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6-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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Immerse yourself in the charm of Siena on this 6-day city break in Italy, where cultural delights and exciting experiences await!

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

The home for your 6-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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Porta Tufi
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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 5 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 Porta Tufi, 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.

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. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Celebrate the start of your 6-day city break in Siena with a toast!

Day 2

Siena
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Siena Cathedral
Pubblico Palace
piazza del Campo
Tower of Mangia
Loggia del Papa, Siena
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Wake up to day 2 of your vacation in Siena. With 4 nights left, you'll have ample time to explore and savor all Siena has to offer.

Let Siena Cathedral set the tone for the day. Spend some time admiring this enchanting church before continuing your journey. Pubblico Palace is your next stop. This frequently visited palace is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Del Campo. This respected public square is a sight to behold. To round off your sightseeing experience, visit Tower Of Mangia and Loggia Del Papa, Siena.

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.

Enjoy a lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

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

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

Day 3

Siena
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Fortezza Medicea
Porta Camollia, Siena
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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 3 nights remaining, there's ample time to explore.

Fortezza Medicea (siena) makes a great addition to your morning plans. This frequently visited monument is a picture-perfect place to see in Siena. Continue your discovery at Porta Camollia, Siena, a standout monument with stories to tell.

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.

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

Treat yourself to a delicious dinner at Ristorante San Desiderio, an excellent option for tonight's dining. Looking for something different? Osteria Le Logge offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Taverna Di Cecco. Known for great service, it’s a fantastic choice for tonight in Siena.

Continue your lively evening at Bar Impero Siena, a perfect place for winding down or revving up the night, depending on which mood you’re in.

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

Day 4

Siena
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Palazzo Salimbeni
Santuario di Santa Caterina
Basilica of San Domenico
Vista Panoramica de Siena
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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 2 nights in Siena and enjoy plenty of time for exploring.

Siena is brimming with adventures.

Palazzo Salimbeni leaves a lasting impression. This palace is one of the most worthwhile places to visit in Siena. Next, head to Santuario Di Santa Caterina, an increasingly popular church, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Basilica Of San Domenico. This culturally significant church is a highly recommended experience. Nearby, you'll also find Vista Panoramica De Siena. Visit these for an interesting touch to your journey.

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.

Have a fantastic dining experience at Bar Pasticceria Nannini Toselli, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Gallo Nero offers an enticing alternative with its varied menu. Additionally, Bar osteria enea is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight 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.

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

Day 5

Siena
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Porta Pispini
Porta Romana
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Wake up to day 5 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!

Visiting Porta Pispini is always a good idea. This increasingly popular historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the historic wonders of Porta Romana, a must-see monument in the city.

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.

Make sure to reserve a table at Ristorante La Finestra, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Sindie, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Numero Unico, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Bar Pinacoteca, ideal for a leisurely evening with a drink in hand.

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

Day 6

Siena - Departure day
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Pinacoteca Nazionale
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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 Pinacoteca Nazionale, a photogenic art gallery 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 in the mood to try something new, consider Osteria Castelvecchio, another top spot with a mouthwatering menu.

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.

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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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