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 AU$678 per night from 5 Aug to 6 Aug
AU$678
5 Aug - 6 Aug
includes taxes & fees
Precise Tale Poggio Alla Sala: Luxury hotel with free breakfast and free WiFi. Guests love the helpful staff!
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on 19 June 2026

Opens in a new windowPrecise Tale Poggio Alla Sala
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
The price is AU$791 per night from 8 July to 9 July
AU$791
8 July - 9 July
includes taxes & fees
Borgo Scopeto Wine & Country Relais: Luxury hotel with free breakfast and free WiFi. Guests love the helpful staff!
"This hotel is the definition of La Dolce Vita! Starting from the beginning, when first arrived to the hotel, they picked up our bags, showed us around the property and responded any questions that we had. Elisa was amazing! She showed us around the property, he gave us recommendations of where to ..."

Reviewed on 1 July 2026

Opens in a new windowBorgo Scopeto Wine & Country Relais
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 12 July to 13 July
AU$131
12 July - 13 July
includes taxes & fees
Hotel Executive: Family-friendly hotel with free WiFi and free parking. Located near a train station.
"Nice clean hotel. Breakfast ok. Good parking"

Reviewed on 6 July 2026

Opens in a new windowHotel Executive
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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.

Your guide to epic deals and sweet holiday packages to Province of Siena

How much are holiday packages to Province of Siena?

You can book an awesome holiday in Province of Siena from just on Wotif. Check our deal cards for details.

What’s included in Wotif’s Province of Siena holiday package deals?

Province of Siena packages can bundle everything: flight + hotel + car hire. But you can go for hotel + car hire without the flight. Or flight + hotel. You do you.

Can I cancel my Province of Siena holiday plans on Wotif?

Yes. Within 24 hours of booking, you can cancel and get your money back on many of our packages. After 24 hours, your airline or hotel may charge a fee. Check your itinerary or our Customer Service Portal to know more.

How do I find the best holiday package to Province of Siena?

Just take a look through all our terrific offers or select your dream spot in Province of Siena, and we’ll serve up some delicious Province of Siena holiday deals that’ll make you swoon and save you cash.

How do I get the best holiday deals to Province of Siena?

We have stacks of ready-made holidays and luxury getaways in Province of Siena, and usually the more flexible you can be on dates, the better the deal. Simply enter your travel details and we’ll find you loads of wallet-friendly deals. You can filter by trip length, hotel stars and flight class and – ta-daa – best break ever. Added bonus: our Price Promise refunds the difference if you find a lower price up to 24 hours before check-in.

When is the best time to visit Province of Siena?

usually has the best bargain breaks when hotel prices are often cheaper, and Province of Siena is quieter. But for more of a buzz, plan your visit in .

Why choose Wotif to book your holiday package to Province of Siena?

Plan your trip to Province of Siena today and you could save on your next escape and pay just . With Wotif, you know you’ve got great flexibility and those awesome Mates Rates deals, too.