Florence to Montepulciano: First Couple Days in Italy!

VIRTVE takes on A Year in Travel, and we’re just getting started! And right now … waking up … [yawn].

The journey begins in Italy. And I already need a cart to be rolled around everywhere because of how full my stomach is.

Night 1:


I flew in to Florence the night I got in and stayed at New Ostel hostel.

I was getting in a day before everyone, and it was perfect for what I needed it for. Costing $32 American dollars (all hostels in Florence are pretty steep), my room had four people in it. It was clean, safe, had good wifi, and a couple of different hang out areas.

If you ever need something basic that isn’t gross, I definitely recommend staying here. To get to the downtown area, the Florence airport makes it really easy for you with a 6 euro shuttle that takes you right there. If you decide to stay at New Ostel, your stop to get off of the shuttle will be the first.

Where the party at?

First night in the town, ironically I met up with my great friend Lilly who I met in Costa Rica a couple of months ago. If you’ve been reading VIRTVE then you know she was also the friend I DJed Shark FM with.

She’s here in Florence studying a semester abroad with fellow students from Chapman University. Crazy how life works out.

I hit her up as soon as I landed to find out what all the cool kids were doing, and it was her roommate’s birthday so they were planning on a long night on the town. Perfect! And what better way to jump right into a new city?!

Wasting no time at all, I quickly showered at New Hostel, locked up my things, and walked the 20 minutes to her apartment.

Wow, let’s just say Florence is romantically gorgeous at night with the street lights, cobble stone, and crooked streets and alleyways.

After a shot-filled pregame session, we went to Shot Cafe (or “Shots”) and then Club Twenty One. Both were Top-40 bars with loud music, flashing lights, college students, and strong drinks.

Day 1

Moving Along

Truth is, I was going to head back straight to Costa Rica after getting back to the States (all that surfing got to me … no seriously), but I was lucky enough to be invited on this Italy and Prague trip with Colton and his family, which got me thinking about staying in Europe for a time that is still TBD…

And then, I plan on going back to Costa! (Yes, I know the plan changes every day.) So anyway, I met up with Colton’s parents the next morning, at their hotel in Florence.

We got our little rental car, which was an adventure in itself, had some lunch, and started the hour and half drive from Florence to Montepuciano to meet up with the rest of the gang!

Montepulciano - Photo: Chelsea Chorpenning

Once we got to the right villa in Montepulciano, *keep in mind, traveling in foreign country always has a steep learning curve* we met up with Colton, his sister, her boyfriend, and her best friend. Pretty extraordinary to have seven people all meet up like this will traveling abroad.

Montepulciano Photo: Chelsea Chorpenning

We did a quick check-in to our magnificent villa that overlooks the rolling countryside, exchanged funny travel stories from all parties involved, checked out our private pool (ballin!), picked some of the grapes to eat in the backyard, and then all realized how much hunger is a side effect of traveling.

Montepulciano - Photo: Chelsea Chorpenning


We made a pretty mad dash into the town, walked around, and decided on Osteria del Borgo.

Montepulciano - Photo: Chelsea Chorpenning

Colton and I split two dishes, the salsicce alla griglia con fagioli all’ ucceletto and risotto con asparagi e zafferano. The food, like all food here, is nothing short of spectacular, and the local Montepulciano wine wasn’t either — but that’s not surprising.

Montepulciano - Photo: Chelsea Chorpenning

Don’t even get me started on the first cappuccino I had. Regular coffee will never be the same.

And Dessert

We stopped for a couple cannolis and creamly gelato on the way out to complete the night. I assume to be the first of many nights to complete in this same fashion.

Montepulciano - Photo: Chelsea Chorpenning

After just a taste of Italy, needless to say, I was feeling hungry for more.

Day 2

Chillin’, maxin’, relaxing all cool

Shooting some B-ball outside the pool. Lounge day! Was so nice to just kick it all day outside by pool.

Montepulciano - Photo: Chelsea Chorpenning

Apps, dinner & canolis

Then, it was back in town. We ordered apps at Rich Steve’s suggested restaurant, Vineria Bistrot Spazio Arte and had apps and wine flights, grabbed dinner at La Fortezza S.A.S. via San Donato for some 12-layered lasagna, and finished another perfect day in Montepulciano paradise with canolis and gelato. Yep, I could get used this…

Montepulciano - Photo: Chelsea Chorpenning

Have you been to Italy? What are some of your favorite hit-up spots or things to do?

The captivating photos of Montelpulciano, Italy you see in this post are all taken by Colton’s sister, and good friend, Chelsea Chorpenning. A Denver-based photographer, Chelsea finds beauty in her natural and constructed surroundings. She shoots weddings, events, portraits, homes, and currently is documenting her trip to Italy. Be sure to browse through more of her gorgeous photography works on her website ChelseaCPhoto.comInstagram, Facebook, and Tumblr. For photo inquiries, shoot her an email at chorpenn@gmail.com.

6 thoughts on “Florence to Montepulciano: First Couple Days in Italy!

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