Summary
Siena is a remarkably historic medieval location situated in the heart of Tuscany.
Positioned in northern Italy, this small city attracts hundreds of thousands of visitors to its UNESCO World Heritage streets annually.
It presents an extraordinary opportunity to experience Renaissance-era art and witness medieval structures in their well-preserved splendor. However, the narrow lanes can become crowded even during quieter times, leading many to seek refuge in the surrounding Tuscan countryside.
Fortunately, Siena is encircled by charming villages and rolling hills, with a diverse array of Italian heritage, culture, and notably, cuisine and wines, awaiting discovery and enjoyment in the vicinity.
Additionally, it is possible to explore Florence, traverse the breathtaking coastline of Cinque Terre, and view the iconic Leaning Tower of Pisa, all just a day trip away from Siena.
1. San Gimignano
Commence your explorations outside Siena by visiting the historic town of San Gimignano.
This area has been inhabited for millennia, with its illustrious past extending back to the 3rd century BC. The primary draw, however, is its UNESCO World Heritage historic center, recognized for its origins in the 13th Century AD.
San Gimignano has adeptly preserved its distinct medieval tower houses through the ages; even today, the skyline is prominently characterized by these majestic structures, with 14 of them still standing valiantly above the town.
Stroll along the ancient streets, explore the towers, and experience a genuine piece of Tuscan history at San Gimignano.
2. Monteriggioni
The fortified town of Monteriggioni is situated amidst the Tuscan hills in the countryside near Siena.
The town has maintained its significant medieval fortifications, entirely encircled by defensive towers and walls.
A visit to Monteriggioni transports you back in time, where Renaissance-era houses and churches still grace the cobblestoned streets.
These fortifications were constructed to protect Siena during its numerous conflicts against the rival city of Florence.
It served as a crucial line of defense for centuries, even inspiring the poet Dante to reference Monteriggioni in his esteemed works.
This site stands out as one of the most intriguing historical attractions to explore around Siena.
3. Lucca
Lucca is yet another splendidly preserved walled city in Tuscany, easily navigable in a day.
The city’s walls are, in fact, the principal reason for a visit.
Although Lucca has expanded and modernized beyond its original defensive perimeter, the walls remain intact, forming a significant feature of the city.
These wide walls have been transformed by locals into a continuous park, providing a picturesque setting for walking or cycling around the old city center.
4. Montalcino
Montalcino is another charming medieval town located in the Tuscan hills. Although it is delightful for its historic architecture and picturesque cobbled streets, a significant reason for visiting is to sample the renowned Brunello Wine produced in the region.
Brunello Wine has a carefully protected recipe, with its production refined over centuries.
Explore the streets of Montalcino and visit the wine bars for tastings, or acquire a few bottles to enjoy the flavors of Tuscany later.
5. Chianti Region Vespa Tour
An unconventional and exhilarating way to discover the historic towns and rolling hills of Tuscany is to partake in a Vespa tour from Siena, venturing into the Chianti Region.
These motorbike tours provide a charming road trip through the stunning countryside, showcasing the best medieval towns, off-the-beaten-path wineries, and notable olive and cheese farms.
It is a unique manner of exploring this beautiful region on the classic Italian Vespa.
6. Livorno
Travel to the coast from Siena to explore Livorno: a seaside city featuring one of Italy’s largest and busiest ports.
This city caters to cruise ships throughout the year and boasts a wide variety of restaurants and bars serving freshly caught seafood and exquisite wines to its visitors.
The port is a remarkable sight, with various vessels, cruise liners, and yachts frequently docking, while the city’s old fortifications line the coast.
Observe the ships in the port and then enjoy dinner at one of the many restaurants along the waterfront.
7. Pisa
Pisa requires no introduction.
Located just an hour and a half from Siena, this city is renowned for the iconic Leaning Tower of Pisa, an essential sight for first-time visitors to Tuscany.
Upon arrival, make your way to the tower to capture that quintessential souvenir photograph, posed as if you were supporting the tilting structure. However, take a moment to linger in Pisa and explore the additional offerings of the city.
Stroll through the old streets, visit the museums, and walk along the picturesque riverbanks.
8. Assisi
Assisi is a town characterized by churches, cathedrals, and basilicas; a place that has significantly contributed to the history of Christianity in Italy and Europe.
The most significant religious location here is the Basilica of Saint Francis of Assisi, dedicated to one of the most esteemed saints in Catholic history.
This vast, multi-tiered structure dates back to the 12th century, and Saint Francis’s remains are interred in a crypt here, making it an essential pilgrimage destination as well as a historically noteworthy medieval basilica.
9. Rapolano Terme
Located half an hour away from Siena, nestled in the countryside, Rapolano Terme offers a wonderful escape from urban life.
Rapolano Terme is an ancient Roman town, originally frequented by the Romans for its hot baths.
Centuries later, this tradition continues; visitors can still explore this quaint town and partake in its rejuvenating hot baths and spas, making it a perfect tranquil retreat from Siena.
10. Colle di Val d’Elsa
A journey to Colle di Val d’Elsa is one of the more straightforward day trips from Siena, as this hilltop town is merely half an hour away and easily reachable, even by public transport.
The town features both old and new sections, with modern architecture contrasting beautifully against the medieval structures.
The age-old craft of crystal glass making has been meticulously preserved here, becoming a valued art form that is showcased to visitors who wish to learn more about its intricacies.
11. Perugia
Perugia serves as the capital of the neighboring Umbria Region, celebrated for its Renaissance architecture alongside ancient Etruscan and Roman remnants.
It is a historic locale, charmingly perched on high hilltops, providing breathtaking views across Umbria.
During the Renaissance, Umbria thrived as an artistic hub, a legacy still evident in the numerous galleries and cultural festivals the city proudly hosts throughout the year.
The most prominent of these is the annual jazz music festival, which takes place every summer.
12. Cortona
In the hills near Siena lies the ancient town of Cortona, characterized by steep streets that always seem to rise upwards.
This area epitomizes quintessential Tuscany, blending ancient Etruscan and Roman influences with Renaissance architecture.
The town offers panoramic views across Tuscany, and the nearby Lake Trasimeno was the site of the historic defeat of the Romans by Hannibal and his elephants.
In recent years, the town has experienced a tourism boom, largely due to its recognition as the setting for the celebrated Hollywood film ‘Under the Tuscan Sun,’ inspiring numerous visitors to discover Tuscany for themselves.
13. Monte Argentario Peninsula
Further from Siena than the majority of the other Tuscan towns, the Monte Argentario Peninsula presents a wonderful retreat from the crowds.
This mountainous region is linked to the mainland by a small land bridge, offering a rugged charm with its stunning, windswept beaches and breathtaking coastal vistas.
It stands apart from the medieval towns and hillside fortresses surrounding Siena, showcasing a unique kind of beauty.
14. Cinque Terre
Cinque Terre represents a lengthy day trip from Siena, yet this stunning coastal area north of Tuscany merits the extra effort to reach.
This UNESCO World Heritage site encompasses five coastal villages nestled amid dramatic cliffs.
It provides an incredible coastal landscape, allowing for authentic experiences while hiking the trails connecting the five towns.
Each town possesses its own unique character, rich with intriguing histories and cultures eager to be explored by inquisitive travelers.
15. Florence
Lastly, a visit from Siena should certainly include the renowned city of Florence.
Historically, these two influential cities served as archrivals, engaged in constant conflict during the medieval period, a rivalry that has profoundly influenced northern Italy’s history and culture.
Ultimately, Florence triumphed over Siena, establishing itself as the capital of the Tuscany region.
The city is replete with museums, historic edifices, castles, and artistic masterpieces.
It represents an authentic Italian marvel that should not be overlooked during your journey through Tuscany.
