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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Revel in the splendor of Siena on this exciting 6-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 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.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out.

This is the time to raise a toast for your 6-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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  • Siena Cathedral
  • Pubblico Palace
  • piazza del Campo
  • Tower of Mangia
  • Loggia del Papa, Siena
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Wake up to day 2 of your exciting city break in Siena. You still have 4 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!

Today’s itinerary in Siena covers several incredible sights, including a church, a palace, a public square, a monument and much more! Start your adventure at Siena Cathedral. This notable church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Pubblico Palace, a must-see palace 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 Piazza Del Campo. This spectacular public square offers an enriching experience. For a change of pace, head to Tower Of Mangia, where you can take in UNESCO world heritage-listed features. Conclude your self-guided sightseeing tour with a visit to Loggia Del Papa, Siena. These sights offer a fulfilling end to a perfect day.

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.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

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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  • Fortezza Medicea
  • Porta Camollia, Siena
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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 3 nights ahead, make the most of your time and create unforgettable memories in Siena.

Begin your adventure at Fortezza Medicea (siena). This is an increasingly popular monument you should not miss. Another must-see is Porta Camollia, Siena, an up-and-coming monument in Siena.

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

Enjoy a delicious meal at Ristorante San Desiderio, a highly-rated dining destination in Siena. If you're eager to try something different, consider Osteria Le Logge, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Let the evening flow smoothly from dinner to drinks at Bar Impero Siena, a top-rated bar in the area.

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 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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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 2 nights in Siena and enjoy plenty of time for exploring.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo Salimbeni. This photogenic palace is sure to ignite your curiosity. Next, dive into the monumental features of Santuario Di Santa Caterina, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Basilica Of San Domenico, a curiosity-inducing church. For a change of scene, check out Vista Panoramica De Siena, known for its stunning features.

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.

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. Immerse yourself in the culinary delights of Ristorante Gallo Nero, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar osteria enea, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand.

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

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Day 5

Day 5

  • Siena
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  • Porta Pispini
  • Porta Romana
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On day 5 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 1 night left in Siena.

Today, you'll explore some of the most beautiful places in Siena, including a historical landmark and a monument. Start your day with a visit to Porta Pispini. This beloved historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Porta Romana, which may be one of the most culturally significant places you will experience today.

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 Ristorante La Finestra, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Sindie? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Numero Unico as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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

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

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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, we recommend visiting Pinacoteca Nazionale, a standout art gallery 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.

Treat yourself to a delightful dinner at PARTICOLARE di Siena, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Castelvecchio? It's another excellent option with a diverse menu.

As your city break in Siena draws to a close, cherish the memories you've made. With your travel plans in place, you're all set for a safe journey home. Until next time, take care and safe travels!

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