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One-Week 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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Discover Siena with this 8-day city break in Italy, blending cultural richness with exhilarating adventures.

In 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. Siena promises an unforgettable journey into Italy's rich heritage.

With this perfectly planned holiday package, you will experience 7 nights in Siena. It's the the ultimate 8-day Siena city break.

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.

Maximize your holiday experience in Siena by customizing each day with exciting tours and tickets. Whether you're tracing history on guided tours or savoring the rich flavors of Italy's traditional cuisine, the city offers a range of immersive experiences. 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. Select a date and start planning your city break in Siena as early as today!

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Day1

Day 1

Siena - Arrival day
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Fortezza Medicea
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Your exciting city break begins as soon as you arrive in the beautiful city of Siena. You’ll stay here for 7 nights and take time to discover what to see in Siena, along with enjoying the city’s best dining and cultural experiences.

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 Fortezza Medicea (siena). Taking a stroll in the city center is a great alternative. 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. Siena offers many excellent restaurants to choose from.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments.

This is the time to raise a toast for your 8-day city break in Siena! Look forward to immersing yourself in the vibrant culture, stunning sights, and local delicacies of the city for the next few days to come!

Day2

Day 2

Siena
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Palazzo Salimbeni
Loggia del Papa, Siena
Tower of Mangia
piazza del Campo
Pubblico Palace
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Rise and shine for day 2 of your city break in Siena! 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.

One of the most locally appreciated attractions included on the itinerary is Palazzo Salimbeni. This photogenic palace will help you start your sightseeing on top. Then, take a leisurely stroll to Loggia Del Papa, Siena and learn what makes this photogenic monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the intriguing Tower Of Mangia. After exploring the monument, head to Piazza Del Campo. This top-rated public square is a highlight in Siena. As your day continues, stop by Pubblico Palace, known for its UNESCO world heritage-designated features.

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

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

After savoring a delicious meal, step into the vibrant nightlife at Maudit Pub, where the evening is just getting started.

Wind down and recharge for tomorrow's escapades in Italy.

Day3

Day 3

Siena
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Musei dell’Accademia dei Fisiocritici
Pinacoteca Nazionale
Piazza del Duomo
Siena Cathedral
Battistero di San Giovanni Battista
Piccolomini Library
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Wake up to day 3 of your vacation in Siena. With 5 nights left, you'll have ample time to explore and savor all Siena has to offer.

Visiting Musei Dell’accademia Dei Fisiocritici is always a good idea. This intriguing museum is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the eye-catching wonders of Pinacoteca Nazionale, a must-see art gallery 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 Duomo. This intriguing public square offers an enriching experience. For a change of pace, head to Siena Cathedral, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Battistero Di San Giovanni Battista and Piccolomini Library These sights offer a fulfilling end to a perfect day.

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

Have a fantastic dining experience at Antica Trattoria Papei, a highly recommended choice for tonight's dinner.

Explore the vibrant nightlife at Bar Impero Siena after your meal, a hub for lively evenings and memorable moments.

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

Day4

Day 4

Siena
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Vista Panoramica de Siena
Basilica of San Domenico
Santuario di Santa Caterina
Fontebranda
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As day 4 dawns in Siena, discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 4 nights left, the possibilities for discovery are endless.

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.

Awaiting your discovery is the curiosity-inducing Vista Panoramica De Siena, a romantic observation deck in Siena. Next, go to Basilica Of San Domenico.

After visiting Vista Panoramica De Siena and Basilica Of San Domenico, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Santuario Di Santa Caterina. This heritage-rich church offers a unique experience. Fontebranda is another noteworthy attraction worthwhile a visit.

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 Osteria Quattro Venti, a highly-rated dining destination in Siena.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out.

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow is a new day!

Day5

Day 5

Siena
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Porta Camollia, Siena
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Wake up to day 5 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!

Make a stop at Porta Camollia, Siena. This frequently visited monument is a must-visit for travelers looking for a unique holiday experience.

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.

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

Keep the evening going at Bar Pinacoteca, a great choice for enjoying the after-dinner hours with a drink.

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

Day6

Day 6

Siena
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Porta Romana
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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 2 nights left in Siena.

Siena is brimming with adventures.

Porta Romana is perfect for a self-paced visit during the day. This historic monument is sure to impress.

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 delightful dinner at Osteria da Divo, highly recommended for tonight's dining.

Let the evening flow smoothly from dinner to drinks at San Paolo Pub, a top-rated bar in the area.

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

Day7

Day 7

Siena
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Porta Tufi
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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.

No visit to Siena is complete without Porta Tufi. This intriguing historical landmark is one of the top attractions in the city.

Before you know it, it’s time to head out for dinner. Treat yourself to a delicious meal at a nice restaurant in Siena.

Enjoy a lovely meal at Ristorante San Desiderio, a top-rated place to have dinner tonight.

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

Day8

Day 8

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, begin at Porta Pispini. This beloved historical landmark is a hotspot among locals.

Depending on how much time you have to spare on your departure day, you may want to do some last-minute shopping at downtown Siena. It's the perfect place for browsing souvenirs and gifts to bring back home with you.

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 local atmosphere over a delicious meal.

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.

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Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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