Travel packages in Italy

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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Siena welcomes you to a refreshing 5-day weekend getaway in Italy, where you can unwind. Experience captivating views and rich culture, making the most of every minute of your short escape.

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 vacation 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.

When it’s time to dine or unwind, Siena offers plenty of options on your weekend trip. Take your pick from the city’s best dining and drinking spots.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start.

Enjoy gaining new experiences in Siena. Celebrate another amazing day of your 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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On this lovely day 2 of your relaxing weekend retreat in Italy, dive into the unique sights and experiences in Siena. With 3 nights still to enjoy, there's so much more to explore and experience.

Whatever your travel style is, Basilica Of San Domenico is an essential stop in Siena. This curiosity-inducing church provides an insightful glimpse into the city's identity. Next, discover Fontebranda, a culturally significant historical landmark, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, a captivating church. When you’re done, don’t forget to make a stop at the famous Piazza Del Campo. Not far away from the public square, you will find the breathtaking Pubblico Palace, perfect for a quick visit. Round off your day at Tower Of Mangia, another gem in Siena with picture-perfect features to discover.

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.

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. Known for great service, it’s a fantastic choice for tonight in Siena.

After enjoying a fulfilling meal, continue your evening at Maudit Pub, ideal for those looking to unwind with a drink in a comfortable setting.

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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Day 3 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 2 nights ahead, filled with unforgettable memories.

Make a stop at Fortezza Medicea (siena). This often recommended monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Porta Camollia, Siena located in Siena for another exciting encounter.

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.

Enjoy a delicious meal at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Following your dinner, dive into the local bar culture at Bar Impero Siena. Enjoy this evening's relaxed ambiance with delightful drinks.

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

Day4

Day 4

Siena
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Porta Tufi
Musei dell’Accademia dei Fisiocritici
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As you wake up to day 4 of your weekend trip in Italy, Siena awaits with new experiences. Make the most of the remaining 1 night by exploring and experiencing all it has to offer.

Siena is brimming with adventures.

Porta Tufi makes a great addition to your morning plans. This worthwhile historical landmark is a standout place to see in Siena. Continue your discovery at Musei Dell’accademia Dei Fisiocritici, an instagrammable museum with stories to tell.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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.

When it’s time to dine or unwind, Siena offers plenty of options on your weekend trip. Take your pick from the city’s best dining and drinking spots.

Don’t miss out on dining at Bar Pasticceria Nannini Toselli, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Gallo Nero, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar osteria enea. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out.

Raise your glass in celebration of your incredible weekend getaway in Italy!

Day5

Day 5

Siena - Departure day
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Palazzo Salimbeni
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Your remarkable weekend getaway in Italy is about to end. Soon, you’ll say goodbye to Siena. Day 5 is your departure day and your chance to catch one last glimpse of the city and Italy's charming sights.

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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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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