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When deciding on an Italian vacation, I imagine most people think of the usual highlights, Rome, Venice, Florence, Milan, Napoli and the like. Not to be overlooked however are the smaller villages and towns which offer an authentic old-world experience. I must say, Siena is one such town I hadn’t heard of until my wife Trudy suggested we add it to our road trip itinerary. Nestled in the heart of Tuscany, this is a city that effortlessly blends medieval charm with vibrant modern life. As you arrive in Siena, you’ll be greeted by its iconic red-brick buildings and narrow winding streets that seem to whisper tales of centuries past. Whether you arrive by train, car, or bus, the journey to Siena is a scenic delight, with rolling hills and picturesque vineyards setting the stage for your adventure. The city is perched on three hills, creating its distinctive topography with steep streets and impressive viewpoints. This hilltop location not only offers stunning panoramic views of the surrounding Tuscan countryside but also adds to Siena’s unique charm and historical significance. The elevation and hilly terrain give the city its characteristic layout, with narrow, winding streets and beautiful, terraced buildings. Siena is situated at an altitude of approximately 322 meters (1,056 feet) above sea level. The walled, Historic Centre of Siena is a UNESCO World Heritage Site.

From our research, we realized that trying to park in the old city would be quite a challenge, so we didn’t attempt it. There is parking in the lower region of the city, some free and some paid so we utilized one of the paid, more secure lots. From this location, there’s about a five-minute uphill walk until you reach the city walls with archways which lead to some escalators. Riding the escalators to Siena is a unique and convenient way to reach the historic city center from the parking areas. Here’s what you can expect:

The old city wall with arches leading to the escalators. These walls, which stretch for about seven kilometers, encircle the historic center of Siena and have been preserved almost completely.

Escalators in Siena

Convenience: The escalators provide a quick and efficient way to get into the city, especially if you have luggage or are traveling with children.

Location: The escalators are located near the Porta Tufi and Porta Fontebranda entrances. These escalators connect the lower parking areas to the upper city, making it easier for visitors to access the main attractions without having to climb steep hills.

Parking: If you’re driving to Siena, you can park your car in one of the designated parking areas near the escalators. Look for signs indicating the escalator access points.

Timings: The escalators operate from early morning until late evening, but it’s always a good idea to check the specific operating hours during your visit.

Accessibility: The escalators are accessible for all visitors, including those with mobility issues, making it a comfortable option for everyone.

The first point of interest once inside the Old City was the Siena Cathedral (Duomo di Siena): A masterpiece of Gothic architecture, the cathedral is adorned with intricate carvings, stunning frescoes, and a breathtaking marble floor. On the day of our visit, there was a service going on, so we were only able to get a glimpse of the inside.

A short walk from the Cathedral brings you to a set of steps. Upon descending, you find yourself in the heart of Siena, the Piazza del Campo, one of Europe’s greatest medieval squares. It has unique shell shape and stunning architecture. Dominating the space is the Torre del Mangia, the iconic clock and bell tower and one of Siena’s most recognizable landmarks. Completed in 1348, the Torre del Mangia is the third tallest bell tower in Italy. This is a great place for relaxing, having a coffee and people watching.

One of the defining events in Siena’s history is the Palio di Siena, a thrilling horse race that takes place twice a year, on July 2nd and August 16th in the Piazza del Campo. This tradition dates back to the 1600’s where the city’s 17 contrade (districts) fiercely compete in this event so it’s more than a spectacle for tourists. The preparations consume the city for months. Blessing ceremonies are held in ancient churches, where horses are led inside (yes, inside!) to receive a holy benediction. The jockeys ride bareback around the square on a mud packed track competing for the coveted Palio banner. We travelled there in October so no chance.

Siena offers a wide range of restaurants, catering to every taste, so we stopped for a quick lunch at Il Campo, a popular restaurant located right on Piazza del Campo. It’s known for its delicious Italian cuisine, including pizza, pasta, and other traditional dishes. The restaurant offers both indoor and outdoor seating, providing a great view of the famous square. While there, we witnessed the parade of the city’s 17 contrade (districts) with residents dressed in traditional medieval costumes, carrying flags and banners representing their respective contrade.

Fresh homemade ravioli with Parmigiana and pesto.

After lunch, there was time for more exploration. There’s something truly enchanting about wandering aimlessly through the back streets and alleyways of Siena. The buildings with their earth toned brick facades seem to tower over you as you stroll the narrow streets. Each twist and turn reveals a new facet of the city’s rich tapestry—a hidden courtyard adorned with vines, ancient well-worn paths, some with arches, and smoothed by centuries of use.

Siena’s shopping scene is a blend of traditional charm and modern convenience, making it a joy to explore. Whether you’re looking for souvenirs, local delicacies, or unique handcrafted items, you’ll find plenty to delight in. We love how the items in the stores are artfully displayed. In our travels now, we’re less about souvenirs and more about specialty food items and there were plenty.

lots of specialty pastas.

We’re glad we added Siena to our itinerary, what a pleasant surprise. There’s so much to do in the region but choosing to visit this Tuscan gem was well worth it. If you’re a lover of history, art, culture, food and wine, we recommend you take a look if you’re ever in the region.