini Library
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Wake up to day 5 of your vacation in Siena. With 3 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 an observation deck, a church, and a library. Begin your sightseeing adventure at the beloved Facciatone. Just a short distance away is Siena Cathedral, an inviting church that draws visitors from far and near.

Continue your journey to Battistero Di San Giovanni Battista, one of the city’s most frequently visited spots that you shouldn’t miss. Another great site to visit is the locally appreciated Piccolomini Library.

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

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

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

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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  • Musei dell’Accademia dei Fisiocritici
  • Pinacoteca Nazionale
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Rise and shine for day 6 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 2 nights remaining, there's ample time to explore and uncover the heart of Siena.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Musei Dell’accademia Dei Fisiocritici. This curiosity-inducing museum provides an insightful glimpse into the city's identity. Next, discover Pinacoteca Nazionale, a historic art gallery, promising a delightful encounter.

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 Osteria da Divo, a top pick for dinner tonight.

Extend your evening after a delightful meal by visiting San Paolo Pub, which offers the perfect atmosphere for a night out.

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

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Day 7

Day 7

  • Siena
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  • Porta Pispini
  • Porta Romana
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Get ready for another exciting day in Siena on day 7 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 1 night ahead, make the most of your time and create unforgettable memories in Siena.

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Porta Pispini, a beloved local hot spot. Another notable attraction to explore is Porta Romana. This up-and-coming monument is known for its awe-inspiring appeal.

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.

Enjoy a delicious meal at Ristorante San Desiderio, a top-rated dining destination in Siena.

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

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Day 8

Day 8

  • Siena - Departure day
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  • Fortezza Medicea
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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 can catch a later flight today, we recommend visiting some of the attractions you may not yet have had the time to explore. This extra time will let you discover more iconic landmarks and hidden gems in Siena.

Fortezza Medicea (siena) is an attraction you could visit on your last day in Siena. This monument has an average rating of 4.5 out of 5 stars from 9,835 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.

As you prepare to leave Siena, remember the moments of joy, discovery, and connection you've experienced in Italy. Carry them with you as souvenirs of your journey, guiding you as you continue to explore and create new memories.

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