Siena is a small town (population 53,000), and it also refers to one of the many provinces (population 273,000) of Italia. Siena belongs to the famous region (there are 20) of Toscana. The bus dropped me off at the Piazza Antonio Gramsci, as car use within the city walls is limited, which makes for a charming pedestrian experience. The town is and entire region is quite hilly, providing for many natural viewpoints. I had to roll my luggage up and down top-10 percentile grades to arrive at my Hotel Athena. I paid a total of $52 for two nights, when the market rate was $144 total. As at a previous hotel, breakfast was included, so this frugal traveler made sure to awake in time to consume more than my fair share.

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While there are comically obvious swathes of Korean tourists in these Italian cities, the bulk of tourists are other Italians. When in Paris, I heard mostly français from other tourists. I reminded myself that when I visit Manhattan, only a small percentage of the visitors made a long airplane trip–the majority are other Americans.

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Many pictures like this. Anywhere I walked in Siena province was like this.


The town has only a few notable attractions: Piazza del Campo and the Cathedral museum complex. Sadly, I did not have time to tour the Cathedral (€8), which I was told was better than the one in Firenze.

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Siena is a fantastic base for exploring the Tuscan region. One can make trips from Firenze too, but Siena is better suited for the lower half of Toscana. Normally, I never go for the tour brochures one sees in hotel lobbies, but I wanted to see the countryside. I had contacted several tours prior to arriving in Siena, and they were all booked. I am glad that I did not go on those tours, which ran in the neighborhood of €160. The first tour I did was not an all-day affair, but it was extremely convenient and thorough enough, lasting from 13:00 to past 18:00. It cost me only €30. I still do not understand how the company makes money when there are no other passengers! One of the places I visited was Sam Gimignano, a UNESCO World Heritage site. The hotel had a sign listing taxicab rates to various locations. The fare for Sam Gimignano was €80 one-way.

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I got a guided tour. I got driven around in a van with Wi-Fi. The driver was in his 20s and spoke passable English. The end of the tour was a wine tasting that was quite filling. My only other wine tours have been in Napa Valley. It seems that the business model of many wine tastings in Toscana is to offer them for free, with the hope that a few tasters will convert into buyers of product. They all give the same speech about free door-to-door shipping, bulk discounts, etc. The pitch reminded me of those timeshare promotions where you receive two hotel nights in exchange for sitting through a two-hour presentation, which I have never done. It also reminded me of a far less heavy-handed tactic that I had observed in Marrakech. The young lady, Ida, doing the presentation was attractive, personable, and engaging. The wine tastings are not skimpy at all. They amounted to 3 to 4 ounces for each of five different wines, only one of them white. The accompanying food was enough that I did not even need dinner. Quite a deal for €30.

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On the tour on my first day, I touched Castellina in Chianti, San Gimignano, and Ulignano. The second day, I did a tour of Torrenieri, Buonconvento, and Montalcino, which is famous for its expensive Brunello wine. This tour was similar to the previous day’s and cost only €38. The first tour was north of Siena town; this tour was south of Siena town. The roads driven felt brand-new, and we did not cover much distance, maybe 100 kilometers total each day, but it felt like much longer because one enters and exists villages quickly. One noticeable difference between my Moroccan tour and these tours was that my Italian drivers did not use two mobile phones simultaneously while doing their job. Only one time did the phone ring during my Tuscan tours, and even then, the driver refused to answer it.

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While my first tour had no other passengers, my second tour had a family from Salvador, Brasil, who was taking their three-month summer break to travel America and Europe. Speaking the tiniest amounts of português and español, along with a basic familiarity of Brazilian politics helped me to become friendly immediately with this family. The father, Silvio, did not speak much English. He had a booming voice and asked the driver many questions from the back of the van. The driver was fluent in Italiano, English, and español, and even spoke some português. I love languages so I was content much of the time listening to tour-guide explanations only in español.

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It is almost a certainty that this family was well off, especially by Brazilian standards, having the wherewithal to travel for several months. The wife spoke only a little English. The two children consisted of an 11-year-old boy who was eager to display his decent English (much better than that of his parents) and a 15-year-old Adriana Lima (who is also from Salvador) lookalike named Bruna. At the end of the tour, Silvio invited me to dinner at a nice restaurant to share some of the Brunello that he purchased at the tasting. He was drunk by this time, but he still insisted on finding a restaurant without a dreaded corkage fee.

2014-12-08 Toscana Real Estate Listing

Real estate listing for a typical Tuscan home.

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San Gimignano (elevation 324 meters). Only 7100 people live here, but there are regular busloads of tourists. This village and others I visited resembled ghost towns with long silent corridors of empty shops and restaurants. I expect the summer season is much different.


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My first wine tasting in the frazione of Ulignano, Province of Siena, Region of Toscana. I drank enough that when the driver came to pick me up, he was alarmed at the redness of my face!



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Beautiful Abbazia di Sant’Antimo, the farthest south in Toscana I traveled. As with so many things in the area, it is more than 1200 years old.


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The Cattedrale di Siena I did not get to tour. Make sure you tour this building, along with the library housed inside.


Siena map

Still much more of Toscana I want to tour!