Free Travel Guide to Siena
Explore Siena: Your Ultimate Guide to the Heart of Tuscany
Picture this: You’re wandering through a city where every stone tells tales of medieval brilliance and ancient splendor. The air hums with the legacy of famous horse races and the craftsmanship of Renaissance masters.
Siena is a place where you can savor a perfectly brewed cappuccino in a charming café and then stroll to admire the iconic Piazza del Campo and the stunning Gothic architecture that defines the city.
It’s a city that cherishes its rich history while buzzing with a vibrant, modern energy. This unique blend of timeless charm and contemporary flair will captivate your senses and spark your curiosity.
And guess what? Wingman is here to make sure you don’t miss a single unforgettable moment in this incredible city.
SIGHTS, SOUNDS, AND SIENA
Siena Trivia - Did You Know?
That Siena’s iconic Palio horse race dates back to the 14th century? This thrilling event, held twice a year, pits the city’s districts against each other in a high-energy, bareback race around the Piazza del Campo! It’s a tradition that adds a dash of excitement to Siena’s historical charm.
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From charming hidden courtyards to the rich history of Siena’s iconic landmarks, our tours offer the perfect mix of excitement and culture.
Lace up your shoes, grab your camera, and join us for an unforgettable adventure through the enchanting streets of Siena!
The Heart of Tuscany – Siena
Siena is a city of unparalleled charm, perfectly preserving its medieval heart and set against a landscape that looks like it was painted by a Renaissance artist.
The city’s historic center, a UNESCO World Heritage site, exudes old-world charm with its narrow, winding streets and beautiful brick buildings. Siena’s artistic heritage is equally impressive and a must-see experience.
Breathe in the beauty, experience the passion, and taste the best wines of Tuscany with Wingman!
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tourist traps and scams
to avoid
in Siena
We know your vacation time is precious, and nothing grinds gears like falling into a tourist trap. So, buckle up as Wingman navigates you away from the “tourist tax” and guides you through a trap-free travel experience with the following slide show…
hidden gems of Siena
Siena is more than just its magnificent cathedral and the bustling Piazza del Campo. It’s a city brimming with hidden corners and lesser-known treasures waiting to be discovered. From peaceful gardens tucked away in ancient neighborhoods to charming sites that tell captivating stories of the past, Siena offers countless unique experiences beyond the typical tourist trail.
Orto de’ Pecci
Tucked behind the medieval walls of Siena, Orto de’ Pecci is a beautiful garden that feels like a hidden oasis. Once a hospital’s kitchen garden, today it’s a serene escape with panoramic views of the city.
Insider Tip: Visit during the late afternoon to enjoy a leisurely stroll and perhaps spot some local wildlife.
Coordinates: 43.3206° N, 11.3300° E
Fontebranda
One of Siena’s oldest and most significant fountains, Fontebranda is a hidden gem that offers a glimpse into the city’s medieval past. Once a vital water source, it’s now a peaceful spot to relax and reflect.
Insider Tip: Bring a book and enjoy a quiet moment by the water’s edge, away from the hustle and bustle of the city center.
Coordinates: 43.3193° N, 11.3285° E
Pinacoteca Nazionale
While everyone flocks to the Duomo, the Pinacoteca Nazionale remains a quieter treasure trove of Sienese art. This gallery showcases masterpieces from the 13th to the 16th century, offering a deep dive into the city’s rich artistic heritage.
Insider Tip: Take advantage of the free entry on the first Sunday of each month to explore without spending a dime.
Coordinates: 43.3167° N, 11.3302° E
Santuario di Santa Caterina
This sanctuary, dedicated to Siena’s patron saint, Catherine of Siena, is a spiritual and historical gem. Nestled in the heart of the city, it includes her family home and a beautiful church with stunning frescoes.
Insider Tip: Spend some time in the peaceful cloister, a perfect spot for quiet contemplation.
Coordinates: 43.3173° N, 11.3312° E
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culinary delights of Siena
From the tender, succulent Bistecca alla Fiorentina to the rich, flavorful layers of Pappardelle al Cinghiale, Siena is a paradise for food lovers. We’ve curated a list of must-visit restaurants where you can savor authentic Tuscan dishes bursting with flavor. Picture biting into a crispy bruschetta topped with ripe tomatoes and basil, or indulging in the freshest truffle pasta paired with a glass of local Chianti. Hungry yet?
Osteria Nonna Gina – Pappardelle al Cinghiale
Experience the hearty flavors of Tuscany at Osteria Nonna Gina, where the Pappardelle al Cinghiale (wild boar pasta) is the star. This family-run gem is known for its warm hospitality and rustic dishes that feel like a hug from Nonna herself.
Insider Tip: Save room for their homemade tiramisu – it’s legendary!
Coordinates: 43.3199° N, 11.3312° E
La Taverna di San Giuseppe – Ribollita
Step into La Taverna di San Giuseppe and indulge in their famous Ribollita, a traditional Tuscan bread soup packed with vegetables and flavor. The charming, historic setting adds to the authentic dining experience.
Insider Tip: Ask for a tour of their wine cellar – it’s a hidden treasure.
Coordinates: 43.3174° N, 11.3309° E
Ristorante Da Enzo – Bistecca alla Fiorentina
For a taste of the quintessential Bistecca alla Fiorentina, Ristorante Da Enzo is the place to be. This beloved spot offers a perfectly grilled T-bone steak that will melt in your mouth, all served in a cozy, inviting atmosphere.
Insider Tip: Pair your Bistecca with a glass of local Chianti for an unforgettable meal.
Coordinates: 43.3181° N, 11.3296° E
Antica Osteria da Divo – Truffle Pasta
Antica Osteria da Divo is where you can indulge in the freshest truffle pasta, a true delicacy. Located in an ancient Etruscan tomb, this unique restaurant offers a dining experience steeped in history and flavor.
Insider Tip: Try their truffle-infused dishes for a taste of luxury.
Coordinates: 43.3180° N, 11.3295° E
cultural insights of Siena
From majestic cathedrals that whisper tales of medieval knights to vibrant festivals that turn plazas into lively stages of music and celebration, Siena is a city where history and contemporary culture come together seamlessly.
Join us as we uncover the hidden gems and celebrated events that capture the essence of this enchanting Italian city.
Museo dell’Opera del Duomo
Step into the Museo dell’Opera del Duomo, a treasure trove of Siena’s artistic heritage. Home to masterpieces by Duccio di Buoninsegna and Donatello, this museum offers a breathtaking journey through centuries of art and history. The stunning views from the museum’s panoramic terrace are an added bonus.
Insider Tip: Climb to the top of the museum’s Facciatone for a spectacular view of the city.
Coordinates: 43.3182° N, 11.3303° E
Teatro dei Rinnovati
Experience the magic of live performance at Teatro dei Rinnovati, a historic theater in the heart of Siena. With its elegant neoclassical architecture and rich cultural programming, this theater is the perfect place to enjoy opera, ballet, and contemporary plays.
Insider Tip: Check the schedule in advance to catch a special performance during your visit.
Coordinates: 43.3170° N, 11.3288° E
Santa Maria della Scala
Visit Santa Maria della Scala, a former hospital turned museum complex that dates back to the 9th century. This expansive site features fascinating exhibits on medieval healthcare, stunning frescoes, and underground tunnels that tell the story of Siena’s past.
Insider Tip: Don’t miss the breathtaking frescoes in the Pellegrinaio Hall, depicting the history of the hospital.
Coordinates: 43.3185° N, 11.3307° E
Cathedral of the City of Siena in Tuscany, Italy
user testimonials
These aren’t just reviews; they’re passports to your next great adventure.
The Wingman audio guide was amazing! It felt like having a personal tour guide in my ear, revealing Siena’s hidden gems and fascinating history.
Loved every minute of the Wingman tour! The stories were captivating and made exploring Siena so much more enriching. Highly recommend
The Wingman audio guide was perfect for our trip. We learned so much and it was so easy to use. Siena came alive with every stop
SIena top sights
1. Piazza del Campo
Fact: Piazza del Campo is renowned for its unique shell shape and serves as the heart of Siena. It is also the site of the famous Palio di Siena, a historic horse race held twice a year, which has been a tradition since the 17th century.
2. Siena Cathedral (Duomo di Siena)
Fact: The Siena Cathedral is famous for its stunning Gothic architecture and intricate marble facade. Inside, you’ll find the Piccolomini Library adorned with vibrant frescoes by Pinturicchio and Michelangelo’s early sculptures.
3. Torre del Mangia
Fact: Standing tall in Piazza del Campo, the Torre del Mangia is one of the tallest secular towers in Italy at 102 meters. Climbing its 400 steps rewards visitors with breathtaking panoramic views of Siena and the surrounding Tuscan countryside.
4. Basilica of San Domenico
Fact: The Basilica of San Domenico is notable for housing the relics of Saint Catherine of Siena, including her head and thumb. The church’s stark, fortress-like exterior contrasts with its rich interior, which includes important artworks and frescoes.
5. Palazzo Pubblico and Museo Civico
Fact: The Palazzo Pubblico, Siena’s historic town hall, is celebrated for its elegant Gothic architecture. The Museo Civico inside the palace contains remarkable frescoes, including the famous “Allegory of Good and Bad Government” by Ambrogio Lorenzetti, which provides insight into medieval political and social ideals.
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