11-Day Italy City Break in Siena With Itinerary
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Take a 11-day city break in Italy and explore Siena like a local. Immerse yourself in the charm of Siena, where every corner holds a new adventure.
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 10 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 11-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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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 in Siena for 10 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 Romana, 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.
Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena.
Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out.
This is the time to raise a toast for your 11-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!
Day 2
- Siena
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- Loggia del Papa, Siena
- Tower of Mangia
- piazza del Campo
- Pubblico Palace
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On day 2 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 9 nights in Siena and enjoy plenty of time for exploring.
Siena is brimming with adventures. Today’s wonderful stops include a monument, a public square, and a palace. Begin your sightseeing adventure at the beloved Loggia Del Papa, Siena and allow yourself time to explore. Just a short distance away you'll find your next stop, Tower Of Mangia, a breathtaking monument that draws visitors from far and near.
Continue your journey to Piazza Del Campo, one of the city’s most impressive spots that you shouldn’t miss. Another great site to visit is the up-and-coming Pubblico Palace.
When you’re ready for dinner, we recommend you try one of the best restaurants in Siena.
Dine in style at Ristorante Tar-Tufo, a top recommendation for dinner tonight.
Let the evening flow smoothly from dinner to drinks at Maudit Pub, a top-rated bar in the area.
Raise a toast and celebrate another memorable day in Siena, Italy!
Day 3
- Siena
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- Piccolomini Library
- Piazza del Duomo
- Siena Cathedral
- Battistero di San Giovanni Battista
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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 8 nights left, the possibilities for discovery are endless.
Prepare for a day full of fun adventures, picturesque spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at Piccolomini Library. This up-and-coming library is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Duomo, one of the city’s best highlights.
Next, check out Siena Cathedral, one of the most captivating places to see in Siena. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Battistero Di San Giovanni Battista. Wander around and soak in the monumental atmosphere this church offers.
When it’s time to eat, Siena has restaurants and bars to suit all budgets.
Savor the flavors at Antica Trattoria Papei, a top pick for dinner tonight.
After savoring a delicious meal, step into the vibrant nightlife at Bar Impero Siena, where the evening is just getting started.
Raise your glass and relax after another amazing day in Siena, Italy.
Day 4
- Siena
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- Fortezza Medicea
- Porta Camollia, Siena
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Wake up to day 4 of your exciting city break in Siena. You still have 7 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 fun adventures, scenic views, and photo-friendly spots in the charming city of Siena. Your adventure starts at Fortezza Medicea (siena), a curiosity-inducing local hot spot. Another notable attraction to explore is Porta Camollia, Siena. This increasingly popular monument is known for its historic appeal.
After or in between exploring, treat yourself to a delicious meal at a nice restaurant in the city. Unwind and enjoy the local flavors and culinary delights while reflecting on the day's adventures.
Enjoy a delicious meal at Osteria Quattro Venti, a top-rated dining destination in Siena.
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.
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.
Day 5
- Siena
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- Vista Panoramica de Siena
- Basilica of San Domenico
- Santuario di Santa Caterina
- Fontebranda
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On day 5 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 fun adventures, romantic experiences, and scenic views. 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. Vista Panoramica De Siena is the first of them. Spend some time admiring this romantic observation deck before continuing your journey. Basilica Of San Domenico is your next stop. This beloved church 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 Santuario Di Santa Caterina. This culturally significant church is a sight to behold. To round off your sightseeing experience, visit Fontebranda.
Before you know it, it’s time to head out for dinner. Treat yourself to a delicious meal at a nice restaurant in Siena.
Treat yourself to a delicious dinner at Fischi per Fiaschi, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice 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 Bar Pinacoteca, a well-loved spot among locals and tourists.
Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow holds new possibilities and discoveries!
Day 6
- Siena
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- Palazzo Salimbeni
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Wake up to day 6 of your vacation in Siena. With 5 nights left, you'll have ample time to explore and savor all Siena has to offer.
Discover a day packed with fun adventures, picturesque spots, and historic treasures in Siena. Begin your sightseeing with Palazzo Salimbeni. This beloved palace is one of the top attractions in the city.
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.
Make sure to reserve a table at Osteria da Divo, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.
Unwind after your meal by stepping into San Paolo Pub. This venue is celebrated for its extensive drink selections and cozy vibes.
Savor the memories of an amazing day in Siena, Italy!
Day 7
- Siena
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- Porta Tufi
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Rise and shine for day 7 of your city break in Siena! Today, delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 4 nights remaining, there's ample time to explore and uncover the heart of Siena.
Siena is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Porta Tufi, an often recommended historical landmark that is worthwhile a visit in the city.
After a long day of sightseeing, try one of the best restaurants in Siena.
Treat yourself to a wonderful meal at Ristorante San Desiderio, a top-rated dining spot in Siena.
No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed.
Day 8
- Siena
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- Pinacoteca Nazionale
- Musei dell’Accademia dei Fisiocritici
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Get ready for another exciting day in Siena on day 8 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 3 nights ahead, make the most of your time and create unforgettable memories in Siena.
Start by visiting Pinacoteca Nazionale, a prime spot to begin your journey. This standout art gallery is sure to impress. Next on your list is Musei Dell’accademia Dei Fisiocritici, another must-visit landmark and frequently visited museum renowned for its heritage-rich features.
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.
Make sure to reserve a table at Osteria Le Logge, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.
Wind down and recharge for tomorrow's escapades in Siena, Italy. With each day comes new experiences to cherish and enjoy.
Day 9
- Siena
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- Facciatone
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On day 9 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, romantic experiences, and breathtaking views. Start at the underrated Facciatone, an UNESCO world heritage-designated observation deck in Siena.
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.
Don’t miss out on dining at Ristorante Taverna Di Cecco, a top-rated dining destination in Siena.
Get some rest at your hotel in preparation for another wonderful day in Siena to come!
Day 10
- Siena
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- Фонтан контради Сельва
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As day 10 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 1 night left, the possibilities for discovery are endless.
Begin your adventure at Fontan Kontradi Sel'va. This is an up-and-coming point of interest you should not miss.
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 dining experience at Bar Pasticceria Nannini Toselli, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city.
Raise a toast and celebrate another memorable day in Siena, Italy!
Day 11
- 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, we recommend visiting Porta Pispini, a picture-perfect historical landmark 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.
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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