To throw yourself into this one-day itinerary in Tuscany in Northern Italy where you will be able to explore three fascinating Tuscan towns, you will first of all need to have a car. You are therefore encouraged to rent a car for one day – if you haven’t already got one. You can for instance try Discover Cars (affiliate link) for a wide range of options across both local and international providers. Secondly, you should be ready to have quite a long sightseeing day in Tuscany – because it will be! As a reward you will get an amazing and unforgettable day in medieval settings in Tuscany in Northern Italy!
Albergo Chiusarelli has a top location in Siena. The hotel is set in a 19th century 3-storey building. It is a renovated hotel in NeoClassical style. Some rooms overlook the town centre. Daily buffet breakfast.
Leon Bianco is located in the heart of San Gimignano in Piazza della Cisterna – an excellent location in the ancient town with great views.
Hotel La Locanda in Volterra offers classic rooms with free Wi-Fi. It is decorated with Etruscan carvings. It is located in the historic centre of Volterra in a converted nunnery near the Roman Theatre and the Porta Fiorentina Gate. Features spa bath or a hydromassage shower.
Start your itinerary from your location in Tuscany in due time, such that you will arrive in Siena around 9 a.m. in the morning. When arriving, leave your car in one of the numerous car parks. For the next 3 hours you will be sightseeing in one of the most charming, medieval towns in Tuscany.
Take your time to visit the Duomo, Siena Cathedral, which is world-famous for its architecture (entry fees apply).
The facade is a real masterpiece by Giovanni Pisano and one of the finest Gothic examples. Just as impressive as the outside is the interior of the Cathedral: black and white banded columns, a picturesquely painted ceiling, bright stained-glass windows as well as stunning mosaic floors. As a highlight the Cathedral features both an outstanding carved marble pulpit and unique statues by Michelangelo and Bernini.
Notice the statue of the she-wolf with Romolus and Remus on display on a column in front of the Cathedral.
Next, twist through the narrow streets and alleys to get to the very heart of Siena, the Piazza del Campo from before the 13th century. It is a fishbone-patterned square with 8 lines of travertine which divide the square into 9 sections, each representing one of the 9 rulers of medieval Siena.
The piazza contains the Gaia Fountain (Gaia means joyful) from 1346 which is a lovely Gothic and Renaissance fountain with decorations by the artist Jacopo della Quercia. Moreover, the piazza also features the beautiful Palazzo Pubblico next to the tower Torre del Mangia. It is the highest tower (102 m / 335 ft) in Tuscany – and once one of the highest secular towers in Italy. The tower had the same height as Siena Cathedral to symbolise that the state and the church had equal power!
The square is the perfect place for people-watching!
It is now time that you got a bit lost in the ancient streets to experience the soul and the charm on your own. Take a look inside some of the shops to get an impression of the local products (and maybe do some tasting?), and notice the narrow passages with their old, quaint structures, and view how the light penetrates the massive stone constructions and creates a unique setting.
Around noon it is time to find the way back to your car to continue your itinerary in this part of Northern Italy with the next stop: San Gimignano.
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By now you have probably got a bit hungry, so first thing after arriving in the UNESCO World Heritage Site San Gimignano is to look for a restaurant to have lunch.
The small town is today unique since it still contains urban structures like squares, wells, houses and palaces dating back to medieval times. It is a walled town with two rare concentric rings of walls from the 10th and the 13th century, respectively.
Take a tour: Siena – Volterra – San Gimignano
Have lunch in one of the Tuscan restaurants in San Gimignano – maybe accompanied by a glass of Vernaccia, the first Tuscan white wine to earn the DOC, Guarantee of Origin.
Stroll around the streets to see how many of the 14 still existing towers you can catch a glimpse of. There are quite a few around the Piazza del Duomo and the Piazza della Cisterna. You may visit the Torre Grossa from 1311 which is the tallest tower at 54 m (177 ft) and which has remained unchanged all during the years. It is open to the public – and allows for a 200-step climb. You enter it just off the Piazza del Duomo. The views from the top over the rolling green hills in the landscape are absolutely breathtaking.
Wandering around San Gimignano and the historic centre full of fascinating quaint towers, you will also come across intriguing local shops selling saffron, white wine, leatherware, ceramics, olive wood utensils and tons of other local products.
The icing on the cake in San Gimignano is to try the world-famous ice cream in Gelateria Dondoli at the Piazza della Cisterna. It is a delicious homemade ice cream – a fine Italian gelato. If you feel like trying a new flavour, go for the saffron gelato! Don’t be surprised if the line is long – it is definitely worth the wait! You may enjoy it right on the picturesque square with a spectacular view of a handful of San Gimignano towers – absorbing the medieval ambiance.
Mid-afternoon it is now time to continue your itinerary in the Tuscan Northern Italy and explore the scenic countryside towards Volterra.
After a breathtaking drive through the hilly Tuscan landscape full of cypress alleys, olive trees and winding roads, you will finally arrive at the ‘flying city’ – Volterra – abruptly elevated above the surrounding terrain.
It is said to be one of the most beautiful towns in Tuscany with an intriguing Etruscan history. The town is enclosed with stone arches as gates dating from ancient times. To be here is like travelling to a true time warp full of enigma from its Etruscan past.
(open mid-March – beginning November. Check the exact dates)
Immediately after arriving in Volterra you will cross over to the Archeological Park. Go here as the first thing you are doing since the park closes around 17:30 (check the openings hours and price)
Alternatively (or if you have more time), you may view the ancient Roman Theatre nearby – dating from the first century AD. It features 19 tiers of seating perfectly built into the sloping ground. You will notice an orchestra pit here as well.
(The Roman theatre closes at 17:30 and earlier in winter. Check the opening hours)
(Probably open until 18:45. Closes earlier in winter. Check the hours)
Don’t deprive yourself of visiting the Etruscan Guarnacci Museum which is next. It is one of the most important museums in town.
Additionally, the first floor features rare examples of Roman mosaics from buildings in Volterra, Etruscan gold, silver and bronze coins, as well as unique Roman Republican and Imperial coins. Most of the displayed objects are found inside the city walls.
After seeing the museum, you will have a much better understanding of Etruscan life!
Now it is time to relax and enjoy your evening and stroll a bit around to absorb the ambiance. Sit for a while at the old city walls together with the locals, admire the ancient gates and visit a few of the small shops selling local products like alabaster items, olive wood cutting boards and local wine.
This is where your one-day Northern Italy itinerary ends.
But … this is one of the real authentic Tuscan towns – so you could also consider staying for the night in a hotel here!
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Small Towns in Northern Italy Itinerary One Day
3 Stunning Small Towns in Northern Italy
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