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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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Embark on a memorable 7-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 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.

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.

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.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere.

This is the time to raise a toast for your 7-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!

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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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 5 nights left in Siena.

Palazzo Salimbeni is perfect for a self-paced visit during the day. This heritage-rich palace is sure to impress. Next on your list is Tower Of Mangia, another must-visit landmark and increasingly popular monument renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Del Campo. This visually striking public square is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Pubblico Palace, an often recommended palace. Nearby, you'll also find Battistero Di San Giovanni Battista, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Siena Cathedral and wrap up your day with its enchanting appeal.

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.

Savor the flavors at Ristorante Tar-Tufo, a top pick for dinner tonight.

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

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

Day 3

Siena
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Vista Panoramica de Siena
Basilica of San Domenico
Santuario di Santa Caterina
Fontebranda
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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 4 nights ahead, make the most of your time and create unforgettable memories in Siena.

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.

Experience Vista Panoramica De Siena, a worthwhile observation deck in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this picture-perfect church.

There are many interesting places to see in Siena, and when you are ready for more, go to Santuario Di Santa Caterina. This is one of the city’s most frequently visited heritage-rich spots of interest. After exploring the church, visit the frequently visited Fontebranda.

You have plenty of options for restaurants and bars in Siena. So when you’re hungry or need a break from exploring, all you have to do is take your pick.

Make sure to reserve a table at Antica Trattoria Papei, 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 Impero Siena, ideal for those looking to unwind with a drink in a comfortable setting.

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

Day 4

Siena
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Porta Camollia, Siena
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Wake up to day 4 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Look forward to a unique sightseeing adventure at the up-and-coming Porta Camollia, Siena and allow yourself time to explore.

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.

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

After your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere.

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

Day 5

Siena
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Porta Romana
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As day 5 dawns in Siena, 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.

Siena is brimming with adventures.

Make time for Porta Romana, an underrated monument that is worthwhile a visit in the city.

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

Dine in style at Fischi per Fiaschi, a top recommendation for dinner tonight.

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

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

Day 6

Siena
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Porta Pispini
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Wake up to day 6 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!

Whatever your travel style is, Porta Pispini is an essential stop in Siena. This frequently visited historical landmark provides an insightful glimpse into the city's identity.

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

Don’t miss out on dining at Osteria da Divo, a top-rated dining destination in Siena.

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

Raise a toast and celebrate another memorable day in Siena, 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, we recommend visiting Porta Tufi, a breathtaking historical landmark 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.

Treat yourself to a delicious dinner at Ristorante San Desiderio, an excellent option for tonight's dining.

As you conclude your city break in Siena, treasure the memories you've made. May they accompany you on your journey homeward!

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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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