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

Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
Fully refundableReserve now, pay when you stay
The price is NZ$929 per night from 1 Apr to 2 Apr
NZ$929
1 Apr - 2 Apr
includes taxes & fees
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 ...
You are paying for the view!!!! This hotel was not worth the money spent in my opinion. The hotel staff was not very accommodating, though the restaurant staff was lovely. We had to bring our luggage up to our room and back down during check in and check out — no one even offered and trust me it ...

Reviewed on 5 Oct 2025

Opens in a new windowBorgo Vescine
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 29 Mar to 30 Mar
NZ$218
29 Mar - 30 Mar
includes taxes & fees
Stay at this business-friendly hotel in Siena. Enjoy free breakfast, free Wi-Fi and room service. Our guests praise the breakfast and the helpful staff in their ...
The hotel was just outside of the town, so the location was good. It was a beautiful property. The breakfast was good. Just be prepared to walk stairs. No lifts. But overall, good.

Reviewed on 22 Mar 2026

Opens in a new windowHotel Chiusarelli
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$204 per night from 29 Mar to 30 Mar
NZ$204
29 Mar - 30 Mar
includes taxes & fees
Stay at this family-friendly hotel in Siena. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
The staff were super great .Took care of all our needs .Suggested the best winery tour .And the food was terrific .

Reviewed on 2 Nov 2025

Opens in a new windowHotel Executive
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