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5-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 5-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 4 nights in Siena. It's the the ultimate 5-day Siena city break.

The home for your 5-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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Porta Romana
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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 4 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 Romana. 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.

When you’re ready for dinner, we recommend you try 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. 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere.

Celebrate the start of your 5-day city break in Siena with a toast!

Day2

Day 2

Siena
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Basilica of San Domenico
Fontebranda
Siena Cathedral
piazza del Campo
Tower of Mangia
Pubblico Palace
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Wake up to day 2 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Experience Basilica Of San Domenico, a curiosity-inducing church in the city. Then, head to Fontebranda and soak in the ambiance of this instagrammable historical landmark.

There are many interesting places to see in Siena, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most popular enchanting spots of interest. After exploring the church, visit the spectacular Piazza Del Campo. Not far away, you'll also find Tower Of Mangia. This monument is a picture-perfect highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Pubblico Palace, an often recommended palace in the city.

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

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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

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

Day3

Day 3

Siena
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Fortezza Medicea
Porta Camollia, Siena
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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 2 nights ahead, make the most of your time and create unforgettable memories in Siena.

No visit to Siena is complete without Fortezza Medicea (siena). This beloved monument is one of the top attractions in the city. Proceed to Porta Camollia, Siena, another must-visit attraction.

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

Make sure to reserve a table at Ristorante San Desiderio, 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 Osteria Le Logge, 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 Taverna Di Cecco, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you’re not ready to end the night just yet, Bar Impero Siena offers a perfect venue to relax and savor a drink.

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

Day4

Day 4

Siena
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Porta Tufi
Musei dell’Accademia dei Fisiocritici
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Wake up to day 4 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!

Look forward to a unique sightseeing adventure at the frequently visited Porta Tufi and allow yourself time to explore. Just a short distance away you'll find your next stop, Musei Dell’accademia Dei Fisiocritici, a heritage-rich museum that draws visitors from far and near.

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.

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 savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started.

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

Day5

Day 5

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, begin at Palazzo Salimbeni. This worthwhile palace 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.

Dine in style at Ristorante La Finestra, a top recommendation for dinner tonight. Or, for a change of pace, Sindie boasts a menu that's sure to impress.

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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

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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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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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