Day and I decided to spend Christmas away, with friends, and we decided on Italy. I had visions of wandering the streets on Christmas Eve, shopping for Christmas dinner and Secret Santa with our friends. Siena is a beautiful medieval walled city in the heart of Tuscany, and as it turns out, the perfect place for our Christmas away, with friends. 

   Siena is a wonderful place to visit, during Christmas or any other time of the year. Siena is rich in history, every bit as important as Rome or Venice, the entire city is virtually an open air museum. And, at the center of Siena and all the history, Piazza del Campo, a UNESCO World Heritage site, and home of the world famous Palio run. More than likely your visit will begin here, in the center of Siena. This was true for Day and I, we hired a car services to pick us up at the airport in Rome, and drive us the two and a half hours to Siena. He couldn’t figure out how to get to our apartment by car, so he dropped us off at the Campo, and we walked the rest of the way. Not a bad place to be dropped off, it was close to our apartment and a great place to take a few photos.

   FYI: When traveling to Siena, you will probably be flying into Rome and taking a train, bus, car service or some combination to Siena, and walking part of the way to your accommodations. Do your homework, get it right, and you might be walking a block or less, get it wrong and you could be walking quite a ways. Check to see how far your accommodations are from the train station, the nearest bus stop, and then decide whether you need a car service or a taxi. Siena is quite hilly, please, if you are elderly or have mobility issues, dragging your luggage around is going to suck, so do your homework.

   In these older European cities, the piazza is the center of the neighborhood, and where locals hang out, bring their kids to play, and socialize, essentially, it’s their backyard. For you and I, this is where our vacation begins.

   Our first full day in Siena was Christmas Eve day, and as usual, Day and I booked a walking tour. We have started using ToursByLocals and our guide was going to be Stella. Before Stella and our tour though, one of my all time favorite things, cappuccino, and for that, a walk to the Campo. The Campo is a big square with plenty of shopping, restaurants and cafes, but it’s the Palazzo Pubblico and the Torre del Mangia that dominate the square (which you can walk to the top of, if 300 plus steps doesn’t bother you). As I said before, the whole square is a UNESCO World Heritage site and home of the world famous Palio run. The Palio run is a horse race, and the single most important event that happens twice a year in Siena. I could write an entire post on the significance and history of the Palio, instead, I have added a couple of links for those who are interested. 

   As always, Day and I booked a walking tour. To be more specific, I booked the tour. Over the years we have developed our roles in travel planning, Day finds flights and accommodations, which she is awesome at, and I search for and book tours. Anyhow, I cannot stress enough how much we like walking tours. The tours are usually 3 or 4 hours long, topics range from photography to history to our favorite, food. We met up with Stella, and for about three hours she walked us around Siena and pointed out all the hidden gems…

gave us tips on the best places to eat and briefed us on the history of the city, the 17 contradas and of course the Palio. The magnificent Siena Cathedral was part of the tour, and later we would return for Midnight Mass. You may want to consider buying a combo ticket and explore some of these sights on your own. The ticket includes a half a dozen sights and is good for three days.

   After the tour, we spent the rest of the day wandering the streets on our own. We shopped for Christmas dinner and Secret Santa. Day and I began planning this trip back in March or April, and what I was most looking forward to, was Christmas Eve. Our day was fantastic, and the evening was everything I hoped it would be, Siena was everything I hoped it would be. We had dinner reservations for 8 pm. and plans on attending Midnight Mass at Siena Cathedral. We dressed a little fancier than usual and left the apartment early so we could wander around, enjoy the sights and possibly a glass of wine before dinner. Walking out of the apartment, and into the streets of Siena, was like stepping back in time a hundred years.

   The streets of Siena are ancient cobblestone streets lined with buildings, hundreds of years old. These buildings are now restaurants, cafes and shops, patronized by tourists and locals shopping, socializing and celebrating under the Christmas lights that decorate every street. The hustle and bustle of Christmas Eve in the streets, the open air markets and Piazzo del Campo was like something out of a Charles Dickens’ novel, enchanting. Our evening continued with Christmas Eve dinner at the restaurant Tar Tufo. Dinner in Italy is an event, reservations are for seven or eight, plenty of wine, three or four courses, and it last three or four hours. The food was fantastic, the wine, plentiful, and the company of friends was heartwarming. Tar Tufos was perfect, and as I said, our dinner event, lasted three hours, leaving just enough time to make it to Siena Cathedral for Midnight Mass.

   Three or four hour dinners are not something most of us are accustomed too, it was late, we were tired and we decided to go to the cathedral to listen to the choir, and leave before mass. Siena Cathedral or the Metropolitan Cathedral of Saint Mary of the Assumption is a beautiful medieval church completed in 1348, and the perfect setting to sit and listen to a choir on Christmas Eve. Yes, we snuck out before mass, as did many, we were all tired and pretty sure we would not be able to make it through mass, but listening to the choir was a perfect ending to a perfect day.

   We spent Christmas Day cooking, eating, drinking wine of course, and playing games. Games included “Cards Against Humanity,” not really in the spirit of the holiday, but we did sing carols, which was fun. We opened gifts, drank more wine and celebrated friendship and travel. We looked at our pictures, made plans for the next day, and talked about the second half of our trip, Rome. We had the 26th to do as wish in Siena. We bought the Siena Combo Ticket and visited the cathedral again, the Crypt, Baptistery or San Giovanni, Museo dell’ Opera, Facciatone and the Oratory of San Bernardino. If this sounds like a lot, it’s not, they are all in the cathedral square, worth a visit and just a few hours of your time. Italy is beautiful, Tuscany is beautiful and the city of Siena is a must for any traveler. Our apartment was close to Piazza del Campo, and nothing was more than an eight minute walk according to Google. We spent three full days in Siena, leisurely wandering around and saw most of the highlights. We went on a walking tour, shopped for Christmas and spent most of Christmas Day inside. You could see Siena in a day, or you could hunker down and spend weeks getting to know Siena, Day and I enjoyed our three days there, it was perfect for us.

   How fortunate are Day and I, Christmas in Siena with friends, it was all I had hoped it would be, and there was more to come. For myself, Day and our six friends, Rome awaits. Come back and read about Rome, the Vatican, the Colosseum and my favorite the Pantheon. Until then, Happy Holidays, cheers to friendship and Explore. Dream. Discover. Travel.

Luv ya,

Curly