Day 8: The Tuscan Hills are alive with wine

Today is my first day without Kerrianne by my side. It was such a great twist of fate that she was able to join me in the first place, so I was sad to see her leave this morning. Despite our obvious personality differences, we are really great travel companions.

It was so helpful and assuring to have her here for the first week as we figured out how to book trains, order coffee, and soak in the Italian scene.

Kerrianne left our hotel just after 5 am and so its been a bit of a long day. Compounded by the fact that despite our amazing view, the room last night was really loud. We appeared to be located directly over a bar that raged until after 2 am. Not super cute. 
Train RideWhat was super cute? Siena. I got here after just about a 90 minute train ride from Florence. The ride itself was reminiscent in a way of the Acela ride through Connecticut – just so pretty you want to stare out the window the whole time. (CT, don’t get all high on yourself… you aren’t as good as Tuscany).

My hotel was easy to find … especially since they’ve thoughtfully spent a fair amount of their ad budget on posting signs between the train station and the hotel. I was a bit worried about how “nice it would be” given all the signage …. But I was pleasantly surprised. Hotel Italia Siena (yes that’s the name) was welcoming, a bit modern, and very friendly.

I can say this for sure because I quite literally burst into tears in the lobby. Let me explain myself… I was quite worried about Kerrianne making her flights and how I hadn’t heard that she made it to the airport in Florence or to her connecting flight in Rome. I was not convinced that Ronald at the Alitalia help desk was correct when he said she made her flights. He thinks I’m crazy btw, but he might be right. So, when the amazingly nice hotel lady said “I just have to ask, what is it like to travel by yourself?”… I burst into tears and I don’t cry. Ever.

Long story short, if you cry during check-in they give you an upgrade. So now I have a terrace and a tub. The terrace has no view, but I don’t care. Also, a Brazilian woman will give you a tissue from the bottom of her purse.

Walking Around Siena
Between arriving and my next activity, I spent a few hours walking around Siena … and once you get over the crowds of tourists… it’s quite beautiful. Tour books call it “medieval” and I can completely see that.

My favorite parts? The amazing doors. Looking up at the buildings. And the old people. Is it obvious yet?

Wine & CastlesI knew that unless I took a tour, I’d spend the entire day thinking about Kerrianne’s flights. So, I figured it would be worth it to pay someone to drive me around the Tuscan countryside and take me to wineries. It was the best decision. (I’m also convinced that the front desk lady told “Fred” not to ask me about my sister, which was fine with me.)

The tour was 5 hours long and included me and my new 7 friends, along with Fred the tour guide. Here are the key moments:
  • Fred says to me “if I may ask, how old are you? You look too young to be traveling alone.” He thought I was his age, which is 22. 
  • There were three 20 year old girls that probably still can’t decide if I’m dumb, fun, or old. They thought there was no way I was 29, thought it was cool that I was doing this trip alone, but also most likely texted about me to each other when I said I didn’t want to go to a club and might have had enough wine. 
  • The Brazilian woman who gave me the tissue in the lobby was on the tour.
  • There was this great couple from Tennessee who provided me some tips on Rome and clearly shared my sense of humor. Plus, the hubs helped me out when I couldn’t finish my wine. The wife was a photographer and clearly was taking some killer pictures… so I awkwardly gave her my email in the van. It was like a first date.
The tour encompassed: a visit to Monteriggoni, winery, gelato at Gelateria l'Antica in Castellina in Cianti, another winery, and two photo op stops.


The two wineries could not have been more different. One of them was modernized and felt like I was in Napa, the other? A 15th century villa with barrels that were 100 years old. I also ate balsamic that was nearly as old as my brother (aged 12+ years), a cheese that had tomato as the rind (amazing), and gelato that tasted like the inside of a Kinder Bueno (not lying at all).
Tomorrow? I’m going to try and get on this San Gimi tour that leaves in the morning. I think it’ll be a good opportunity to see more countryside out of the city and remove the hassle of taking the train. If not, I’ll hop on the train to Montepulciano and maybe see some more sights in Siena. Fred (the tour guide) raved about this Fortezza Medicea at the other side of Siena. He originally recommended it for an evening stroll but I knew my Dad would not be pleased about that. So instead, I took a bubble bath. See you tomorrow Fortezza Medicea in full daylight!

1 comment

  1. Photographer wife from Tennessee, here! Finally got home and settled in and could check out your blog. Love it:) I'm just starting to edit pics and get all my thoughts down for the blog. Definitely should have done it as I went! So glad you gave me your info, and totally wasn't awkward at all lol. My website/blog is and I'm planning the first post for friday. Hope you can stop by:)


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