Luxury 3-Day Italy City Break in Siena

Your exciting luxury holiday begins as soon as you arrive in beautiful Siena. You will stay in the city for 2 nights and choose from some of the best luxury hotels in downtown Siena that are guaranteed to make you feel special.

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 3 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 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.

Locals also recommend Osteria degli Svitati as one of the best restaurants to have dinner at in Siena. Osteria degli Svitati is rated an average of 4.7 out of 5 stars by 911 customers, including locals as well as travelers.

Alternatively, for another culinary experience you will remember, book a table at Osteria Il Carroccio. This popular restaurant has an average rating of 4.7 out of 5 stars by 895 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.

The options in Siena don’t end there. You could also spend some time at the excellent San Paolo Pub. Rated 4.3 out of 5 stars by 704 customers, this bar is one of the best places to relax after a long, adventure-filled day.

This is the time to raise a toast to the beginning of your special 3-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 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 Porta Camollia, Siena. About 2,460 reviewers have rated this city gate and attraction an average of 4.5 out of 5 stars.

The popular Palazzo Salimbeni is another unique sight you can experience in Siena today. This attraction is a palazzo, rated an average of 4.5 out of 5 stars by 2,537 visitors.

Make your way to the fantastic piazza del Campo, perhaps the most famous square in Siena. This attraction is rated an average of 4.8 out of 5 stars by 3,290 travelers.

As the day moves along, be sure to also drop by the magnificent Siena Cathedral. This attraction and domus has an average rating of 4.8 out of 5 stars from 21,656 reviews.

Lastly, but not least, make a visit to the lovely Basilica of San Domenico. This is a popular minor basilica and highlight on travelers’ itineraries in Siena. Basilica of San Domenico has an average rating of 4.6 out of 5 stars from 3,290 visitors.

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 Antica Salumeria Salvini, which is a popular restaurant with an exciting menu. This restaurant has an average rating of 4.7 out of 5 stars by 720 customers.

Another top-rated restaurant to consider is Antica Trattoria Papei. This restaurant is popular with locals as well as travelers and is rated an average of 4.3 out of 5 stars by 3,761 customers.

Grotta Santa Caterina da Bagoga 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 1,669 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 Bar Impero Siena. This bar is considered one of the best in Siena and is rated an average of 4.2 out of 5 stars by 988 customers.

You may also want to check out Sindie. Equally popular, this bar offers a great drink list and a nice atmosphere for your evening endeavors. Sindie is rated an average of 4.7 out of 5 stars by 124 customers.

Alternatively, head out to Meet Life Cafè. This bar has an average rating of 4.4 out of 5 stars by 416 customers and is a top choice among travelers as well as locals.

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.

Porta Romana is a fantastic attraction you could visit on your last day in Siena. This city gate and popular site of interest has an impressive average rating of 4.4 out of 5 stars from 2,383 visitors.

If you look forward to enjoying one last delicious meal in Siena, consider a top-rated restaurant like Osteria Nonna Gina. This restaurant is rated at an average of 4.6 out of 5 stars by 1,247 customers.

Another highly recommended alternative in Siena is Osteria Cice. Previous customers have praised and rated this restaurant an average of 4.5 out of 5 stars in 1,313 reviews.

If you’re in the mood for something else, go to Osteria da Divo. This restaurant is a popular choice among locals as well as travelers and has received an average rating of 4.4 out of 5 stars by 1,062 customers.

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!