6-Day Italy City Break in Siena With Itinerary

1 / 15
Photo of Siena cathedral against a bright blue sky in Italy.
Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
photo of view of Stylish woman walks on background of cityscape of Siena old town. Concept of travel famous cities in Tosacny region of Italy
photo of view of  Aerial view of Montepulciano, a medieval and Renaissance hill town in the Italian province of Siena in southern Tuscany, Italy
photo of view of Facade decoration of the cathedral of Siena, Italy.
photo of view of historic buildings and landmarks in magnificent medieval Siena,Tuscany, Italy.
photo of view of Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view of Cathedral of the City of Siena in Tuscany region of Italy at sunset.
photo of view of Beautiful traveler girl exploring the historic city of Siena in Tuscany. Young tourist woman smiling at camera in Siena Cathedral square, Tuscany, Italy.
photo of view ofYoung woman having lunch with pizza and wine, sitting with dog at outdoor restaurant with beautiful view on the old town of Siena. Concept of italian cuisine and travel
photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
photo of view ofBeautiful view of campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena in the sunny day, Tuscany, Siena province, Italy
Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
From A to Z
Travel agent
24/7 fast service

Description

Take a 6-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 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!

Read more

Travel details

Set your travel details to find the best price

Flights

Round trip
Round trip
Travel dates

Travelers

Rooms

Flights

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

Car

Choose from the best car rental deals or see all options

Itinerary summary

See a summary of the itinerary that you can fully customize

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

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1

  • Siena - Arrival day
  • More
  • Porta Tufi
  • More

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.

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 wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Celebrate the start of your 6-day city break in Siena with a toast!

Read more
Day 2

Day 2

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

Wake up to day 2 of your vacation in Siena. With 4 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 family-friendly attractions, romantic experiences, and scenic views! Start at Siena Cathedral, a locally renowned church that is worthwhile a visit in the city. Nearby, you’ll find Pubblico Palace, enchanting visitors with its picture-perfect appeal. Continue your exploration at Piazza Del Campo. This public square is one of the city’s most spectacular spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Tower Of Mangia. After exploring the monument, head to the frequently visited Loggia Del Papa, Siena.

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

Enjoy a lovely meal at Osteria Quattro Venti, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Fischi per Fiaschi is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Cap off your dinner by heading to Maudit Pub, ideal for a leisurely evening with a drink in hand.

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

Read more
Day 3

Day 3

  • Siena
  • More
  • Fortezza Medicea
  • Porta Camollia, Siena
  • 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 3 nights left in Siena.

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and picturesque spots. 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. Fortezza Medicea (siena) is the first of them. Spend some time admiring this culturally significant monument before continuing your journey. Porta Camollia, Siena is your next stop. This curiosity-inducing monument is one of the best-rated sights in Siena.

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.

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. Immerse yourself in the culinary delights of Osteria Le Logge, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Taverna Di Cecco, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

Read more
Day 4

Day 4

  • Siena
  • More
  • Palazzo Salimbeni
  • Santuario di Santa Caterina
  • Basilica of San Domenico
  • Vista Panoramica de Siena
  • More

Rise and shine for day 4 of your city break in Siena! Today, 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 and uncover the heart of Siena.

Start by visiting Palazzo Salimbeni, a prime spot to begin your journey. This heritage-rich palace is sure to impress. Next on your list is Santuario Di Santa Caterina, another must-visit landmark and intriguing church renowned for its culturally significant 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 Basilica Of San Domenico. This breathtaking church is an essential place to visit for anyone looking for the full Siena experience. We also recommend visiting Vista Panoramica De Siena, a frequently visited observation deck.

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

Enjoy a delicious meal at Bar Pasticceria Nannini Toselli, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Gallo Nero, another top spot with a tantalizing menu. You might also want to secure a reservation at Bar osteria enea. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks.

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.

Read more
Day 5

Day 5

  • Siena
  • More
  • Porta Pispini
  • Porta Romana
  • More

As day 5 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.

Savor the day by visiting some of the best places to see in Siena, including a historical landmark and a monument. Start your adventure at Porta Pispini. This up-and-coming historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta Romana located in Siena for another exciting encounter.

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 Ristorante La Finestra, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Sindie, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Numero Unico. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

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

Read more
Day 6

Day 6

  • Siena - Departure day
  • More
  • Pinacoteca Nazionale
  • 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, we recommend visiting Pinacoteca Nazionale, a history-steeped 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 for something new, try Osteria Castelvecchio, another premier location with a delectable menu.

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!

Read more

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
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.