My favorite sketching spots in Italy

Sketching in Spello, from Sesto the Traveling Sketchbook

With over 10 years of traveling through Italy, I've collected quite a number of sketches and watercolors. To date, I have 8 filled sketchbooks, most of which I bound by hand with mixed paper inside so I can paint, journal, collage and draw all in one place (Psst! Each Wanderful Retreat guest gets their own blank sketchbook to document their adventures!). 

These sketchbooks are some of my most treasured souvenirs and possessions. Totally on the list of things I'd grab if there was ever a fire. Within the sketchbooks though, I definitely have some favorite sketches. Moments that were too good not to document. Sketches that captured amazing places, meals or memories. And some spots that I just can't resist sketching again, again and again, even a decade later.

To keep track of all my sketchbooks, I started naming them. My first two sketchbooks from my travels were premade sketchbooks and I wanted my third (Terzo) to be special since it would be my first time traveling back to Italy since my Internship ended. Terzo was the first handbound sketchbook I made that started the addiction and the love of naming these sketchbooks. They've become my travel companions, umbrellas and seat cushion at times, and my most favorite thing to bring home and share with friends and family. 

Since Terzo, there's been Quarto, Quinto, Sesto, Settimo and Ottavo (each meaning 4th, 5th, 6th, 7th and 8th in Italian). My most recent sketchbook tends to always be my current favorite but each sketchbook definitely has some favorite pages.

2013, Lucca with Terzo
In 2013, I spent the fall in Lucca at my friend Vanessa's apartment to just spend some time in Italy visiting friends. This was the first year I ever traveled with a sketchbook I had made myself, let alone a mixed paper sketchbook. While it doesn't have too many sketches that are still favorites, I do love flipping through it to see how I played with drawing and sketching in the same spread, side by side! 

Since I had so much solo, unscheduled time this trip, there's a series of produce studies I did in watercolor from this year in Terzo. As well as lots of more detailed fountain pen sketches of places I was eating at around Lucca. This spot was my friend Elena's former restaurant, Emporio del Sale. It was an amazing spot to hang out at and sketch with a glass of prosecco! This was also my first year traveling with Instagram so I wasn't really in the swing of documenting sketches out in the wild! 

2014, Pisa with Quarto
In the summer/fall of 2014, I stayed in Lucca for a few months to help my friend Vanessa with her apartment rentals. In between checking folks in and out, I made day trips to nearby towns including Pisa. 

This trip to Pisa was one of my first times I had visited since I was a student in 2009 and it was the first time I actually made a point to sketch the famed crooked tower. 

To date this is still one of my favorite fountain pen sketches, especially when paired with the people observations on the opposing page. 

2016, Orvieto with Quinto
This was a big year for me and sketching, and hosting retreats! 2016 was the first year I ever hosted retreats in Italy (Florence only that year) which meant that I had a whole week in Italy with very little time to sketch! What followed afterwards in the few weeks I traveled solo once the retreats wrapped was pretty monumental for how I fill sketchbooks while traveling. 

Left with waaay too many blank pages, I started journaling/doodling everything I did/ate/saw during the day to help fill the pages. I absolutely LOVE how this looks scattered between watercolors and sketches and continue to do this in every sketchbook I travel with longterm. Plus it's just a great way to pass the time when traveling solo. 

2017, Castiglion Fiorentino with Sesto
This was the first year the retreats came home to Castiglion Fiorentino! I was SO excited to finally show folks around my Italian hometown this year, as well as be able to teach everyone to sketch my favorite sites and streets.

One of the iconic views of town is from the Vassari Loggia arches at the top of town, overlooking the Val d'Chio with the bell tower of La Collegiata nearby. I've sketched this view probably more times than anything else except the Pantheon in Rome and it was so fun to lead our guests through their first time painting it.

2018, Cinque Terre with Settimo
After the Villa and Lucca retreats wrapped up, my family met up with me in Lucca before we headed out on our own adventure! We visited Florence, Orvieto, Castiglion Fiorentino, Rome and Riomaggiore in the Cinque Terre region.

It had been years since I actually stayed the night in one of these gorgeous 5 towns nestled along the cliffs and shores of the Mediterranean. I loved being able to wake up early, walk down to the harbor and sketch it without the throngs of tourists invading my view. 

​Plus I got to visit with the harbor cats before anyone else ;) 

2019, Rome with Ottavo
Last year, 2019, was an EPIC year for my sketchbook! Before I even got to Italy to host the retreats in Castiglion Fiorentino and Lucca, I was able to travel with my boyfriend and his family through Berlin, Amsterdam and London. Ottavo already had quite a dent in it before heading to Italy for 2.5 weeks before then heading to meet up with my boyfriend again in Kenya for a safari, and then a river trek in Zambia!

The night before my flight to Nairobi, Kenya, I stayed in Rome and spent the afternoon/evening wandering and sketching all my favorite spots in town, including the Pantheon. I have sooo many sketches of this building, both in and out and I don't think I'll ever get bored of sketching and painting it. 

Stay tuned for Nono (my 9th sketchbook) this fall! ;)