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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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Embark on a memorable 8-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 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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes.

Celebrate the start of your 8-day city break in Siena with a toast!

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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Get ready for another exciting day in Siena on day 2 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 6 nights ahead, make the most of your time and create unforgettable memories in Siena.

Enjoy all that Palazzo Salimbeni has to offer. This is a curiosity-inducing palace you should not miss. Another must-see is Loggia Del Papa, Siena, an intriguing monument in Siena.

When you’re ready for the next sight, head to Tower Of Mangia. From there, take a leisurely stroll to Piazza Del Campo, another of the city’s famous attractions. We recommend continuing your self-guided tour at Pubblico Palace, an UNESCO world heritage-designated place of interest 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.

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

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

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

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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As day 3 dawns in Siena, discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 5 nights left, the possibilities for discovery are endless.

Musei Dell’accademia Dei Fisiocritici makes a great addition to your morning plans. This curiosity-inducing museum is a photogenic place to see in Siena. Continue your discovery at Pinacoteca Nazionale, a standout art gallery 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 Piazza Del Duomo. This locally appreciated public square offers a romantic encounter with Siena. Next, make your way to Siena Cathedral to add another highlight to your day. After that, visit Battistero Di San Giovanni Battista, a beloved church that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piccolomini Library, a beloved library in the city. 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.

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 delicious dinner at Antica Trattoria Papei, an excellent option for tonight's dining.

Keep the excitement of the evening going by visiting a bar or two. Bar Impero Siena is an excellent place to start.

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

No visit to Siena is complete without Vista Panoramica De Siena. This frequently visited observation deck is one of the top attractions in the city. Proceed to Basilica Of San Domenico, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Santuario Di Santa Caterina. This locally appreciated church is a traveler-favorite. Not far away, you’ll find Fontebranda, another key site on your sightseeing itinerary.

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

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

Continue the enjoyment post-dinner at Charlie Mixology Bar Di Aldinucci Riccardo, a cherished local gathering spot renowned for its welcoming atmosphere.

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

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!

Porta Camollia, Siena leaves a lasting impression. This monument is one of the most locally appreciated places to visit 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 delicious meal at Fischi per Fiaschi, a highly-rated dining destination in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Pinacoteca stands out as an excellent choice for a post-dinner cocktail.

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

Day6

Day 6

Siena
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Porta Romana
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Rise and shine for day 6 of your city break in Siena! Delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 2 nights remaining, there's ample time to explore.

Experience Porta Romana, an underrated monument in the city.

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

Have a fantastic dining experience at Osteria da Divo, a highly recommended choice for tonight's dinner.

Continue your evening by exploring the vibrant nightlife scene at San Paolo Pub, a prime destination for a thrilling night out.

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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On day 7 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.

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.

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

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.

Treat yourself to a delightful dinner at Ristorante San Desiderio, highly recommended for tonight's dining.

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

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 locally appreciated 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.

Treat yourself to a delightful dinner at Osteria Le Logge, highly recommended for tonight's dining.

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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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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