Travel packages in Italy

City breaks in Italy

11-Day Italy City Break in Siena With Itinerary

1 / 15

Photo of Siena cathedral against a bright blue sky in Italy.

Perfect travel plans

Everything included

Fully customizable

Description

Included

Flights

Hotel

Select dates

Car rental

Select dates

Tours & tickets

Select dates

Travel plan

From A to Z

Travel agent

24/7 fast service

Description

Immerse yourself in the charm of Siena on this 11-day city break in Italy, where cultural delights and exciting experiences await!

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 10 nights in Siena. It's the the ultimate 11-day Siena city break.

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.

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!

Travel details

Set your travel details to find the best price

Flights

Compare and choose from the best flights to Siena, landing in Florence

Include flights

Car

Choose from the best car rental deals or see all options

Include car

Personalize your itinerary

Customize tours under each day and destination

Day1

Day 1

Siena - Arrival day
More

Porta Romana
More

Your exciting city break begins as soon as you arrive in the beautiful city of Siena. You’ll stay here for 10 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 to eat, treat yourself to a nice meal at a top-rated restaurant in the city.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere.

Celebrate the start of your 11-day city break in Siena with a toast!

Day2

Day 2

Siena
More

Loggia del Papa, Siena
Tower of Mangia
piazza del Campo
Pubblico Palace
More

Rise and shine for day 2 of your city break in Siena! Delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 9 nights remaining, there's ample time to explore.

One of the most worthwhile attractions included on the itinerary is Loggia Del Papa, Siena. This symbolic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Tower Of Mangia and learn what makes this UNESCO world heritage-designated monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the impressive Piazza Del Campo. After exploring the public square, head to Pubblico Palace. This beloved palace is a highlight in Siena.

After or in between exploring, treat yourself to a delicious meal. Siena offers many excellent restaurants to choose from.

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

Let the evening flow smoothly from dinner to drinks at Maudit Pub, a top-rated bar in the area.

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

Day3

Day 3

Siena
More

Piccolomini Library
Piazza del Duomo
Siena Cathedral
Battistero di San Giovanni Battista
More

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 8 nights left in Siena.

Enjoy all that Piccolomini Library has to offer. This is a frequently visited library you should not miss. Another must-see is Piazza Del Duomo, an often recommended public square in Siena.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Battistero Di San Giovanni Battista, another of the city’s worthwhile attractions.

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 Antica Trattoria Papei, highly recommended for tonight's dining.

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

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

Day4

Day 4

Siena
More

Fortezza Medicea
Porta Camollia, Siena
More

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!

Fortezza Medicea (siena) is an ideal stop early in the day. This underrated monument is a must-visit in the city. When you’re ready for your next discovery, continue to Porta Camollia, Siena, which may be one of the most culturally significant places you will experience today.

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

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Charlie Mixology Bar Di Aldinucci Riccardo, known for its inviting atmosphere.

Reflect on the adventures of the day as you unwind in the comfort of your hotel in Siena. Tomorrow is a new day!

Day5

Day 5

Siena
More

Vista Panoramica de Siena
Basilica of San Domenico
Santuario di Santa Caterina
Fontebranda
More

As day 5 dawns in Siena, discover the city's vibrant culture, delicious cuisine, and captivating sights at your own pace. With 6 nights left, the possibilities for discovery are endless.

Vista Panoramica De Siena leaves a lasting impression. This observation deck is one of the most underrated places to visit in Siena. Next, head to Basilica Of San Domenico, a curiosity-inducing church, known for its majestic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Santuario Di Santa Caterina. This photogenic church is a highly recommended experience. Nearby, you'll also find Fontebranda Visit these for an interesting touch to your journey.

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.

Savor the flavors at Fischi per Fiaschi, a top pick for dinner tonight.

Extend your evening after a delightful meal by visiting Bar Pinacoteca, which offers the perfect atmosphere for a night out.

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

Day6

Day 6

Siena
More

Palazzo Salimbeni
More

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 5 nights ahead, make the most of your time and create unforgettable memories in Siena.

Palazzo Salimbeni is perfect for a self-paced visit during the day. This photogenic palace is sure to impress.

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.

Dine in style at Osteria da Divo, a top recommendation for dinner tonight.

Keep the excitement of the evening going by visiting a bar or two. San Paolo Pub is an excellent place to start.

Wind down and recharge for tomorrow's escapades in Italy.

Day7

Day 7

Siena
More

Porta Tufi
More

On day 7 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.

Porta Tufi brings Siena's character to life. This awe-inspiring historical landmark is a highlight of any visit in the city.

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 Ristorante San Desiderio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

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

Day8

Day 8

Siena
More

Pinacoteca Nazionale
Musei dell’Accademia dei Fisiocritici
More

Wake up to day 8 of your vacation in Siena. With 3 nights left, you'll have ample time to explore and savor all Siena has to offer.

Awaiting your discovery is the curiosity-inducing Pinacoteca Nazionale, a respected art gallery in Siena. Next, go to Musei Dell’accademia Dei Fisiocritici.

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.

Enjoy a lovely meal at Osteria Le Logge, a top-rated place to have dinner tonight.

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

Day9

Day 9

Siena
More

Facciatone
More

Rise and shine for day 9 of your city break in Siena! Delve deeper into the city's offerings, from its iconic landmarks to its hidden gems. With 2 nights remaining, there's ample time to explore.

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.

Facciatone is must-visit observation deck and a great option for a daytime tour of the area.

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

Enjoy a delicious meal at Ristorante Taverna Di Cecco, a highly-rated dining destination in Siena.

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

Day10

Day 10

Siena
More

Фонтан контради Сельва
More

On day 10 of your fun city break in Siena, you’ll experience more of the best attractions and activities in the city. You now have 1 night left in Siena.

Siena is brimming with adventures.

Whatever your travel style is, Fontan Kontradi Sel'va is an essential stop in Siena. This often recommended point of interest provides an insightful glimpse into the city's identity.

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

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.

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

Day11

Day 11

Siena - Departure day
More

Porta Pispini
More

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 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.

Have a fantastic dining experience at Ristorante Gallo Nero, a highly recommended choice for tonight's dinner.

As you conclude your city break in Siena, treasure the memories you've made. May they accompany you on your journey homeward!

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

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.

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.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

Similar travel packages

Discover other popular vacations in Italy

From 0

Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.