One-Week Italy City Break in Siena With Itinerary

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Discover the essence of Siena with a 8-day city break in Italy, blending cultural richness with exhilarating adventures.

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 7 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 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. 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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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Fortezza Medicea
Palazzo SalimbeniLoggia del Papa, SienaTower of Mangiapiazza del CampoPubblico Palace
Musei dell’Accademia dei FisiocriticiPinacoteca NazionalePiazza del DuomoSiena CathedralBattistero di San Giovanni BattistaPiccolomini Library
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
Porta Camollia, Siena
Porta Romana
Porta Tufi
Porta Pispini

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Day 1

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 in Siena for 7 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 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.

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

Savor the flavors at Enoteca I Terzi, a top pick for dinner tonight.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink.

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

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Day 2

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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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 6 nights left in Siena.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and history-rich sites. 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. Palazzo Salimbeni is the first of them. Spend some time admiring this heritage-rich palace before continuing your journey. Loggia Del Papa, Siena is your next stop. This underrated monument 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 Tower Of Mangia. This culturally significant monument is a sight to behold. To round off your sightseeing experience, visit Piazza Del Campo and Pubblico Palace.

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 delicious dinner at Ristorante Tar-Tufo, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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

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

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Day 3

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, embark on another day of exploration and adventure. 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.

Start by visiting Musei Dell’accademia Dei Fisiocritici, a prime spot to begin your journey. This heritage-rich museum is sure to impress. Next on your list is Pinacoteca Nazionale, another must-visit landmark and often recommended art gallery renowned for its visually striking 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 Duomo. This romantic public square is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Siena Cathedral, a popular church. 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 Piccolomini Library and wrap up your day with its history-steeped appeal.

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.

Enjoy a delicious meal at Antica Trattoria Papei, a top-rated dining destination in Siena.

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

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

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Day 4

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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and scenic views in the charming city of Siena. Your adventure starts at Vista Panoramica De Siena, a worthwhile local hot spot. Another notable attraction to explore is Basilica Of San Domenico. This intriguing church 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 Santuario Di Santa Caterina. This culturally significant church offers a fascinating experience that many visitors find memorable. Fontebranda is also worth visiting.

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 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.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in.

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 5

Day 5

  • Siena
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  • Porta Camollia, Siena
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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 3 nights remaining, there's ample time to explore and uncover the heart of Siena.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Porta Camollia, Siena is the perfect place to start. This monument is one of the most locally appreciated places to visit in Siena.

Visit these for an interesting touch to your journey.

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.

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

Round off your dining experience by visiting Bar Pinacoteca, a prime location for a drink.

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

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Day 6

Day 6

  • Siena
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  • Porta Romana
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Wake up to day 6 of your vacation in Siena. With 2 nights left, you'll have ample time to explore and savor all Siena has to offer.

Siena is home to plenty of attractions that offer fun adventures, breathtaking views, and picturesque spots! Start at Porta Romana, an increasingly popular monument that is worthwhile a visit in the city.

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

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

If you’re not ready to end the night just yet, San Paolo Pub offers a perfect venue to relax and savor a drink.

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

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Day 7

Day 7

  • Siena
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  • Porta Tufi
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Wake up to day 7 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!

Start your day with a visit to Porta Tufi. This locally appreciated historical landmark is a must-visit in the city.

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

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

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 8

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 up-and-coming historical landmark is a popular place to see in the city.

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.

Savor the flavors at Osteria Le Logge, a top pick for dinner tonight.

As your city break in Siena draws to a close, cherish the memories you've made. With your travel plans in place, you're all set for a safe journey home. Until next time, take care and safe travels!

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