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7-Day 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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Explore Siena on this 7-day city break in Italy and experience a fusion of culture and excitement.

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 6 nights in Siena. It's the the ultimate 7-day Siena city break.

The home for your 7-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 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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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 6 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), 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.

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 Enoteca I Terzi, a top-rated dining spot in Siena.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink.

Celebrate the start of your 7-day city break in Siena with a toast!

Day 2

Siena
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Palazzo Salimbeni
Tower of Mangia
piazza del Campo
Pubblico Palace
Battistero di San Giovanni Battista
Siena Cathedral
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Wake up to day 2 of your vacation in Siena. With 5 nights left, you'll have ample time to explore and savor all Siena has to offer.

Make time for Palazzo Salimbeni, an underrated palace that is worthwhile a visit in the city. Nearby, you’ll find Tower Of Mangia, enchanting visitors with its culturally significant appeal. Continue your exploration at Piazza Del Campo. This public square is one of the city’s most spectacular spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pubblico Palace. After exploring the palace, head to the locally appreciated Battistero Di San Giovanni Battista. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Siena Cathedral, a place of history-steeped interest in Siena.

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 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.

As the day draws to a close, enjoy Siena at night. Rest well for more adventures tomorrow.

Day 3

Siena
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Vista Panoramica de Siena
Basilica of San Domenico
Santuario di Santa Caterina
Fontebranda
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Rise and shine for day 3 of your city break in Siena! Delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 4 nights remaining, there's ample time to explore.

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.

Vista Panoramica De Siena makes a great addition to your morning plans. This locally appreciated observation deck is a romantic place to see in Siena. Continue your discovery at Basilica Of San Domenico, a picture-perfect 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 Santuario Di Santa Caterina. This worthwhile church offers a standout encounter with Siena. Next, make your way to Fontebranda 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 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 lovely dining experience at Antica Trattoria Papei, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.

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

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

Day 4

Siena
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Porta Camollia, Siena
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On day 4 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 3 nights left in Siena.

Catch Porta Camollia, Siena before the crowds roll in. This breathtaking monument is sure to ignite your curiosity.

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

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena.

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

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

Day 5

Siena
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Porta Romana
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Wake up to day 5 of your exciting city break in Siena. You still have 2 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!

Siena is brimming with adventures.

Check out the frequently visited monument, Porta Romana. As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city.

After or in between exploring, treat yourself to a delicious meal. Siena offers many excellent restaurants to choose from.

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.

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

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

Day 6

Siena
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Porta Pispini
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As day 6 dawns in Siena, discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 1 night left, the possibilities for discovery are endless.

Experience Porta Pispini, a locally appreciated historical landmark in the city.

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

Enjoy a lovely meal at Osteria da Divo, a top-rated place to have dinner tonight.

Explore the vibrant nightlife at San Paolo Pub after your meal, a hub for lively evenings and memorable moments.

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

Day 7

Siena - Departure day
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Porta Tufi
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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 Tufi. This often recommended 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 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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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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