Star Trip in Southern Tuscany from Siena
I have traveled in Italy many times, but it was precisely on my last trip that I realized
that every place we reach in Italy seems to be beautiful and with delicious food. Even
quiet, uncrowded towns, those that do not skip resting
during siesta time, enjoy impressive views and a backdrop that is entirely filled with the
so-beloved Italian charm.
The villages and towns of Tuscany are proof of this.
The towns are ancient and very impressive,
with narrow and picturesque alleys filled with beautiful viewpoints, small shops,
boutiques, wine, cheeses, pizzas, ice cream, and a relaxed, old-time atmosphere.
Many travel to the capital of Tuscany,
the city of Florence
(Firenze), but in southern Tuscany as well, you can set out
on very successful star trips from the city of Siena.
Siena
The city of Siena is considered one of the most beautiful cities in Tuscany. The following video gives a short taste of the city's landscapes.
Siena is known for its shell-shaped Piazza del Campo. The huge square, where today you will find surrounding shops, cafes, restaurants, and souvenir stalls, was once the center of social and civic life in Siena, dating back to the 12th century. Around the square, there are also impressive buildings like the Fountain Gaia and the Town Hall.

It is worthwhile to climb to the top of the Torre del Mangia tower that rises above the ancient buildings. To reach it, you have to climb 400 steps. From the top of the tower, an impressive view of the square, the city, and its surroundings is revealed.


The Siena Duomo Cathedral is also very impressive - its construction began in the 11th century and lasted for over 300 years. The cathedral facade is covered in white and black marble, and above it stand out the large dome alongside the tower with the triangular spire.
Tours and Attractions in Siena
Booking recommended tours and attractions from Viator:
♦ Guided walking tour of the best of Siena including Duomo entry -
Skip the Line: Siena Duomo and City Walking
Tour
Lasts about 2 hours.
Cooking courses and hot air balloon flights in Siena:

Recommended Hotels in Siena:
The most luxurious hotel in Siena:
Grand Hotel Continental Siena - Starhotels Collezione
5-star hotel in the historic center of the city. Elegant restaurant with traditional gourmet cuisine. The hotel features quality art pieces and fresco paintings on the ceilings. Parking available. Free Wi-Fi.
4-star hotel in the old city near its walls. Elegant Italian restaurant. Free parking and Wi-Fi.
Outside the city near Siena:
10 km north of Siena, in the heart of Tuscan nature:
Certosa di Pontignano Residenza d'Epoca
Hotel with restaurant and bar. Free parking and Wi-Fi. Breakfast available. Large garden, ping pong table, free bicycles for guests' use.
About 15 km from the city, in a pastoral location, 4-star standard:
Quality 4-star hotel with a large pool, restaurant, tennis court, large garden. Free parking and internet.
Or an aparthotel in the suburbs of Siena about two km from its historic center:
Aparthotel of various sizes with equipped kitchenette. Air conditioning. Outdoor pool. Free parking and Wi-Fi.
Destinations and Trips Outside Siena
For those staying in Siena for several days, it is recommended to also take guided tours in the vicinity of Siena. Below are several suggestions for recommended guided tours from the Viator website departing from Siena:
♦ Small-group guided trip to Montepulciano and Pienza -
Small-Group Montepulciano and Pienza Day Trip from
Siena
Departs from Siena. Includes a meal at a farm. Lasts 8 hours.
♦ Trip to the city of towers San Gimignano and Volterra -
Small-Group
San
Gimignano and Volterra Day Trip from Siena
Small group trip departing from Siena. Lasts 8 hours and includes lunch.
♦ Private guided walking tour in the landscapes of Tuscany -
Private Tour: Guided Hike in Tuscany with
Transport from
Siena
Private tour. Lasts 7 hours. Includes transportation to the destination from Siena.
Includes a picnic lunch with a glass of wine.
Montalcino
South of Siena (42 km) you will find the town of Montalcino, a small town situated on top of a hill and surrounded by a medieval wall. The first thing you will notice upon entering the town is of course the impressive fortress inside which you will find many wine shops offering tastings of wines from private wineries of the town's people or from Tuscan wineries.

The fortress was built in the 14th century and the views from it are very impressive.


After visiting the fortress, it is also worth visiting the clock tower adjacent to the Piazza dei Priori square and the central Piazza del Popolo designed in Gothic style.

Pienza
Just as wine and cheese complement each other, so too does the town of Pienza complement the town of Montalcino. Therefore, it will be natural to continue the day trip and arrive at Pienza (located 23 km east of Montalcino) which is characterized by a Renaissance style. This is a charming, preserved town declared a UNESCO World Heritage site.
Booking a guided trip from Siena to Pienza and Montepulciano from the Viator website:
♦ Small-group guided trip to Montepulciano and Pienza -
Small-Group Montepulciano and Pienza Day Trip from
Siena
Departs from Siena. Includes a meal at a farm. Lasts 8 hours.

Today, the town is especially famous for its many delicatessens featuring local Pecorino cheese, Pecorino Toscano. It is worthwhile to take a tasting tour in the town and enjoy a huge variety of cheeses with different aging times and interesting additions, like the truffles popular in this area.


The town features narrow, winding alleys and offers an impressive view.


Montepulciano
A short scenic drive (14 km) east of Pienza, leads to the town of Montepulciano, which can be entered through one of two main gates: Porta al Prato or Porta delle Farine. The first gate leads to the main street, which features a variety of shops and impressive Renaissance-style buildings.
Booking a guided trip from Siena to Montepulciano and Pienza from the Viator website:
♦ Small-group
guided trip to Montepulciano and Pienza
-
Small-Group Montepulciano and Pienza Day Trip from
Siena
Departs from Siena. Includes a meal at a farm. Lasts 8 hours.

In the center of the town is the large and impressive Piazza Grande, around which is also the Duomo, a large cathedral impressive in its glory, and the Palazzo Comunale city palace.
Cycling enthusiasts will find a few meters from this square an electric bike rental shop named Urban Bikery where I recommend renting a bike and touring independently for a full day (about 6 hours) in the hills and picturesque towns in the surrounding area including vineyards and wineries. Along with the bike, you will receive a smartphone with a recommended route map that will guide you to the various destinations. www.urbanbikery.it
Short video of the cycling trip in Tuscany:
Duomo:

Shrine of Saint Agnese Church:

This article focused on cities and towns in southern Tuscany. There are of course
many other equally beautiful and famous destinations in Tuscany:
Florence,
San Gimignano,
Pisa, Lucca
and the Chianti region.
Of course, you can combine a trip in Tuscany with
a visit to Rome,
Umbria, and Cinque
Terre, and of course with a cruise
departing from the cruise port near Rome, Civitavecchia
.
Written by: O. E. Bar