Luxury 7-Day Italy City Break in Siena

Your exciting luxury holiday begins as soon as you arrive in beautiful Siena.

Siena has plenty of sights, monuments, and places of interest for you to explore throughout your vacation. Luckily, you have plenty of time to do so for the next 7 days. Catch an early flight to get started with your sightseeing in Siena right away.

An attraction we recommend you check out today is Fortezza Medicea (Siena). This spectacular fortress and travel destination has an average rating of 4.5 out of 5 stars from 9,835 visitors.

After a long day of traveling and sightseeing, we recommend you treat yourself to a meal at one of the best restaurants in Siena.

Check out Osteria degli Svitati. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.7 out of 5 stars from 911 reviews.

Locals also recommend Osteria Il Carroccio as one of the best restaurants to have dinner at in Siena. Osteria Il Carroccio is rated an average of 4.7 out of 5 stars by 895 customers, including locals as well as travelers.

Alternatively, for another culinary experience you will remember, book a table at Antica Trattoria Papei. This popular restaurant has an average rating of 4.3 out of 5 stars by 3,761 customers.

As your first day in Siena is coming to an end, retreat to a bar for some celebration.

One of travelers' and locals' favorite bars in the city is La Taverna di San Giuseppe. This claim is supported by 1,767 customers who have rated it an average of 4.7 out of 5 stars.

If you want to continue your night somewhere else, head to another popular place like Ristorante Gallo Nero. This bar is a local favorite, with great drinks, lovely service, and an average rating of 4.4 out of 5 stars by 829 customers.

This is the time to raise a toast to the beginning of your special 7-day luxury holiday in Siena!

Wake up 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 5 nights you have left of your luxury holiday in Siena.

Start the day with a visit to one of the most recommended attractions in the city, the remarkable piazza del Campo. About 64,175 reviewers have rated this square and attraction an average of 4.8 out of 5 stars.

The popular Siena Cathedral is another unique sight you can experience in Siena today. This attraction is a domus, rated an average of 4.8 out of 5 stars by 21,656 visitors.

Make your way to the fantastic Fortezza Medicea (Siena), perhaps the most famous fortress in Siena.

This is a highlight on travelers’ itineraries in Siena.

To make your day extra special, check out the available tours and tickets in the city. You can choose from a curated selection of the most popular tours and activities in Siena below. Add the tickets to your luxury holiday package to guarantee a spot on your preferred tour in the city.

After or in between exploring Siena, treat yourself to a delicious meal at one of the best restaurants in the city.

An excellent option is Osteria da Divo, which is a popular restaurant with an exciting menu. This restaurant has an average rating of 4.4 out of 5 stars by 1,062 customers.

Another top-rated restaurant to consider is Ristorante Taverna Di Cecco. This restaurant is popular with locals as well as travelers and is rated an average of 4.4 out of 5 stars by 822 customers.

PARTICOLARE di Siena is another restaurant that is certain to become a favorite in Siena. This irresistible restaurant has an average rating of 4.6 out of 5 stars by 598 customers.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

If you’re not yet ready to call it a day, pop into San Paolo Pub. This bar is considered one of the best in Siena and is rated an average of 4.3 out of 5 stars by 704 customers.

You may also want to check out Torrefazione Fiorella. Equally popular, this bar offers a great drink list and a nice atmosphere for your evening endeavors. Torrefazione Fiorella is rated an average of 4.8 out of 5 stars by 370 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.

Day 3 of your luxury itinerary in Siena will be filled with memorable experiences. With magnificent attractions, delicious food, and great entertainment, you're guaranteed a lovely day in the city. Make the most out of the 4 nights you have left of your luxury holiday in Siena.

Begin this beautiful day with a visit to a top-rated square and attraction in Siena, the piazza del Campo. About 64,175 visitors have rated this attraction an average of 4.8 out of 5 stars.

The popular Siena Cathedral is another top sight in Siena that locals and travelers often enjoy spending time at. This attraction is a domus, rated an average of 4.8 out of 5 stars by 21,656 visitors.

Fortezza Medicea (Siena) is a spectacular fortress and highlight on travelers’ itineraries in Siena.

Exploring Siena's best attractions and hidden gems can make you quickly lose track of time. Make sure to grab something to eat and use this opportunity to learn more about Siena's culinary culture.

Ristorante San Desiderio is one of the most popular restaurants in Siena. Most people can find something that fits their taste from Ristorante San Desiderio’s excellent menu. Approximately 657 customers have rated this popular restaurant an average of 4.4 out of 5 stars.

If you’re in the mood for something different, check out Osteria Castelvecchio. This Siena-based restaurant is one of locals’ favorites and has an average rating of 4.5 out of 5 stars from 582 customers.

Another top-rated restaurant that serves a menu of appetizing food and drinks is Ristorante La Finestra. This popular restaurant has an average rating of 4.4 out of 5 stars from 602 customers.

If you’re up for getting a drink, consider going to BLANDIS - Wine & Cafè. Around 291 customers have given this incredible bar an average rating of 4.7 out of 5 stars.

Locals of Siena also enjoy the drinks at Sindie. This place is rated an average of 4.7 out of 5 stars by 124 customers and is one of the best you can experience in the city.

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!

Wake up to day 4 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 3 nights you have left of your luxury holiday in Siena.

Start the day with a visit to one of the most recommended attractions in the city, the remarkable piazza del Campo. About 64,175 reviewers have rated this square and attraction an average of 4.8 out of 5 stars.

The popular Siena Cathedral is another unique sight you can experience in Siena today. This attraction is a domus, rated an average of 4.8 out of 5 stars by 21,656 visitors.

Make your way to the fantastic Fortezza Medicea (Siena), perhaps the most famous fortress in Siena.

This is a highlight on travelers’ itineraries in Siena.

To make your day extra special, check out the available tours and tickets in the city. You can choose from a curated selection of the most popular tours and activities in Siena below. Add the tickets to your luxury holiday package to guarantee a spot on your preferred tour in the city.

After or in between exploring Siena, treat yourself to a delicious meal at one of the best restaurants in the city.

An excellent option is Osteria Le Logge, which is a popular restaurant with an exciting menu. This restaurant has an average rating of 4.3 out of 5 stars by 547 customers.

Another top-rated restaurant to consider is Fischi per Fiaschi. This restaurant is popular with locals as well as travelers and is rated an average of 4.6 out of 5 stars by 356 customers.

Enoteca I Terzi is another restaurant that is certain to become a favorite in Siena. This irresistible restaurant has an average rating of 4.4 out of 5 stars by 425 customers.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

If you’re not yet ready to call it a day, pop into Osteria Quattro Venti. This bar is considered one of the best in Siena and is rated an average of 4.6 out of 5 stars by 304 customers.

You may also want to check out Maudit Pub. Equally popular, this bar offers a great drink list and a nice atmosphere for your evening endeavors. Maudit Pub is rated an average of 4.4 out of 5 stars by 224 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.

Day 5 of your luxury itinerary in Siena will be filled with memorable experiences. With magnificent attractions, delicious food, and great entertainment, you're guaranteed a lovely day in the city. Make the most out of the 2 nights you have left of your luxury holiday in Siena.

Begin this beautiful day with a visit to a top-rated square and attraction in Siena, the piazza del Campo. About 64,175 visitors have rated this attraction an average of 4.8 out of 5 stars.

The popular Siena Cathedral is another top sight in Siena that locals and travelers often enjoy spending time at. This attraction is a domus, rated an average of 4.8 out of 5 stars by 21,656 visitors.

Fortezza Medicea (Siena) is a spectacular fortress and highlight on travelers’ itineraries in Siena.

Exploring Siena's best attractions and hidden gems can make you quickly lose track of time. Make sure to grab something to eat and use this opportunity to learn more about Siena's culinary culture.

Ristorante Numero Unico is one of the most popular restaurants in Siena. Most people can find something that fits their taste from Ristorante Numero Unico’s excellent menu. Approximately 379 customers have rated this popular restaurant an average of 4.3 out of 5 stars.

If you’re up for getting a drink, consider going to Charlie Mixology Bar di Aldinucci Riccardo. Around 138 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!

Wake up to day 6 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 1 night you have left of your luxury holiday in Siena.

Start the day with a visit to one of the most recommended attractions in the city, the remarkable piazza del Campo. About 64,175 reviewers have rated this square and attraction an average of 4.8 out of 5 stars.

The popular Siena Cathedral is another unique sight you can experience in Siena today. This attraction is a domus, rated an average of 4.8 out of 5 stars by 21,656 visitors.

Make your way to the fantastic Fortezza Medicea (Siena), perhaps the most famous fortress in Siena.

This is a highlight on travelers’ itineraries in Siena.

To make your day extra special, check out the available tours and tickets in the city. You can choose from a curated selection of the most popular tours and activities in Siena below. Add the tickets to your luxury holiday package to guarantee a spot on your preferred tour in the city.

After or in between exploring Siena, treat yourself to a delicious meal at one of the best restaurants in the city.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

Equally popular, this bar offers a great drink list and a nice atmosphere for your evening endeavors.

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.

Your special luxury holiday in Siena is coming to an end and it’s soon time to say goodbye to the city.

Depending on how much time you have before your departure, this is your chance to get one last glimpse of Siena. Catch a later flight to enjoy some additional time exploring the city. Your luxury accommodation will be conveniently located for some last-minute shopping or sightseeing.

If you still have time, we recommend visiting some of the attractions you may not yet have had the time to explore.

Piazza del Campo is a fantastic attraction you could visit on your last day in Siena. This square and popular site of interest has an impressive average rating of 4.8 out of 5 stars from 64,175 visitors.

If you would rather see something else, Siena Cathedral is a great alternative. With an average rating of 4.8 out of 5 stars by 21,656 visitors, it's easy to understand why so many travelers feel inclined to check this domus out.

To soak in the last of your luxury vacation in Siena, you can also make a visit to Fortezza Medicea (Siena). This outstanding fortress is rated an average of 4.5 out of 5 stars by 9,835 visitors.

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!