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

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$179 per night from 3 Mar to 4 Mar
NZ$179
3 Mar - 4 Mar
includes taxes & fees
Stay at this business-friendly hotel in Siena. Enjoy free Wi-Fi, free parking and a rooftop terrace. Our guests praise the breakfast and the helpful staff in ...
Great hotel, beautiful view and excellent service from the personnel.

Reviewed on 28 Jan 2026

Opens in a new windowHotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$562 per night from 2 Mar to 3 Mar
NZ$562
2 Mar - 3 Mar
includes taxes & fees
Stay at this luxury hotel in Siena. Enjoy free Wi-Fi, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
Room, bathroom and breakfast were wonderful. WiFi was not great. Lovely location and pretty property.

Reviewed on 27 Jan 2026

Opens in a new windowGrand Hotel Continental Siena – Starhotels Collezione
Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
Stay at this luxury hotel in Radda in Chianti. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs ...

Reviewed on 24 Sept 2025

Opens in a new windowBorgo Vescine
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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.