Province of Siena Holiday Packages

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Holidays To SIena

Italy’s got so many famous cities, it can be hard to decide which ones to visit: Rome, Milan, Venice and more.

How about…none of those? Holidays to Siena, just south of Florence, have all the art and architecture without the crowds. In fact, the city’s medieval art and churches are some of the most important in the country. With a mixture of small-town charm and big-city pride, Siena can’t wait to show you what it’s all about.

Things to Do in Siena

All roads in Siena (or at least a lot of them) lead to Piazza del Campo. Aside from stunning architecture like the Gaia Fountain and the 102m Mangia Tower, the square has loads of important history and events. No gladiators here these days, though just the ancient traditional Palio di Siena, a bareback horse race, complete with all the medieval fanfare. Book a Siena package deal for early July or mid-August to see this world-famous race.

Architecture aficionados will also want Siena packages in this area to see the city’s two most important churches. The Siena Cathedral is an intricately carved Gothic marble church make sure you enter through the Door of Forgiveness if you’ve done some things you regret on this holiday. In the nave, you can stare at the ceiling details for hours—and no one would even think you were strange. Just north of Siena Cathedral is St. Dominic's Basilica, which contains a grisly secret: the relics of St. Catherine of Siena, including her mummified head and thumb.

Fans of churches and architecture will want to pay a visit to the capital of Tuscany as well our Florence holiday packages will really complete your tour of medieval times.

Shopping, Dining & Nightlife

Take the high street when shopping in Siena—or rather, streets. Book one of Wotif’s Siena car hire options to carry all your finds, as the shopping is a bit spread out. Start at Via di Citta near the Piazza del Campo, where you’ll find old-fashioned country stores to pick up chocolate and pastries for the coworkers—and an espresso for yourself. Heading north, stop at Banchi di Sopra for upscale shops selling Italian leather and luxury brands, then end your trip at the casual stores of Via Montanini.

You’re in Italy, so you really can’t go wrong when it comes time to refuel. Head back to the area around St. Dominic's Basilica for hard-to-find regional classics like tegamata di maiale, a Sienese pork casserole, or Piazza del Campo for cheap dishes like pizza, panini and pasta e fagioli.

Siena has been called a “sleeping beauty” thanks to its architectural grandeur and relatively sleepy nightlife. There are a few areas, though, where the slumber is broken. Book Siena package deals near Via Pantaneto for pubs, live music and late-night dining, or near Piazza Del Sale if fine wine bars and conversation are more your thing.

What’s Next?

The beauty of Siena has to be seen to be believed—and once you experience it, you may not want to leave! Plan your Siena holiday on Wotif, and you just might save enough cash to stay a few more days.

Top Province of Siena hotels

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
The price is NZ$643 per night from 11 May to 12 May
NZ$643
includes taxes & fees
11 May - 12 May
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
"This is a beautiful location and the facilities are stunning. Really everything is picture perfect and you are only 20 minutes from Montepulciano and 30 minutes from Pienza. Both are amazing to explore and offer excellent dining options. The concierge recommended Tuscan Sweet Dreams to take us to ..."

Reviewed on 8 Apr. 2025

Precise Tale Poggio Alla Sala
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is NZ$334 per night from 12 May to 13 May
NZ$334
includes taxes & fees
12 May - 13 May
Stay at this 4-star business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
"Loved staying here! Great location. Our room had a fabulous view of Tuscany landscape"

Reviewed on 26 Apr. 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is NZ$310 per night from 29 May to 30 May
NZ$310
includes taxes & fees
29 May - 30 May
Stay at this 4-star hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
"Great location, comfortable beds, and good breakfast"

Reviewed on 26 Apr. 2025

NH Siena
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.