Luxury 4-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 4 days. Catch an early flight to get started with your sightseeing in Siena right away.

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 La Taverna di San Giuseppe. This restaurant offers a fantastic menu and impeccable service, deserving of its average rating of 4.7 out of 5 stars from 1,767 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 Ristorante Gallo Nero. This claim is supported by 829 customers who have rated it an average of 4.4 out of 5 stars.

If you want to continue your night somewhere else, head to another popular place like San Paolo Pub. This bar is a local favorite, with great drinks, lovely service, and an average rating of 4.3 out of 5 stars by 704 customers.

This is the time to raise a toast to the beginning of your special 4-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 2 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 Antica Trattoria Papei, which is a popular restaurant with an exciting menu. This restaurant has an average rating of 4.3 out of 5 stars by 3,761 customers.

Another top-rated restaurant to consider is Osteria da Divo. This restaurant is popular with locals as well as travelers and is rated an average of 4.4 out of 5 stars by 1,062 customers.

Ristorante Gallo Nero 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 829 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 Torrefazione Fiorella. This bar is considered one of the best in Siena and is rated an average of 4.8 out of 5 stars by 370 customers.

You may also want to check out BLANDIS - Wine & Cafè. Equally popular, this bar offers a great drink list and a nice atmosphere for your evening endeavors. BLANDIS - Wine & Cafè is rated an average of 4.7 out of 5 stars by 291 customers.

Alternatively, head out to Sindie. This bar has an average rating of 4.7 out of 5 stars by 124 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.

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 1 night 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 Taverna Di Cecco is one of the most popular restaurants in Siena. Most people can find something that fits their taste from Ristorante Taverna Di Cecco’s excellent menu. Approximately 822 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 PARTICOLARE di Siena. This Siena-based restaurant is one of locals’ favorites and has an average rating of 4.6 out of 5 stars from 598 customers.

Another top-rated restaurant that serves a menu of appetizing food and drinks is Ristorante San Desiderio. This popular restaurant has an average rating of 4.4 out of 5 stars from 657 customers.

If you’re up for getting a drink, consider going to Osteria Quattro Venti. Around 304 customers have given this incredible bar an average rating of 4.6 out of 5 stars.

Locals of Siena also enjoy the drinks at Maudit Pub. This place is rated an average of 4.4 out of 5 stars by 224 customers and is one of the best you can experience in the city.

Another top-rated alternative for a celebratory drink is Charlie Mixology Bar di Aldinucci Riccardo. This bar has an average rating of 4.3 out of 5 stars by 138 customers.

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!

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.

If you look forward to enjoying one last delicious meal in Siena, consider a top-rated restaurant like Osteria Castelvecchio. This restaurant is rated at an average of 4.5 out of 5 stars by 582 customers.

Another highly recommended alternative in Siena is Ristorante La Finestra. Previous customers have praised and rated this restaurant an average of 4.4 out of 5 stars in 602 reviews.

If you’re in the mood for something else, go to Osteria Le Logge. This restaurant is a popular choice among locals as well as travelers and has received an average rating of 4.3 out of 5 stars by 547 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!