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Weekend getaways in Italy

4-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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Experience a refreshing escape in Italy on this 4-day weekend getaway in Siena! Immerse yourself in the city’s energy, seeing its best sites and visiting famous landmarks.

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 4-day travel plan is designed to make the most of your weekend getaway in Siena. With 3 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. You'll visit the unique Fortezza Medicea (siena), explore the fascinating Basilica Of San Domenico, and make lovely memories at the fantastic Palazzo Salimbeni. 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 4-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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Day 1

Siena - Arrival day
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Porta Pispini
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Your exciting weekend getaway in Italy begins as you arrive in Siena. Explore the destination's charm while spending 3 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 Pispini, or just taking a stroll in the city center. 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 eat, dine at one of the best local restaurants in Siena and satisfy your appetite for a lovely meal. You can then enjoy the perfect end to this day of your weekend getaway in Italy at one of the best bars in the city.

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.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand.

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!

Day 2

Siena
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Basilica of San Domenico
Fontebranda
Siena Cathedral
piazza del Campo
Pubblico Palace
Porta Romana
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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 2 nights still to enjoy, there's so much more to explore and experience.

Look forward to a unique sightseeing adventure at the up-and-coming Basilica Of San Domenico and allow yourself time to explore. Just a short distance away you'll find your next stop, Fontebranda, a heritage-rich historical landmark that draws visitors from far and near.

Continue your journey to Siena Cathedral, one of the city’s most notable spots that you shouldn’t miss. Another great site to visit is the widely recognized Piazza Del Campo. When you're finished at the public square, Pubblico Palace awaits your visit. This palace is a breathtaking highlight on today's itinerary. Last up is a monument - the locally appreciated Porta Romana.

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.

Enjoy a lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Extend your evening after a delightful meal by visiting Maudit Pub, which offers the perfect atmosphere for a night out.

Enjoy gaining new experiences in Siena. Celebrate another amazing day of your weekend getaway in Italy!

Day 3

Siena
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Fortezza Medicea
Porta Camollia, Siena
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Welcome to day 3 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.

Fortezza Medicea (siena) is an ideal stop early in the day. This frequently visited monument is a must-visit in the city. When you’re ready for your next discovery, continue to Porta Camollia, Siena, which may be one of the most breathtaking places you will experience today.

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.

Transform your weekend getaway in Italy into a memorable experience by exploring the fantastic restaurants and bars in Siena. Discover the city’s diverse culinary scene, savor local flavors, and soak in the friendly atmosphere.

Savor the flavors at Ristorante San Desiderio, a top pick for dinner tonight. Alternatively, Osteria Le Logge beckons with its unique menu offerings. Also, consider Ristorante Taverna Di Cecco. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

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

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!

Day 4

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 4 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.

Take advantage of your accommodation's proximity to Siena’s shopping district for some last-minute bargain hunting. Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

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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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.

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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