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3-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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Embark on a memorable 3-day city break in Siena, Italy!

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 2 nights in Siena. It's the the ultimate 3-day Siena city break.

The home for your 3-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 2 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.

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

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight. Alternatively, Ristorante Tar-Tufo beckons with its unique menu offerings. Also, consider Antica Trattoria Papei. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

Celebrate the start of your 3-day city break in Siena with a toast!

Day 2

Siena
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Pubblico Palace
Tower of Mangia
piazza del Campo
Siena Cathedral
Fontebranda
Basilica of San Domenico
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Wake up to day 2 of your exciting city break in Siena. You still have 1 night 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!

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 up-and-coming Pubblico Palace, a historic palace in Siena. Next, go to Tower Of Mangia.

After visiting Pubblico Palace and Tower Of Mangia, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Campo. This visually striking public square offers a unique experience. Siena Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Fontebranda, one of the most symbolic places to visit in Siena. If you still have some time left for sightseeing, we also recommend stopping by Basilica Of San Domenico.

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 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.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 3

Siena - Departure day
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Palazzo Salimbeni
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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 Palazzo Salimbeni, a history-steeped palace 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 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.

If you're eager to try something different, consider Osteria Le Logge, another top spot with a tantalizing 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.

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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.

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.

We guarantee

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

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