6-Day Italy City Break in Siena With Itinerary

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Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
photo of view of Stylish woman walks on background of cityscape of Siena old town. Concept of travel famous cities in Tosacny region of Italy
photo of view of  Aerial view of Montepulciano, a medieval and Renaissance hill town in the Italian province of Siena in southern Tuscany, Italy
photo of view of Facade decoration of the cathedral of Siena, Italy.
photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
photo of view of Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
photo of view of Beautiful traveler girl exploring the historic city of Siena in Tuscany. Young tourist woman smiling at camera in Siena Cathedral square, Tuscany, Italy.
photo of view ofYoung woman having lunch with pizza and wine, sitting with dog at outdoor restaurant with beautiful view on the old town of Siena. Concept of italian cuisine and travel
photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view ofBeautiful view of campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Siena province, Italy
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Take a 6-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 5 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 6-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 Tufi
Siena CathedralPubblico Palacepiazza del CampoTower of MangiaLoggia del Papa, Siena
Fortezza MediceaPorta Camollia, Siena
Palazzo SalimbeniSantuario di Santa CaterinaBasilica of San DomenicoVista Panoramica de Siena
Porta PispiniPorta Romana
Pinacoteca Nazionale

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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 5 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 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.

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

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out.

Celebrate the start of your 6-day city break in Siena with a toast!

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Day 2

Day 2

  • Siena
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  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • Tower of Mangia
  • Loggia del Papa, Siena
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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 4 nights left in Siena.

Savor the day by visiting some of the best places to see in Siena, including a church, a palace, a public square, a monument and much more! Start your adventure at Siena Cathedral. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Pubblico Palace located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Campo. Its enchanting features will captivate you. After the public square, continue your tour of the city with a visit to Tower Of Mangia. Visitors usually appreciate the UNESCO world heritage-listed features of this monument. Next up is Loggia Del Papa, Siena, a highly recommended monument.

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.

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

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

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 3

Day 3

  • Siena
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  • Fortezza Medicea
  • Porta Camollia, Siena
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Wake up to day 3 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!

Get ready for a day filled with fun adventures, breathtaking views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Fortezza Medicea (siena), an intriguing local hot spot. Another notable attraction to explore is Porta Camollia, Siena. This underrated monument is known for its historic appeal.

When you’re ready to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Treat yourself to a delicious dinner at Ristorante San Desiderio, an excellent option for tonight's dining. Looking for something different? Osteria Le Logge offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Taverna Di Cecco. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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

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

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Day 4

Day 4

  • Siena
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  • Palazzo Salimbeni
  • Santuario di Santa Caterina
  • Basilica of San Domenico
  • Vista Panoramica de Siena
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As day 4 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, photo-friendly spots, and history-rich sites. The first attraction of today is Palazzo Salimbeni. This locally appreciated palace is a photogenic place to see in Siena. Continue your discovery at Santuario Di Santa Caterina, a photogenic church 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 Basilica Of San Domenico. This often recommended church offers a historic encounter with Siena. Next, make your way to Vista Panoramica De Siena to add another highlight to your day. 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 it’s time to eat, Siena has restaurants and bars to suit all budgets.

Enjoy a lovely dining experience at Bar Pasticceria Nannini Toselli, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Gallo Nero, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Bar osteria enea. It’s yet another ideal choice to enhance your time in Siena tonight.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink.

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

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Day 5

Day 5

  • Siena
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  • Porta Pispini
  • Porta Romana
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Wake up to day 5 of your vacation in Siena. With 1 night left, you'll have ample time to explore and savor all Siena has to offer.

Prepare for a day full of family-friendly attractions, scenic views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Porta Pispini. This increasingly popular historical landmark is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Porta Romana, one of the city’s best highlights.

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 wonderful meal at Ristorante La Finestra, a top-rated dining spot in Siena. If you're in the mood for something new, try Sindie, another premier location with a delectable menu. You might also want to book a table at Ristorante Numero Unico. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Pinacoteca, a well-loved spot among locals and tourists.

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 - Departure day
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  • Pinacoteca Nazionale
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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, begin at Pinacoteca Nazionale. This underrated art gallery is a popular place to see in the city.

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.

If you're in the mood to try something new, consider Osteria Castelvecchio, another top spot with a mouthwatering menu.

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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