Luxury 6-Day Italy City Break in Siena

Your exciting luxury holiday begins as soon as you arrive in the beautiful city of Siena. You will stay in the city for 5 nights and choose from some of the best luxury hotels in downtown Siena that are guaranteed to make you feel special.

Tonight, you will be treated to a stay at one of the best luxury hotels in Siena. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Your sightseeing of the day begins at Porta Romana, a remarkable city gate where it’s easy to get lost in exploration. This top attraction is rated an average of 4.4 out of 5 stars in 2,383 reviews.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Check out Osteria La Sosta di Violante. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.7 out of 5 stars from 2,042 reviews.

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Siena.

When an after-dinner drink sounds enticing, visit La Taverna di San Giuseppe, one of the best bars in the city of Siena. This bar has an average rating of 4.7 out of 5 stars from 1,767 customers.

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

Wake up refreshed to day 2 of your luxury holiday in Siena. Today, you're going to experience the perfect blend of discovery, excitement, and indulgence. Take the opportunity to see the best sights, join the most exciting activities, and sample the finest restaurants in the city. Cherish the 4 nights you have left of your luxury holiday in Siena.

A top pick for your self-guided sightseeing tour today is Duomo di Siena. Previous visitors have rated this domus an average of 4.8 out of 5 stars in 21,656 reviews.

Pubblico Palace is a local recommendation that you also can pay a visit today. This museum is rated an average of 4.7 out of 5 stars in 1,400 reviews.

Another attraction you won't want to miss is Piazza del Campo. This square is rated an average of 4.8 out of 5 stars in 64,175 reviews.

Tower of Mangia is another outstanding experience in Siena. Around 673 travelers have rated this point of interest an average of 4.6 out of 5 stars.

If you long for more, Loggia del Papa, Siena is not far away. This sightseeing destination is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.5 out of 5 stars in 235 reviews.

There are plenty of experiences you can choose from in Italy that will add excitement to your vacation. When you’re keen to discover what else Siena has in store for you, use this day to go on a tour. This tour allows curious travelers like you to experience the best of the country. You can make the most of your time in Italy by scrolling down and selecting tours and activities to include on your itinerary for the day.

After a long day of traveling and sightseeing, we recommend you treat yourself to a meal at one of the best restaurants in Siena. Enjoy the local flavors and culinary delights as you reflect on the day's adventures.

Don't forget to book a table at Osteria degli Svitati, a well-known eatery in Siena. This popular restaurant and its sumptuous cuisine have won the hearts of food lovers. Its commitment to a delicious menu is evident in its 4.7 out of 5-star rating from 911 satisfied guests.

Go back to your hotel, take a stroll through the city, or head out to a bar to celebrate another fantastic day of your luxury vacation in Siena.

To have one of the best bar experiences in Siena, we recommend going to the wonderful Ristorante Gallo Nero. This bar offers a variety of phenomenal dishes and drinks and has been rated an average of 4.4 out of 5 stars by 829 customers.

This is a favorite place to hang out among locals, and an excellent place to visit if you wish to make new acquaintances while enjoying a refreshing drink.

No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed. Cheers to a fantastic day of your luxury vacation in Siena, Italy!

Begin day 3 in Siena with a renewed sense of adventure and anticipation. Today, delve deeper into the city's rich culture and vibrant atmosphere. Explore hidden gems, engage in immersive activities, and savor the flavors of local cuisine as you continue to make unforgettable memories.

Your sightseeing of the day begins at Fortezza Medicea, a remarkable fortress where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 9,835 reviews.

Next, satisfy your wanderlust at Porta Camollia. This city gate has an average rating of 4.5 out of 5 stars from 2,460 travelers.

To immerse yourself in more memorable moments in Siena, check out the best-rated tours the region offers. You can discover and choose from all of the top-rated activities you can do on this day in Siena below.

After a long day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Make sure to reserve a table at Osteria Il Carroccio, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Its dedication to culinary innovation is evident in its 4.7 out of 5-star rating from 895 satisfied guests.

As your day in Siena is coming to an end, retreat to a bar where you can celebrate the start of your exciting luxury holiday in Italy.

If you’re up for classic drinks with a modern flair, consider going to San Paolo Pub. Around 704 customers have given this incredible bar an average rating of 4.3 out of 5 stars.

Go over your photos from the day, raise a toast, and rest your tired legs. Another wonderful day of your luxury holiday in Siena awaits!

As the sun rises on day 4 in Siena, greet the day with excitement. Today offers the perfect opportunity to delve deeper into the city's rich history and vibrant culture. Whether you're embarking on guided tours, discovering famous attractions, or simply relaxing in the city's scenic beauty, every moment is an invitation to indulge in luxury and discovery.

Start your sightseeing with a visit to Palazzo Salimbeni. This palazzo is a popular stop on travelers’ itineraries in Siena, with an average rating of 4.5 out of 5 stars by 2,537 visitors.

Santuario Casa di Santa Caterina is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 1,201 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Basilica Cateriniana San Domenico. Visitors have rated this minor basilica an average of 4.6 out of 5 stars in 3,290 reviews.

Vista Panoramica de Siena is another unique site you can experience today. This attraction is a sightseeing destination rated an average of 4.8 out of 5 stars in 194 reviews.

Immerse yourself in the local scene through top-rated tours and activities. You can choose from a wide variety of easy to challenging tours and easily add them to your travel package below.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Elevate your experience by savoring a meal in Antica Trattoria Papei, a distinguished dining establishment in Siena. It has a rating of 4.3 out of 5 stars, thanks to the positive reviews of 3,761 satisfied guests and a menu that’s committed to quality and flavor.

As your first day in Siena is coming to an end, retreat to a bar for some celebration. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

When you’ve finished your meal, visit Bar Impero Siena for a well-deserved after-dinner drink. One of the best bars in the city, Bar Impero Siena has an average rating of 4.2 out of 5 stars from 988 customers.

Raise a toast to another amazing day of your luxury holiday in Siena! Get some rest at your hotel in preparation for yet another fantastic day in Italy.

Welcome day 5 of your luxury escape in Siena with a sense of anticipation and delight. Today invites you to embark on a journey of discovery as you uncover the city's best sights and indulge in its finest offerings. Whether you're exploring historic sites, sampling local delicacies, or simply basking in the beauty of your surroundings, every moment promises to be extraordinary.

Start your sightseeing with a visit to Pinacoteca Nazionale di Siena. This art museum is rated an average of 4.3 out of 5 stars from 507 visitors. Pinacoteca Nazionale di Siena welcomes around 8,127 visitors every year.

Musei dell’Accademia dei Fisiocritici is another popular attraction you could visit today. This museum has a rating of 4.8 out of 5 stars from 280 visitors.

Porta Tufi is also highly recommended by travelers. This city gate has a rating of 4.5 out of 5 stars from 906 visitors.

You can learn more about Siena today by going on a tour. Siena offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.

Exploring new places can make you hungry. When you’re ready for dinner, we recommend trying one of the finest restaurants in Siena.

Don't miss out on experiencing Grotta Santa Caterina da Bagoga, a renowned dining spot in Siena. This restaurant's rich flavors have left a lasting impression on diners. Its dedication to culinary perfection is evident in its 4.6 out of 5-star rating from 1,669 satisfied guests.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks. Immerse yourself in the local culture by sampling a signature cocktail or regional specialty.

One of the top bars in Siena is Sindie. This claim is supported by 124 customers who have rated it an average of 4.7 out of 5 stars.

No matter where in Siena you end up, an amazing evening of relaxation and enjoyment is guaranteed. Cheers to a fantastic day of your luxury vacation in Siena, Italy!

Your luxurious city break in Siena is coming to an end, and it's soon time to say goodbye to the city. But before you leave, make sure to capture a few more memories and perhaps find that special souvenir to remind you of your unforgettable journey.

On your last day in Italy, take time to indulge in shopping at Siena’s popular marketplace. Thanks to your accommodation’s strategic location, city’s bustling commercial district is only a stone’s throw away, giving you ample time to leisurely explore the area, filled with local shops.

Take time to find the perfect present, reminding you of the charms of Italy. Each store here is brimming with unique finds.

Make the most of what's left of your luxury vacation and head out to the stunning Porta Pispini. This extraordinary point of interest and attraction is rated an average of 4.5 out of 5 stars in 1,437 reviews, and is an excellent choice for your last sightseeing in Siena.

Don’t travel hungry. Take the opportunity to savor the local cuisine in Siena one last time before you head to the airport.

Check out Osteria Nonna Gina. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.6 out of 5 stars from 1,247 reviews.

You will then say farewell to Siena and begin your journey home. Now with a camera roll full of photos and your memory filled with happy moments from your unforgettable luxury holiday in Siena, Italy!