Top 9 Landmarks
to visit in San Gimignano
for cruisers to Livorno in 2023

The landmarks of San Gimignano are one of the main reasons to visit this medieval town in Tuscany. The famous towers are extraordinary and the view from the top stunning.

Overview for Cruisers

But even if the cruise traveler doesn't have the stamina to climb to the top for breathtaking (in more than one sense) views, a walk along the Via San Giovani, with stops by the Piazza Duomo and Piazza Cisterna is a memorable experience.

If planing to visit San Gimignano on a ship excursion aka Shorex, the cruise traveler will not have much time to explore as far as the Rocca di Montestaffoli, but shouldn't miss a stroll on Via San Mateo.

1. Porta San Giovanni
(Gate of San Giovanni)

There are quite a few different gateways in San Gimignano’s 13th-century walls, but none is as popular or more historically significant than the Gate of San Giovanni.

An imposing portal that is about 750 years old, the Gate is a favorite photography spot for visitors who want to take a bit of San Gimignano’s medieval architectural home with them.

2. Via San Giovanni
(San Giovanni Street)

For those looking to experience San Gimignano’s romantic medieval atmosphere, a stroll down the San Giovanni Street is a must. The sloped, cobbled road located along the Porta San Giovanni gateway is the city’s main thoroughfare.

Rising up on either side of the street are numerous picturesque 13th and 14th-century buildings and towers that include San Francesco’s Church, Pratellesi Palace, Cugnanesi Tower, Becci’s Arch, and Becci’s Tower. Those meandering along San Giovanni Street can choose whether or not they’d like to stop and take a look at these stunning medieval structures, but they won’t be able to help feeling like they’be been transported back in time.

3. Via San Matteo
(San Matteo Street)

Like San Giovanni Street, walking along San Matteo Street offers visitors a delightful San Gimignano experience. A paved road stretching from the Piazza del Duomo, it runs adjacent to numerous historical buildings – the most notable of which is the Palazzo del Podesta.

San Matteo Street also offers up some delightful little shops housed in picturesque medieval buildings. For those seeking out some off-the-beaten-track attractions, the street also runs past the Pettini Tower, San Bartolo Church, and the Salvucci Tower. The street ends at the Porta San Matteo, the second most important gate in San Gimignano’s medieval wall.

4. Piazza del Duomo
(Cathedral Square)

The Piazza del Duomo is lined by the Collegiata, the Palazzo Comunale, the Torre Grossa and the Palace of Podesta facing the Cathedral – some of San Gimignano’s main attractions.

As a result, the piazza is often crowded with tourists. If not in a hurry to see these landmarks, the piazza is a wonderful place to sit at a café table and relax while people watching and soaking up the medieval town’s unique atmosphere.

5. Palazzo Comunale aka Palazzo del Popolo
(Town Hall)

The Palazzo Comunale, also known as the Palazzo del Popolo, was built between 1289 and 1298 on the Piazza del Duomo. The Palazzo was expanded upon in the 14th century and now features a facade that is made half of stone and half of brick.

Located close to the Collegiata church, it has been the seat of civic power since its founding. Today the building also houses a museum and art gallery that includes works by Benozzo Gozzoli, Lippo Memmi, Coppo di Marcovaldo, Filippino Lippi, Pinturicchio, and Il Sodomo. The Palazzo Comunale also provides access to the Torre Grossa, the tallest tower in the city, which affords fabulous views of the surrounding countryside.

6. Palazzo del Podestà
(Podesta Palace)

The Palazzo del Podestà was built in 1239 across the piazza from the Collegiata and acted as the city’s town hall before the Palazzo Comunale fulfilled the role.

The municipality built the Palazzo’s tower in 1255 to settle the battle between the city’s warring families to determine who can build the tallest tower. The solution was short-lived. Today the Palazzo del Podestà houses a museum filled with works by artists that include Coppo di Marcovaldo, Domenico Michael, Filippino Lippi, Pinturicchio, Memmo Filippuccio, and Lippo Memmi.

7. Torre Grossa
(Great Tower)

San Gimignano’s ancient town walls and gateways may be striking, but the city is best known for its incredible towers. At the height of their construction, more than 70 towers rose out of San Gimignano’s medieval city blocks.

Only 14 of these towers remain today, but they are still a sight to behold, even earning a spot amongst UNESCO’s World Heritage Sites. Half of the remaining towers line the Piazza del Duomo.

The tallest one of the bunch, between the Cathedral and the Palazzo del Popolo, is the Torre Grossa, which rises to a height of 55 meters off the ground. It may be a steep climb to the top of the tower, but the incredible view is well worth the exertion. The Palazzo del Podesta’s Torre della Rognosa is also another tower worth visiting.

8. Piazza della Cisterna
(Cistern Square)

The Piazza della Cisterna is San Gimignano’s historical main square. Shaped like a triangle, the piazza was constructed in 1237 and expanded in 1346.

It is named for the octagonal well in its center, which provided clean water for the town’s citizens. Tracks from centuries of chains and ropes used to drag water jugs can be seen etched into the piazza’s stones.

The main attractions lining the Piazza della Cisterna include the very photogenic Torre del Diavolo and Torri Ardinghelli, as well as the Torture Museum and Palazzo Tortoli. Visitors will also find a variety of bustling shops and cafes lining the piazza.

9. Rocca di Montestaffoli
(Montestaffoli Castle)

The Rocca di Montestaffoli lies west of the Piazza del Duomo on the highest point of the hill against the town walls. It was once a massive castle with two drawbridges and five turrets built in 1353 by the Florentines.

The Rocca di Montestaffoli was demolished in 1555 by the Sienese government and only fragments of the walls and one tower remain. In 1978, the Rocca di Montestaffoli became a park and the area’s large grassy area makes it a perfect place for a picnic. For those looking for a bit more of an adventure, the remaining tower is stable enough to climb up. The lookout at the top affords stunning views of San Gimignano and the surrounding countryside.