Siena3Magical Siena. Beautiful Sienna. Flavorful Sienna …. Amazing Sienna.

Under the Bright Tuscan Sun, sits the beautiful and storied, walled hill town of Siena. An hour trains ride from Florence sets you up at the base, and a quick taxi ride has you reaching the city heights in no time.

There’s so much to love about this city. Beautiful winding alleys filled with historical buildings, fanciful artisan shops, incredible dining experiences, neighborhoods filled with pride, drop dead gorgeous Cathedral and Baptistry, and one of the largest open piazzas in the round I’ve ever experienced flanked by a drop dead gorgeous Bell Tower and City hall. There is much to love and admire about Siena, and I had only wished I spent much more than just 3 days there back in May 2018, but even with just 3 days, it left a very long lasting impression on my heart.

Siena: A Brief History courtesy of Wikipedia

The historic centre of Siena has been declared by UNESCO a World Heritage Site.[4] It is one of the nation’s most visited tourist attractions, with over 163,000 international arrivals in 2008.[5] Siena is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year. Siena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900–400 BC) when it was inhabited by a tribe called the Saina.

Siena did not prosper under Roman rule. It was not sited near any major roads and lacked opportunities for trade. Its insular status meant that Christianity did not penetrate until the 4th century AD, and it was not until the Lombards invaded Siena and the surrounding territory that it knew prosperity.[citation needed] After the Lombard occupation, the old Roman roads of Via Aurelia and the Via Cassia passed through areas exposed to Byzantine raids, so the Lombards rerouted much of their trade between the Lombards’ northern possessions and Rome along a more secure road through Siena. Siena prospered as a trading post, and the constant streams of pilgrims passing to and from Rome provided a valuable source of income in the centuries to come.[citation needed]

The oldest aristocratic families in Siena date their line to the Lombards’ surrender in 774 to Charlemagne. At this point, the city was inundated with a swarm of Frankish overseers who married into the existing Sienese nobility and left a legacy that can be seen in the abbeys they founded throughout Sienese territory.[citation needed] Feudal power waned, however, and by the death of Countess Matilda in 1115 the border territory of the March of Tuscany which had been under the control of her family, the Canossa, broke up into several autonomous regions. This ultimately resulted in the creation of the Republic of Siena.

The Republic existed for over four hundred years, from the 12th century until the year 1555. During the golden age of Siena before the Black Deathin 1348, the city was home to 50,000 people.[6]Care of Wikipedia

Getting There:

There are many ways to get to Siena. The bus is supposedly a great option , so is a car if you’re into cruising the gorgeous Tuscan coutnryside. We decided instead to take one of the many regional trains that stop at the city instead.

I left after a wonderful week indulging in yet another very famous Tuscan Town                  ( although most never seem to realize this ) Florence: The Beautiful Tuscan Capital To Siena. I have had my share of reading, and yet nothing was able to properly prepare me for the majesty of the city.  We arrived off of TrenItalia’s Regional train: Train: Regionale 11745 leaving from  Firenze Santa Maria Novella station , and a little over an hour later we were pulling up at the base of the Hill.  A quick exit and a fast hop in a taxi ride up and up to the town, we were dropped off what I thought would be fairly close to our accommodation. However, our taxi dropped us of a tiny incline and we had to lug our luggage up the steep ramp like walk way until I came across a majestic view of Siena’s Baptistry.


I researched until I had a nose bleed, where we would be staying. After a few hours of searching, I came across this quaint and gorgeous little apartment , located directly across the Baptistry, located in Piazza San Giovanni. In the pictures it looked so darn beautiful and pretty. We landed on top of Piazza San Giovanni, with the majestic Baptistry smacking us in the face saying…. ” Hey you, look at me, I’m pretty” , and found our door. Rang it up , and our host came down to meet us. One quick flight of stairs, and we were there in our gorgeous little apartment in the heart of Siena, with big smiles on our faces, as this place was even better than the photos. She gave us the lay of the land, offered us some gifts from her family’s Olive Oil Farm, and we exchanged some with her ourselves, and we said our thank you and goodbyes. The apartment decorated in a beautiful style with Sienese Tile ,  was filled with every little thing you could think of including 3 very important things: 1. Washer and Dryer, 2. Nespresso Coffee, 3. Tons of Toilet Paper… Grazie!!!   Siena Apartment Airbnb

After unloading our luggage in preparation for the 3 days we would have here, we grabbed our map and rushed out the door. We couldn’t wait to explore this gorgeous City.

Day 1 : May 12, 2018

Siena1We did what we always do when first arriving to a place, we walked around our little neighborhood to see what is around us. 3 little restaurants with a menu to die for, The steps leading up to the Baptistry, even Steeper steps leading up to the Duomo Cathedral above, a few Sienese artisan stores selling scarves, soaps, olive oil, clay art and a bunch of other things, and a winding road leading in two intriguing directions.

We decided to go up instead of out, and climbed the beautiful marble looking steps up , up , up to the Duomo. Wow!!!! The architecture is so beautiful. The sky was also so ethereal making the setting of this place even more heavenly. The piazza in front of the Duomo was packed. And while we were so eager to visit it , we decided to go have lunch instead. There was one thing that I noticed immediately, it was the Rainbow flag with the word Peace in Italian on it. I knew this was a great sign, as how can you not love a place that promotes Peace.



Directly across the Duomo’s entrance is a building which houses a ticketing booth. We went there to pick up an OPA SI Pass   which allows you to buy a multiples ticket that encompasses the Cathedral ( Duomo ) The Baptistry, The Crypt, the Museo Del Opera, and a bunch of other little places all within the complex. We bought our tickets so that we could visit it later on after lunch.


siena5The city is magical and a perfect place to explore. As we veered right while facing the Duomo’s steps, we found ourselves engulfed In the awe of all the beautiful artisanal shops. Beautiful colored plates, tiles, address markers, clothing stores, you name it it was there. I had to stop in one and buy our address numbers in beautiful Azure , White and yellow trimmings. An awesome memento . Across the little store I was at was a very steep step hill with a bunch of restaurants stilling so perfectly on it. We decided to sit down and eat and quench our thirst with a gorgeous bottle of Chianti ..

There was a plethora of amazing options , but I just had to try what the locals eat. Ribollita… Literally meaning to Reboil. Ribollita is a famous Tuscan bread soup, a hearty potage made with bread and vegetables. There are many variations but the main ingredients always include leftover bread, cannellini beans, lacinato kale, cabbage, and inexpensive vegetables such as carrot, beans, chard, celery, potatoes and onion.  It was amazing!!!!!


All fueled up after a good 2 hour lunch with a fabulous meal and equally fabulous wine, we back tracked our steps, a bit and made our way down the winding alleys . While passing through again, I started to notice a few things. Meat shops selling their finest fresh meats, and aged meats, cobbled stone pathways, a beautiful well out of nowhere, monochromatic flat portraits of the Virgin Mary adorning door fronts, and very colorful flags with a picture or a porcelain attached to it of an animal. In our journey for that short walk, we saw a duck and an owl . I had to know what this meant. So a quick fire up to google, and I  came across the word Contrada.  It just so happens that we came to Siena at the most perfect time.


The walled town of Siena is split up into 3 areas, that are then split into 17 different Wards/ Districts called Contrade.  It is to this Contrada that can only be obtained by birth, that the citizen of that district owe its most loyalty and membership to. Twice a year, in the hot summer months the Contrada celebration comes to a precipice with the Palio Di Siena . This race famously known as the Palio, is a Bare back horse race competition that is held in the Piazza del Campo where the winner of either race brings much love and honor to their Contrade. siena10

Now that I know all about the Contrada, it only made sense that we visit where the spectacle of the Palio happens.

Piazza Del Campo:

Piazza Del Campo

Wow … I can see now how they can actually hold a horse race here. It is huge! Flanked by beautiful buildings , a plethora of restaurants and sun bathers, a gorgeous fountain, and the City hall with its even higher Bell tower.

I shouldn’t have said anything to Debra, because I knew what would come next. ” Eh we go climb the tower” Oi!!!!! Okay… Lets go exercise off the food and wine.  And off we went. A tiny fee allows you to start your climb up the tower. And up and up you go. But the end result is absolutely worth it. You get a commanding view of the city, and the rolling Tuscan Hills in the back ground. What a beautiful city this is and how vast and large it is.  We took some lovely photos, rested a bit and enjoyed the cool early summer / late spring breeze and made our way down back to earth.

There were children everywhere in formation with their teachers, lovers cleaning off the faces of their significant other, full on bikini clad women soaking up the early summer sun, and loud and boisterous all male parties going on in some of the restaurants on the round. There was singing, clapping, and chanting, beer clanking, wine toasting and lots of red faces. We thought it time for a rest and Apperetivo… Spritz con Aperol Per Fevore!

We soaked it all up, no not just our wine, but the beautiful day, the surroundings, the fabulous people next to us all of it. We were here, in beautiful Siena and its only Day 1 and only 3 pm. That’s when we heard it…. Cadence drumming. I’m thinking to myself, the last time I heard drumming like that was during the Assencion procession of the Virgin Mary in Granada. Spain: A tapas of beautiful people and landscapes

And there they were , A Contrade, all dressed up in their medieval blue attire waiving their Blue and White flags and making their processional rounds in front of snickering people, loud cheers, and applause. It was a sight to see.

Contrada parade on Piazza Del Campo

After that festive parade that went on for 25 minutes (that’s how many people were in that contra ) we decided to back track yet again up the steep hill , past the winding window shops, until we reached the now very reasonably  and less packed Cathedral of Siena or as the locals call it: The Duomo




Siena Cathedral is a medieval church in Siena, Italy, dedicated from its earliest days as a Roman Catholic Marian church, and now dedicated to the Assumption of Mary. Wikipedia We entered through a side door located on the step front of the church.

This Medieval 13th Century Church has a form of a Latin cross, with a bell tower and Nave, with the interior and exterior comprised of greenish / blackish marble in alternating stripes with Red Marble accents.  The art here is priceless, with works from Michelangelo, Bernini’s Lantern,  Nothing can prepare you for the beauty of this cathedral . It is of no wonder why the Sienese people have been so world famous for their architecture and beautiful art. .siena4

There is so much to tell and so much to see that I could spend the whole day explaining each and every crevice of this spectacular cathedral and what to see. But why not leave somethings left unsaid. 🙂 Go and Visit!

After the Duomo, we decided to head back down to the Baptistry, since its right there and for a quick bathroom break at our apartment across the way.

Battistero di San Giovanni: The Baptistry of Saint JohnSiena1

Much more of a smaller scale than its parent, the Duomo, The Baptistry is still filled with everything to mesmerize your eyes, and tantalize your senses .The interior, the rectangular hall, divided into a nave and two aisles by two columns, contains a hexagonal baptismal font in bronze, marble and enamel created by master sculptor Donatello .

Baptistry Di Sant Giovani

After a quick stop home and a lovely rest and refresh, we headed back out following the path down now away from the city center as we kept hearing music, and cheering. The contrada flags started to change and everything became a sea of Green, red and white decked out people …



We were in the Goose neighborhood. There were rows of tables set up on one street with a fully cooked pig being chopped up, rows and rows of wine bottles and glasses, ladies young and old with their hands on their hearts, singing their cheers while trying to sell pastries, dancers swinging their hips, children playing and trying to sing along, and sword wielding ax holding Medieval dressed young Paiges. It was a beautiful and surprising sight to see. Perfect Timing!!!!!

The sun was now setting , its around  9:30 pm . We hopped around a bit until we could find a nice little cozy spot to fill our stomachs with wine and Pasta with Tartufo and headed to bed. What an amazing first day.

Tomorrow we head off To Montalcino and a few Fine Brunello wine Vineyards on our Tuscan Wine Tour. How exciting.


Day 2siena20

I don’t know why or how it happened, but I was up at 5:00 am. By this time, I’ve been sleeping very normal , and getting up around 6:30 instead , but for some reason I was up and full of energy. Debra was still sound a sleep. Our tour doesn’t start with our meet up until 9:30 am, and what am I to do? I could still hear off in the distance the sounds of the party we passed through last night in one of the Contrade. Hilarious…. other then that it was pretty quiet.

I got minimally dressed with some warming gear, made a cup of coffee, and headed out to sit on the steps of the baptistry to enjoy my coffee and a nice cigarette. The Town was absolutely silent. Not even the morning birds were up yet. Oh these Italians they know how to live, even the birds are on the same schedule. It’s so different to experience a city with no on around. It was cold but yet so refreshing. I got up from my step, and decided to go visit the city ALONE. I climbed up to the Duomo, which was also absolutely empty. I sat across from it and stared at its facade. Taking in the majesty , the beauty, the heavenly awe-inspiring architecture as it stood in perfect harmony with the night sky. So many things crossed my mind. Are there Creatures of the Night? Will there be that one drunkard walking around? What or who lives behind those windows up there were the Peace Rainbow flag is blowing? Is this what life is like in Siena so early in the morning? And there it was, a tiny tint and hint of a blue sky. Morning is coming. …

I continued following the path we took yesterday, all the way down to the Campo, where I started to see rubbish collectors, sweepers, and morning walkers. Ahhhh so there is life so early in the morning here in the city? I meandered around to places we haven’t been yet. So full of curiosity.. While nothing was open, the walls of the city spoke to me as if it was welcoming me to her heart. It was really quite a lovely walk. Siena2

By the time I got back, the morning sky was in full bloom. It’s 6:30 now, time to shower and wake up Debra. I wanna go have a fierce cappuccino and some sort of breakfast. Slowly Debra awoke, and we were out of the house by 8 am. We stopped at a little pub that was finally open a bit down from our place but on our route to our meeting point with the small tour company we hired for the day.

Our meeting point was the San Domenico Church of Siena. Under “The large Tree”

Basilica San Domenico :

Basilica San Domenico

The San Domenico Basilica church is very picturesque church that sits on its own little hill. I could see it from my apartment, flanked by Euro Style Palm trees and red earth brick ( probably what the color Sienna is truly referring to)  The church , like its sister cathedral was built in the 13th Century and expanding in the 15th Century. It is home to the Dominican order of nuns, and a most interesting set of Relics of Saint Catherine of Siena. While we were visiting there was a tiny mass being held there.

It’s 5 minutes to 9:30 now, I need to use the bathroom and its almost time to meet out tour guides.  Directly across the “Large Tree” were a few pubs and pastry shops . I bought a quick cafe and used the restroom just in case as I heard our first drive was a long one.

Tuscan Escapes By Papilio Tours

The Beautiful Tuscan Countryside

We booked With tuscan escapes for a small group tour to the Tuscan Countryside. I mean who hasn’t watched under the Tuscan Sun and wondered if it truly is as beautiful as the movie. We had some options to choose from, but Debra who loves Brunello wines said that that would probably be the best wine tour for us. I would’ve loved the Chianti tour instead.  We were met by 2 drivers/ Guides under the “Large Tree” and 5 other couples. So 12 people total and in 2 vans. Not bad at all.

Our tour started heading down the hill passing beautiful Villas, crossing over quaint bridges and heading straight into the Tuscan Sun. The landscape here is unbelievably beautiful . It’s so dream like. 35 minutes later, we were pulling into our first Vineyard ( who I can’t remember the name save the life of me) . It was nice to get out and stretch our legs. We sampled 6 different San Giovani Grape Brunellos, and learned a bit about how these San Giovani grapes earn the label Brunello. Next we headed for the quaint little town of Montalcino.


Castelo De Montalcino 

Montalcino sits high on a little mountain top, and is in the Provence of Siena. Famous for Brunello wine, historical outposts, and quaint shops made it for a lovely stretch of the legs and a little shopping adventure. We were given a good 45 minutes to enjoy the city and we made every single little minute count.

Next stop was a tiny eco friendly vineyard , that does their cultivating totally eco friendly, where the vines have a symbiotic relationship with the grass, earth, and flowers surrounding it. Here we had some home cooking lunch meal. While not absolutely spectacular, it was still delicious and fabulous experience. I think the menu is skewed toward and American Pallet. Too bad. we did have another tasting here, and that was nice.

Last vineyard stop was a really elaborate Vineyard. Very fancy processing, and Chic studio to sample wine. We were at the Creator of Illy Coffee’s Vineyard and in my opinion, the least favorite of the 3 we’ve visited. It was a little pretentious  and soulless, and the wine was just OKAY> I’ve now come to realize that I don’t care very much for Brunello wine, and would prefer a good Chianti Classico or Reserva any day over it! I’m glad I bought a bottle at the first vineyard we went to, as it was actually the best of the 3.


The last stop we did was to this beautiful valley and rustic Abbey in the countryside.

Abbazia Di Sant’ Antimosiena19

Set deep in a valley sits the gorgeous evocative abbey built in the 12th century. The drive along the winding country road leading to the monastery offers  incredible pleasure for your eyes: vineyards, olive groves, green hills, and isolated farmhouses here and there. The Abbey, built in travertine stone, stands in perfect isolation on a plain among secular olive groves and lovely wheat fields. It made for excellent photo opportunities. The Abbey is still in use, yet truly holds to its rustic form.siena21

OUr Guides


Sadly that was the end of our day journey. We landed back into town around 6:45 pm. So it was a really full day.  Fortunately for us, the sun in Italy doesn’t set until around 9:30pm . So we still had plenty of time to enjoy the rest of our day.

When we landed, there was a huge open market going on, so of course, we decided to go check it out. It was a large flower market and them some blah swap meet type underwear and tacky clothes for sale. But the flower market was gorgeous. We walked back into the center of town, taking in all the shops and stopping of course for our daily apperitivo, Aperol spritz.Siena3

The city was a buzz. There were more people than we saw the day before.


We explored a bit more, coming across small church piazzas, and another little basilica down the way.siena4

We needed to think about dinner which is slowly approaching. Of Course we were on Italian dining times by now, so a 9:30 dinner would be optimal . So I fired up the Fork app ( you can learn more about it and eating in Italy at: Where, When, What & How to Eat in Italy ) I found a really cool looking restaurant located not too far from our apartment located in a basement.  So we rushed home and changed clothes and headed out for the 4 minute walk to dinner.

Debra and I in Montalcino

La Compagnia Dei Vinatterisiena22

What a fabulous dinner we had. Of Course I had to try another famous Sienese dish, Pici: Pici is thick, hand-rolled pasta, like fat spaghetti. The strangest thing happened to us. We were sitting down, sipping our wine and enjoying the fabulous wine, we heard a very familiar accent. Debra said : ” Omg I think that guy is from Hawaii” So I asked, ” excuse me , you from Hawaii? ” in my best local accident. And sure enough he was. So we talked and swapped experience with him and his wife. He’s from my Island and was the nicest guy and perfect way to end our stay in Siena, than with a lovely conversation with someone from our home.


Day 3

Fortunately today was a good day to wake up early because, unfortunately, we were leaving this gorgeous city early for a train back to Firenze on our way to Rome. It was really sad to leave as we felt we haven’t even remotely scratched the surface. However, Our stay in our gorgeous apartment, and our lovely time we had here had filled my up with so many wonderful memories that I’m able to write this from memory almost a year later. We hired our taxi with the help of our host, who happened to pick us up right at our front door, what a difference from Day 1. hahahaha. My last glimpse of the city was like taking mental photographs forever etched in my mind.

Thank you so very much for following my adventure, whether it be later than it should’ve been. If you’re thinking of Siena, I say don’t think, just do, and you will absolutely not regret it.