7-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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Take this 7-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 6 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 7-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 SalimbeniTower of Mangiapiazza del CampoPubblico PalaceBattistero di San Giovanni BattistaSiena Cathedral
Vista Panoramica de SienaBasilica of San DomenicoSantuario di Santa CaterinaFontebranda
Porta Camollia, Siena
Porta Romana
Porta Pispini
Porta Tufi

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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 6 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 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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena.

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

Celebrate the start of your 7-day city break in Siena with a toast!

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Day 2

Day 2

  • Siena
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  • Palazzo Salimbeni
  • Tower of Mangia
  • piazza del Campo
  • Pubblico Palace
  • Battistero di San Giovanni Battista
  • Siena Cathedral
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Wake up to day 2 of your exciting city break in Siena. You still have 5 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!

Prepare for a day full of family-friendly attractions, picturesque spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Palazzo Salimbeni. This up-and-coming palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Tower Of Mangia, one of the city’s best highlights.

Next, check out Piazza Del Campo, one of the most widely recognized places to see in Siena. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pubblico Palace. Wander around and soak in the culturally significant atmosphere this palace offers. Then, head to Battistero Di San Giovanni Battista, a top-rated church that adds another dimension to your day. Finally, visit the well-known Siena Cathedral, the last of our attraction recommendations for today.

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.

Have a fantastic dining experience at Ristorante Tar-Tufo, a highly recommended choice for tonight's dinner.

After savoring a delicious meal, step into the vibrant nightlife at Maudit Pub, where the evening is just getting started.

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 3

Day 3

  • Siena
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  • Vista Panoramica de Siena
  • Basilica of San Domenico
  • Santuario di Santa Caterina
  • Fontebranda
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On day 3 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 4 nights left in Siena.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, 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 visually striking observation deck before continuing your journey. Basilica Of San Domenico is your next stop. This up-and-coming 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 respected 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.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Impero Siena, known for its inviting atmosphere.

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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  • Porta Camollia, Siena
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Wake up to day 4 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Siena. Begin your sightseeing with Porta Camollia, Siena. This curiosity-inducing monument is one of the top attractions in the city.

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

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.

Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, a top-rated bar in the area.

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

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Day 5

Day 5

  • Siena
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  • Porta Romana
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On day 5 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.

Start your adventure at Porta Romana. This locally appreciated monument is a place that is appreciated by travelers and locals alike.

These sights offer a fulfilling end to a perfect day.

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 lovely meal at Fischi per Fiaschi, a top-rated place to have dinner tonight.

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

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow holds new possibilities and discoveries!

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Day 6

Day 6

  • Siena
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  • Porta Pispini
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Get ready for another exciting day in Siena on day 6 of your city break! From historical sites to modern attractions, there's something for everyone to enjoy. With 1 night ahead, make the most of your time and create unforgettable memories in Siena.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most beloved attractions included on the itinerary is Porta Pispini. This picture-perfect historical landmark will help you start your sightseeing on top.

Throughout the day, make sure to take breaks to appreciate the surroundings.

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 Osteria da Divo, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, San Paolo Pub stands out as an excellent choice for a post-dinner cocktail.

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

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Day 7

Day 7

  • Siena - Departure day
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  • Porta Tufi
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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 Tufi. This frequently visited 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.

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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