STOP 1Cattedrale di Santa Maria Assunta
The Cattedrale di Santa Maria Assunta reaches a height of 77 meters. This Catholic cathedral is a medieval church in Siena, Italy, and is now dedicated to the Assumption of Mary. The inception of the building was in 1196, and it was designed in the Gothic architecture style. As you look at the structure, you can see that it remains an unfinished building. It is a significant example of the Gothic style and a central part of the city's history and religious life.
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STOP 2Orto Botanico
Look closely at the varied plant life before you see the full scale of the Orto Botanico. This botanical garden was established in 1856 and is operated by the University of Siena. As you walk through the grounds, you are visiting a site that is officially Italian national heritage. It is a place where nature and academia meet in the heart of the city. I find the greenery here a welcome break from the stone streets, though I usually have to stay out of the way of the students.
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STOP 3Palazzo Vestri
Let me show you Palazzo Vestri. This building is a palace that stands as a part of the city's architectural character. It is a place where you can see the specific design and scale used for such residences in this area. I find that the facade makes for a great spot to pause and look around.
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STOP 4Porta Pispini
Let me show you Porta Pispini, a city gate built into the medieval walls of Siena in Tuscany. You can find it on the east side of town, specifically where Via Pìspini meets Via Aretina in the terzo of San Martino. This portal is recognized as Italian national heritage. It took its name from a nearby fountain, the Fonte de' Pispina, which was built between 1534 and 1538. I've always found the way the gate anchors the contrada del Nicchio to be quite charming.
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STOP 5Porta Romana
Let me show you Porta Romana, a city gate started in 1327. It is one of the portals in the medieval Walls of Siena and is recognized as an Italian national heritage. You can find it located on Via Cassia in the Tuscany region of Italy. If you head through the gate, it leads south out of town to Via Enea Silvio Piccolomini and exits near the Basilica of San Clemente. I've noticed the breeze is always a bit fresher once you pass through these old stones.
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STOP 6Porta Tufi
Started in 1325, Porta Tufi is a city gate that opens to a road leading south of the city. You can find it on Strada di Tufi, which is now Via Pier Andrea Mattioli, in the Tuscany region of Italy. It remains one of the portals still standing in the medieval Walls of Siena and is located on a peninsula of walls near Sant'Agostino. I've seen plenty of tourists miss the way it anchors the edge of the old center.
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STOP 7Pinacoteca Nazionale di Siena
Let me show you the Pinacoteca Nazionale. This national museum in Siena is housed within the Brigidi and Buonsignori palaces. Once you step inside, you can pick out a collection of late medieval and Renaissance paintings from Italian artists. The buildings themselves are highlights; the Brigidi palace was built in the 14th century and the Palazzo Bichi-Buonsignori in the 15th century. I find it interesting that a 2022 restoration revealed the Bichi-Buonsignori façade is mostly original. It is a quiet spot compared to the main square, drawing 8,127 annual visitors.
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STOP 8Porta San Marco
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STOP 9Chiesa di Sant'Agostino
Chiesa di Sant'Agostino is a Roman Catholic church building located in Siena, within the Tuscany region of Italy. This site is recognized as an Italian national heritage site. Visitors can observe the Gothic architecture style used throughout the structure. Construction on this church building was started in 1258, making it a long-standing part of the local landscape. It remains a place of worship and a point of interest for those visiting the region of Tuscany.
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STOP 10Palazzo Tolomei
Palazzo Tolomei is a palace in the region of Tuscany, Italy. This Gothic style urban palace is found on Via Banchi di Sopra, situated within the contrada of Civetta. It is recognized as Italian national heritage and is located in the Terzo di Camollia of Siena. I always think the street layout here makes for a great bank shot. If you take a moment to look at the facade, you can see the characteristics of the Gothic style that define this urban residence in the heart of the city.
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STOP 11Porta Ovile
You might mistake this for a simple wall or a random break in the fortifications, but it is actually Porta Ovile. It is a city gate that allows you to see the historic boundaries of the area. Because of its historical value, the site is classified as an Italian national heritage. I always find the stonework here interesting to look at while I am waiting for a snack, and it is a great spot to stop and orient yourself before moving further into the city streets.
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STOP 12Il Campo
This isn't just any open space; it is Il Campo, the main public space of the historic center of Siena in Tuscany, Italy. The square is shaped like a scallop shell and is surrounded by the Palazzo Pubblico, the Torre del Mangia, and various palazzi signorili. If you walk to the northwest edge of the piazza, you can find the Fonte Gaia. The name of the square comes from the Italian word campanile and campanilismo. I've noticed the slope of the pavement makes for a very interesting roll for a golf ball.
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STOP 13Basilica di San Francesco
Located in Siena, Tuscany, the Basilica di San Francesco is a basilica church that stands as a prominent landmark in the city. It is a minor basilica designed in the Romanesque architecture style. This site is designated as an Italian national heritage, reflecting its importance to the country. The inception of the building was in 1475. Visitors to the area can observe the specific architectural details that characterize this period of construction and its place within the wider urban layout of Siena.
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STOP 14Stanze della Memoria
Let me show you Stanze della Memoria, which is a private history museum. This site was founded in 2007 and is recognized as Italian national heritage, making it a point of pride for the local area. You can pick out the unique atmosphere of the exhibits as you explore the space, though it stays quite intimate compared to the larger city attractions. It currently welcomes 768 annual visitors who come to learn about the history preserved here. I think the small crowd makes it a great spot to avoid the usual tourist rush while you take in the sights.
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STOP 15Porta Camollia
Let me show you Porta Camollia, a city gate found on via Camollia. It is one of the northern portals built into the medieval walls of Siena. When you move through the gate and head inside the city, you will find yourself in the Contrada of Istrice. I've noticed the street layout here makes it a great spot to get your bearings before heading deeper into the center. It is a sturdy piece of the city's perimeter that still defines how people enter the heart of the old town today.
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STOP 16Fortezza Medicea
You might expect another ornate villa, but this is the Fortezza Medicea, a fortress. It was built in the city between 1561 and 1563 using the Renaissance architecture style. Duke Cosimo ordered the construction of the site, which began in 1561. Today, the fortress is recognized as an Italian national heritage site. I have noticed the walls make for a great spot to watch the city from above, though I usually prefer the higher ledges for a better view of the street activity below.
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STOP 17Palazzo Salimbeni
Let me show you the Terzo di Camollia of Siena, where you will find Palazzo Salimbeni. This palace sits on the Piazza Salimbeni and is designed in the Sienese school style. Giuseppe Partini is the architect of this Gothic style urban palace, which is also an Italian national heritage. It currently houses the main offices of the Banca Monte dei Paschi di Siena. I always find the architecture here quite striking compared to the more common city blocks, and it is a great spot to pause and admire the facade.
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STOP 18Chiesa di Santo Spirito
You will first notice the Renaissance architecture style of Chiesa di Santo Spirito. This Roman Catholic church building is an Italian national heritage site located in piazza Santo Spirito in Siena. The construction of the church was started in 1498. If you are navigating the narrow streets of the city, you can find the building located where Via dei Pispini meets Vicolo del Sasso. It is a place of significance for those interested in the transition of architectural styles in Italy.
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STOP 19Basilica di San Clemente in Santa Maria dei Servi
The Basilica di San Clemente in Santa Maria dei Servi is a minor basilica featuring the Gothic art style. It is a Roman Catholic church located in the Terzo of San Martino in the city of Siena, Tuscany, Italy. This site is recognized as part of a UNESCO World Heritage Site. While the basilica is Gothic, you can also notice that the Church of Santa Maria dei Servi is in the Romanesque style. These two architectural styles provide a clear look at the different periods of design used for this religious site in the heart of the city.
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