A historic town with terracotta-roof buildings, a prominent church, and a hilltop fortress.

Siena Vacations from $1,188

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The Latest Siena Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 11 - Oct 17

    Aurum Uffizi + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    7.6/10 - Good (1,003 reviews)
    "Clean room, close to all major attractions, friendly staff ready to help always, good breakfast."
    Reviewed July 13, 2026
    Roundtrip New York (NYC) - Florence (FLR)
    JFK - FLR1 stop FLR - JFK1 stop
    $1,741
    $1,188
    per traveler
    found 20 hours ago
    Aurum Uffizi
  • Oct 11 - Oct 17

    Aurum Firenze + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    7.4/10 - Good (1,011 reviews)
    "Good location. Travel family of 4. If you only need basics it is perfect. Breakfast was a surprise, it was fresh and good overall. Enjoyed to stay there just for sleeping."
    Reviewed July 18, 2026
    Roundtrip New York (NYC) - Florence (FLR)
    JFK - FLR1 stop FLR - JFK1 stop
    $1,756
    $1,197
    per traveler
    found 20 hours ago
    Aurum Firenze
  • Sep 18 - Sep 23

    Hotel Regency + Flight

    Historic Centre of Florence
    4 nights
    5.0 star property
    9.4/10 - Exceptional (457 reviews)
    "The staff at the hotel were really at our service. The knew my name, responded quickly and were happy to help. The breakfast area is a beautiful place to eat. The marble bathroom was stunning and are the bedroom was decorated in such a grand way. I would stay there again happily."
    Reviewed June 19, 2026
    Roundtrip New York (NYC) - Florence (FLR)
    JFK - FLR1 stop FLR - JFK1 stop
    $2,995
    $2,087
    per traveler
    found 10 hours ago
    Hotel Regency
  • Oct 11 - Oct 17

    The Moon Boutique Hotel & Spa + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.6/10 - Exceptional (576 reviews)
    "Wonderful stay, attentive staff, very clean room. The spa facilities are very high quality and had a lovely massage. Good choices for breakfast. I would certainly recommend staying here, the spa was a particular highlight that is free for guests to use."
    Reviewed July 2, 2026
    Roundtrip New York (NYC) - Florence (FLR)
    JFK - FLR1 stop FLR - JFK1 stop
    $1,966
    $1,372
    per traveler
    found 20 hours ago
    The Moon Boutique Hotel & Spa
  • Sep 19 - Sep 25

    Residenza Florentia + Flight

    Historic Centre of Florence
    5 nights
    1.0 star property
    8.4/10 - Very Good (53 reviews)
    "Staff was helpful, the property was not very well maintained."
    Reviewed June 1, 2026
    Roundtrip New York (NYC) - Florence (FLR)
    EWR - FLR1 stop FLR - JFK1 stop
    $1,886
    $1,327
    per traveler
    found 1 day ago
    Residenza Florentia

Where to stay in Siena

Find the best Siena areas and neighborhoods for the activities you enjoy most. Learn more about Siena
Learn more about Siena

Siena City Centre

Step back in time as you wander through Siena's medieval center, a UNESCO World Heritage site where history comes alive. Gothic buildings frame the shell-shaped Piazza del Campo, home to the twice-yearly Palio horse race. The striped marble cathedral showcases stunning Bernini sculptures and intricate floor mosaics. Vehicle-free streets allow you to explore the contrade districts at your own pace. Duck into artisan workshops selling leather goods and hand-painted ceramics between visits to museums. Church bells echo across terracotta rooftops while traditional Tuscan trattorias serve pici pasta and wild boar.

Siena Historical Center

Step back in time among the rose-colored medieval buildings of Siena Historical Center. Wander through the iconic shell-shaped Piazza del Campo or climb Torre del Mangia for breathtaking views across terracotta rooftops. The striking black-and-white marble cathedral stands as a masterpiece of Italian Gothic architecture. The neighborhood's pedestrian-only cobblestone streets create an immersive journey through Tuscan history. Traditional trattorias serve authentic pici pasta and local wines between ancient stone walls. Visit during early morning to experience the area before the tour groups arrive. The famous Palio horse race brings this UNESCO World Heritage site to vibrant life twice yearly.

Camollia

Step through the medieval gates of Camollia to discover Siena's northern historic district. This charming neighborhood features narrow cobblestone streets lined with ancient palazzos and Gothic arches. The hilltop Basilica dell'Osservanza rewards visitors with panoramic views of the Tuscan countryside. Traditional trattorias serve hearty Tuscan cuisine like ribollita and pici pasta. Local artisans craft ceramics and leather goods in small family workshops. The peaceful residential atmosphere offers an authentic slice of Italian life away from tourist crowds.

Ravacciano

Ravacciano offers a peaceful retreat from Siena's tourist bustle while keeping city attractions within reach. This authentic Italian neighborhood reveals everyday local life with its family-run trattorias and morning espresso culture. Small parks and olive trees line the narrow streets where cream and ochre buildings create a charming atmosphere. The neighborhood sits on Siena's eastern edge, a 25-minute walk to the historic center. Traditional shops follow Italian rhythms with afternoon closures, while evenings bring a tranquil quiet rarely found in tourist zones. Budget-friendly accommodations make this residential haven ideal for travelers seeking genuine Tuscan experiences.

San Prospero

Step into San Prospero, a medieval treasure in Siena's UNESCO-protected heart. Wander cobblestone streets lined with weathered stone churches and traditional Tuscan palazzos. Gothic arches frame hidden courtyards where locals gather away from tourist paths. This pedestrian-only neighborhood rewards explorers with authentic Italian life. Family-run trattorias serve handmade pici pasta and local Chianti Classico. Artisan workshops display hand-painted ceramics and fine leather goods behind historic stone facades.

Discover the most popular places to visit in Siena

What to do in Siena

Siena Hotel Deals

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.

Frequently Asked Questions

How much does a Siena vacation package cost?

Offering great value package deals from $1,188 on Expedia, you'll be pleasantly surprised at how much a vacation to Siena costs! Expedia's packages simplify travel planning and maximize your savings.

What are the cheapest months to go to Siena?

If you're looking to book a cheap Siena vacation package, consider planning a trip in November, December and January. You're likely to find lower rates on flights and hotels during these months — ideal for travelers wishing to save money.

How many days is enough for Siena?

With around 2 days, you'll have enough time to experience popular neighborhoods such as Siena Historical Center and Siena City Centre during your Siena vacation. Be sure to also add Civic Museum and Museo dell'Opera del Duomo to your sightseeing itinerary. Looking for more adventures? Consider exploring outside of Siena on day trips and tours.

Is it worth booking a vacation package to Siena?

Whether you'd like to explore key attractions such as Siena Cathedral and Torre del Mangia on your Siena vacation, or coming for its excellent history, culture and family-friendly attractions, there's something for everyone here. With so much to do, you'll soon discover why so many people think Siena is a good vacation destination.

How to find the best Siena package deals?

Bagging a cheap Siena package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Siena package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a Siena vacation as a package?

An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can personalize your Siena escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Siena?

Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Siena getaway.

How to plan a trip to Siena?

  1. Choose your travel dates: What you'd like to do in Siena and your favorite season will help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Siena.
  3. Explore Siena with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Siena. You can also save your favorite places, collaborate with friends and family and manage all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Siena, you can work out the perfect length of your vacation. Create a rough plan and give yourself enough time to cover everything you want to do.
  5. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Siena vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on Siena's highlights. Find all the exciting things to do in Siena with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Siena vacation packages?

Jet off on your ideal getaway to Siena with our Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they sell out.

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Things to do in and around Siena

Siena offers a rich blend of cultural, outdoor, and romantic experiences perfect for tourists. You can explore the charming streets, indulge in wine tastings, and enjoy luxurious spa treatments. Consider booking Siena vacation packages or guided tours to enhance your visit. Don't miss out on wine tour packages to savor the region's famous wines while immersing yourself in the local culture.

Shopping

Siena offers charming local shops for unique gifts and souvenirs. If you're up for a drive, The Mall Luxury Outlet, 27 miles away, and Fashion Groove, 26 miles away, provide a variety of brands and family-friendly vibes. RI Crea RE, located 24 miles from Siena, is also worth a visit.

Recreation

Experience the thrill of local sports at Siena Stadium and Stadio Artemio Franchi, both offering vibrant atmospheres. For a cultural escape, enjoy a romantic show at Teatro dei Rinnovati, where entertainment meets family-friendly vibes in a stunning setting.

Adventure

Experience the thrill of karting at Siena Circuit, located 7 miles from the city, perfect for adrenaline junkies. Hike the scenic Sentierelsa Trail, 12 miles away, to immerse yourself in nature. For an exhilarating zipline adventure, visit Saltalbero Adventure Park, situated 13 miles from Siena.

Nightlife

Siena's nightlife is charming and vibrant. Visit Il Fiaschetto, a cozy drinking pub located 26 miles from the heart of Siena, where you can enjoy romantic vibes and lively entertainment. Sip on local wines and mingle with friendly locals for an unforgettable evening.

Find the best attractions in Siena

Siena, Tuscany, is a charming destination perfect for culture lovers, outdoor enthusiasts, and romantic getaways. Visitors can explore historic churches, grand palaces, and lively piazzas. Key attractions include the stunning Siena Cathedral, the local province, and the Siena Stadium. With its rich cultural experiences and family-friendly activities, Siena promises an unforgettable vacation for travelers seeking to immerse themselves in Italy's enchanting history and beauty.

  • Piazza del Campo: This iconic square is the heart of Siena, renowned for its unique shell shape and vibrant atmosphere. Surrounded by medieval buildings, it's a perfect spot to soak in local culture, enjoy a coffee, or witness the thrilling Palio horse race held twice a year.
  • Siena Cathedral: A masterpiece of Gothic architecture, Siena Cathedral boasts stunning frescoes and intricate marble floors. Its striking façade and the breathtaking Piccolomini Library make it a must-see for art and history enthusiasts alike.
  • Banca Monte dei Paschi di Siena: Established in 1472, this historic bank is the world's oldest surviving bank. Its elegant architecture and rich history reflect Siena's financial importance, offering a glimpse into the city’s economic past.

Best time to go to Siena

The best time to visit Siena can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Siena falls in July, when visitor numbers are slightly high and weather is sunny with no rain. The coolest average temperature in Siena falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Siena

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Siena.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.