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Weekend getaways in Italy

5-Day Italy Weekend Getaway in Siena With Itinerary

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Photo of Siena cathedral against a bright blue sky in Italy.

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Go on a 5-day weekend getaway to Siena, Italy, and experience the best weekend holiday in Europe! Discover Italy’s charming streets, delightful cuisine, and unforgettable sights.

In Tuscany, Siena stands as a medieval masterpiece. Discover the historic Palio horse race, the stunning Piazza del Campo, and the magnificent Siena Cathedral in this magnificent city. Stroll through its charming alleys and immerse yourself in this classic Italian city's timeless traditions and artistic treasures. Siena promises an unforgettable journey into Italy's rich heritage.

To help you take it all in, this 5-day travel plan is designed to make the most of your weekend getaway in Siena. With 4 nights in Siena, you'll have just enough time to enjoy iconic landmarks, vibrant neighborhoods, and timeless charm, without feeling rushed.

Your accommodation will be conveniently located for easy access to many of the best places to visit in Siena. Expect a comfortable stay with essential amenities, allowing you to rest well between sightseeing.

You'll also have plenty of time to stroll through local markets and shopping streets. Go souvenir shopping to your heart's content, and take a bit of Italy home with you to remind you of your weekend getaway in Siena.

Your itinerary will take you to the best sights and spots in Siena. By the end of your weekend getaway in Italy, you'll return home happy, with plenty of photos and memories to look back on and share.

Following your day-by-day sightseeing, this 5-day travel plan includes everything you need for a memorable weekend in Siena. The itinerary is fully customizable, allowing you to add tours, tickets, and activities to each day and make the most of your time in Siena.

To enhance your trip even further, you can also include a car rental in your weekend getaway package in Italy. This added flexibility lets you explore hidden gems and experience more of Italy at your own pace.

And to make your experience even smoother, you’ll have access to 24/7 travel support from your personal agent. We’ll provide a step-by-step guide through our mobile app, where all your travel documents are stored and organized.

Booking a complete weekend getaway in Siena has never been this fast and easy. The best services in Siena fill up quickly, so select a date and start planning your weekend getaway to Italy today!

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Day1

Day 1

Siena - Arrival day
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Porta Romana
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Your exciting weekend getaway in Italy begins as you arrive in Siena. Explore the destination's charm while spending 4 nights at one of the best hotels and places to stay in Siena.

Siena is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Porta Romana. Taking a stroll in the city center is a great alternative. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

When the afternoon arrives, make your way to the hotel of your choice in downtown Siena. Check-in at hotels in Italy normally starts around 2 to 3 PM. Each accommodation option in Siena offers a unique blend of comfort and style in addition to prime access to the city’s top attractions.

Once you've soaked up the sights, continue your day by exploring the vibrant culinary and social scene in the city. Cap off day 1 of your weekend getaway in Italy with a wonderful meal and a refreshing drink at one of the best spots in Siena.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists.

Experience the unique vibe of Siena tonight. Relax and enjoy your rewarding weekend getaway in Italy!

Day2

Day 2

Siena
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Basilica of San Domenico
Fontebranda
Siena Cathedral
piazza del Campo
Tower of Mangia
Pubblico Palace
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Day 2 of your weekend getaway in Italy brings another exciting opportunity to discover the wonders of Siena. Start your morning with a delicious breakfast and get ready for 3 nights ahead, filled with unforgettable memories.

Your adventure in Siena is only getting started when you visit Basilica Of San Domenico, an increasingly popular local hot spot. Another notable attraction to explore is Fontebranda. This underrated historical landmark is known for its stunning appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Siena Cathedral. This inviting church offers a fascinating experience that many visitors find memorable. Piazza Del Campo is also worth visiting, along with Tower Of Mangia. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Pubblico Palace. This curiosity-inducing palace provides a fitting finale to your sightseeing.

Tours add variety to your weekend getaway in Siena. For a more memorable vacation, be sure to check out the popular tours and activities you can add to your package.

Once you've soaked up the sights, continue your day by exploring the vibrant culinary and social scene in the city. Cap off day 2 of your weekend getaway in Italy with a wonderful meal and a refreshing drink at one of the best spots in Siena.

Treat yourself to a delightful dinner at Osteria Quattro Venti, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Fischi per Fiaschi? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Keep the evening going at Maudit Pub, a great choice for enjoying the after-dinner hours with a drink.

This is the perfect time to relax and enjoy your weekend getaway in Italy to the fullest. Savor every minute of your stay in Siena!

Day3

Day 3

Siena
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Fortezza Medicea
Porta Camollia, Siena
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On day 3 of your weekend getaway in Italy, soak up the atmosphere of Siena. Make the most of your remaining 2 nights by exploring the local food scene and nightlife, making your journey even more memorable.

Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

To truly experience Siena, make sure to drop by Fortezza Medicea (siena). This frequently visited monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Porta Camollia, Siena, one of the city’s best highlights.

Tours add variety to your weekend getaway in Siena. For a more memorable vacation, be sure to check out the popular tours and activities you can add to your package.

You’ll have plenty of restaurant and bar options in Siena during your weekend getaway. So when you’re done exploring, and it’s time to eat, all you have to do is take your pick of the city’s best dining and drinking spots.

Dine in style at Ristorante San Desiderio, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Le Logge boasts a menu that's sure to impress. Also, be sure to check out Ristorante Taverna Di Cecco. Known as a local hotspot, it’s a great choice for tonight in Siena.

Let the evening flow smoothly from dinner to drinks at Bar Impero Siena, a top-rated bar in the area.

A quick trip to any of the popular local bars in Siena will enhance your travel experience in the city. Cheers to a pleasant weekend getaway in Italy!

Day4

Day 4

Siena
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Porta Tufi
Musei dell’Accademia dei Fisiocritici
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Welcome to day 4 of your weekend getaway in Italy! Today, discover more of Siena's character as you visit its best spots. With 1 night still ahead, there’s plenty of time to enjoy everything this captivating destination has to offer.

Experience Porta Tufi, an intriguing historical landmark in the city. Then, head to Musei Dell’accademia Dei Fisiocritici and soak in the ambiance of this eye-catching museum.

Tours add variety to your weekend getaway in Siena. For a more memorable vacation, be sure to check out the popular tours and activities you can add to your package.

A weekend getaway in Italy isn't complete without experiencing the food and nightlife scene in Siena. Fortunately, the city has many fantastic bars and restaurants that cater to all travel budgets.

Treat yourself to a delicious dinner at Bar Pasticceria Nannini Toselli, an excellent option for tonight's dining. Looking for something different? Ristorante Gallo Nero offers a tantalizing alternative with its diverse menu. And don’t miss Bar osteria enea. Known for great service, it’s a fantastic choice for tonight in Siena.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in.

Sit back, relax, and enjoy every minute of your 5-day weekend getaway in Siena. Raise your glass to a lovely time in Italy!

Day5

Day 5

Siena - Departure day
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Palazzo Salimbeni
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Your remarkable 5-day weekend getaway in Siena is about to end, and soon you’ll say goodbye to the city. Day 5 is your departure day and your chance to catch one last glimpse of the city and Italy's charming sights. Depending on how much time you have until you start your journey home, we recommend visiting some more attractions.

If you prefer to go sightseeing before leaving Italy, the popular Palazzo Salimbeni is an extraordinary attraction you could visit on your last day in Siena.

Before you conclude your weekend getaway in Siena, drop by a top-rated restaurant for a last chance at a memorable dining experience in the city. Savor the local food culture over a fantastic meal.

You’ll then say farewell to Italy and begin your journey home, now filled with memories of your unforgettable weekend getaway in Siena!

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Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

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Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

Secure your spot

Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

Get instant confirmation

Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.

Personalize your itinerary

Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.

Easily make changes

Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.

Enjoy seamless planning

With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.

Explore with confidence

From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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Your trip is protected, personalized, and priced right. No surprises, no stress.

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