Province of Siena Vacations & Trips from $1,209

Book a Hotel + Flight or Car together to unlock savings

Your Province of Siena Vacation

Lock in a vacation package to Province of Siena and enjoy what it means to travel on your own terms. You'll be impressed by its walking trails, nature and views. With so many things to explore on a trip to Province of Siena, it can be tricky to know where to begin. Kick off your travels in Siena at Monteriggioni Castle and Palazzo Pubblico — two leading attractions here. Another city worth adding to your itinerary is Montepulciano. Be sure not to miss Val di Chiana and Piazza Grande. Whether you're traveling on a shoestring or in the lap of luxury, Expedia are here to help you customize your next Province of Siena vacation.

Top destinations in Province of Siena

A historic square with stone buildings, a prominent tower, and outdoor seating areas.
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San Gimignano

San Gimignano

The Latest Province of Siena Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Borghese Palace Art Hotel

Borghese Palace Art Hotel

4 out of 5
Historic Centre of Florence
Price was $1,520, price is now $1,209 per person
$1,209
per person
Jan 17 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.6/10 Excellent! (1,000 reviews)

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,760, price is now $1,236 per person
$1,236
per person
Jan 17 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Amazing location. So cool to be literally across from the Duomo. Easy walk to so many places to shop and eat. Free sparkling and still water was great. Snacks and free gelato! Staff was the most friendly and helpful. Highly recommend this place!

Reviewed on Nov 3, 2026

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Price was $3,176, price is now $2,229 per person
$2,229
per person
Jan 3 - Jan 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Price was $1,633, price is now $1,242 per person
$1,242
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (1,011 reviews)
Most beautiful place and outstanding staff. Luxury with care and kindness. Thanks to the entire team for the Wonderful stay in Florence.

Reviewed on Nov 9, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,684, price is now $1,287 per person
$1,287
per person
Dec 12 - Dec 18
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (612 reviews)

Best Places to Vacation in Province of Siena

1. Experience Siena with a travel package

Siena, located in the heart of Tuscany, Italy, offers a rich cultural experience for visitors. The city's stunning cathedral, historical monuments, and museums provide a glimpse into its rich history. Explore the charming streets and discover beautiful churches, while enjoying the local cafes and wineries. Take part in destination activities, tours, and sightseeing to fully immerse yourself in the local atmosphere. Siena's geographic affinities make it an ideal destination for art enthusiasts and those seeking a cultural vacation. Experience the vibrant culture and history that Siena has to offer.

  • The peak season is from July to September
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Siena

2. Book your ideal San Gimignano with a vacation package

San Gimignano, located in the picturesque region of Tuscany, Italy, offers a unique cultural vacation experience. The town's historical charm is evident in its well-preserved medieval architecture, including its iconic towers. Visitors can explore numerous museums and churches, immersing themselves in the rich history and art of the area. The tranquil countryside provides the perfect backdrop for leisurely walks and wine tastings at local wineries. With its hilly landscape and stunning views, San Gimignano offers a truly immersive cultural experience that combines history, art, and the beauty of the Tuscan countryside.

  • The peak season is from November to January
  • The off-peak season is from January to March
  • Travelers tend to stay 3 days in San Gimignano

3. Enjoy Montepulciano with a travel package

Montepulciano, located in Tuscany, Italy, offers a captivating atmosphere for a cultural vacation. The town is renowned for its wineries, historical sites, and picturesque countryside. Visitors can immerse themselves in the local culture by exploring the charming streets, visiting museums and art galleries, and enjoying traditional festivals. The region is also known for its delicious cheese and offers a variety of cafes and restaurants to indulge in local cuisine. With its secluded and peaceful ambiance, Montepulciano provides a perfect setting for sightseeing, tours, and experiencing the rich cultural heritage of Tuscany.

  • The peak season is from July to September
  • The off-peak season is from January to March
  • Travelers tend to stay 3 days in Montepulciano

4. Create memories in Montalcino with a vacation package

Montalcino, located in the heart of Tuscany, Italy, offers a romantic atmosphere and experience for couples on vacation. The town is known for its picturesque wineries, where visitors can indulge in delicious wines and take in the stunning countryside views. For adventure seekers, there are opportunities for hiking and exploring the hilly terrain. History buffs will appreciate the medieval castle and monuments that dot the town. Relaxation can be found at the local spas, offering rejuvenating treatments. Montalcino also provides the perfect backdrop for romantic walks, especially during sunrise. Overall, Montalcino is a charming destination for couples seeking a romantic getaway.

  • The peak season is from March to May
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Montalcino

6. Plan your dream getaway to Castelnuovo Berardenga

Castellina in Chianti in Tuscany, Italy, offers a charming and romantic atmosphere for your vacation stay. Surrounded by rolling hills and lush countryside, this small town is perfect for a secluded and relaxing getaway. The area is renowned for its wineries, allowing you to indulge in wine tasting and explore the beautiful vineyards. You can also enjoy activities such as hiking in the nearby forests, swimming in the refreshing waters, and birdwatching. Take in the sights and immerse yourself in the local culture with destination activities, tours, and sightseeing. Castellina in Chianti is the ideal destination for a truly romantic and luxurious vacation experience.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Castelnuovo Berardenga

5. Find your perfect Pienza vacation

Pienza, located in the beautiful region of Tuscany, Italy, offers a charming atmosphere perfect for a cultural vacation. With its breathtaking countryside, luxury accommodations, and hilly landscapes, Pienza provides a picturesque backdrop for your visit. Immerse yourself in the rich history and architecture by exploring the town's churches, castle, and cathedral. Indulge in the local wineries and taste the exquisite wines that the region is famous for. Take in the small-town charm as you wander through the streets and admire the stunning scenery. Pienza offers a variety of destination activities, tours, and sightseeing opportunities for travelers to enjoy.

  • The peak season is from July to September
  • The off-peak season is from November to January
  • Travelers tend to stay 3 days in Pienza

Find the Best Province of Siena Vacation Packages

Province of Siena Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Fiumicino - Leonardo da Vinci Intl. Airport (FCO)
Population
42,900
Top Sights
Monte Amiata, Terme di Montepulciano Spa and Piscine Termali Theia

Province of Siena Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $104 total per night from Nov 29 to Nov 30
$104 total
Nov 29 - Nov 30
Total with taxes and fees
Hotel Athena
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
Get rates
Precise Tale Poggio Alla Sala
Hotel Minerva

Hotel Minerva

3 out of 5
Via Garibaldi, 72 Siena SI
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $98 total per night from Nov 11 to Nov 12
$98 total
Nov 11 - Nov 12
Total with taxes and fees
Hotel Minerva
See all 6,009 properties in Province of Siena
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.
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Frequently asked questions

What's included in a Province of Siena vacation package?
A Province of Siena vacation package in Siena lets you combine flights, hotel stays, and rental cars. Most hotels in Siena offer free breakfast, and most also provide airport shuttle service to and from Florence (FLR-Peretola) airport. Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Province of Siena vacation package?
When you bundle, you can save up to 30%*. To save money on a Province of Siena package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What is the best time to visit Province of Siena?
The best time for a Province of Siena vacation package in Siena is typically from May through September, with September being the peak month for visitors, followed by June and May. During September, average highs are around 78°F, and in June, they reach about 81°F, making it pleasant for exploring.

If you prefer a quieter trip with fewer crowds, consider visiting in January, when average highs are around 48°F. Please note that these conditions reflect Siena specifically, and weather or crowd levels may differ in other parts of the Province of Siena.
Which destinations should I consider for a Province of Siena vacation?
When planning a Province of Siena vacation, consider basing your stay in one of these charming destinations, each offering a unique experience:
  • Siena: This city is an excellent main base for cultural exploration and outdoor activities, with a wide range of lodging choices.
  • San Gimignano: Ideal for romantic getaways, this medieval town is known for its cultural attractions and scenic views.
  • Montepulciano: Another top choice for romantic trips, offering a blend of outdoor activities and cultural experiences, particularly in its wine country.
  • Castellina in Chianti: Perfect for those seeking a romantic escape in the heart of the Chianti region, with opportunities for outdoor activities and cultural immersion.
Is Province of Siena better suited for a beach vacation or a cultural trip?
The Province of Siena is primarily an outdoor and nature destination, known for its scenic views and a wide range of outdoor activities like hiking and wine tours, and is also strongly suited for cultural trips.

Cities like Siena are rich in cultural attractions, including the historic Piazza del Campo and the magnificent Siena Cathedral. Many vacation packages in the Province of Siena combine the region's natural beauty with opportunities for cultural exploration, such as Tuscan cooking classes or wine and food tasting experiences. This makes a Province of Siena vacation ideal for travelers seeking a blend of scenic landscapes, outdoor adventures, and rich cultural heritage.
Which airport should I use for a Province of Siena vacation?
For a Province of Siena vacation, the primary airports to consider are Rome Fiumicino - Leonardo da Vinci International Airport (FCO) and Florence Peretola Airport (FLR). Both serve the wider Tuscany region, including the Province of Siena, and will require onward travel to your specific destination within the province.
What are the top things to do in the Province of Siena?
A Province of Siena vacation is best explored from a base like Siena, which offers a blend of cultural attractions and outdoor activities. From there, you can discover:

Your Province of Siena vacation package can be customized around these activities. Browse and book things to do in the Province of Siena on Expedia.
Can I change or cancel my Province of Siena vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Province of Siena vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Province of Siena vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Province of Siena vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Province of Siena?
To find last-minute vacation packages to Province of Siena, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Province of Siena vacation packages?
Free cancellation on a Province of Siena vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Province of Siena vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Province of Siena getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Province of Siena vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Stay near popular Province of Siena attractions

A historic square with cobblestone pavement, surrounded by multi-story buildings with traditional architecture.

Piazza del Campo

9.6/10 (1,995 reviews)
Sit at a café and experience the atmosphere of Siena’s main square, known for its medieval architectural grandeur and famous horse races.
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What to do in Province of Siena

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$22
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Chianti Wine and Food Safari

SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence

$146
per adult
100% of travellers recommend
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
Pasta-making class at a Cesarina's home with tasting - Siena

Pasta-making class at a Cesarina's home with tasting - Siena

$201
per adult
Pasta-making class at a Cesarina's home with tasting - Siena
See all activities in Province of Siena
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.