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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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Escape to Italy and unwind from the week's stresses with this 5-day weekend getaway to Siena. Enjoy the local culture and take in breathtaking views during your short break.

In the heart of 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.

This fantastic 5-day travel plan is your chance to see the best travel destinations in Italy over the course of a weekend. You’ll stay for 4 nights in Siena, taking in its beauty and energy while maximizing your time in Italy.

Spend your wonderful weekend break in Italy visiting the most popular sightseeing destinations. Expect to see other remarkable attractions in Italy and get a glimpse of the country's unique history and culture.

Your accommodation will be conveniently located for easy access to many of the best places to see and do in Italy. You'll 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 vacation in Siena.

Your itinerary will take you to the best sights and spots in the city of 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 to and share.

This 5-day travel plan covers all you need for an amazing time in Italy. Your itinerary is customizable, giving you the opportunity to create the perfect weekend getaway in Siena. Add tours, tickets, and activities to each day of your itinerary and make the most of your time in Italy.

For your convenience, you can also add a car rental to your weekend getaway package to Italy. This way, you can discover hidden gems and explore Italy at your own pace.

On top of all that, you’ll also have access to 24/7 travel support from your personal agent. We’ll provide you with a step-by-step guide you can easily access on our mobile app, where 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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Days

Destination

Attractions

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Day

City & Overnight

Attractions

Day 1

Porta Romana

Day 2

Basilica of San Domenico•Fontebranda•Siena Cathedral•piazza del Campo•Tower of Mangia•Pubblico Palace

Day 3

Fortezza Medicea•Porta Camollia, Siena

Day 4

Porta Tufi•Musei dell’Accademia dei Fisiocritici

Day 5

Palazzo Salimbeni

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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 city'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, 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.

Transform your weekend getaway in Italy into a memorable experience by exploring the fantastic restaurants and bars in Siena. Dive into the city’s diverse dining and drinking spots to savor its local flavors and enjoy a friendly atmosphere.

Don’t miss out on dining at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink.

Relish in novel experiences as you continue your weekend getaway in the city of Siena. Toast to another amazing day in Italy!

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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As you continue your weekend adventure in Italy on day 2, the charm of Siena awaits. Enjoy the remaining 3 nights as you continue exploring new sights and making lasting memories.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a church, a historical landmark, a public square, a monument, a palace and much more! Begin your adventure at Basilica Of San Domenico. This is an underrated church you should not miss. Another must-see is Fontebranda, an up-and-coming historical landmark in Siena.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Piazza Del Campo, another of the city’s top-rated attractions. We recommend continuing your self-guided tour at Tower Of Mangia, an UNESCO world heritage-designated place of interest in the city. If time allows, add Pubblico Palace to your itinerary. This locally appreciated palace offers the perfect finishing touch to your 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 a wide range of restaurants and bars on your weekend trip. Take your pick from the city’s best dining and drinking spots. Savor a great meal, sip refreshing drinks, and enjoy the nightlife scene before calling it a night in Italy.

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Round off your dining experience by visiting Maudit Pub, a prime location for a drink.

Soak in the unique vibe of the city of Siena tonight! Relax with a drink after your rewarding weekend getaway experience in Italy!

Day 3

Siena
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Fortezza Medicea
Porta Camollia, Siena
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Welcome to day 3 of your exciting weekend getaway in Italy. Today, let Siena reveal more of its personality as you visit its best spots. Relish the remaining 2 nights of your vacation as you dive deeper into this captivating destination.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Fortezza Medicea (siena). This increasingly popular monument provides an insightful glimpse into the city's identity. Next, discover Porta Camollia, Siena, a breathtaking monument, promising a delightful 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.

Make sure to reserve a table at Ristorante San Desiderio, 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 Osteria Le Logge, 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 Ristorante Taverna Di Cecco, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Bar Impero Siena after your meal, a hub for lively evenings and memorable moments.

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
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Porta Tufi
Musei dell’Accademia dei Fisiocritici
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Today marks day 4 of your relaxing weekend break in Italy. Embrace the beauty and spirit of Siena as you look forward to 1 night filled with joy and adventure.

Today, you'll explore some of the most beautiful places in Siena, including a historical landmark and a museum. Start your day with a visit to Porta Tufi. This beloved historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Musei Dell’accademia Dei Fisiocritici, which may be one of the most photogenic 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.

Treat yourself to a delightful dinner at Bar Pasticceria Nannini Toselli, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Gallo Nero? It's another excellent option with a diverse menu. Consider reserving a table at Bar osteria enea as well. Known for its consistent customer satisfaction, it’s an ideal pick 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 and relax as you savor every minute of your stay in Siena. Celebrate Italy and your 5-day weekend getaway!

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.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Siena's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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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