6-Day Italy City Break in Siena With Itinerary

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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 the heart of 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.

With this perfectly planned holiday package, you will experience the ultimate Siena city break. This trip includes 5 nights in Siena at one of the best hotels in the city. Let us take care of the details so you can fully enjoy all the attractions and activities the city has to offer. Whether you're seeking to discover the rich cultural heritage of Siena or indulge in its delicious culinary scene, this holiday package has got you covered.

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 the footsteps of history through iconic landmarks, savoring the rich flavors of Italy's traditional cuisine, or uncovering the city's best-kept secrets on guided tours, Siena promises an adventure tailored to every traveler's passion. With a diverse selection of immersive experiences to choose from, 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, so it's advisable to book your holiday package in advance. Select a date and start planning your city break in Siena as early as today. Join us and discover the enchanting beauty of Siena, Italy!

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Porta Tufi
Siena CathedralPubblico Palacepiazza del CampoTower of MangiaLoggia del Papa, Siena
Fortezza MediceaPorta Camollia, Siena
Palazzo SalimbeniSantuario di Santa CaterinaBasilica of San DomenicoVista Panoramica de Siena
Porta PispiniPorta Romana
Pinacoteca Nazionale

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Day 1

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 in Siena for 5 nights.

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.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area.

This is the time to raise a toast for your 6-day city break in Siena! Savor the moment and look forward to immersing yourself in the vibrant culture, stunning sights, and local delicacies of the city for the next few days to come!

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Day 2

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 exciting city break in Siena. You still have 4 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!

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Siena. Your adventure starts at Siena Cathedral, a well-known local hot spot. Another notable attraction to explore is Pubblico Palace. This locally appreciated palace is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Piazza Del Campo. This romantic public square offers a fascinating experience that many visitors find memorable. Tower Of Mangia is also worth visiting, along with Loggia Del Papa, Siena. These standout landmarks offer unique experiences that add to the day’s enjoyment.

When you’re ready for dinner, we recommend you try one of the best restaurants in Siena.

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.

To truly maximize your evening out, consider visiting Maudit Pub after dinner. This bar is known for offering some of the best drinks and vibes in the city.

Raise a toast and celebrate another memorable day in Siena, Italy!

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Day 3

Day 3

  • Siena
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  • Fortezza Medicea
  • Porta Camollia, Siena
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As day 3 dawns in Siena, embark on another day of exploration and adventure. Discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 3 nights left, the possibilities for discovery are endless.

Siena is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Fortezza Medicea (siena), an up-and-coming monument that is worthwhile a visit in the city. Nearby, you’ll find Porta Camollia, Siena, enchanting visitors with its culturally significant appeal.

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.

Don’t miss out on dining at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

After your meal, keep the night alive at a bar like Bar Impero Siena, known for its lively atmosphere.

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

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Day 4

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.

Set out on a day brimming with family-friendly attractions, picturesque spots, and historic treasures. Start at the intriguing Palazzo Salimbeni, an instagrammable palace in Siena. Next, go to Santuario Di Santa Caterina.

After visiting Palazzo Salimbeni and Santuario Di Santa Caterina, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of San Domenico. This stunning church offers a unique experience. Vista Panoramica De Siena is another noteworthy attraction worthwhile a visit.

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

Savor the flavors at Bar Pasticceria Nannini Toselli, a top pick for dinner tonight. Alternatively, Ristorante Gallo Nero beckons with its unique menu offerings. Also, consider Bar osteria enea. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

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

As the day draws to a close, bask in the tranquility of Siena by night. With memories made and adventures ahead, rest well and embrace the journey anew tomorrow.

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Day 5

Day 5

  • Siena
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  • Porta Pispini
  • Porta Romana
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Rise and shine for day 5 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 1 night remaining, there's ample time to explore and uncover the heart of Siena.

Today’s agenda in Siena includes a historical landmark and a monument. Porta Pispini is must-visit historical landmark and a great starting point for the day. Next, continue your journey to Porta Romana, an often recommended monument, located just a leisurely stroll away.

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.

Enjoy a lovely meal at Ristorante La Finestra, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Sindie is another top choice with a popular menu. You could also check for a table at Ristorante Numero Unico. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Following your dinner, dive into the local bar culture at Bar Pinacoteca. Enjoy this evening's relaxed ambiance with delightful drinks.

Wind down and recharge for tomorrow's escapades in Siena, Italy. With each day comes new experiences to cherish and enjoy.

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Day 6

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 respected 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 or sightseeing. Downtown Siena offers excellent shopping opportunities and is the perfect place to browse for souvenirs and gifts to bring home. Take a walk and discover unique items you can purchase to remind you of your city break in Siena.

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 vibrant 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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